Effect of methyl derivatives of β-CD on solubility and efficacy of drugs.
\r\n\tAnimal food additives are products used in animal nutrition for purposes of improving the quality of feed or to improve the animal’s performance and health. Other additives can be used to enhance digestibility or even flavour of feed materials. In addition, feed additives are known which improve the quality of compound feed production; consequently e.g. they improve the quality of the granulated mixed diet.
\r\n\r\n\tGenerally feed additives could be divided into five groups:
\r\n\t1.Technological additives which influence the technological aspects of the diet to improve its handling or hygiene characteristics.
\r\n\t2. Sensory additives which improve the palatability of a diet by stimulating appetite, usually through the effect these products have on the flavour or colour.
\r\n\t3. Nutritional additives, such additives are specific nutrient(s) required by the animal for optimal production.
\r\n\t4.Zootechnical additives which improve the nutrient status of the animal, not by providing specific nutrients, but by enabling more efficient use of the nutrients present in the diet, in other words, it increases the efficiency of production.
\r\n\t5. In poultry nutrition: Coccidiostats and Histomonostats which widely used to control intestinal health of poultry through direct effects on the parasitic organism concerned.
\r\n\tThe aim of the book is to present the impact of the most important feed additives on the animal production, to demonstrate their mode of action, to show their effect on intermediate metabolism and heath status of livestock and to suggest how to use the different feed additives in animal nutrition to produce high quality and safety animal origin foodstuffs for human consumer.
",isbn:"978-1-83969-404-2",printIsbn:"978-1-83969-403-5",pdfIsbn:"978-1-83969-405-9",doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!1,hash:"8ffe43a82ac48b309abc3632bbf3efd0",bookSignature:"Prof. László Babinszky",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/10496.jpg",keywords:"Technological Feed Additives, Feed Industry, Quality of Compound Feed, Non-Antibiotic Growth Promoter, Product Quality, Additive Enzymes, Digestibility of Nutrients, NSP Enzymes, Farm Animals, Livestock, Immunity, Microbiome",numberOfDownloads:null,numberOfWosCitations:0,numberOfCrossrefCitations:null,numberOfDimensionsCitations:null,numberOfTotalCitations:null,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"November 24th 2020",dateEndSecondStepPublish:"December 22nd 2020",dateEndThirdStepPublish:"February 20th 2021",dateEndFourthStepPublish:"May 11th 2021",dateEndFifthStepPublish:"July 10th 2021",remainingDaysToSecondStep:"2 months",secondStepPassed:!0,currentStepOfPublishingProcess:4,editedByType:null,kuFlag:!1,biosketch:"Professor Emeritus from the University of Debrecen, Hungary who authored 297 publications (papers, book chapters) and edited 3 books. Member of various committees and chairman of the World Conference of Innovative Animal Nutrition and Feeding (WIANF).",coeditorOneBiosketch:null,coeditorTwoBiosketch:null,coeditorThreeBiosketch:null,coeditorFourBiosketch:null,coeditorFiveBiosketch:null,editors:[{id:"53998",title:"Prof.",name:"László",middleName:null,surname:"Babinszky",slug:"laszlo-babinszky",fullName:"László Babinszky",profilePictureURL:"https://mts.intechopen.com/storage/users/53998/images/system/53998.jpg",biography:"László Babinszky is Professor Emeritus of animal nutrition at the University of Debrecen, Hungary. From 1984 to 1985 he worked at the Agricultural University in Wageningen and in the Institute for Livestock Feeding and Nutrition in Lelystad (the Netherlands). He also worked at the Agricultural University of Vienna in the Institute for Animal Breeding and Nutrition (Austria) and in the Oscar Kellner Research Institute in Rostock (Germany). 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Knuckey and Bruno P. Meloni",authors:[{id:"87625",title:"Prof.",name:"Bruno",middleName:null,surname:"Meloni",fullName:"Bruno Meloni",slug:"bruno-meloni"},{id:"87987",title:"Prof.",name:"Neville",middleName:null,surname:"Knuckey",fullName:"Neville Knuckey",slug:"neville-knuckey"},{id:"87988",title:"Dr.",name:"Kym",middleName:null,surname:"Campbell",fullName:"Kym Campbell",slug:"kym-campbell"}]},{id:"30324",title:"Hypothermia as an Alternative for the Management of Cerebral Ischemia",slug:"hypothermia-as-an-alternative-for-the-management-of-cerebral-ischemia",signatures:"Felipe Eduardo Nares-López, Gabriela Leticia González-Rivera and María Elena Chánez-Cárdenas",authors:[{id:"92781",title:"Dr.",name:"María Elena",middleName:null,surname:"Chánez-Cárdenas",fullName:"María Elena Chánez-Cárdenas",slug:"maria-elena-chanez-cardenas"},{id:"98025",title:"Mr.",name:"Felipe Eduardo",middleName:null,surname:"Nares-López",fullName:"Felipe Eduardo Nares-López",slug:"felipe-eduardo-nares-lopez"},{id:"98026",title:"Ms.",name:"Gabriela Leticia",middleName:null,surname:"Gonzalez-Rivera",fullName:"Gabriela Leticia Gonzalez-Rivera",slug:"gabriela-leticia-gonzalez-rivera"}]},{id:"30325",title:"Timing of Hypothermia (During or After Global Cerebral Ischemia) Differentially Affects Acute Brain Edema and Delayed Neuronal Death",slug:"optimal-duration-of-hypothermia-for-reperfusion-injury-following-cerebral-ischemia-based-on-experime",signatures:"Masaru Doshi and Yutaka Hirashima",authors:[{id:"90671",title:"Dr.",name:"Masaru",middleName:null,surname:"Doshi",fullName:"Masaru Doshi",slug:"masaru-doshi"}]},{id:"30326",title:"Molecular Mechanisms Underlying the Neuroprotective Effect of Hypothermia in Cerebral Ischemia",slug:"molecular-mechanisms-involved-in-the-neuroprotective-effect-of-hypothermia-in-cerebral-ischemia",signatures:"Yasushi Shintani and Yasuko Terao",authors:[{id:"90657",title:"Dr.",name:"Yasushi",middleName:null,surname:"Shintani",fullName:"Yasushi Shintani",slug:"yasushi-shintani"}]},{id:"30327",title:"Cortical Neurogensis in Adult Brains After Focal Cerebral Ischemia",slug:"cortical-neurogenesis-in-adult-brains-after-focal-cerebral-ischemia",signatures:"Weigang Gu and Per Wester",authors:[{id:"90299",title:"Dr.",name:"Weigang",middleName:null,surname:"Gu",fullName:"Weigang Gu",slug:"weigang-gu"},{id:"97918",title:"Prof.",name:"Per",middleName:null,surname:"Wester",fullName:"Per Wester",slug:"per-wester"}]},{id:"30328",title:"Brain Plasticity Following Ischemia: Effect of Estrogen and Other Cerebroprotective Drugs",slug:"brain-regeneration-following-ischemia-effect-of-estrogen-and-other-cerebroprotective-drugs",signatures:"Edina A. Wappler, Klára Felszeghy, Mukesh Varshney, Raj D. Mehra, Csaba Nyakas and Zoltán Nagy",authors:[{id:"97286",title:"Dr.",name:"Zoltán",middleName:null,surname:"Nagy",fullName:"Zoltán Nagy",slug:"zoltan-nagy"},{id:"101636",title:"Dr.",name:"Edina A.",middleName:null,surname:"Wappler",fullName:"Edina A. Wappler",slug:"edina-a.-wappler"},{id:"122330",title:"Dr.",name:"Klára",middleName:null,surname:"Felszeghy",fullName:"Klára Felszeghy",slug:"klara-felszeghy"},{id:"122331",title:"Prof.",name:"Csaba",middleName:null,surname:"Nyakas",fullName:"Csaba Nyakas",slug:"csaba-nyakas"},{id:"122332",title:"Prof.",name:"Raj",middleName:"D",surname:"Mehra",fullName:"Raj Mehra",slug:"raj-mehra"},{id:"122353",title:"Dr.",name:"Mukesh",middleName:"Kumar",surname:"Varshney",fullName:"Mukesh Varshney",slug:"mukesh-varshney"}]},{id:"30329",title:"The Promise of Hematopoietic Stem Cell Therapy for Stroke: Are We There Yet?",slug:"the-promise-of-hematopoietic-stem-cell-therapy-for-stroke-are-we-there-yet-",signatures:"Aqeela Afzal and J. Mocco",authors:[{id:"65922",title:"Dr.",name:"J",middleName:null,surname:"Mocco",fullName:"J Mocco",slug:"j-mocco"},{id:"98635",title:"Dr.",name:"Aqeela",middleName:null,surname:"Afzal",fullName:"Aqeela Afzal",slug:"aqeela-afzal"}]},{id:"30330",title:"Toward a More Effective Intravascular Cell Therapy in Stroke",slug:"toward-a-more-effective-intravascular-cell-therapy-in-stroke",signatures:"Bhimashankar Mitkari, Erja Kerkelä, Johanna Nystedt, Matti Korhonen, Tuulia Huhtala and Jukka Jolkkonen",authors:[{id:"90821",title:"Dr.",name:"Jukka",middleName:null,surname:"Jolkkonen",fullName:"Jukka Jolkkonen",slug:"jukka-jolkkonen"},{id:"96312",title:"MSc.",name:"Bhimashankar",middleName:null,surname:"Mitkari",fullName:"Bhimashankar Mitkari",slug:"bhimashankar-mitkari"},{id:"96313",title:"Dr.",name:"Erja",middleName:null,surname:"Kerkelä",fullName:"Erja Kerkelä",slug:"erja-kerkela"},{id:"96314",title:"Dr.",name:"Johanna",middleName:null,surname:"Nystedt",fullName:"Johanna Nystedt",slug:"johanna-nystedt"},{id:"96315",title:"Dr.",name:"Matti",middleName:null,surname:"Korhonen",fullName:"Matti Korhonen",slug:"matti-korhonen"},{id:"96316",title:"MSc.",name:"Tuulia",middleName:null,surname:"Huhtala",fullName:"Tuulia Huhtala",slug:"tuulia-huhtala"}]},{id:"30331",title:"Thrombolysis for Ischemic Stroke in Patients Aged 90 Years or Older",slug:"thrombolysis-for-ischemic-stroke-in-patients-aged-90-years-or-older",signatures:"M. Balestrino, L. Dinia, M. Del Sette, B. Albano and C. Gandolfo",authors:[{id:"87201",title:"Dr.",name:"Maurizio",middleName:null,surname:"Balestrino",fullName:"Maurizio Balestrino",slug:"maurizio-balestrino"}]},{id:"30332",title:"Mechanical Embolectomy",slug:"mechanical-embolectomy",signatures:"Jiří Lacman and František Charvát",authors:[{id:"99796",title:"Dr.",name:"Frantisek",middleName:null,surname:"Charvat",fullName:"Frantisek Charvat",slug:"frantisek-charvat"},{id:"99986",title:"Dr.",name:"Jiri",middleName:null,surname:"Lacman",fullName:"Jiri Lacman",slug:"jiri-lacman"}]},{id:"30333",title:"Decreased Cerebral Perfusion in Carotid Artery Stenosis, Carotid Angioplasty and Its Effects on Cerebral Circulation",slug:"cerebral-perfusion-and-interaction-with-carotid-angioplasty",signatures:"Antenor Tavares and José Guilherme Caldas",authors:[{id:"91098",title:"PhD.",name:"Antenor",middleName:"Tavares",surname:"Junior",fullName:"Antenor Junior",slug:"antenor-junior"},{id:"98211",title:"Dr.",name:"Jose",middleName:"Guilherme",surname:"Caldas",fullName:"Jose Caldas",slug:"jose-caldas"}]},{id:"30334",title:"Medical and Surgical Management of Intracranial Hypertension",slug:"medical-and-surgical-management-of-intracranial-hypertension",signatures:"James Scozzafava, Muhammad Shazam Hussain and Seby John",authors:[{id:"92560",title:"Dr.",name:"Giuseppe",middleName:"J",surname:"Scozzafava",fullName:"Giuseppe Scozzafava",slug:"giuseppe-scozzafava"},{id:"135628",title:"Dr.",name:"Muhammad S",middleName:null,surname:"Hussain",fullName:"Muhammad S Hussain",slug:"muhammad-s-hussain"},{id:"135630",title:"Dr.",name:"Seby",middleName:null,surname:"John",fullName:"Seby John",slug:"seby-john"}]},{id:"30335",title:"An Innovative Technique of Decompressive Craniectomy for Acute Ischemic Stroke",slug:"decompressive-craniectomy-for-cerebral-ischemia",signatures:"Marcelo M. Valença, Carolina Martins, Joacil Carlos da Silva, Caio Max Félix Mendonça, Patrícia B. Ambrosi and Luciana P.A. Andrade-Valença",authors:[{id:"90013",title:"Prof.",name:"Marcelo",middleName:"Moraes",surname:"Valença",fullName:"Marcelo Valença",slug:"marcelo-valenca"}]}]}]},onlineFirst:{chapter:{type:"chapter",id:"70358",title:"Effect of Cyclodextrin Derivatization on Solubility and Efficacy of Drugs",doi:"10.5772/intechopen.90364",slug:"effect-of-cyclodextrin-derivatization-on-solubility-and-efficacy-of-drugs",body:'\nCyclodextrins (CDs), first isolated by Antoine in 1891, are categorized as cyclic oligosaccharides in which glucose units are repeatedly connected through α-1,4-glycosidic linkages. Their unique property is the availability of various hydroxyl groups that serve as active site to form a variety of derivatives and linkages. CDs possess the capability of forming inclusion complexes with various molecules by incorporating them in their inner hydrophobic cavity, which not only alters the biological and physicochemical properties but also expands their magnitude of application [1, 2, 3].
\nInclusion complexation is basically the formation of hydrogen bonds and Van der Waals’ and hydrophobic interactions along with removal of water molecules [4, 5]. CDs are getting popular as food additives, owing to their solubilizing and protecting properties; they can be effectively used for incorporating vitamins, flavors, fragrances, essential oils, and dyes. They not only provide the controlled release of drugs and other incorporated molecules but also mask the obnoxious taste and odor [6, 7, 8, 9].
\nThe order of water solubility for commonly used cyclodextrins is as follows: β-CD (18.5 gL−1) < α-CD (145gL−1) < γ-CD (232 gL−1). The crystal state of natural CDs indicates strong molecular bonding (high crystal lattice energy) which in turn results in low aqueous solubility. β-CD has limited application as a solubilizing agent due to its low aqueous solubility, despite low cost, ease of availability, and appropriate cavity size. The most likely justification of lower solubility of β-CD is inadequate hydration by water molecule due to intramolecular hydrogen bond interaction offered by optimally arranged secondary hydroxyl groups [10]. Another possible elucidation of low aqueous solubility is the formation of aggregates that leads to unfavorable interactions with the hydrogen bonded structure of water molecule as proposed by Colman and coworkers [11]. β-CD shows Bs-type behavior in phase solubility graph when added to the aqueous drug solution or suspension due to precipitation of respective CD inclusion complex.
\nThe solubilizing power of parent CDs can be enhanced by adopting many different strategies, but the most interesting of them is the derivatization of CDs. The hydroxyl groups of CDs can be substituted to yield a variety of derivatives with significantly high aqueous solubility [12, 13, 14]. This chapter discusses the various strategies to functionalize the CDs and the resultant improvement in the aqueous solubility of formed complexes.
\nParent CDs can be modified through structural modifications by incorporating hydrophilic moieties that will ultimately result in significant increase in aqueous solubility. Furthermore, the inclusion complexes formed by modified CDs have higher complexation efficiencies than that of parent CDs. Rekharsky and Inoue reported various examples of thermodynamic parameters of inclusion complexes involving derivatized CDs [5].
\nIt is noteworthy that derivatization of CDs does not always enhance the complexation. The inhibition and promotion of complexation solely depends upon the type of substituents. Although the strong electrostatic force of attraction between the cationic substituents and organic anion was predicted to promote complexation, paradoxical effect was observed when the complexation of 2-naphthalene sulfonate was reduced with polyamine derivatives of β-CD. An unfavorable entropic effect may be involved that results in decrease in complexation [15]. On the other hand, a favorable electrostatic interaction occurs that leads to formation of zwitterionic corona by substituting both cationic and anionic groups at the primary face that will ultimately enhance the complexation of amino acids [16].
\nThe interdependence of numerous molecular parameters including type of substituent at the CDs, contribution of hydrophobic, and charge character of the guest moiety and competitive self-complexation (possible inclusion complexation of substituent moiety inside the core of CD) was discussed in detail by Kean and his coworkers [17]. While dealing with ionic species, electrostatic effects are usually dominated which exert a paradoxical effect. Based on this status quo, the inclusion complexation of charged CD with organic ions must be evaluated on the basis of electrostatic interactions. The properties of modified CDs are governed by the location of hydroxyl groups on the parent CDs that are going to be substituted. Three different hydroxyl groups that exert different reactivities are located on the glucose repeating unit of a CD molecule, including one primary hydroxyl group attached to C6 (at the narrow side) and two secondary hydroxyl groups attached to C2 and C3 (at wider side).
\nMost common derivatives of CDs are discussed in this section.
\nThere is variety of ways to perform methylation of native cyclodextrins:
\nFormerly methyl derivatives were synthesized by using either methyl iodide or dimethyl sulfate [18]. These two reagents are highly toxic and unsafe so may be detrimental to the environment as well as human being. Based on this status quo, it is mandatory to seek new and novel synthetic method to replace these toxic chemicals.
\nDimethyl carbonate being eco-friendly could be an attractive alternate in this scenario [19]. The synthesis involves addition of β-CD in dimethylformamide solution followed by stirring until clear solution is obtained. Potassium carbonate is added as catalyst followed by dropwise addition of dimethyl carbonate, and mixture is allowed to stir for the next 48 hours. The catalyst and dimethyl carbonate are removed to produce syrupy consistency. At the end, this concentrate is treated with acetone followed by its removal by filtration. Finally, the product is treated with ether two to three times, and after filtration white powdered product is obtained as indicated in Figure 1.
\nSynthesis of methyl β-CD [21].
An important feature of methyl β-CD is its degree of substitution that has marked effect on drug solubilization, so it must be carefully investigated [20]. Table 1 gives the use of methyl derivatives of β-CD with effect on solubility and efficacy of various drugs.
\nAuthor | \nDrug | \nAdditives (if used) | \nEffects | \n
---|---|---|---|
Schipper et al. [22] | \nInsulin | \n— | \nImproved nasal absorption | \n
Schipper et al. [23] | \nSalmon calcitonin | \n— | \nEnhanced nasal penetration | \n
Sigurdsson et al. [24] | \nDexamethasone | \n— | \nLocalized drug delivery to anterior eye segment | \n
Soares-Sobrinho et al. [25] | \nBenznidazole | \nPVP, HPMC | \nEnhanced solubility, reduced toxicity | \n
Mathiron et al. [26] | \nMidazolam | \n— | \nImproved solubility, protective effect on drug degradation | \n
Chao et al. [27] | \nOfloxacin | \n— | \nSignificant increase in solubility, improved pharmacological efficacy | \n
Vieira et al. [28] | \nEfavirenz | \nPVP | \nImproved dissolution profile, increased stability | \n
Rassu et al. [29] | \nDeferoxamine mesylate | \n— | \nImproved bioavailability, avoidance of systemic exposure | \n
Terauchi et al. [30] | \nSimvastatin | \n— | \nImproved solubility, effective bone regeneration therapy | \n
Effect of methyl derivatives of β-CD on solubility and efficacy of drugs.
This pharmaceutically significant methylated derivative of β-CD has the following advantages:
Easy availability (as dry powder/aqueous solution 50%)
Good water solubility
Cost-effective
High inclusion capacity for hydrophobic drugs
The replacement of hydroxyl groups of CD by 2-hydroxypropyl moiety can be done by the reaction of CD with propylene oxide in an alkaline aqueous solution (Figure 2a) [31]. An isopropylene (oligomeric hydroxypropylene) side chain is formed for high degree of substitution (Figure 2b).
\nReaction scheme for HPβCD synthesis: (a) low DS, (b) high DS [32].
The characterization of finally synthesized hydroxypropyl derivatives involves determination of average number of substituents on the cyclodextrin molecule (degree of substitution). According to latest US and European pharmacopoeias, the acceptable range for DS is 2.8–10.5 for HPβCD. Degree of substitution can be measured by a variety of techniques including near-infrared reflectance spectroscopy, nuclear magnetic resonance (NMR), microcalorimetric titration [33], mass spectrometry (MS), differential scanning calorimetry (DSC) [34], and reductive-cleavage and methylation analysis.
\nEncapsin™ and Molecusol™ are the trade names of commercially available form of hydroxyalkyl derivative (2-hydroxypropyl-β-CD). Various clinical trials have been performed with this derivative besides its use in technological, toxicological, and pharmaceutical experiments [35]. Being the most thoroughly studied derivative, FDA has approved Sporanox™ by Janssen using the same derivatives as molecular carrier. The hydroxypropyl derivative of β-CD and ɣ-CD have been widely used for solubility enhancement and leading to increase in efficacy of various drugs as illustrated in Tables 2 and 3.
\nAuthor | \nDrug | \nOther additives (if present) | \nEffects | \n
---|---|---|---|
Kaur et al. 2004 [36] | \nAcetazolamide | \nPVA, PVP, HPMC, Carbopol 940 | \nImproved solubility, effective drug permeation, improved corneal transport | \n
Chowdary et al. [37] | \nCelecoxib | \nPVP, HPMC, PEG | \nImproved solubility, higher CE by ternary complexation | \n
El-Maradny et al. [38] | \nMeloxicam | \nPVP, L-ARG | \nImproved solubility, quick pain relieving effect, faster drug release with ternary complex | \n
Manali Shah et al. [39] | \nEtoricoxib | \nPVP, L-ARG | \nEnhanced dissolution profile, improved oral bioavailability | \n
Asbahr et al. [40] | \nFinasteride | \nPVP, chitosan | \nPositive effect on drug solubility, inc. in bulk of formulation so can be used in solid dosage forms | \n
Mummidi and Jayanthi [41] | \nIsradipine | \nPVP, HPMC, PEG | \nMarked increase in solubilizing efficiency, improved dissolution with ternary complexes | \n
Pacheco et al. [42] | \nAlbendazole | \nPVA | \nEnhanced solubility, improved intrinsic dissolution rate | \n
Jadhav and Pore [43] | \nBosentan | \nArginine (ARG) | \nEnhanced solubility and dissolution profile | \n
Effects of HPβCD on solubility and efficacy of drugs.
Author | \nDrug | \nOther additives (if present) | \nEffects | \n
---|---|---|---|
Zhou et al. [44] | \nBaicalein | \n— | \nHigher drug absorption, better stability, enhanced release profile | \n
Soica et al. [45] | \nOleanolic acid, ursolic acid | \n— | \nEnhanced aqueous solubility, marked antiproliferative activity | \n
Misiuk and Jasiuk 2014 [46] | \nBupropion | \n— | \nImproved release, rapid absorption, enhanced encapsulation efficiency | \n
Misiuk et al. [47] | \nCeftazidime | \n— | \nImproved aqueous solubility, improved stability as suggested by NMR study | \n
Wathoni et al. [48] | \nCurcumin | \n— | \nIncreased solubility, enhanced antioxidant activity | \n
Effects of HPɣCD on solubility and efficacy of drugs.
Almost more than 180 articles had focused on the preparation and use of charged (anionic) CD derivatives by the end of July 1998.The glucopyranose unit present in the native CD ring could be directly substituted with charged moiety, or a neutral spacer group may be used for the insertion [49]. Such functional groups can be inserted at different degrees of substitution (DS) and have variable sizes, so the final product of modified CD derivative may be influenced by electronic and steric factors.
\nThe sulfopropyl and sulfobutyl derivatives of beta-CDs are produced by reacting native CD with propane sultone and butane sultone, respectively, in an alkaline aqueous solution as shown in Figure 3.
\nSynthesis of SBE-β-CD [50].
Sulfobutylated β-CD with seven substituents is considered as suitable derivative and is commercially available under the trade name of Captisol™ by CyDex. Resveratrol is complexed with sulfobutylether derivatives of β-CD and increased the anticancer activity with increase in solubility of resveratrol as well [51].
\nA class of water-soluble CD derivatives having anti-angiogenic, biological, and anticancer properties is sulfated CDs. As the tumor growth is dependent on angiogenesis, the use of these derivatives could be a unique approach for the treatment of solid tumors, as reported by Folkman et al. in early 1970 [52]. In addition to these properties, they also possess antilipemic, antiviral, and anti-inflammatory effects [53].
\nReaction of CD in absolute dimethylformamide with pyridine sulfur trioxide gives better yield of sulfated derivatives of CDs [54]. Besides their use as solubility enhancers, these derivatives also provide protection against gentamicin-induced nephrotoxicity and have no hemolytic properties, so can be effectively used in clinical studies [55]. Figure 4 presents the scheme of preparation of sulfated β-CD.
\nSynthesis of sulfated β-CD [56].
The following guidelines should be strictly followed during the synthesis of CD derivatives in order to get the better solubility and complexing ability:
Although the substituents at primary hydroxyl side may influence other uses, they do not exert much effect on the complexation. The pH of the medium is decisive that either the secondary hydroxyl side or primary side will be substituted. Moderately basic medium will favor secondary hydroxyl substitution, whereas primary hydroxyl side will get substituted in strong basic medium [57].
To avoid the deformation of cavity shape, avoid the bulky substitution which may crowd each other. Although the CD torus is made of anhydroglucose repeating units which are quite rigid, they are connected to each other through single glycosidic bonds. As torus is stabilized by hydrogen bonds between the secondary hydroxyls on adjacent glucose unit, the stabilizing effect of hydrogen bonding is diminished by secondary hydroxyl substitution. Finally, the anhydroglucose units may tilt out the defined torus shape due to introduction of steric strain between substituting units present on the adjacent anhydroglucose residues [35].
The water-soluble CDs are used either in solid form or in concentrated solution state. Some substituting groups have the tendency to incorporate in the core of CDs, so they compete with active drug molecules for inclusion complexation. Therefore, it is mandatory to select those substituents that are unable to fit in the cavity of CDs [58].
A glucopyranose unit of cyclodextrin ring contains how many substituted hydroxyl groups are defined as its degree of substitution. One mole of glucopyranose unit contains three reactive hydroxyl groups so the maximum possible numbers of substituents are 18, 21, and 24 for α-, β-, and γ- CDs, respectively. Controlling the degree of substitution is important in producing the desired properties in functionalized CDs.
Using different functional groups, modified CDs could play a pivotal role in improving limited drug stability and boosting aqueous solubility and dissolution behavior of drugs with poor water solubility. In order to use full potential of CDs as a drug delivery carrier, the nature and degree of functionalization play an important role. However, the future research should focus on the use of green chemistry for CDs’ functionalization, and the attention should also be paid to the toxicokinetic profiling of the modified CDs to establish their safety and efficacy at the same time.
\nThere is no conflict of interest among the listed authors.
.
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