\r\n\t• Role of technological innovation and corporate risk management \r\n\t• Challenges for corporate governance while launching corporate environmental management among emerging economies \r\n\t• Demonstrating the relationship between environmental risk management and sustainable management \r\n\t• Contemplating strategic corporate environmental responsibility under the influence of cultural barriers \r\n\t• Risk management in different countries – the international management dimension \r\n\t• Global Standardization vs local adaptation of corporate environmental risk management in multinational corporations. \r\n\t• Is there a transnational approach to environmental risk management? \r\n\t• Approaches towards Risk management strategies in the short-term and long-term.
",isbn:"978-1-83968-906-2",printIsbn:"978-1-83968-905-5",pdfIsbn:"978-1-83968-907-9",doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!1,hash:"9b65afaff43ec930bc6ee52c4aa1f78f",bookSignature:"Dr. Muddassar Sarfraz and Prof. Larisa Ivascu",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/10226.jpg",keywords:"Global Risk Management, Risk Assessment, Climate Risk, Environmental Management, International Business, Business Sustainability, Corporate Governance, Financial Market, Financial Risks, Sustainable Economic Environment, Business Valuation, Organizational Behavior",numberOfDownloads:53,numberOfWosCitations:0,numberOfCrossrefCitations:0,numberOfDimensionsCitations:0,numberOfTotalCitations:0,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"September 24th 2020",dateEndSecondStepPublish:"October 22nd 2020",dateEndThirdStepPublish:"December 21st 2020",dateEndFourthStepPublish:"March 11th 2021",dateEndFifthStepPublish:"May 10th 2021",remainingDaysToSecondStep:"3 months",secondStepPassed:!0,currentStepOfPublishingProcess:4,editedByType:null,kuFlag:!1,biosketch:"Dr. Muddassar Sarfraz focuses on corporate social responsibility, human resource management, strategic management, and business management. He is a member of the British Academy of Management (UK), Chinese Economists Society (USA), World Economic Association (UK), American Economic Association (USA), and an Ambassador of the International MBA program of Chongqing University, PR China, for Pakistan.",coeditorOneBiosketch:"Dr. Larisa Ivascu's area of research includes sustainability, management, and strategic management. She has published over 190 papers in international journals. She is vice-president of the Society for Ergonomics and Work Environment Management, Timisoara, and a member of the World Economics Association (WEA), International Economics Development and Research Center (IEDRC), Engineering, and Management Research Center (CCIM).",coeditorTwoBiosketch:null,coeditorThreeBiosketch:null,coeditorFourBiosketch:null,coeditorFiveBiosketch:null,editors:[{id:"260655",title:"Dr.",name:"Muddassar",middleName:null,surname:"Sarfraz",slug:"muddassar-sarfraz",fullName:"Muddassar Sarfraz",profilePictureURL:"https://mts.intechopen.com/storage/users/260655/images/system/260655.jpeg",biography:"Dr Muddassar Sarfraz is working at the Binjiang College, Nanjing University of Information Science and Technology, Wuxi, Jiangsu, China. He has obtained his PhD in Management Sciences and Engineering from the Business School of Hohai University. He holds an International Master of Business Administration (IMBA) from Chongqing University (China) and Master of Business Administration (HR) from The University of Lahore. He has published tens of papers in foreign authoritative journals and academic conferences both at home and abroad.\nHe is the Book Editor of Sustainable Management Practices, Analyzing the Relationship between Corporate Governance, CSR, Sustainability, and Cogitating the Interconnection between Corporate Social Responsibility and Sustainability. He is the Associate and Guest Editor of Frontiers in Psychology, International Journal of Humanities and Social Development Research and the Journal of Science and Innovative Technologies. He is an Editorial Board Member of the International Journal of Human Resource as well as a member of the British Academy of Management (UK), Chinese Economists Society (USA), World Economic Association (UK), American Economic Association (USA), and an Ambassador of the International MBA program of Chongqing University, PR China, for Pakistan. \nHis research focuses on corporate social responsibility, human resource management, strategic management, and business management.",institutionString:"Binjiang College, Nanjing University of Information Science &Technology, Wuxi, Jiangsu",position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"0",totalChapterViews:"0",totalEditedBooks:"1",institution:null}],coeditorOne:{id:"288698",title:"Prof.",name:"Larisa",middleName:null,surname:"Ivascu",slug:"larisa-ivascu",fullName:"Larisa Ivascu",profilePictureURL:"https://s3.us-east-1.amazonaws.com/intech-files/0030O00002bRfMOQA0/Profile_Picture_1594716735521",biography:"Dr Larisa IVAȘCU is currently an associate professor at the Politehnica University of Timisoara. 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\n\t\t\t
1. Introduction
\n\t\t\t
Investigation of compounds having the asymmetric carbon in their structure has a fundamental significance for understanding all processes that occur in living organisms. Biologically active compounds as amino acids, sugars, peptides, proteins and polysaccharides posses a different stereochemistry. All of these compounds are involve in chiral interactions in biochemical systems functioning in living organisms. Animal and human peptides consist of almost only left-handed (L) amino acids as building blocks for peptides. Right-handed (D) amino acids occur in unicellular lower organisms. A huge interest in chirality results also from the fact that present pharmaceutical and chemical industry to large extent is based on the synthesis of compounds that may have a different stereochemistry. Enantiomeric pharmaceuticals, pesticides or food additives can have a different influence on living organisms. The first observations on the pharmacological role of enantiomers are assigned to Abderhalde and Müller, who described in 1908 a difference in raising blood pressure by enantiomers of epinephrine. These observation started research on the effects of the enantiomers in the context of the pharmacological effect.
\n\t\t\t
Clinical tests indicate that the replacement of racemate by a single active enantiomer of pharmaceutical allows to use of lower doses of drugs, increasing the therapeutic efficacy of individual doses. It helps to avoid possible harmful interactions with other drugs, to minimize the differences in drug metabolism between species and reduce the toxicity caused by supplementation of inactive isomers (Agranat et al., 2002; Baumann et al., 2002). There has been a trend towards to ensure that pharmaceuticals that were invented, approved and marketed as a racemate or a mixture of diastereomers, have been re-marketed as single enantiomers. Such compounds are called "chiral switches" (Caner et al., 2004; Hutt & Valentová, 2003)
\n\t\t\t
The enantiomers of the same compound, indistinguishable by physical and chemical properties show sometimes different physiological effects. There are a number of examples demonstrated the need to test the impact of individual enantiomers, and in some cases, the chiral purity control of the compound. Enantiomers may differ in smell which can be exemplified by carvone, S and R-enantiomer have the scent of caraway and mint respectively (Laska et al., 1999). They may have a different taste - for example, isoleucine and asparagine, have a bitter taste as a form of L and sweet in the form of D (Zawirska-Wojtasiak, 2006) and activity effects on organisms, such as ephedrine and adrenaline. The stimulating effect of (+) ephedrine is 80% of the effect caused by (-) ephedrine (Herráez-Hernández & Campíns-Falco, 2001). There have also been known cases in which one of the enantiomers of a compound have a beneficial influence for the body and the other caused serious problems. The most famous example was the drug with analgesic and calming effect - thalidomide administered to pregnant women in the racemic form. It was found that the R enantiomer has a therapeutic effect, while the other enantiomer was strongly teratogenic. It elicited phocomelia, disease involving the disappearance of the long bones of limbs (Nakanishi et al., 2004; Lenz, 1988). Currently, researches on the use of this drug for cancer are conducted. It is used to treat multiple myeloma, especially in the elderly. Its inhibiting effect on the formation of blood vessels around tumours was also noted. Also, the enantiomers of many other drugs have different effects. L-DOPA is used to treat Parkinson\'s disease, while the D-enantiomer exhibits strong toxicity. Similarly, in the case of penicillamine, D-enantiomer is used as an antiarthritic drug, and the L-enantiomer is highly toxic (Eichelbaum & Gross, 1996). Also, a number of drugs belonging to the group of antidepressants and psychotropic drugs have a different effect of both enantiomers (Lane & Baker, 1999).
\n\t\t\t
Literature presents many examples showing that enantiomers differ in activity, rate of reaction or time of dissolution. The example of difference in time of dissolution can be fungicide metalaxyl. In a neutral pH the R enantiomer in its active form shows over four times higher dissolution constant than S enantiomer. (R)-(+)-isomer of organophosphorus pesticide methamidophos reveals the higher insecticidal activity against flies than other enantiomer and racemate (Miyazaki et al.,1988). On the other hand (S)-(-)-methamidophos appear more toxic after application against German cockroaches in a short time. During first 5 hours the same dose of S enantiomer caused death of 75% of insects whereas R enantiomer caused death of only 20%.
\n\t\t\t
Research of the individual enantiomers can be a valuable indicator of the quality of different food products. D amino acid content in natural samples of milk, juice and honey is an indication of bacterial contamination, prolonged storage time of products or poor quality of fruit used in the production of juice. The content of D or L enantiomers of lactic acid in fermented products provides the type of bacteria responsible for the process. Similarly the presence of D-asparagine in yogurt samples indicates the presence of specific bacteria. Also, chiral alcohols can be used to control product quality. For determination of 2-butanol in distilled spirits, R-enantiomer derived from bacteria that may be present in the mash, and S enantiomer is produced only by yeast. The content of R-2-butanol is a marker of bacterial contamination. Also from chiral linalool (affecting the taste of oranges), the S form is present in sweet oranges, and R is the typical to bitter. It can be an indicator of adulteration of the concentrate’s composition (Marchelli et al., 1996).
\n\t\t\t
Enantiomers of some compounds can be used also to trace sources of water contamination. A non-selective beta blocker mainly used in the treatment of hypertension-propranolol exists in untreated sewage as a racemate. During successive steps of sewage treatment the amount of R enantiomer in relation to both enantiomers decreased to even less then 40% regardless the concentration of compound. Determination of enantiomeric fraction (the ratio of the concentration of one of the isomers to the total concentration) can be useful indicator to evaluate if examined water is significantly affected by untreated sewage, for example as a result of leaking sewers and to apportion the contribution of treated and untreated sewage into surface waters (Fono & Sedlak, 2005).
\n\t\t\t
In a similar manner the source of groundwater contamination in Switzerland by specifying the content of enantiomers of the herbicide Mecoprop was determined. In order to protect crops in agriculture, it is sold as a pure enantiomer, while the same compound was also used to protect roofs against fouling by plants. In latter case a racemate was used. Enantiomer ratio of 0.5 was an indication that about 50% of the herbicide in surface water origin from roofs security system, and not - as expected - mostly from agriculture (Bucheli et al., 1998).
\n\t\t\t
There are also works in which attempts to use information about the racemization rate in the study to determine the age of archaeological finds on the basis of the ratio of amino acids enantiomers contained in samples of bone, shell or teeth. In living organisms, the ratio of amino acid D / L is zero. After the death of the body\'s proteins break down and the process of racemization begins. It leads to increase the ratio of amino acids D / L up to one. This process is lengthy and depends on many factors such as the structure of the amino acid sequence of amino acids in the protein, pH, buffering effect, humidity, temperature, as well as the presence of catalysts. Due to the large number of parameters that must be controlled, this technique is challenged by many researchers, even though it is used for 30 years and has resulted in many interesting publications (Robins et al. 2001).
\n\t\t\t
Optically pure compounds are also used in chiral synthesis. In 2001, Sharpless, Knowles and Noyori received the Nobel Prize for research on the oxidation and hydrogenation reactions using optically active compounds which have found application in the production of many antibiotics and anti-inflammatory and cardiac drugs (Kaniewska 2009).
\n\t\t\t
The enantiomers of the same compound are characterized by almost identical physical properties. For this reason they can not be separated by widely used methods such as fractional distillation or fractional crystallization except that the solvent is optically active. Methods used for separation and determination of individual isomers are based on interaction with substances exhibiting optical activity. Currently used methods for the analysis of optically active compounds are mainly separation methods such as gas chromatography (GC), liquid chromatography (LC) and high performance liquid chromatography (HPLC) using chiral stationary phases, chiral selectors in the mobile phase or flow reactors for derivatization and highly efficient electromigration techniques as capillary electrophoresis (CE) using chiral selectors. Other methods are mass spectroscopy, NMR to the study of molecular recognition, as well as some spectroscopic techniques. These techniques require expensive equipment and the analysis is in most cases time-consuming.
\n\t\t\t
Biosensors are widely used for analytical application for example in clinical of food analysis, environmental monitoring or chemical processes. They are characterized by good precision and sensitivity. The measurement is fast and stable. Biosensors can be miniaturized and used in portable analysers. They contain the biological material which often has the stereoselective or stereospecific properties. For this reason, biosensors may be competitive to the separation methods for the analysis of optically active compounds.
\n\t\t
\n\t\t
\n\t\t\t
2. Enantioselective enzymatic biosensors
\n\t\t\t
\n\t\t\t\t
2.1. Electrochemical biosensors
\n\t\t\t\t
Among natural receptors in construction of biosensors most often enzymes are employed. The reasons are the wide range of measurable parameters that can be utilized as result of biocatalytic process (chemical products, ions, protons, light, electrons) and a large number of available, isolated enzymes (Subrahmanyam et al. 2002). Numerous number of enzymes employed for long years in design of biosensors catalyses enantioselectively reactions of particular isomers of substrates, but very few reports can be found on their enantioselectivity and potential applications. The most examples can be find in reviews (Schlügerl et al. 1996; Stefan et al. 1999)).
\n\t\t\t\t
Enzymes as compounds involved in life processes catalyze the reactions in which the substrate is a compound in the form of pure enantiomer. Enzymes may exhibit, depending on the method and mechanism of interaction with substrates, the absolute, or stereochemical specificity. The specificity may relate the D and L forms, geometric isomers, the position of binding, the coenzyme spatial settings, and the asymmetry of the complex enzyme-substrate. Stereochemical specificity is the perfect matching of the substrate configuration of the spatial points of interaction in the active centre. Active complex is generated only in the case of appropriate size. Enzymes catalyse reactions by creating new reaction pathways of lower energy transition state. The first step is usually to produce an enzyme-substrate complex. Substrate binds to the enzyme active site, which is a small recess or slot for the characteristic structure of the enzyme. Binding specificity depends on the specific arrangement of atoms in the active site. The fit is possible only if the substrate have an appropriate shape. In the case of chiral compounds the velocity of the reaction of substrate molecule with the enzyme is usually different for both enantiomers. Enantioselectivity factor value (E) can be determined from the equation (1) (Chen C. S. et al. 1982)
The difference of reaction rates of competing substrates due to the difference in Gibbs free energy of the subsequent stages of the reaction (Fig. 1) (Overbeeke et al., 1998).
\n\t\t\t\t
Figure 1.
Gibbs free energy change in subsequent reactions catalysed by the enantioselective enzyme
\n\t\t\t\t
Then the enantioselectivity is determined from the expression (2):
The most often developed, so far, are systems with pair of enzymes specific for each enantiomer. One of the mostly used examples are amino acid oxidases. D-amino acid oxidase, by the presence of adenine flavin dinucleotide (FAD) as cofactor, catalyses the oxidation of D amino acids to imino acids which are immediately hydrolyzed to the corresponding α-keto acids and ammonium ions (Moreno et al. 1996). D-AAOx does not catalyze the oxidation of the opposite enantiomer and it is not inhibited by L amino acids. The properties of D-amino acid oxidase differ depending on the species. For example, the structure of the active centre of enzyme derived from mould is more open, which is the cause of a much broader range of catalytic activity (Pollegioni et al. 2002).
\n\t\t\t\t\t
Enantiomers of amino acids were determined electrochemically with the biosensors that differ by way of immobilization, enzyme systems, or a kind of mediator. D-AAOx or L-AAOx were involved to the construction of biosensor sensitive to D or L amino acids. Value of the signal obtained for over 20 common L-amino acids and six important D-amino acids were presented in (Sarkar et al. 1999) and compared with the results obtained in (Kacaniklic et al. 1994). In the first case an enzyme was immobilized on the screen-printed electrode with the addition of polyethylamine (PEI) to the working electrode paste. The working electrode incorporated rhodinized carbon to facilitate hydrogen peroxide oxidation. Sensor showed response to six of the seven tested D amino acids, except D-proline. Only the average response of the biosensor for the relevant amino acid at a concentration of 0.1 mol L-1 was presented. In the latter case the enantioselective enzyme was coimmobilized with the horseradish peroxidase in the graphite paste with the addition of polyethylamine. In another example D-or L-AAOx were immobilized together with horseradish peroxidase and ferrocene as a mediator in the graphite-Teflon paste. The sensor consists of two electrodes – each with a different amino acid oxidase, L or D was used to determine amino acids in the racemic samples, or to determine the L amino acid in samples of grapes. Measurements were carried out in batch and flow (Dominguez et al. 2001). For the rapid determination of D and L amino acids the system of D-or L-AAOx biosensors immobilized in a membrane protein with glutaraldehyde was used. The chiral selectivity of the reactor was checked. The system was used for determination of amino acids in samples of two beers during the process of fermentation (Varadi et al. 1999). For determination of D-alanine a system of two sensors was used. System contained a reactor with DAAOx immobilized by glutaraldehyde on glass porous CPG (long chain alkyl amino-controlled pore glass) coupled with a sensor with the pyruvate oxidase (PyOx). D-amino acid oxidase catalysed the oxidation of D-amino acids, including the formation of pyruvate from D-alanine. This compound was then oxidized in a reaction catalysed by the pyruvate oxidase and the amount of oxygen consumed in this reaction corresponded to the contents of D-alanine in the sample (Inaba et al. 2003a). A different design of a sensor based on the same reactions was also used. Pyruvate oxidase was immobilized in the membrane on the surface of the Clark oxygen electrode. Suitable amino acid oxidase D-or L- in the buffer was added to a sample of amino acids and oxygen-saturated solution was incubated with catalase. After a specified time, the concentration of pyruvic acid formed was measured using electrode with PyOx (Inaba et al. 2003a). DAAOx was also immobilized on Prussian blue film by electrochemical codeposition. The electroactive layer was covered with Nafion. Biosensor was calibrated with D-alanine, but had no specific answer to this amino acid (Shi & Dong, 1995)
\n\t\t\t\t\t
The screen-printed electrodes with the Prussian Blue as a mediator were used to prepare the biosensor for D-amino acids (Wcislo et al. 2007). The surface of the working electrode covered with the mediator has been additionally protected by the Nafion layer and then modified by evaporation of mixture containing DAAOx, bovine serum albumin and glutaraldehyde. The short response time and good reproducibility was obtained in measurements of D-alanine and some chosen D-amino acids. Biosensor showed the linear response to D-alanine in the phosphate buffer with addition of FAD in the concentration range 10-300 μM. L-alanine did not give any response (Fig. 2). The biosensor was examined towards some other D amino acids and all L amino acids. The total amount of D-amino acids was estimated for the samples of milk and juices.
\n\t\t\t\t\t
Figure 2.
The amperometric response of screen-printed enzymatic biosensor to enantiomers of alanine. Measurements made by placing a drop of measuring solution on the SPE sensor at –0.05 V polarizing potential. Solution of alanine made in 50 mM phosphate buffer of pH 7.4 containing 0.1 M KCl and 10 μM FAD (Wcislo et al. 2007).
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The graphite paste biosensors with immobilized L-AAOx were employed for enantioselective detection of S-capropril (Stefan et al. 2003a). With amino acid oxidases also multi-enzyme biosensors were developed for determination of various drugs from the group of angiotensin-converting enzyme inhibitors such as cilizapril, pentopril (Aboul-Enein et al., 1999a), enalapril, ramipril, trandolapril (Stefan et al., 1998) and perindopril (Aboul-Enein et al., 1999b). For determination of D- or L-methotrexate (substituted glutamic acid) D-AAOx or L-AAOx were immobilized together with glutamate oxidase and horseradish peroxidase in the graphite paste. Different combinations of enzymes were examined. Mono-, bi- and trienzyme electrodes were constructed. The best enantioselectivity was obtained for three enzyme system with L-AAOx (selectivity coefficient pKamp = 3.09). The selectivity of all biosensors was checked by both separate and mixed solution method. In mixed solution method the ratio between the concentration of the main and the interfering enantiomer was 1:10 (Stefan et al. 2003b). For the same multi-enzymatic system also a covalent immobilization with glutaraldehyde on the graphite support was examined with carbodiimide and thermal hardening, but immobilization in graphite paste was found simpler and providing better results in terms of enantioselectivity. Similar methods of enzyme immobilization have been used for detection of pipecolic acid. The graphite paste biosensor consist D or L amino acid oxidase or the one of the amino acid oxidase combined with horseradish peroxidase in order to improve detection of hydrogen peroxide. The best result was obtained for bienzyme biosensor containing L-AAOx with HRP (selectivity coefficient pKamp = 3.82). The values of amperometric selectivity coefficients for all the biosensors designed for L and D pipecolic acid were higher than 2. Proposed biosensors were used in clinical analysis to detect L or D-pipecolic acid in serum samples (Stefan et al. 2003c).
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Another similar pair of enzymes sensitive to enantiomers is D- and L-lactate dehydrogenases (D-, L-LDH). Biosensors with these enzymes immobilized on porous carbon electrodes with the use of osmium complex (Os(bpy)3)(PF6)2 as mediator have been used for determination of D and L-lactic acids. Changes in the concentration of lactic acid enantiomers measured by cyclic voltammetry were linear for L-enantiomer in the range of 0.1 -10 mmol L-1 and D-enantiomer of 1-20 mmol L-1. The enantioselectivity was determined by marking of error of one of the enantiomers determination at 10 fold excess of another. In the case of biosensor with L-lactate dehydrogenase, L-lactic acid was determined with an error of 4.9% with 10 fold excess of D-lactic acid. In the opposite situation the error was 5.4% (Motonaka et al. 1998). In the design of enzyme field effect transistor with D-LDH, the enzyme was immobilized on pH sensitive gate. The enantioselectivity of the biosensor is presented in Fig. 3. The authors admited, however, that the equilibrium of these reactions was shifted to the left and therefore the reaction product had to be removed. The signals were also influenced by pH, buffer capacity, temperature and flow-rate (Kullick et al. 1994). In a similar way biosensors with D- and L-malate dehydrogenases have been prepared (Schlügerl et al 1996).
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Figure 3.
The potentiometric response of D-LDH FET biosensor to enantiomers of lactate (Kullick et al. 1994).
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In cases where there are no specific enzymes for both enantiomers another method of determination can be used. Two biosensors can be simultaneously employed – one sensing with similar sensitivity both D and L species, and another one, sensitive to particular enantiomer. A multichannel system with eight pH field effect transistors has been developed for determination of hydrophobic esters of amino acids. Esterase EC 3.1.1.1 was used as a non-enantioselective enzyme while α-chymotrypsin only catalysed the reaction of L-amino acid esters. The first biosensor could detect the total amount of amino acid esters and the second gave the information about the enantiomeric ratio in the sample. The same authors present the example of the sensor containing the esterase and lipase for the enantioselective determination of β-hydroxy acid esters, where lipase catalysed the reaction of D-β-hydroxy esters (Kullick et al. 1994). The authors also mention the possibility of construction of system of two enzymes – amidase and aminoacylaze - which catalyze the reactions of deacylation. Amidase catalyzes the non-selective reaction of N-acetyl amino acids and aminoacylaze selectively catalyses only N-acetyl-L-amino acids (Schlügerl et al. 1996)
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Also a biosensor design has been reported, where with the use of non-enantioselective enzyme, the enantioselectivity has been gained by the modification of sensing electrode surface with appropriate conducting polymer, which additionally serves as support for immobilization of enzyme. The surface of glassy carbon electrode was modified by electropolymerization of the chiral dicarbazole-biotin. The modification provided differentiation of current magnitude for anodic oxidation of L- and D-norepinephrine of about 50% at 0.5 V vs. SCE. Electrode was modified by six enzyme layers constructed by six cycles of sussesive deposition of avidine and biotinylated polyphenol oxidase (PPO). The immobilization resulted in obtaining of biosensor for measurements of D-norepinephrine with 4.8 times larger sensitivity than for L isomer at 0.2 V vs. SCE (Cosnier et al. 2003).
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Finely there are enzymes with well defined enantioselectivity still not involved to biosensor design. One of the examples is Quinohaemoprotein alcohol dehydrogenase (Jongejan et al., 2000). The enzyme is enantioselective in the oxidation of secondary alcohols. A strong preference is observed for the S-2-alcohols. The enantioselectivity increases with increasing chain length. The same enzyme was immobilized on the surface of electrode and used in that form for preparative purposes (Somers et al., 1998). Although another type of alcohol dehydrogenases were used for biosensor design (Jiang et al. 2009) Quinohaemoprotein alcohol dehydrogenase as yet didn’t find any analytical application.
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2.1.2. Chiral inhibition
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There is a large representation of chiral compounds among pesticides. 25% of the active pesticide ingredients appear in the form of enantiomers (Garrison, 2006). A vast majority of these compounds is produced and sold as a racemate. The operating principle for a large number of phosphoogranic pesticides is precisely acetylcholinesterase inhibition. Unimmobilized enzyme inhibition studies using phosphoogranic pesticides in solution and in vivo in water microorganisms, indicate differences in the inhibition rate and toxicity against selected organisms for the enantiomers of the compounds used for tests. These differences may depend on the origin of the enzyme. Depending on whether it was tested in vitro or in living organisms opposite inhibition was observed. (-)-Profenofos has more than 8-fold greater toxicity on Daphnia manga in vivo, while (+)-Profenofos in vitro shows a rate of inhibition over 71 times stronger towards HR-AChE (Nillos et al., 2007). In the case of fenoxon sulfoxide, IC50 (half maximal inhibitor concentration) has been presented. This factor was estimated for two enzymes: HR-AChE and EE AChE with the average figures at 6.9 µM and 6.5 µM for R (+) fenoxon sulfoxide and 230 µM and 111 µM for S (-) fenoxon sulfoxide respectively (Gadepalli et al., 2007). Another example of chiral phosphoogranic pesticide is the nematicide fosthiazate. The examination of individual enantiomers’ reactivity showed a 1.4 difference in the inhibition of EE AChE in vitro and a 3.1 fold difference in toxicity against Daphnia manga (Lin K. D. Linet al., 2007). Significant differences of AChE inhibition can also be observed for the insecticide chloramidofos, which has 2 pairs of diastereoisomers; depending on the chosen pair of enantiomers the differences range from 1.1 to 18.1 (for measurements in vitro) and from 1.2 to 13 (in vivo) (Zhou et al., 2007).
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The operating principle of malathion and malaoxon also is based on the inhibition of acetylcholinesterase. The differences in the inhibition rate dependent on the enantiomer applied, as well as on the origin of the enzyme have been observed. R malaoxon inhibited RB AChE (rat brain) 8.6 times faster than S malaoxon (Berkman et al., 1993a). In turn, BE AChE (bovine erythrocytes) difference in the rate of inhibition of R / S is 22.5 (Rodriguez et al., 1997).
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Below we present for the first time in literature a screen printed biosensor which can be used to measure the inhibition of the immobilized enzyme in both batch and flow analysis.
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Screen printed electrode mediated with Prussian Blue and protected by Nafion layer was used to prepare the bienzymatic biosensor. The membrane was obtained by mixing acetylcholinesterase, choline oxidase and BSA solution phosphate buffer with the addition of KCl, and then with glutaraldehyde solution in water. The scope of straightness for the signal received in batch measurements was 10-500 µM for acetylcholine chloride. Static measurements indicated that the enzyme immobilized by the R-enantiomer is inhibited stronger than the one immobilized with the S-enantiomer by approximately 1.25 times. For malathion the inhibition ratio for the enantiomers R / S was 1.3 (Fig 4A).
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Batch measurements were also carried out for B394-strain acetylcholinesterase – a mutant strain of the enzyme isolated from the fruit fly. The biosensor with immobilized B394 strain acetylcholinesterase showed practically no difference in inhibition by the two pesticides (malaoxon and malathion) (Fig 4B)\n\t\t\t\t\t
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For the flow measurements the biosensor with EEAChE showed linear response to the analyte in the range of concentration from 50 to 800 μM. The ratio of the original signal of the biosensor inhibited by R and S enantiomers of malaoxon in flow analysis after the first injection was 2.7. Then, after the second injection of the inhibitor solution, it was as high as 22 and the subsequent injections caused practically no signal from the enzyme immobilized on the surface of the biosensor by R-enantiomer (Fig 4C). The enzyme inhibited by S-enantiomer, on the other hand, still showed some activity. The presented study also confirms that the differences in inhibition depend on the chiral origin of the enzyme (Kaniewska 2009).
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3. Enantioselective immunosensors
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It is well known that antibodies can differentiate enantiomers of antigens (Landsteiner & van der Scheer, 1928). Bedsides numerous other selectors as cyclodextrins, crown ethers, macrocyclic antibiotics, Pirkles, proteins or cellulose commonly used for obtaining a chiral stationary phases for HPLC, chiral separation can be obtained by immobilizing suitably raised stereoselective antibodies onto a stationary phase (Hofstetter et al., 2002; Kim H. et al., 2004).
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The development of the affinity-based biosensors is on of the fastest growing area in the biosensor field (Rogers 2000). Various strategies have been developed for design of separation-free electrochemical immunosensors, based mostly on heterogeneous immunoassay procedures (Killard & Smyth, 2000).
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3.1. Electrochemical immunosensors
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The possibility of the construction of enantioselective immunosensors was indicated by the use a stereoselective antibody sensitive to the chiral centre of α-amino acids (Hofstetter et al., 1998). The interactions of rabbit antibodies was detected for amino acids in an enzyme-linked immunosorbent assay (ELISA). The enantiospecificity was observed for free amino acids p-aminophenylalanine and phenylalanine, whose structures overlap with the hapten, but also it was exhibited for other amino acids, aromatic and aliphatic. The same antibodies were employed for the development of a highly enantioselective electrochemical immunosensor. Stereoselective binding of an anti-D-amino acid antibody to the hapten-modified sensor surface resulted in capacitance changes that were detected with high sensitivity by a potentiostatic step method enabled to detect impurities of D-phenylalanine as low as 0.001%. The L-enantiomer was not bound by the antibody (Zhang S. et al. 2006).
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Another example of electrochemical sensor is based on the stereoselective interaction of proline with carcinoembrionic antibody (anti-CEA). The selected pure enantiomer of proline was assembled on the glassy carbon electrode surface. Then the anti-CEA was loaded and
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Figure 4.
The percentage of inhibition of AChE immobilized on the surface of the biosensors by malaoxon enantiomers. (A) Inhibition of EE AChE in batch measurement. A signal measurement was performed for three samples of the substrate (concentration 100 μM), preceded by baseline measurements. Then the electrode was incubated for 20 minutes in a solution of a given concentration of the pesticide. (B) Inhibition of B394 strain AChE in batch measurements. Signal measurement was performed for three samples in the substrate concentration of 1mmol L-1 preceded by baseline measurements. (C) Inhibition of EE AChE immobilized on the surface of biosensors inhibited by malaoxon enantiomers (40 nM concentration) in the flow system. 100 μL of solution of the substrate at a concentration of 400 μM and 100 μL of inhibitor solution were injected. Subsequent injections were preceded by rinsing the biosensor phosphate buffer (Kaniewska 2009).
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the ready immunosensors were tested over different concentration of carcinoembryonic antigen (CEA) (Fig 5.). The experimental results demonstrated that electrodes modified with D-proline had a better recognition function to anti-CEA, which is in good correlation with images of electrode surface obtained by atomic force microscopy. Authors suggested that designing chiral surfaces of amino acids may bring a new direction for biomaterials and help to understand the origin of stereoselectivity in pharmaceutical systems and clinic diagnoses (Chen M. et al.2009).
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An amperometric immunosensor based on a graphite paste was presented in (Stefan & Aboul-Enein 2002). Mouse monoclonal anti-(+)-3,3’,5,5’-tetraiodo-L-thyronine (anti-L-T4) was used to the construction of immunosensor sensitive to thyroid hormone L-T4 known also as L-thyroxine. The selectivity coefficient obtained over D-T4 was 1.7 10-4.
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3.2. Other type of detection
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Anti-D-AA antibodies have been employed for the determination of trace amounts of enantiomeric impurities of amino acids in the design of immunosensor based on different detection methods. The binding of stereoselective antibodies sensitive to the chiral centre of D-phenylalanine tested by a competitive enzyme-linked immunosorbent assay enabled to detect D- phenylalanine concentrations as low as 0.1 mM in the presence of 10 mM L-phenylalanine which corresponds to an enantiomer excess of 99.998% (Hofstetter et al., 2000).
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Figure 5.
Calibration plots of the cathodic peak current response vs. concentration of CEA (0.5-80 ng/mL) with D (closed squares) and L (open circles) modified immunoelectrodes under optimal conditions (Chen M. et al.2009).
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The same interactions were used in construction of immunosensors based on surface plasmon resonance detection. Applications of immunoglobulins in a sensor design allowed to detect a low-molecular-weight analytes as amino acids by the SPR method. Compounds called D1 (p-amino-D-phenylalanine) and L1 (p-amino-L-phenylalanine) were immobilized onto separate channels of the sensor coated by the streptavidin covalently linked to carboxymethyl-dextran. Polyclonal rabbit antibody sensitive to D-amino acids interacted with the sensor while no increase of the SPR signal was observed for antibody sensitive to L-amino acids. Chiral discrimination was shown for the enantiomers of tyrosine, DOPA (3,4-dihydroxyphenylalanine), norleucine (Fig 6.) and tryptophan. The immunosensor allowed to detect 0.01% of the minor enantiomer present in the major enantiomer sample (Hofstetter et al., 1999).
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Also a magnetic relaxation switching appears can be applied as a detection method for the construction of chiral immunosensors. This method allows for a rapid determination of enantiomeric excess in a high-throughput format. The MRS immunosensor was based on magnetic nanoparticles consisted of superparamagnetic iron oxide core with an aminated cross-linked dextran coating (CLIO) labelled with a derivative of D-phenylalanine. A decrease of more than 100 ms in the relaxation time was obtained by self-assembly of antibodies specific to D-amino acids (anti-D-AA) added to the CLIO-D-Phe. Upon addition of mixtures of the phenylalanine enantiomers to the CLIO-D-Phe/anti-D-AA self assembled structures, the presence of D-Phe impurities resulted in the dispersion of the nanoparticles by competing with the CLIO-D-Phe conjugates for antibody binding sites. The immunosensor allowed to detect 0.1 µM D-Phe in the presence of 10 mM L-Phe, which is an equivalent to 99,998% enantiomer excess (Fig 7.) (Tsourkas et al., 2004).
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For the less sensitive determination of enantiomeric impurities a simple and inexpensive membrane-based optical immunosensor was invented. The immunosensor was based on a competitive reaction between an analyte and a biotin-derivatized analogue for the binding
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Figure 6.
Stereoselective binding of antibody to various amino acids: D-tyrosine (closed triangles), L-tyrosine (open triangles), D-DOPA (open circles), L-DOPA (closed circles), D-norleucine (closed diamonds), L-norleucine (open diamonds). The SPR values were converted into percentage of inhibition.
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sites of a stereoselective membrane immobilized antibody. The antibody-bound was detected with peroxidase-conjugated avidin that converted a colourless substrate into an insoluble dye. The colour intensity was inversely related to the concentration of an analyte. The immunosensor allowed for quantitative determination of chiral phenylalanine up to an enantiomer excess 99.9% (Hofsetter et al. 2005)
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Figure 7.
Inhibition of the CLIO-D-Phe/anti-D-AA self assembly in the presence of increasing concentrations of L- or D-Phe as detected by changes in the T2 relaxation time (Tsourkas A. et al 2004)
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Figure 8.
Time trace of cantilever defections resulting from the binding of enantiomers of amino acids to micro cantilevers modified with covalently anti-L-amino acid antibody (1-4) or human immunoglobulin G (5,6) 1-50 mg/L L-tryptophan, 2,5- 50mg/L L-phenylalanine, 3- 50 mg/L D-tryptophan, 4,6- 50 mg/L D-phenylalanine. (Dutta et al. 2003).
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These antibodies have been also employed for enantioselective sequential-injection chemiluminescence immunoassay of triiodothhyronine and tetraiodothyronine with immunoreactor with immobilized haptens. It has been shown that the detection of <0.01% of the L enantiomers in samples of D enantiomers is possible in less than 5 minutes including regeneration of immunoreactor (Silvaieh et al. 2002). Anti-D-AA was used in microfabricated cantilevers for enantioselective detection of amino acids based on inducing surface stress by intermolecular forces arising from analyte adsorption on surface-immobilized antibodies (Dutta et al. 2003). The temporal response of the cantilever allowed the quantitative determination of enantiomeric purity up to an enantiomeric excess of 99.8%. Based on the slope of response curves or anti-D-amino acid antibody, the selectivity coefficients for D- enantiomer towards L-isomer were 6.5, 7.7, and 37.5 for D-phenylalanine, D-tryptophan (Fig 8.) and D-methionine respectively. The largest enantioselectivity has been observed for D-valine (104).
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4. Enantioselective bioreceptors
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4.1. Mass-based biosensors
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There are many examples of sensors exhibiting the enantioselective properties based on quartz crystal microbalance technique for example sensor for L-histidine (Zhang Z. et al. 2005), (+) methyl lactate (Ng et al. 2002), L-cysteine (Chen Z. et al. 2000), L-phenylalanine (Huang et al. 2003) or (-) menthol (Tanese et al. 2004). However the combination of biological macromolecules and QCM technique has been rarely reported for the studies of chiral discrimination.
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Two sensors were developed by immobilization of human serum albumin (HAS) and bovine serum albumin (BSA) onto gold electrode combined with quartz plate by self-assembled monolayer technique. The decreased frequency demonstrated interactions between albumines and enantiomers of R,S-1-(3-Metoxyphenyl)ethylamine (R,S-3-MPEA), R,S-1-(4-Metoxyphenyl)ethylamine (R,S-4-MPEA), R,S-tetrahydronaphthylamine (R,S-TNA), R,S-2-octanol (R,S-2-OT) and R,S-methyl lactate (R,S-MEL). The binding affinity of BSA and HSA for all five pairs of enantiomers was stereodependent. The effectiveness of the QCM sensor was described by the chiral discrimination factor αQCM, defined as a quotient of the frequency decrease for enantiomer R and S respectively. For both sensors the highest discrimination factor were obtained for R,S-TNA. The value were for BSA sensor αQCM =1.34 while for HSA sensor αQCM =1.57 (Su et al. 2009).
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4.2. Optical biosensors
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The Surface Plasmon Resonance method was used for monitoring real time interactions of enantiomeric drug compounds to biomolecules immobilized on the surface of the sensor chip. The example of such biosensor for the first time was used to check the binding of the unnamed chiral drugs to human and rat albumins. However the enantiomers showed slight differences in their affinities towards the immobilized albumins, authors admitted that they were not able to detect whatever subtle differences could be due to differences in the enantiomers or it could be due to experimental errors (Ahmad et al. 2003). The next SPR biosensors were used to a detailed investigation of enantioselective interactions between protein and chiral small drugs. The binding of β-blockers alprenolol and propranolol to Cel7a cellulase was used as a model system. Cel7a was immobilized onto the sensor chip by PDEA-mediated thiol coupling. The single enantiomers of β-blockers were injected in a series with broad concentration range and a different pH of the solution was examined. The results were compared with the previously validated HPLC perturbation method. (Arnell et al., 2006). Similar interactions of drugs were examined for the SPR biosensors with two types of proteins-transport and target, immobilized onto the sensor chip. Different type of strong, intermediated and week interactions were exhibited by the models of binding of propranolol enantiomers to α1-acid glycoprotein (AGP), R- and S-warfarin to human serum albumin (HSA) and RS and SR-melagratan to thrombin, AGP and HSA. Strong binding occurred in the case of RS-melagratan-trombin interaction. The other enantiomer did not interact at all with the protein (Sandblad et al., 2009)
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4.3. Ion channel biosensors
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The enantioselectivity was also reported for coulometric ion channel sensor for glutamic acid. The sensor was based on the use of glutamate receptor ion channel protein. The glutamate receptor was immobilized within an artificial bilayer lipid membrane formed by applying the folding method across a small circular aperture bored through a thin polyimide-film. The detection of L-glutamic acid was performed at a concentration as low as 10-8 M. The observed enantioselectivity for the channel activation was attributed to a combined effect of both the relative strength of binding isomers to the receptor protein and the relative potency of bound isomers to induce the ion channel current (Minami et al., 1991).
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5. Enantioselective aptamers
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DNA aptamers are a new group of chiral selectors. They are a single-stranded oligonucleotide sequences that can fold into a 3D shape with binding pocket and clefts that allow them to bind many molecular targets as proteins, amino acids, peptides, cells and viruses with specificity that allows them to distinguish even strictly structurally related molecules. Aptamers are able to bind the target molecules with a very high affinity, equal or sometimes even superior to those of antibodies. Comparing to antibodies they present also some important advantages as well defined sequences produced by reproducible solid phase synthesis which allows an accurate modulation of their selectivity and binding parameters. Aptamers are much smaller than antibodies, permitting a higher density of molecules to be attached to surfaces. Their production does not require animal’s immunization. It’s also possible to obtain aptamers towards molecules that do not stimulate immunoresponce or that are toxic. Selections are not limited by physiological constraints allowing aptamers that bind their targets in extreme conditions to be isolated. Aptamers will refold to regain functionality after exposure to denaturing conditions (Mosing & Bowser, 2007). They are attractive host molecules, because they can be tailored to a variety of guest targets by the method of systematic evolution of ligands by exponential enrichment (SELEX) (Giovannoli et al., 2008).
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Figure 9.
SPR analyses of enantioselective binding interactions of selected aptamer with complex of avidine and biotinylated L-glutamic acid- α,γ-di-t-butylester (closed circles), D-glutamic acid- α,γ-di-t-butylester (open circles), glycine t-butyl ester (open triangles) and aptamers complex with avidine and biotin (open diamonds) (Ohsawa et al., 2008)
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Aptamers can be successfully used to the biosensor design. As a biocomponents in biosensors they offers a multitude of advantages, such as the possibility of easily regenerate the function of immobilized aptamers, their homogeneous preparation and the possibility of using different detection methods due to easy labeling (Tombelli et al., 2005). A different detection techniques can be use for the aptasensor design as for example electrochemical (Liu et al., 2010), optical (Lee & Walt, 2000) or mass-based (Minunni et al., 2004). Although many examples of aptamer biosensor are presented in the literature only few of them considers the enantioselective properties.
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The enzymatically prepared the biotinylated aptamers were immobilized on the sensor chip attached with streptavidin. Two of three selected amptamers showed enantioselective recognition of the dicarboxylic acid moiety of glutamic acid. The binding affinity and enantioselectivity were successfully evaluated by SPR measurements, and the binding ability of these aptamers was eliminated by the absence of arginyl groups, indicating that modified groups are indispensable due to their binding affinity and enantioselectivity. The enantioselective response of selected aptamer is presented in Fig 9. (Ohsawa et al., 2008).
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Another example presented in (Perrier et al., 2010) is based on the induced-fit binding mechanism of end-labelled nucleic acid aptamers to the small molecule. The anti-adenosine DNA aptamer, labelled by a single fluorescein dye was employed as a model functional nucleic acid probe. Target binding is converted into a significant increase of the fluorescence anisotropy signal presumably produced by the reduction of the local motional freedom of the dye and detected by fluorescence polarization sensor. In case of target molecule the difference in the anisotropy fluorescence signal generated by D and L enantiomers was not enough to allow the enantioselective detection of adenosine. The presented DNA aptamer was also able to bind the adenine nucleotides such as adenosine monophosphate AMP. In latter case aptasensor exhibited important enantioselective properties. Titration curves obtained by the addition of D-AMP show an FP response while for L-AMP does not cause any significant response Fig 10.
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Figure 10.
Titration curves of the 3’-F-21-Apt probe with increasing concentration of enantiomers D-Ade (closed squares), L-Ade (open squares), D-AMP (closed triangles) and L-AMP (open triangles). Δr is a difference between the measured anisotrophy in the presence and in the absence of analyte (Perrier et al., 2010).
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Aptamers are increasingly being used as chiral selectors in separation techniques as capillary electrophoresis or HPLC. Recently new aptamers for different specific molecular targets are selected. Some of them posses enantioselective properties for example for D-peptides (Michaud et al., 2003), histidine (Ruta et al., 2007a), arginine ( Ruta et al., 2007b; Brumbt et al., 2005), thalidomide (Shoji et al., 2007) or ibuprofen (Kim Y. S. et al., 2010). These aptamers can potentially be used to construct chiral biosensors. Despite of successful chiral separation by aptamer modified stationary phase (Ravelet et al., 2005) or aptamers based capillary electrophoresis there still exists deficiencies in the understanding of the molecular basis of their chiral recognition. In (Lin P. H. et al., 2009) authors study the binding mechanism of DNA aptamers with L-argininamide by spectroscopic and calorimetric methods.
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5. Conclusion
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The design and optimization of sensors based on the use of active biological materials, biosensors and immunosensors for rapid, selective and sensitive determination of chiral compounds seems to be an extremely promising direction of development. As it was presented to the construction of such sensors a different detection methods may be involved. Guideline in the selection of biologically active material can be results of research conducted by separation methods using chiral antibodies or aptamers. Especially development of aptasensor which are a relatively new technique seems to be promising. The number of available biological active materials suitable to the construction of biosensors could be increased by enzyme screening and protein design. It is quite possible that with very well optimized enantioselectivity, stability and reproducibility biochemical sensors may become in the future valuable instruments for quick control of chiral purity for biotechnology and pharmaceutical industry.
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\n\t\n',keywords:null,chapterPDFUrl:"https://cdn.intechopen.com/pdfs/16423.pdf",chapterXML:"https://mts.intechopen.com/source/xml/16423.xml",downloadPdfUrl:"/chapter/pdf-download/16423",previewPdfUrl:"/chapter/pdf-preview/16423",totalDownloads:2241,totalViews:168,totalCrossrefCites:1,totalDimensionsCites:5,hasAltmetrics:0,dateSubmitted:"November 3rd 2010",dateReviewed:"March 10th 2011",datePrePublished:null,datePublished:"July 18th 2011",dateFinished:null,readingETA:"0",abstract:null,reviewType:"peer-reviewed",bibtexUrl:"/chapter/bibtex/16423",risUrl:"/chapter/ris/16423",book:{slug:"biosensors-emerging-materials-and-applications"},signatures:"Trojanowicz and Marzena Kaniewska",authors:[{id:"27423",title:"Dr.",name:"Marek",middleName:null,surname:"Trojanowicz",fullName:"Marek Trojanowicz",slug:"marek-trojanowicz",email:"trojan@chem.uw.edu.pl",position:null,institution:null},{id:"34661",title:"Dr.",name:"Marzena",middleName:null,surname:"Kaniewska",fullName:"Marzena Kaniewska",slug:"marzena-kaniewska",email:"mkaniewska@chem.uw.edu.pl",position:null,institution:null}],sections:[{id:"sec_1",title:"1. Introduction",level:"1"},{id:"sec_2",title:"2. Enantioselective enzymatic biosensors",level:"1"},{id:"sec_2_2",title:"2.1. Electrochemical biosensors",level:"2"},{id:"sec_2_3",title:"2.1.1. Chiral catalysis",level:"3"},{id:"sec_3_3",title:"2.1.2. Chiral inhibition",level:"3"},{id:"sec_6",title:"3. Enantioselective immunosensors",level:"1"},{id:"sec_6_2",title:"3.1. Electrochemical immunosensors",level:"2"},{id:"sec_7_2",title:"3.2. Other type of detection",level:"2"},{id:"sec_9",title:"4. Enantioselective bioreceptors",level:"1"},{id:"sec_9_2",title:"4.1. Mass-based biosensors",level:"2"},{id:"sec_10_2",title:"4.2. Optical biosensors",level:"2"},{id:"sec_11_2",title:"4.3. Ion channel biosensors",level:"2"},{id:"sec_13",title:"5. Enantioselective aptamers",level:"1"},{id:"sec_14",title:"5. Conclusion",level:"1"}],chapterReferences:[{id:"B1",body:'\n\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tAboul-Enein\n\t\t\t\t\t\t\tH. 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G.\n\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t2004 Poly(phenyleneethynylene) polymers bearing glucose substituents as promising active layers in enantioselective chemiresistors., Sensors and Actuators B, 100\n\t\t\t\t\t1-2 , (June 2004) 17\n\t\t\t\t\t21 , 0925-4005\n\t\t\t\t\n\t\t\t'},{id:"B85",body:'\n\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tTombelli\n\t\t\t\t\t\t\tS.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tMinunni\n\t\t\t\t\t\t\tM.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tMascini\n\t\t\t\t\t\t\tM.\n\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t2005 Review. Analytical applications of aptamers. Biosensors and Bioelectronics,\n\t\t\t\t\t20\n\t\t\t\t\t12 (June 2005), 2424\n\t\t\t\t\t2434 , 0956-5663\n\t\t\t\t\n\t\t\t'},{id:"B86",body:'\n\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tTsourkas\n\t\t\t\t\t\t\tA.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tHofstetter\n\t\t\t\t\t\t\tO.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tHofstetter\n\t\t\t\t\t\t\tH.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tWeissleder\n\t\t\t\t\t\t\tR.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tJosephson\n\t\t\t\t\t\t\tL.\n\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t2004 Magnetic relaxation swich immunosensors detect anantiomeric impurities. Angewandte Chemie-International Edition, 43\n\t\t\t\t\t18 (n.d.), 2395\n\t\t\t\t\t2399 , 0044-8249\n\t\t\t\t\n\t\t\t'},{id:"B87",body:'\n\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tVaradi\n\t\t\t\t\t\t\tM.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tAdanyi\n\t\t\t\t\t\t\tN.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tSzabó\n\t\t\t\t\t\t\tE. E.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tTrummer\n\t\t\t\t\t\t\tN.\n\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t1999 Determination of the ratio of D- and L-amino acids in brewing by an immobilised amino acid oxidase enzyme reactor coupled to amperometric detection. Biosensors and Bioelectronics, 14\n\t\t\t\t\t3 (March 1999), 335\n\t\t\t\t\t340 , 0956-5663\n\t\t\t\t\n\t\t\t'},{id:"B88",body:'\n\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tWcisło\n\t\t\t\t\t\t\tM.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tCompagnone\n\t\t\t\t\t\t\tD.\n\t\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\tTrojanowicz\n\t\t\t\t\t\t\tM.\n\t\t\t\t\t\t\n\t\t\t\t\t\n\t\t\t\t\t2007 Enantioselective screen-printed amperometric biosensor for determination of D-amino acids. 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'}],corrections:null},book:{id:"147",title:"Biosensors",subtitle:"Emerging Materials and Applications",fullTitle:"Biosensors - Emerging Materials and Applications",slug:"biosensors-emerging-materials-and-applications",publishedDate:"July 18th 2011",bookSignature:"Pier Andrea Serra",coverURL:"https://cdn.intechopen.com/books/images_new/147.jpg",licenceType:"CC BY-NC-SA 3.0",editedByType:"Edited by",editors:[{id:"6091",title:"Prof.",name:"Pier Andrea",middleName:null,surname:"Serra",slug:"pier-andrea-serra",fullName:"Pier Andrea Serra"}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"},chapters:[{id:"16418",title:"Signal Analysis and Calibration of Biosensors for Biogenic Amines in the Mixtures of Several Substrates",slug:"signal-analysis-and-calibration-of-biosensors-for-biogenic-amines-in-the-mixtures-of-several-substra",totalDownloads:1743,totalCrossrefCites:1,signatures:"Toonika Rinken, Priit Rinken and Kairi Kivirand",authors:[{id:"24687",title:"Dr.",name:"Toonika",middleName:null,surname:"Rinken",fullName:"Toonika Rinken",slug:"toonika-rinken"},{id:"33937",title:"MSc.",name:"Kairi",middleName:null,surname:"Kivirand",fullName:"Kairi Kivirand",slug:"kairi-kivirand"},{id:"66501",title:"Mr",name:"Priit",middleName:null,surname:"Rinken",fullName:"Priit Rinken",slug:"priit-rinken"}]},{id:"16419",title:"Molecular Design of Multivalent Glycosides Bearing GlcNAc, (GlcNAc)2 and LacNAc - 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1. Introduction
Crude oil has remained the major source of world energy supply despite considerable efforts on other sources of energy [1]. Due to rapid industrialization, there is an increase in world energy demand leading the need to produce increasing volume of crude oil to support this demand. Meanwhile, the oil and gas industry is concerned with the shortage of new conventional oil reserves and low production from existing conventional reservoirs. On average, one-third of conventional reservoirs can be recovered through primary and secondary (i.e. waterflooding) oil recovery processes. The remaining oil-in-place is the target for enhanced oil recovery (EOR). Several EOR methods have been developed to recover bypassed and residual oil in the reservoir. These are majorly categorized into thermal and non-thermal EOR methods. Thermal EOR are unsuitable for reservoirs with great depth or thin pay zones. Hence, non-thermal EOR methods such as gas flooding, chemical flooding and microbial methods have received important attention over the last decades for oil recovery processes [2, 3, 4].
Of the numerous EOR methods, chemical EOR has been considered as the most promising because of its high efficiency, technical and economic feasibilities. Chemical EOR methods increase the efficiency of oil production by increasing the volumetric sweep efficiency of the injected waterflood. By tuning the efficiency of the injected chemical floods, the microscopic (pore scale) displacement efficiency and/or macroscopic (sweep) efficiency of the reservoir is increased leading to an increase in oil production. Chemicals for injection include alkali, surfactants, and polymers. Alkali and surfactants increase oil recovery by improving microscopic displacement at the pore scale; while polymers enhance the volumetric sweep efficiency of the reservoir [5].
Despite its highly reported efficiency and widely acclaimed potentials, chemical EOR has several limitations. The chemicals injected degrade and/or precipitate in the presence of resident reservoir brines and elevated temperature conditions. Besides, retention of the chemicals occurs during their flow in porous media which decreases it process efficiency and may lead to formation damage. To overcome this shortcoming, new salt and temperature-tolerant chemicals of various kinds have been developed and tested for their EOR potentials. Nonetheless, most of the newly developed chemicals have been jettisoned as they were found to increase the cost of the overall EOR process.
Nanotechnology is the application of nanoparticles characterized by a size ranging from 1 to 100 nm (see Figure 1) [6, 7]. In the oil and gas industry, applications of nanotechnology ranges from drilling processes, flow assurance, hydraulic fracturing, cementing, to EOR [8]. For EOR process, the engineered nanomaterials are mixed with fluids that are injected into the reservoir to boost oil production [9].
Figure 1.
Schematic of increasing surface area of nanoparticle with decreasing particle size [6].
Nanoparticles and conventional EOR chemicals blends have been reported to possess important properties that are not observed in the individual chemical or nanoparticle [10]. For example, surfactant nanofluids (or nanosurfactant), a blend of nanoparticle and surfactant were reported to improve the efficiency of the surfactant at lowering the interfacial tension (IFT) of oil/water (o/w) interface and lower their adsorption during their transport in porous media [11]. Besides, emulsions and foams stabilized by nanoparticles are found to be thermodynamically stable and easily transported in reservoirs [12]. Meanwhile, polymeric nanofluids demonstrated to have improved rheological behavior and stability at characteristic reservoir temperature and salinity conditions [4]. This chapter presents an overview of nanotechnology applications in chemical EOR. First, the challenges of chemical EOR are briefly discussed. Subsequently, the mechanism and efficiency of nanotechnology application in chemical EOR is discussed. Finally, the experimental and laboratory studies of the newly devised EOR technique are outlined.
2. Challenges of chemical EOR methods
2.1 Degradation and precipitation
An oil reservoir exists at a specific temperature, salinity, and pH. The prevailing conditions of the reservoir influence the efficiency of the injected chemicals and consequently of the EOR process [13]. Most injected chemicals degrade and become unstable at high salinity, elevated temperature, and low pH conditions [14]. For polymers, under saline conditions, screening of the charged polymer molecules by cations contained in the reservoir brine occurs. This reduces the hydrodynamic radius and polymer chain entanglement causing the contraction of the macromolecules that ultimately results in the loss of polymer solution viscosity [15, 16]. Meanwhile, high temperature causes hydrolysis of the polymer and its precipitation in the presence of divalent ions [17]. In the case of surfactant and alkali solutions, depending on the rock type, precipitation of the chemicals occurs in the presence of divalent cations [18]. Low pH reservoir conditions might interact and acidify injected chemical solutions [15].
2.2 Adsorption and retention
Depending on the type of chemical injected into the reservoir, adsorption and retention of chemical occur during flow through porous media, which negatively affects the efficiency of the EOR process [19]. Chemicals react with the rock surface through electrostatic attraction, steric interaction, and van der Waal forces that reduces the concentration of the injected chemical solutions. Adsorption is prevalent for surfactant and alkali chemicals, while polymer is mainly retained due to mechanical entrapment because of the size of the polymer macromolecules [3, 18, 20]. The adsorption process occurs when the interface is energetically favored by the surfactant and/or alkali in comparison to the bulk phase. Thus, the adsorption at the solid–liquid interface takes place by the transfer of the molecule of the chemical to the solid–liquid interface from the bulk solution phase [21]. Meanwhile, polymer retention and inaccessible pore volume dictates the propagation of polymer flow in the reservoir [22]. Retention of polymer is alluded to any mechanism that leads to reduction or removal of polymer molecules from transported aqueous phase. The nature of polymer retention in reservoir rock is depicted in Figure 2. Overall, adsorption and/or retention of chemicals in porous media governs the efficiency and economic viability of the EOR process. Several factors affecting adsorption or retention of chemical EOR includes; electrolyte concentration (salinity), temperature, pH, composition of reservoir fluids, and the presence of clay mineral content [21, 23].
Figure 2.
Retention of polymers in porous media. Sourced from [19].
3. Application of Nanotechnology in chemical EOR
Nanotechnology application in chemical EOR is used to overcome the shortcomings and improve the process efficiency of chemical EOR methods. Though most works are still at the laboratory scale, the synergic application of nanoparticles and chemicals have led to the formation of novel nanomaterials with exceptional qualities [6]. Recently, field trials have been reported in Columbia oilfield [24]. Depending on the nanoparticle type and chemical used, the formulated nanomaterials have demonstrated better stability and superior quality which enhances their performance during simulated reservoir conditions. So far, the most common nano-chemical studies are polymeric nanofluids and surfactant nanofluids.
3.1 Surfactant nanofluid
Surfactant nanofluid, a combination of nanoparticle and surfactant, increases the microscopic displacement efficiency through the mechanisms of IFT reduction and wettability alteration [11, 25, 26]. This nanofluid could be used for the generation or formation of stable foams and emulsions in the reservoir. Stable foams ensure fluid diversion from thief zones to lower permeability regions in the reservoir, while emulsions ensure conformance efficiency of the injectant [27, 28]. Furthermore, surfactant nanofluids have been reported to have lower adsorption onto rock surface compared to ordinary surfactant solutions [29, 30].
IFT and wettability are major parameters for quantifying fluids distribution and movement in the reservoir [31]. After secondary oil recovery, a portion of the oil is trapped in the reservoir due to capillary forces. This capillary force is measured by a dimensionless capillary number defined as [32]:
Nc=μvσ.cosθE1
Where μ is the displacing fluid viscosity, v is the displacing Darcy velocity, θ is the contact angle, and σ is the IFT between the displacing fluid (water) and the displaced fluid (oil). Nc is closely related to residual oil saturation and oil recovery. NC increases as residual oil saturation decreases. Consequently, a higher Nc will result in a higher oil recovery [32, 33]. The capillary trapped oil can be released by either lowering the IFT of the o/w interface or through the wettability alteration mechanism [33]. Surfactant molecules due to their amphiphilic nature lowers IFT and alters wettability of porous media by adsorbing at the o/w interface [5, 32]. Nanoparticles also performs the same task in similitude to surfactant molecules, though at a different efficiency. The synergic effect of blending nanoparticles and surfactants have been shown to enhance the surfactant flooding process by lowering IFT and altering the wettability more efficiently than the individual nanoparticle or surfactant solution. On the other hand, the surfactant enhances the stability of the nanoparticles, thus, increasing the efficiency [11].
Driven primarily by electrostatic interaction, the surfactant adsorbs on the nanoparticles surface forming surfactant-coated nanoparticles [11]. Nonetheless, the relative concentration of nanoparticles and surfactant in the solution determines the properties of the mixture. A lower concentration ratio of surfactant to nanoparticle in the mixture means that only a small fraction of the nanoparticle surface will be coated by surfactant. Conversely, a higher concentration ratio of surfactant to nanoparticles implies the surfactant molecules will form a bilayer on the particle surface [11, 34]. A single-chain surfactant on nanoparticle is required to form maximum nanoparticle flocculation and hydrophobic nature required for an optimal performance.
3.1.1 IFT reduction
To quantify the performance of surfactant nanofluid on IFT of o/w interface, Le et al. evaluated the impact of silica (SiO2) nanoparticles and anionic surfactant for IFT reduction using a spinning drop tensiometer. Their results indicated that at a total concentration of 1000 ppm and at a surfactant to SiO2 ratio of 8:2, a four-fold IFT reduction was achieved by the nanosurfactant. Hence, they proposed the application of surfactant nanofluids for EOR in high temperature and high salinity (HTHS) conditions [35]. Mohajeri et al. evaluated the effect of zirconium oxide (ZrO2) nanoparticles on anionic sodium dodecyl sulfate (SDS) surfactant and cationic cetyltrimethylammonium bromide (CTAB) surfactant [25]. They reported that the contribution of ZrO2/SDS yielded an IFT reduction of 81% while ZrO2/CTAB decreased the IFT of o/w interface by 70%. Zargartalebi et al. probed the effect of SiO2 nanoparticles and anionic SDS to quantify the effect of the nanoparticle on IFT, adsorption and oil recovery potential of the surfactant molecules. They observed that nanoparticles effectively improve surfactant performance by enhancing the governing mechanism. Furthermore, flooding results shows that oil recovery increased significantly due to the inclusion of nanoparticles in the surfactant solution [26].
The mechanisms of nanosurfactant for reducing IFT at o/w interface has been explored. Researchers noted that the adsorption of the surfactant on the nanoparticle surface occurs as a result of the mix, leading to a hydrophobic character of the nanoparticle surface. Due to their Brownian motion, the nanoparticle acts as carriers for the surfactant molecules from the bulk of the fluid to the interface. At the interface, the minimization of the interfacial energy by the nanosurfactant leads to IFT reduction. As compared to ordinary surfactant whose molecule desorbs from the interface after some time, the nanoparticle prevents desorption of surfactant molecules from the interface, hence, better IFT reduction [11].
3.1.2 Wettability alteration
The reduction of interfacial energy at the rock/oil/brine interface by nanosurfactant also results in higher wettability alteration. Besides, the relative permeability curves of oil and water also changes after contact with the surfactant nanofluid; the relative permeability to water and oil decreases and increases respectively [34]. Mohajeri et al. studied the effect of ZrO2/surfactants on wettability alteration in a fractured micromodel. The sessile drop experiments and wettability alteration measurements showed that coating the micromodel with heavy oil makes an oil-wet surface. Moreover, coating of the oil-wet micromodel with surfactant or nanoparticle altered the wettability of the surface to water-wet condition, while coating the surface with the blend ZrO2/surfactant altered the wettability to strongly water-wet condition [25].
Additionally, the use of nanosurfactants as wettability alteration agents have proved useful for improving oil recovery from carbonates reservoir, which are characterized by poor oil recovery owing to its inherent natural fractures and hydrophobic nature that makes water imbibition into its rock matrix difficult, because of capillary pressure effects. Nwidee et al. assessed the effect of nanosurfactant formulation for wettability alteration of oil-wet limestone over a wide range of temperatures (0–70°C). ZrO2 and nickel oxide (NiO) were used as the nanoparticles while CTAB and triton X-100 were used as surfactants for the formulation. Due to their strong electrostatic interaction, ZrO2/CTAB and NiO/CTAB display greater affinity for the rock surface and demonstrated better wettability alteration efficiency for all temperature conditions considered in this study [36].
Surfactant nanofluids have also been used to improve wettability alteration of sandstone cores to boost oil recovery. Giraldo et al. tested alumina-surfactant nanofluid to improve oil recovery in sandstone cores via wettability alteration using contact angle and imbibition tests. Their results show that the effectiveness of surfactant as wettability modifier was improved with the addition of 100 ppm of alumina nanoparticles. Additionally, the effective oil permeability increased by 33%, and consequently, a higher oil recovery was recorded [37]. Huibers et al. measured changes in wettability of sandstone cores of saturated with light and heavy crude oil using surfactant nanofluid composed of SiO2 nanoparticle and Tween 20 nonionic surfactant in Berea and Boise sandstone cores. Using direct imaging and contact angle measurements, 0.001 wt.% SiO2 nanoparticles yielded an increase in contact angle of 101.6% for light oil saturated cores, while the optimum concentration for heavy oil was not ascertained at the nanoparticle concentration range investigated [38].
3.1.3 Adsorption reduction
One of the major challenges of surfactant EOR is the loss of surfactant molecules to adsorption onto the formation rock during the flooding process. Surfactant adsorption can make the chemical EOR process economically unfeasible. Therefore, reducing the surfactant adsorption improves the oil recovery process. Previous studies have investigated the use of polymers such as sodium polyacrylate as sacrificial agent to reduce surfactant adsorption during flow in porous media [39]. Recently, the adsorption reduction effect of nanoparticles has been investigated during the co-injection of nanoparticles with surfactant for oil recovery. Nanoparticles showed good potential for inhibiting surfactant adsorption via competitive adsorption mechanism by blocking the active site of the porous media while the surfactant flows through the porous media contacting the resident fluids in the reservoir. Yekeen et al. observed that the presence of SiO2 and Al2O3 nanoparticles decreased surfactant adsorption on kaolinite in the presence of reservoir brines. The addition of Al2O3 nanoparticles reduced the SDS adsorption on kaolinite by 38%, while the addition of SiO2 nanoparticles reduced the SDS adsorption by 75% [40].
Wu et al. conducted static and dynamic adsorption experiments to investigate the inhibition mechanism of SiO2 nanoparticle during co-injection with surfactant. An optimum aging time, solid–liquid ratio, nanoparticle concentration, and surfactant concentration were determined for the adsorption process. Static adsorption experiments showed that 0.5 wt.% of SiO2 nanoparticle concentration reduced the adsorption of SDS from 2.84 to 1.61 mg/g. Dynamic adsorption experiments conducted at 20°C showed that the adsorption and dynamic retention of single SDS solution were 1.16 and 0.30 mg/g respectively. The addition of 0.3 wt.% SiO2 nanoparticle concentration reduced the adsorption and dynamic retention of the surfactant by 43.6% to 0.66 and 0.06 mg/g, respectively. Furthermore, oil recovery displacement experiments in sand packs using a nanosurfactant solution showed a 4.68% incremental oil recovery factor over the oil recovery attained by the injection of conventional surfactant solution [29]. Suresh et al. extended the adsorption studies on nanosurfactant to higher salinity and elevated temperature (80°C) conditions using thermogravimetric analysis (TGA) to determine the surfactant concentration in the produced fluids. The dynamic adsorption of the surfactant was calculated from the difference between injected and effluent concentration of the surfactant. Results showed that the addition of 0.5 wt.% SiO2 nanoparticle to the surfactant solution reduced the surfactant adsorption by a factor of 3 times from 0.810 to 0.265 mg/g [30].
3.1.4 Foam and emulsion stability
Foams used for oil recovery are generated by co-injecting a gas (e.g., carbon dioxide, nitrogen or air) and a foaming agent containing liquid into the reservoir [41]. In the porous media, foams act as a dispersion of gas in liquid separated by a lamella, with the gas phase residing in the upper side while the bulk liquid is located at the bottom of the foam structure [42]. They perform two diverse roles in the reservoir namely; (1) mobility control, (2) fluid diversion. These mechanisms aid foam to overcome the challenges of gas EOR such as gravity override and viscous fingering phenomena. The liquids used as conventional foaming agents includes surfactants, polymers, and proteins. When used with polymers, foams are used to plug high permeability areas, while the polymer is diverted to lower permeability regions, thus, improving the volumetric sweep efficiency of the reservoir. In the case of surfactant-stabilized foams, a stable foam is formed due to a decrease in the required energy to form the gas–liquid interface [43]. Moreover, the synergic combination with surfactant lowers the interfacial tension of the capillary trapped oil, hence, facilitates oil displacement [44, 45]. Conventional foams have been shown to be thermodynamically unstable in the presence of oil and resident reservoir brines. This implies that the foam coalesces leading to of the reduced efficacy of the process. The addition of nanoparticles to the surfactant solution seems to generate more stable foams with longer half-life and ability to withstand harsh reservoir conditions [43]. Due to the solid nature of nanoparticles, the foams they stabilize are highly resistant to unfavorable reservoir conditions. Nanoparticles adsorb at the lamellae interface of the foam with a strong adhesion energy that makes their attachment irreversible (see Figure 3) [41, 46].
Figure 3.
Foams stabilized (a) without nanoparticles showing signs of foam drainage, (b) with nanoparticles stabilizing the lamellae [46].
Sun et al. studied the influence of nanoparticles on the generation, propagation, and stability of SiO2/SDS-stabilized foam in micromodels and sandpack porous media [47]. In the case of the SDS-stabilized foam, the shape of the oil droplet could not be changed by the foam because the microforce acting on the oil droplet was small. This subsequently leads to bubbles rupture and coalescence leaving a substantial amount of oil trapped in the porous media. In the case of SiO2/SDS foam, a large amount of oil was displaced by the foam due to the higher microforce acting on the oil droplet. The higher microforce was attributed to the enhanced viscoelasticity of the bubble surface by the attached nanoparticles. Yekeen et al. studied the influence of SiO2 and Al2O3 nanoparticles on surfactant-foam stability and propagation in the presence of oil. They noted that the presence of nanoparticle increases foam half-life. Additionally, the SiO2-SDS and Al2O3-SDS foam achieved nearly 100% microscopic efficiency even in the presence of oil. Finally, they identified mechanisms of foam flow as lamellae division and bubble-to-multiple bubble lamellae division, while the dominant mechanism of oil displacement and residual oil saturation are direct displacement and emulsification of oil [40]. Tables 1 and 2 summarizes laboratory and experimental results of nanoparticles-stabilized and nanoparticle-surfactant stabilized foams.
Laboratory and experimental investigation of nanoparticle/nanoparticle-surfactant stabilized foams.
aIncremental oil recovery over waterflood.
bIncremental oil recovery over surfactant-stabilized foam.
On the other hand, the interactions of surfactants with oil during flow through porous media may generate emulsions. Emulsions generated in situ have potential for mobility and conformance control in the reservoir, which are desirable properties for improving the oil recovery process. Further, the feasibility of injecting emulsions has also been explored, exhibiting appropriate potential for oil recovery. Nonetheless, conventional emulsions show poor stability at high pressure and high temperature conditions. As temperature increases, the average droplet size of the dispersed phase increases which eventually plug pore throats in the reservoir [75]. Recently, the binary mix of nanosurfactant with oil have been evaluated for emulsion generation showing better stability performance in the reservoir for oil recovery applications. Besides, the presence of nanoparticle significantly improved the stability and mobility of the emulsions.
Pei et al. investigated the synergetic effect of SiO2 nanoparticle and CTAB for o/w emulsions applications. Phase behavior testing, rheology evaluation, and micro-visualization studies showed that nano-surfactant-stabilized emulsion demonstrated a high bulk viscosity and desirable mobility for recovering heavy oil [50]. Kumar et al. synthesized a Pickering emulsion stabilized by SiO2 nanoparticle and sodium dodecylbenzene sulfonate (SDBS) surfactant. The synthesized Pickering emulsion displayed better thermal stability at the high pressure (0–5 MPa) and high temperature (30–100°C) conditions investigated, and showed a higher oil recovery when injected into the sandpack [75].
3.2 Polymeric nanofluids
Depending on the method of preparation, polymeric nanofluids are categorized into two types; polymer-coated nanoparticles and polymer nanoparticles. Polymer-coated nanoparticles were developed due to overcome the aggregation and agglomeration problems of nanoparticles at reservoir conditions. It involves grafting polymers onto the surface of nanoparticles to improve dispersibility. In addition, their properties can be customized for particular applications [34]. Meanwhile, polymer nanoparticles are prepared by the hybrid dispersion of nanoparticles in polymer solutions. These polymer nanoparticles emerged as a means of inhibiting polymer degradation in typical reservoir conditions [4]. The mechanisms of polymeric nanofluids performance during EOR applications include improved rheology and stability, wettability alteration, and lower polymer adsorption [6].
3.2.1 Improved rheology and stability for mobility control
Rheology is defined as the study of flow and deformation behaviors of fluids under stress [76]. For EOR applications, an improved rheological behavior of injectant is required to inhibit viscous fingering phenomena and maintain a suitable mobility ratio in the reservoir; which requires that the displacing fluid maintain its viscosity and chemical integrity in the presence of resident reservoir brines [77]. Polymer and nanoparticles undergo degradation in the presence of reservoir brines. The cations present in the brine interact with the carboxylate and amide groups in the polymer molecule resulting in viscosity loss [78]. In the case of nanoparticles, the electrostatic attraction among nanoparticles are increased in the presence of brine fostering their aggregation and agglomeration; which implies the loss of surface functionality that is required for EOR [79]. However, the combination of polymer and nanoparticles results in a synergistic effect that improves the rheology of the polymer and the stability of the nanoparticle [4].
The preparation of polymer-nanoparticles blends involves the mixing of the nanoparticle and the polymer solution or grafting of the polymer on the nanoparticle [80, 81]. Subsequently, interactions occur between the nanoparticle and the carboxylate and amide group in the polymer molecules. Therefore, nanoparticles act as physical crosslinkers among the polymer chains forming three-dimensional network of stable flocs that increases the viscosity of the suspension [82]. At high temperature, polymer-nanoparticles blends exhibit better rheological performance due to the enhanced bridging induced flocculation [82, 83]. Furthermore, in the presence of reservoir brines, nanoparticles shield the polymer backbone from the cations of the brine by inducing ion-dipole interactions that inhibit the degradation of the polymer molecules [81].
Lai et al. noted that the shear and mechanical resistance of acrylamide polymer solution can be increased by adding modified nano-SiO2, because the presence of SiO2-NP caused a reduction of the hydrodynamic radius of the polymer molecules [84]. Hu et al. studied the rheological properties on an oilfield polyacrylamide (HPAM) -SiO2 NP under different aging times, salinity, and temperature conditions. The results demonstrated that the presence of the SiO2-NP significantly improved the viscosity and viscoelastic properties of the HPAM under high temperature and high salinity (HTHS) conditions [80]. Haruna et al. grafted HPAM molecules with graphene oxide (GO) nanosheets and evaluated the rheological and stability properties of the formulated polymeric nanofluid. They reported enhancement of the suspension viscosity behavior, as well as high-temperature stability and improved elastic properties of the dispersion [85].
As for polymer-coated nanoparticles, depending on the grafting method, the polymeric chains protrude from the nanoparticle surface. Hence, hydrodynamic interactions occur between the grafted nanoparticle when subjected to shear. Besides, polymeric chains grafted on the surface of the nanoparticle overlap with another polymer chain adsorbed on another nanoparticle. The overlapping of several grafted nanoparticles results in the strengthening of the network structure of the polymer -nanoparticle system. Consequently, hydro clusters are formed, which results in an increase of stability and viscosity [86]. Liu et al. grafted a layer of amphiphilic-polymeric chains on nano-SiO2 core shell via a facile water-free radical polymerization and evaluated its rheological properties and oil recovery performance. The synthesized polymer-coated nanoparticle formed a three-dimensional microstructure and intermolecular associations characterized by long-term stability and better rheological properties than the individual polymer or nanoparticles. Furthermore, a 20% incremental oil recovery was recorded after flooding the polymer-coated nanoparticle solution at a concentration of 1500 mg/L in sandstone cores [87]. Table 3 summarizes some laboratory and experimental studies of improved rheological properties and oil displacement properties of polymeric nanofluids.
Laboratory results of oil recovery applications by polymeric nanofluid [6].
3.2.2 Adsorption inhibition
Polymeric nanofluids also show reduced adsorption onto porous media due to the synergic interaction between the polymer and nanoparticles. Foster et al. used the grafting through approach to tether tuneable quantities of poly(2-acrylamido-2-methylpropanesulfonic acid) (PAMPS) and poly([3-(methacryloxylamino)propyl]dimethyl(3-sulfopropyl)ammoniumhydroxide)(PMPDSA) homopolymer (PMPDSA) onto iron oxide nanoparticle surfaces. Steric stabilization of the synthesized polymer-coated nanoparticle was observed which remained stable at HTHS conditions. Moreover, adsorption experiments on crushed Berea sandstone cores showed that the adsorption of polymer-coated iron oxide nanoparticles was infinitesimal and almost negligible [96]. Cheraghian et al. performed static adsorption experiments to investigate the impact of nano-SiO2 and nanoclay on the adsorption inhibition of polyacrylamide onto sandstone rocks. Polymer nanoparticles containing SiO2 nanoparticle showed lower adsorption onto sandstone rock surface compared to the polymer containing nanoclay [97].
3.2.3 Wettability alteration
Wettability alteration plays a vital role in enhancing the microscopic displacement efficiency. In the case of polymeric nanofluids, an interplay of electrostatic repulsive forces occur at the interface of the nanoparticles., Two-dimension layered structure of nanoparticles occur due to Brownian motion when brought into contact with an oil-wet solid surface, creating a wedge film because of the ordering of nanoparticles at the three-phase (solid-oil–water) contact region. This results in an increase of the disjoining pressure,which causes the spreading of the nanofluid phase at the wedge of the vertex, altering the wettability of the surface [6]. Maurya et al. grafted polyacrylamide on the surface of SiO2 using the free radical polymerization approach and investigated its wettability potential on an oil-wet sandstone rock surface. They indicated that the polymer grafted nanoparticle altered the wettability of the sandstone surface to a more water-wet condition [86]. Maghzi et al. performed wettability alteration studies employing polymer nanoparticles consisting of SiO2 nanoparticle and polyacrylamide polymer solution in a five-spot glass micromodel. The polymer nanoparticle altered the surface of the micromodel from an average contact angle of 112° (oil-wet) to 20° (water-wet). More details of wettability alteration by polymeric nanofluids can be found in the literature [6, 34].
4. Conclusions
This chapter summarizes some of the recent advances in the application of nanotechnology in chemical EOR processes to boost oil production. The mechanisms of oil recovery through nanotechnology were reviewed. Several experimental studies were summarized and discussed. Results of various experiments shows that the incorporation of nanotechnology with chemical EOR shows good potential to improve pore scale mechanisms in the case of surfactant. Adsorption of surfactant on rock pores is inhibited while greater IFT reduction and better wettability alteration were achieved. Furthermore, nanotechnology improved the rheological properties of polymer and stability of emulsions and foams indicating the good potentials of improving sweep efficiency of injected chemicals especially in the presence of harsh reservoir conditions. Finally, future research should focus on modeling the flow behavior of nanomaterials through porous media, which is required for the designing and field implementation of nano-chemicals EOR.
\n',keywords:"chemical enhanced oil recovery, nanotechnology, surfactant, polymer, nanoparticles",chapterPDFUrl:"https://cdn.intechopen.com/pdfs/69126.pdf",chapterXML:"https://mts.intechopen.com/source/xml/69126.xml",downloadPdfUrl:"/chapter/pdf-download/69126",previewPdfUrl:"/chapter/pdf-preview/69126",totalDownloads:516,totalViews:0,totalCrossrefCites:0,dateSubmitted:"January 13th 2019",dateReviewed:"June 19th 2019",datePrePublished:"September 19th 2019",datePublished:null,dateFinished:null,readingETA:"0",abstract:"Chemical enhanced oil recovery (EOR) has been adjudged as an efficient oil recovery technique to recover bypassed oil and residual oil trapped in the reservoir. This EOR method relies on the injection of chemicals to boost oil recovery. Recently, due to the limitations of the application of chemical EOR methods to reservoirs having elevated temperatures and high salinity and hardness concentrations, nanotechnology have been applied to enhance its efficiency and improve oil productivity. The synergistic combination of nanoparticles and conventional EOR chemicals has opened new routes for the synthesis and application of novel materials with sterling and fascinating properties. In this chapter, an up-to-date synopsis of nanotechnology applications in chemical EOR is discussed. A detailed explanation of the mechanism and applications of these novel methods for oil recovery are appraised and analyzed. Finally, experimental and laboratory results were outlined. This overview presents extensive information about new frontiers in chemical EOR applications for sustainable energy production.",reviewType:"peer-reviewed",bibtexUrl:"/chapter/bibtex/69126",risUrl:"/chapter/ris/69126",signatures:"Afeez Gbadamosi, Radzuan Junin, Muhammad Manan, Augustine Agi and Jeffrey Oseh",book:{id:"7609",title:"Enhanced Oil Recovery Processes",subtitle:"New Technologies",fullTitle:"Enhanced Oil Recovery Processes - New Technologies",slug:"enhanced-oil-recovery-processes-new-technologies",publishedDate:"December 18th 2019",bookSignature:"Ariffin Samsuri",coverURL:"https://cdn.intechopen.com/books/images_new/7609.jpg",licenceType:"CC BY 3.0",editedByType:"Edited by",editors:[{id:"120519",title:"Prof.",name:"Ariffin",middleName:null,surname:"Samsuri",slug:"ariffin-samsuri",fullName:"Ariffin Samsuri"}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"}},authors:null,sections:[{id:"sec_1",title:"1. Introduction",level:"1"},{id:"sec_2",title:"2. Challenges of chemical EOR methods",level:"1"},{id:"sec_2_2",title:"2.1 Degradation and precipitation",level:"2"},{id:"sec_3_2",title:"2.2 Adsorption and retention",level:"2"},{id:"sec_5",title:"3. Application of Nanotechnology in chemical EOR",level:"1"},{id:"sec_5_2",title:"3.1 Surfactant nanofluid",level:"2"},{id:"sec_5_3",title:"3.1.1 IFT reduction",level:"3"},{id:"sec_6_3",title:"3.1.2 Wettability alteration",level:"3"},{id:"sec_7_3",title:"3.1.3 Adsorption reduction",level:"3"},{id:"sec_8_3",title:"Table 1.",level:"3"},{id:"sec_10_2",title:"3.2 Polymeric nanofluids",level:"2"},{id:"sec_10_3",title:"Table 3.",level:"3"},{id:"sec_11_3",title:"3.2.2 Adsorption inhibition",level:"3"},{id:"sec_12_3",title:"3.2.3 Wettability alteration",level:"3"},{id:"sec_15",title:"4. Conclusions",level:"1"},{id:"sec_18",title:"Nomenclature",level:"1"}],chapterReferences:[{id:"B1",body:'Afolabi F, Ojo T, Udeagbara S, Gbadamosi A. 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Characterization of SPN Pickering emulsions for application in enhanced oil recovery. Journal of Industrial and Engineering Chemistry. 2017;54:304-315. DOI: 10.1016/j.jiec.2017.06.005'},{id:"B76",body:'Rezaei A, Abdi-Khangah M, Mohebbi A, Tatar A, Mohammadi AH. Using surface modified clay nanoparticles to improve rheological behavior of Hydrolized Polyacrylamid (HPAM) solution for enhanced oil recovery with polymer flooding. Journal of Molecular Liquids. 2016;222:1148-1156. DOI: 10.1016/j.molliq.2016.08.004'},{id:"B77",body:'Wei B, Romero-Zerón L, Rodrigue D. Oil displacement mechanisms of viscoelastic polymers in enhanced oil recovery (EOR): A review. Journal of Petroleum Exploration and Production Technologies. 2014;4:113-121. DOI: 10.1007/s13202-013-0087-5'},{id:"B78",body:'Liu P, Mu Z, Wang C, Wang Y. Experimental study of rheological properties and oil displacement efficiency in oilfields for a synthetic Hydrophobically modified polymer. Scientific Reports. 2017;7:8791. DOI: 10.1038/s41598-017-09057-9'},{id:"B79",body:'Kamal MS, Adewunmi AA, Sultan AS, et al. Journal of Nanomaterials. 2017;2017:15. DOI: 10.1155/2017/2473175'},{id:"B80",body:'Hu Z, Haruna M, Gao H, Nourafkan E, Wen D. Rheological properties of partially hydrolyzed polyacrylamide seeded by nanoparticles. Industrial and Engineering Chemistry Research. 2017;56:3456-3463. DOI: 10.1021/acs.iecr.6b05036'},{id:"B81",body:'Maghzi A, Kharrat R, Mohebbi A, Ghazanfari MH. The impact of silica nanoparticles on the performance of polymer solution in presence of salts in polymer flooding for heavy oil recovery. Fuel. 2014;123:123-132. DOI: 10.1016/j.fuel.2014.01.017'},{id:"B82",body:'Maurya NK, Mandal A. Studies on behavior of suspension of silica nanoparticle in aqueous polyacrylamide solution for application in enhanced oil recovery. Petroleum Science and Technology. 2016;34:429-436. DOI: 10.1080/10916466.2016.1145693'},{id:"B83",body:'Giraldo LJ, Giraldo MA, Llanos S, Maya G, Zabala RD, Nassar NN, et al. The effects of SiO2 nanoparticles on the thermal stability and rheological behavior of hydrolyzed polyacrylamide based polymeric solutions. Journal of Petroleum Science and Engineering. 2017;159:841-852. DOI: 10.1016/j.petrol.2017.10.009'},{id:"B84",body:'Lai N, Guo X, Zhou N, Xu Q. Shear resistance properties of modified Nano-SiO2/AA/AM copolymer oil displacement agent. Energies. 2016;9:1037. DOI: 10.3390/en9121037'},{id:"B85",body:'Haruna MA, Pervaiz S, Hu Z, Nourafkan E, Wen D. Improved rheology and high-temperature stability of hydrolyzed polyacrylamide using graphene oxide nanosheet. Journal of Applied Polymer Science. 2019;0(1–13):47582. DOI: 10.1002/app.47582'},{id:"B86",body:'Maurya NK, Kushwaha P, Mandal A. Studies on interfacial and rheological properties of water soluble polymer grafted nanoparticle for application in enhanced oil recovery. Journal of the Taiwan Institute of Chemical Engineers. 2017;70:319-330. DOI: 10.1016/j.jtice.2016.10.021'},{id:"B87",body:'Liu R, Pu W, Sheng JJ, Du D. Star-like hydrophobically associative polyacrylamide for enhanced oil recovery: Comprehensive properties in harsh reservoir conditions. Journal of the Taiwan Institute of Chemical Engineers. 2017;80:639-649. DOI: 10.1016/j.jtice.2017.08.043'},{id:"B88",body:'Ponnapati R, Karazincir O, Dao E, Ng R, Mohanty KK, Krishnamoorti R. Polymer-functionalized nanoparticles for improving Waterflood sweep efficiency: Characterization and transport properties. Industrial and Engineering Chemistry Research. 2011;50:13030-13036. DOI: 10.1021/ie2019257'},{id:"B89",body:'Cheng Y, Zhao M, Zheng C, Guo S, Li X, Zhang Z. Water-dispersible reactive Nanosilica and poly(2-acrylamido-2-methyl-1-propanesulfonic acid sodium) Nanohybrid as potential oil displacement agent for enhanced oil recovery. Energy & Fuels. 2017;31:6345-6351. DOI: 10.1021/acs.energyfuels.7b00743'},{id:"B90",body:'Behzadi A, Mohammadi A. Environmentally responsive surface-modified silica nanoparticles for enhanced oil recovery. Journal of Nanoparticle Research. 2016;18:1-19. DOI: 10.1007/s11051-016-3580-1'},{id:"B91",body:'Liu R, Pu W-F, Du D-J. Synthesis and characterization of core–shell associative polymer that prepared by oilfield formation water for chemical flooding. Journal of Industrial and Engineering Chemistry. 2017;46:80-90. DOI: 10.1016/j.jiec.2016.10.018'},{id:"B92",body:'Ye Z, Qin X, Lai N, Peng Q, Li X, Li C. Synthesis and performance of an acrylamide copolymer containing Nano-SiO2 as enhanced oil recovery chemical. Journal of Chemistry. 2013;2013:1-33'},{id:"B93",body:'Lai N, Wu T, Ye Z, Zhang Y, Zhou N, Zeng F. Hybrid hyperbranched polymer based on modified Nano-SiO2 for enhanced oil recovery. Chemistry Letters. 2016;45:1189-1191. DOI: 10.1246/cl.160554'},{id:"B94",body:'Maghzi A, Mohebbi A, Kharrat R, Ghazanfari MH. Pore-scale monitoring of wettability alteration by silica nanoparticles during polymer flooding to heavy oil in a five-spot glass micromodel. Transport in Porous Media. 2011;87:653-664. DOI: 10.1007/s11242-010-9696-3'},{id:"B95",body:'Yousefvand H, Jafari A. Enhanced oil recovery using polymer/nanosilica. Procedia Materials Science. 2015;11:565-570. DOI: 10.1016/j.mspro.2015.11.068'},{id:"B96",body:'Foster EL, Xue Z, Roach CM, Larsen ES, Bielawski CW, Johnston KP. Iron oxide nanoparticles grafted with sulfonated and Zwitterionic polymers: High stability and low adsorption in extreme aqueous environments. ACS Macro Letters. 2014;3:867-871. DOI: 10.1021/mz5004213'},{id:"B97",body:'Cheraghian G, Khalili Nezhad SS, Kamari M, Hemmati M, Masihi M, Bazgir S. Adsorption polymer on reservoir rock and role of the nanoparticles, clay and SiO2. International Nano Letters. 2014;4:114. DOI: 10.1007/s40089-014-0114-7'}],footnotes:[],contributors:[{corresp:"yes",contributorFullName:"Afeez Gbadamosi",address:"gbadamosiafeezo@abuad.edu.ng",affiliation:'
Department of Chemical and Petroleum Engineering, School of Engineering, Afe Babalola University, Nigeria
Department of Petroleum Engineering, Universiti Teknologi Malaysia, Malaysia
Department of Chemical and Petroleum Engineering, School of Engineering, Afe Babalola University, Nigeria
Department of Petroleum Engineering, Universiti Teknologi Malaysia, Malaysia
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IntechOpen books are indexed by the following abstracting and indexing services:
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BKCI is a part of Web of Science Core Collection (WoSCC) and the world’s leading citation index with multidisciplinary content from the top tier international and regional journals, conference proceedings, and books. The Book Citation Index includes over 104,500 editorially selected books, with 10,000 new books added each year. Containing more than 53.2 million cited references, coverage dates back from 2005 to present. The Book Citation Index is multidisciplinary, covering disciplines across the sciences, social sciences, and arts & humanities.
Produced by the Web Of Science group, BIOSIS Previews research database provides researchers with the most current sources of life sciences information, including journals, conferences, patents, books, review articles, and more. Researchers can also access multidisciplinary coverage via specialized indexing such as MeSH disease terms, CAS registry numbers, Sequence Databank Numbers and Major Concepts.
Produced by the Web Of Science group, Zoological Record is the world’s oldest continuing database of animal biology. It is considered the world’s leading taxonomic reference, and with coverage back to 1864, has long acted as the world’s unofficial register of animal names. The broad scope of coverage ranges from biodiversity and the environment to taxonomy and veterinary sciences.
Provides a simple way to search broadly for scholarly literature. Includes peer-reviewed papers, theses, books, abstracts and articles, from academic publishers, professsional societies, preprint repositories, universities and other scholarly organizations. Google Scholar sorts articles by weighing the full text of each article, the author, the publication in which the article appears, and how often the article has been cited in other scholarly literature, so that the most relevant results are returned on the first page.
Microsoft Academic is a project exploring how to assist human conducting scientific research by leveraging machine’s cognitive power in memory, computation, sensing, attention, and endurance. Re-launched in 2016, the tool features an entirely new data structure and search engine using semantic search technologies. The Academic Knowledge API offers information retrieval from the underlying database using REST endpoints for advanced research purposes.
The national library of the United Kingdom includes 150 million manuscripts, maps, newspapers, magazines, prints and drawings, music scores, and patents. Online catalogues, information and exhibitions can be found on its website. The library operates the world's largest document delivery service, providing millions of items a year to national and international customers.
The digital NSK portal is the central gathering place for the digital collections of the National and University Library (NSK) in Croatia. It was established in 2016 to provide access to the Library’s digital and digitized material collections regardless of storage location. The digital NSK portal enables a unified search of digitized material from the NSK Special Collections - books, visual material, maps and music material. From the end of 2019, all thematic portals are available independently: Digital Books, Digitized Manuscripts, Digitized Visual Materials, Digital Music Materials and Digitized Cartographic Materials (established in 2017). Currently available only in Croatian.
The official DOI (digital object identifier) link registration agency for scholarly and professional publications. Crossref operates a cross-publisher citation linking system that allows a researcher to click on a reference citation on one publisher’s platform and link directly to the cited content on another publisher’s platform, subject to the target publisher’s access control practices. This citation-linking network covers millions of articles and other content items from several hundred scholarly and professional publishers.
Dimensions is a next-generation linked research information system that makes it easier to find and access the most relevant information, analyze the academic and broader outcomes of research, and gather insights to inform future strategy. Dimensions delivers an array of search and discovery, analytical, and research management tools, all in a single platform. Developed in collaboration with over 100 leading research organizations around the world, it brings together over 128 million publications, grants, policy, data and metrics for the first time, enabling users to explore over 4 billion connections between them.
The primary aim of DOAB (Directory of Open Access Books) is to increase discoverability of Open Access books. Metadata will be harvestable in order to maximize dissemination, visibility and impact. Aggregators can integrate the records in their commercial services and libraries can integrate the directory into their online catalogues, helping scholars and students to discover the books.
OAPEN is dedicated to open access, peer-reviewed books. OAPEN operates two platforms, the OAPEN Library (www.oapen.org), a central repository for hosting and disseminating OA books, and the Directory of Open Access Books (DOAB, www.doabooks.org), a discovery service for OA books.
OpenAIRE aims at promoting and implementing the directives of the European Commission (EC) and the European Research Council on the promotion and funding of science and research. OpenAIRE supports the Open Access Mandate and the Open Research Data Pilot developed as part of the Horizon 2020 projects.
An integrated information service combining reference databases, subscription management, online journals, books and linking services. Widely used by libraries, schools, government institutions, medical institutions, corporations and others.
SFX® link resolver gives patrons and librarians a wealth of features that optimize management of and access to resources. It provides patrons with a direct route to electronic full-text records through OpenURL linking, delivers alternative links for further resource discovery, access to journals, and more. Released in 2001 as the first OpenURL resolver, SFX is continuously enhanced to support the newest industry developments and meet the evolving needs of customers. The records include a mix of scholarly material – primarily articles and e-books – but also conference proceedings, newspaper articles, and more.
A non-profit, membership, computer library service and research organization dedicated to the public purposes of furthering access to the world's information and reducing information costs. More than 41,555 libraries in 112 countries and territories around the world use OCLC services to locate, acquire, catalogue, lend and preserve library materials.
The world’s largest collection of open access research papers. CORE's mission is to aggregate all open access research outputs from repositories and journals worldwide and make them available to the public. In this way CORE facilitates free unrestricted access to research for all.
Perlego is a digital online library focusing on the delivery of academic, professional and non-fiction eBooks. It is a subscription-based service that offers users unlimited access to these texts for the duration of their subscription, however IntechOpen content integrated on the platform will always be available for free. They have been billed as “the Spotify for Textbooks” by the Evening Standard. Perlego is based in London but is available to users worldwide.
MyScienceWork provides a suite of data-driven solutions for research institutions, scientific publishers and private-sector R&D companies. MyScienceWork's comprehensive database includes more than 90 million scientific publications and 12 million patents.
CNKI (China National Knowledge Infrastructure) is a key national information construction project under the lead of Tsinghua University, and supported by PRC Ministry of Education, PRC Ministry of Science, Propaganda Department of the Communist Party of China and PRC General Administration of Press and Publication. CNKI has built a comprehensive China Integrated Knowledge Resources System, including journals, doctoral dissertations, masters' theses, proceedings, newspapers, yearbooks, statistical yearbooks, ebooks, patents, standards and so on. CNKI keeps integrating new contents and developing new products in 2 aspects: full-text academic resources, software on digitization and knowledge management. Began with academic journals, CNKI has become the largest and mostly-used academic online library in China.
As one of the largest digital content platform in China,independently developed by CNPIEC, CNPeReading positions herself as “One Platform,Vast Content, Global Services”. Through their new cooperation model and service philosophy, CNPeReading provides integrated promotion and marketing solutionsfor upstream publishers, one-stop, triune, recommendation, online reading and management servicesfor downstream institutions & libraries.
ERIC (Education Resources Information Center), sponsored by the Institute of Education Sciences (IES) of the U.S. Department of Education, provides access to education literature to support the use of educational research and information to improve practice in learning, teaching, educational decision-making, and research. The ERIC website is available to the public for searching more than one million citations going back to 1966.
The ACM Digital Library is a research, discovery and networking platform containing: The Full-Text Collection of all ACM publications, including journals, conference proceedings, technical magazines, newsletters and books. A collection of curated and hosted full-text publications from select publishers.
BASE (Bielefeld Academic Search Engine) is one of the world's most voluminous search sengines especially for academic web resources, e.g. journal articles, preprints, digital collections, images / videos or research data. BASE facilitates effective and targeted searches and retrieves high quality, academically relevant results. Other than search engines like Google or Bing BASE searches the deep web as well. The sources which are included in BASE are intellectually selected (by people from the BASE team) and reviewed. That's why data garbage and spam do not occur.
Zentralblatt MATH (zbMATH) is the world’s most comprehensive and longest-running abstracting and reviewing service in pure and applied mathematics. It is edited by the European Mathematical Society (EMS), the Heidelberg Academy of Sciences and Humanities and FIZ Karlsruhe. zbMATH provides easy access to bibliographic data, reviews and abstracts from all areas of pure mathematics as well as applications, in particular to natural sciences, computer science, economics and engineering. It also covers history and philosophy of mathematics and university education. All entries are classified according to the Mathematics Subject Classification Scheme (MSC 2020) and are equipped with keywords in order to characterize their particular content.
IDEAS is the largest bibliographic database dedicated to Economics and available freely on the Internet. Based on RePEc, it indexes over 3,100,000 items of research, including over 2,900,000 that can be downloaded in full text. RePEc (Research Papers in Economics) is a large volunteer effort to enhance the free dissemination of research in Economics which includes bibliographic metadata from over 2,000 participating archives, including all the major publishers and research outlets. IDEAS is just one of several services that use RePEc data.
As the authoritative source for chemical names, structures and CAS Registry Numbers®, the CAS substance collection, CAS REGISTRY®, serves as a universal standard for chemists worldwide. Covering advances in chemistry and related sciences over the last 150 years, the CAS content collection empowers researchers, business leaders, and information professionals around the world with immediate access to the reliable information they need to fuel innovation.
BKCI is a part of Web of Science Core Collection (WoSCC) and the world’s leading citation index with multidisciplinary content from the top tier international and regional journals, conference proceedings, and books. The Book Citation Index includes over 104,500 editorially selected books, with 10,000 new books added each year. Containing more than 53.2 million cited references, coverage dates back from 2005 to present. The Book Citation Index is multidisciplinary, covering disciplines across the sciences, social sciences, and arts & humanities.
Produced by the Web Of Science group, BIOSIS Previews research database provides researchers with the most current sources of life sciences information, including journals, conferences, patents, books, review articles, and more. Researchers can also access multidisciplinary coverage via specialized indexing such as MeSH disease terms, CAS registry numbers, Sequence Databank Numbers and Major Concepts.
Produced by the Web Of Science group, Zoological Record is the world’s oldest continuing database of animal biology. It is considered the world’s leading taxonomic reference, and with coverage back to 1864, has long acted as the world’s unofficial register of animal names. The broad scope of coverage ranges from biodiversity and the environment to taxonomy and veterinary sciences.
Provides a simple way to search broadly for scholarly literature. Includes peer-reviewed papers, theses, books, abstracts and articles, from academic publishers, professsional societies, preprint repositories, universities and other scholarly organizations. Google Scholar sorts articles by weighing the full text of each article, the author, the publication in which the article appears, and how often the article has been cited in other scholarly literature, so that the most relevant results are returned on the first page.
Microsoft Academic is a project exploring how to assist human conducting scientific research by leveraging machine’s cognitive power in memory, computation, sensing, attention, and endurance. Re-launched in 2016, the tool features an entirely new data structure and search engine using semantic search technologies. The Academic Knowledge API offers information retrieval from the underlying database using REST endpoints for advanced research purposes.
The national library of the United Kingdom includes 150 million manuscripts, maps, newspapers, magazines, prints and drawings, music scores, and patents. Online catalogues, information and exhibitions can be found on its website. The library operates the world's largest document delivery service, providing millions of items a year to national and international customers.
The digital NSK portal is the central gathering place for the digital collections of the National and University Library (NSK) in Croatia. It was established in 2016 to provide access to the Library’s digital and digitized material collections regardless of storage location. The digital NSK portal enables a unified search of digitized material from the NSK Special Collections - books, visual material, maps and music material. From the end of 2019, all thematic portals are available independently: Digital Books, Digitized Manuscripts, Digitized Visual Materials, Digital Music Materials and Digitized Cartographic Materials (established in 2017). Currently available only in Croatian.
The official DOI (digital object identifier) link registration agency for scholarly and professional publications. Crossref operates a cross-publisher citation linking system that allows a researcher to click on a reference citation on one publisher’s platform and link directly to the cited content on another publisher’s platform, subject to the target publisher’s access control practices. This citation-linking network covers millions of articles and other content items from several hundred scholarly and professional publishers.
Dimensions is a next-generation linked research information system that makes it easier to find and access the most relevant information, analyze the academic and broader outcomes of research, and gather insights to inform future strategy. Dimensions delivers an array of search and discovery, analytical, and research management tools, all in a single platform. Developed in collaboration with over 100 leading research organizations around the world, it brings together over 128 million publications, grants, policy, data and metrics for the first time, enabling users to explore over 4 billion connections between them.
The primary aim of DOAB (Directory of Open Access Books) is to increase discoverability of Open Access books. Metadata will be harvestable in order to maximize dissemination, visibility and impact. Aggregators can integrate the records in their commercial services and libraries can integrate the directory into their online catalogues, helping scholars and students to discover the books.
OAPEN is dedicated to open access, peer-reviewed books. OAPEN operates two platforms, the OAPEN Library (www.oapen.org), a central repository for hosting and disseminating OA books, and the Directory of Open Access Books (DOAB, www.doabooks.org), a discovery service for OA books.
OpenAIRE aims at promoting and implementing the directives of the European Commission (EC) and the European Research Council on the promotion and funding of science and research. OpenAIRE supports the Open Access Mandate and the Open Research Data Pilot developed as part of the Horizon 2020 projects.
An integrated information service combining reference databases, subscription management, online journals, books and linking services. Widely used by libraries, schools, government institutions, medical institutions, corporations and others.
SFX® link resolver gives patrons and librarians a wealth of features that optimize management of and access to resources. It provides patrons with a direct route to electronic full-text records through OpenURL linking, delivers alternative links for further resource discovery, access to journals, and more. Released in 2001 as the first OpenURL resolver, SFX is continuously enhanced to support the newest industry developments and meet the evolving needs of customers. The records include a mix of scholarly material – primarily articles and e-books – but also conference proceedings, newspaper articles, and more.
A non-profit, membership, computer library service and research organization dedicated to the public purposes of furthering access to the world's information and reducing information costs. More than 41,555 libraries in 112 countries and territories around the world use OCLC services to locate, acquire, catalogue, lend and preserve library materials.
The world’s largest collection of open access research papers. CORE's mission is to aggregate all open access research outputs from repositories and journals worldwide and make them available to the public. In this way CORE facilitates free unrestricted access to research for all.
Perlego is a digital online library focusing on the delivery of academic, professional and non-fiction eBooks. It is a subscription-based service that offers users unlimited access to these texts for the duration of their subscription, however IntechOpen content integrated on the platform will always be available for free. They have been billed as “the Spotify for Textbooks” by the Evening Standard. Perlego is based in London but is available to users worldwide.
MyScienceWork provides a suite of data-driven solutions for research institutions, scientific publishers and private-sector R&D companies. MyScienceWork's comprehensive database includes more than 90 million scientific publications and 12 million patents.
CNKI (China National Knowledge Infrastructure) is a key national information construction project under the lead of Tsinghua University, and supported by PRC Ministry of Education, PRC Ministry of Science, Propaganda Department of the Communist Party of China and PRC General Administration of Press and Publication. CNKI has built a comprehensive China Integrated Knowledge Resources System, including journals, doctoral dissertations, masters' theses, proceedings, newspapers, yearbooks, statistical yearbooks, ebooks, patents, standards and so on. CNKI keeps integrating new contents and developing new products in 2 aspects: full-text academic resources, software on digitization and knowledge management. Began with academic journals, CNKI has become the largest and mostly-used academic online library in China.
As one of the largest digital content platform in China,independently developed by CNPIEC, CNPeReading positions herself as “One Platform,Vast Content, Global Services”. Through their new cooperation model and service philosophy, CNPeReading provides integrated promotion and marketing solutionsfor upstream publishers, one-stop, triune, recommendation, online reading and management servicesfor downstream institutions & libraries.
ERIC (Education Resources Information Center), sponsored by the Institute of Education Sciences (IES) of the U.S. Department of Education, provides access to education literature to support the use of educational research and information to improve practice in learning, teaching, educational decision-making, and research. The ERIC website is available to the public for searching more than one million citations going back to 1966.
The ACM Digital Library is a research, discovery and networking platform containing: The Full-Text Collection of all ACM publications, including journals, conference proceedings, technical magazines, newsletters and books. A collection of curated and hosted full-text publications from select publishers.
BASE (Bielefeld Academic Search Engine) is one of the world's most voluminous search sengines especially for academic web resources, e.g. journal articles, preprints, digital collections, images / videos or research data. BASE facilitates effective and targeted searches and retrieves high quality, academically relevant results. Other than search engines like Google or Bing BASE searches the deep web as well. The sources which are included in BASE are intellectually selected (by people from the BASE team) and reviewed. That's why data garbage and spam do not occur.
Zentralblatt MATH (zbMATH) is the world’s most comprehensive and longest-running abstracting and reviewing service in pure and applied mathematics. It is edited by the European Mathematical Society (EMS), the Heidelberg Academy of Sciences and Humanities and FIZ Karlsruhe. zbMATH provides easy access to bibliographic data, reviews and abstracts from all areas of pure mathematics as well as applications, in particular to natural sciences, computer science, economics and engineering. It also covers history and philosophy of mathematics and university education. All entries are classified according to the Mathematics Subject Classification Scheme (MSC 2020) and are equipped with keywords in order to characterize their particular content.
IDEAS is the largest bibliographic database dedicated to Economics and available freely on the Internet. Based on RePEc, it indexes over 3,100,000 items of research, including over 2,900,000 that can be downloaded in full text. RePEc (Research Papers in Economics) is a large volunteer effort to enhance the free dissemination of research in Economics which includes bibliographic metadata from over 2,000 participating archives, including all the major publishers and research outlets. IDEAS is just one of several services that use RePEc data.
As the authoritative source for chemical names, structures and CAS Registry Numbers®, the CAS substance collection, CAS REGISTRY®, serves as a universal standard for chemists worldwide. Covering advances in chemistry and related sciences over the last 150 years, the CAS content collection empowers researchers, business leaders, and information professionals around the world with immediate access to the reliable information they need to fuel innovation.
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