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More than half of the publishers listed alongside IntechOpen (18 out of 30) are Social Science and Humanities publishers. IntechOpen is an exception to this as a leader in not only Open Access content but Open Access content across all scientific disciplines, including Physical Sciences, Engineering and Technology, Health Sciences, Life Science, and Social Sciences and Humanities.
\\n\\nOur breakdown of titles published demonstrates this with 47% PET, 31% HS, 18% LS, and 4% SSH books published.
\\n\\n“Even though ItechOpen has shown the potential of sci-tech books using an OA approach,” other publishers “have shown little interest in OA books.”
\\n\\nAdditionally, each book published by IntechOpen contains original content and research findings.
\\n\\nWe are honored to be among such prestigious publishers and we hope to continue to spearhead that growth in our quest to promote Open Access as a true pioneer in OA book publishing.
\\n\\n\\n\\n
\\n"}]',published:!0,mainMedia:null},components:[{type:"htmlEditorComponent",content:'
Simba Information has released its Open Access Book Publishing 2020 - 2024 report and has again identified IntechOpen as the world’s largest Open Access book publisher by title count.
\n\nSimba Information is a leading provider for market intelligence and forecasts in the media and publishing industry. The report, published every year, provides an overview and financial outlook for the global professional e-book publishing market.
\n\nIntechOpen, De Gruyter, and Frontiers are the largest OA book publishers by title count, with IntechOpen coming in at first place with 5,101 OA books published, a good 1,782 titles ahead of the nearest competitor.
\n\nSince the first Open Access Book Publishing report published in 2016, IntechOpen has held the top stop each year.
\n\n\n\nMore than half of the publishers listed alongside IntechOpen (18 out of 30) are Social Science and Humanities publishers. IntechOpen is an exception to this as a leader in not only Open Access content but Open Access content across all scientific disciplines, including Physical Sciences, Engineering and Technology, Health Sciences, Life Science, and Social Sciences and Humanities.
\n\nOur breakdown of titles published demonstrates this with 47% PET, 31% HS, 18% LS, and 4% SSH books published.
\n\n“Even though ItechOpen has shown the potential of sci-tech books using an OA approach,” other publishers “have shown little interest in OA books.”
\n\nAdditionally, each book published by IntechOpen contains original content and research findings.
\n\nWe are honored to be among such prestigious publishers and we hope to continue to spearhead that growth in our quest to promote Open Access as a true pioneer in OA book publishing.
\n\n\n\n
\n'}],latestNews:[{slug:"stanford-university-identifies-top-2-scientists-over-1-000-are-intechopen-authors-and-editors-20210122",title:"Stanford University Identifies Top 2% Scientists, Over 1,000 are IntechOpen Authors and Editors"},{slug:"intechopen-authors-included-in-the-highly-cited-researchers-list-for-2020-20210121",title:"IntechOpen Authors Included in the Highly Cited Researchers List for 2020"},{slug:"intechopen-maintains-position-as-the-world-s-largest-oa-book-publisher-20201218",title:"IntechOpen Maintains Position as the World’s Largest OA Book Publisher"},{slug:"all-intechopen-books-available-on-perlego-20201215",title:"All IntechOpen Books Available on Perlego"},{slug:"oiv-awards-recognizes-intechopen-s-editors-20201127",title:"OIV Awards Recognizes IntechOpen's Editors"},{slug:"intechopen-joins-crossref-s-initiative-for-open-abstracts-i4oa-to-boost-the-discovery-of-research-20201005",title:"IntechOpen joins Crossref's Initiative for Open Abstracts (I4OA) to Boost the Discovery of Research"},{slug:"intechopen-hits-milestone-5-000-open-access-books-published-20200908",title:"IntechOpen hits milestone: 5,000 Open Access books published!"},{slug:"intechopen-books-hosted-on-the-mathworks-book-program-20200819",title:"IntechOpen Books Hosted on the MathWorks Book Program"}]},book:{item:{type:"book",id:"715",leadTitle:null,fullTitle:"Learning Disabilities",title:"Learning Disabilities",subtitle:null,reviewType:"peer-reviewed",abstract:"Learning disability is a classification that includes several disorders in which a person has difficulty learning in a typical manner. Depending on the type and severity of the disability, interventions may be used to help the individual learn strategies that will foster future success. Some interventions can be quite simplistic, while others are intricate and complex. This book deserves a wide audience; it will be beneficial not only for teachers and parents struggling with attachment or behavior issues, but it will also benefit health care professionals and therapists working directly with special needs such as sensory integration dysfunction.",isbn:null,printIsbn:"978-953-51-0269-4",pdfIsbn:"978-953-51-5105-0",doi:"10.5772/1224",price:139,priceEur:155,priceUsd:179,slug:"learning-disabilities",numberOfPages:376,isOpenForSubmission:!1,isInWos:1,hash:"7cf7910a2068cff1fdcdfd5ed3c25cc7",bookSignature:"Wichian Sittiprapaporn",publishedDate:"March 14th 2012",coverURL:"https://cdn.intechopen.com/books/images_new/715.jpg",numberOfDownloads:61529,numberOfWosCitations:20,numberOfCrossrefCitations:12,numberOfDimensionsCitations:17,hasAltmetrics:0,numberOfTotalCitations:49,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"March 14th 2011",dateEndSecondStepPublish:"April 11th 2011",dateEndThirdStepPublish:"August 16th 2011",dateEndFourthStepPublish:"September 15th 2011",dateEndFifthStepPublish:"January 13th 2012",currentStepOfPublishingProcess:5,indexedIn:"1,2,3,4,5,6",editedByType:"Edited by",kuFlag:!1,editors:[{id:"73395",title:"Dr.",name:"Phakkharawat",middleName:null,surname:"Sittiprapaporn",slug:"phakkharawat-sittiprapaporn",fullName:"Phakkharawat Sittiprapaporn",profilePictureURL:"https://mts.intechopen.com/storage/users/73395/images/2283_n.jpg",biography:"Assistant Professor Dr. Phakkharawat Sittiprapaporn is a Thai Cognitive Neuroscientist who has published in many national and international publications. His other achievements include authoring chapters in other books and reviewing articles for reputed national and international indexed journals. Assistant Professor Dr. Phakkharawat Sittiprapaporn was born in Udornthani, Thailand in 1970. He received the B.A. (Hons.) (English) and M.A. (Linguistics) from Srinakharinwirot University and Mahidol University, Bangkok, Thailand in 1993 and 1997, respectively. He received a Ph.D. degree in Neurosciences from Mahidol University, Thailand, in 2002 and became a postdoctoral fellow at the Clinical Cognitive Neuroscience Center (CCNC), Seoul National University, College of Medicine, Seoul, Korea, in 2006. After working as a lecturer in Neurosciences at the Neuro-Behavioural Biology Center, Institute of Science and Technology for Research and Development, Mahidol University, from 2003 to 2005, he was invited to join the Music Therapy Division, College of Music, Mahidol University, Bangkok, in 2008. Since January 2010, he has joined the Faculty of Medicine, Mahasarakham University. He also went for a postdoctoral research fellow at the University of Kansas Medical Center, Kansas, USA. He concurrently held an Assistant Professor at the School of Anti-Aging and Regenerative Medicine, Mae Fah Luang University, Thailand. He also takes in chart of the head of the Brain Sciences and Engineering Research Unit (BSEI), Mae Fah Luang University, Thailand. 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Payan-Carreira",dateSubmitted:"April 21st 2020",dateReviewed:"September 10th 2020",datePrePublished:"October 8th 2020",datePublished:"January 20th 2021",book:{id:"8545",title:"Animal Reproduction in Veterinary Medicine",subtitle:null,fullTitle:"Animal Reproduction in Veterinary Medicine",slug:"animal-reproduction-in-veterinary-medicine",publishedDate:"January 20th 2021",bookSignature:"Faruk Aral, Rita Payan-Carreira and Miguel Quaresma",coverURL:"https://cdn.intechopen.com/books/images_new/8545.jpg",licenceType:"CC BY 3.0",editedByType:"Edited by",editors:[{id:"25600",title:"Prof.",name:"Faruk",middleName:null,surname:"Aral",slug:"faruk-aral",fullName:"Faruk Aral"}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"}},authors:[{id:"38652",title:"Dr.",name:"Rita",middleName:null,surname:"Payan-Carreira",fullName:"Rita Payan-Carreira",slug:"rita-payan-carreira",email:"rtpayan@gmail.com",position:null,institution:{name:"University of Évora",institutionURL:null,country:{name:"Portugal"}}},{id:"309250",title:"Dr.",name:"Miguel",middleName:null,surname:"Quaresma",fullName:"Miguel Quaresma",slug:"miguel-quaresma",email:"miguelq@utad.pt",position:null,institution:{name:"University of Trás-os-Montes and Alto Douro",institutionURL:null,country:{name:"Portugal"}}}]}},chapter:{id:"73504",slug:"calf-sex-influence-in-bovine-milk-production",signatures:"Miguel Quaresma and R. Payan-Carreira",dateSubmitted:"April 21st 2020",dateReviewed:"September 10th 2020",datePrePublished:"October 8th 2020",datePublished:"January 20th 2021",book:{id:"8545",title:"Animal Reproduction in Veterinary Medicine",subtitle:null,fullTitle:"Animal Reproduction in Veterinary Medicine",slug:"animal-reproduction-in-veterinary-medicine",publishedDate:"January 20th 2021",bookSignature:"Faruk Aral, Rita Payan-Carreira and Miguel Quaresma",coverURL:"https://cdn.intechopen.com/books/images_new/8545.jpg",licenceType:"CC BY 3.0",editedByType:"Edited by",editors:[{id:"25600",title:"Prof.",name:"Faruk",middleName:null,surname:"Aral",slug:"faruk-aral",fullName:"Faruk Aral"}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"}},authors:[{id:"38652",title:"Dr.",name:"Rita",middleName:null,surname:"Payan-Carreira",fullName:"Rita Payan-Carreira",slug:"rita-payan-carreira",email:"rtpayan@gmail.com",position:null,institution:{name:"University of Évora",institutionURL:null,country:{name:"Portugal"}}},{id:"309250",title:"Dr.",name:"Miguel",middleName:null,surname:"Quaresma",fullName:"Miguel Quaresma",slug:"miguel-quaresma",email:"miguelq@utad.pt",position:null,institution:{name:"University of Trás-os-Montes and Alto Douro",institutionURL:null,country:{name:"Portugal"}}}]},book:{id:"8545",title:"Animal Reproduction in Veterinary Medicine",subtitle:null,fullTitle:"Animal Reproduction in Veterinary Medicine",slug:"animal-reproduction-in-veterinary-medicine",publishedDate:"January 20th 2021",bookSignature:"Faruk Aral, Rita Payan-Carreira and Miguel Quaresma",coverURL:"https://cdn.intechopen.com/books/images_new/8545.jpg",licenceType:"CC BY 3.0",editedByType:"Edited by",editors:[{id:"25600",title:"Prof.",name:"Faruk",middleName:null,surname:"Aral",slug:"faruk-aral",fullName:"Faruk Aral"}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"}}},ofsBook:{item:{type:"book",id:"9277",leadTitle:null,title:"Manifolds",subtitle:null,reviewType:"peer-reviewed",abstract:"
\r\n\tA manifold can be defined as a topological space in which the global properties may vary widely and have a complicated structure, but near each point it resembles a Euclidean space. The concept of manifold is central to modern physical mathematics as it provides tools and techniques for the analysis of complex physical systems using simple topological properties of Euclidean spaces. From Riemann's acceptance that a Euclidean space structure was suitable to study the physical knowledge of his time, until the most recent efforts to produce highly accurate higher dimensional manifolds, there has been a tremendous cross-fertilization of theory, ideas and applied numerical algorithms on manifolds based on a vivid interplay between differential geometry, topology, analysis, algebra and physics.
\r\n\r\n\tThis book intends to provide the reader with a comprehensive overview of the current state-of-the-art in this fascinating and critically important field of mathematics, presenting some of the most important developments of the last years alongside its applications in areas such as computer-graphics, robotics, augmented-reality, machine learning, quantum mechanics and general relativity, to name only a few.
",isbn:null,printIsbn:"979-953-307-X-X",pdfIsbn:null,doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!1,hash:"57ab2a7967f4f13906f1a7aa3c998d44",bookSignature:"Dr. Bruno Carpentieri",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/9277.jpg",keywords:"Smooth Manifolds, Foundational Theorems, Differential Forms, Integration, Topological Spaces, Group Theory, Calculus on Manifolds, Riemannian Geometry, Dirac Operators, Differential-Algebraic Equations, Geometric Integration Algorithms, Computer-Graphics",numberOfDownloads:null,numberOfWosCitations:0,numberOfCrossrefCitations:null,numberOfDimensionsCitations:null,numberOfTotalCitations:null,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"June 12th 2020",dateEndSecondStepPublish:"July 3rd 2020",dateEndThirdStepPublish:"September 1st 2020",dateEndFourthStepPublish:"November 20th 2020",dateEndFifthStepPublish:"January 19th 2021",remainingDaysToSecondStep:"8 months",secondStepPassed:!0,currentStepOfPublishingProcess:5,editedByType:null,kuFlag:!1,biosketch:"Bruno Carpentieri furthered his Ph.D. studies at the National Polytechnic Institute of Toulouse, he gained professional experiences at the Karl-Franzens University of Graz, at CRS4 in Sardinia, at the University of Groningen and finally as a Reader in Applied Mathematics at the Nottingham Trent University before joining his current affiliation.",coeditorOneBiosketch:null,coeditorTwoBiosketch:null,coeditorThreeBiosketch:null,coeditorFourBiosketch:null,coeditorFiveBiosketch:null,editors:[{id:"92921",title:"Dr.",name:"Bruno",middleName:null,surname:"Carpentieri",slug:"bruno-carpentieri",fullName:"Bruno Carpentieri",profilePictureURL:"https://mts.intechopen.com/storage/users/92921/images/system/92921.png",biography:"Bruno Carpentieri obtained a Laurea degree in Applied Mathematics in 1997 from Bari University, then he furthered his Ph.D. studies in Computer Science at the National Polytechnic Institute of Toulouse. After some professional experiences as a postdoctoral researcher at the Karl-Franzens University of Graz, as a consultant for an European project in cardiac modelling at CRS4 in Sardinia, as an Assistant Professor at the University of Groningen and finally as a Reader in Applied Mathematics at the Nottingham Trent University, since May 2017 he is holding an Associate Professor appointment in Applied Mathematics at the Faculty of Computer Science, University of Bozen-Bolzano. 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From chapter submission and review, to approval and revision, copyediting and design, until final publication, I work closely with authors and editors to ensure a simple and easy publishing process. I maintain constant and effective communication with authors, editors and reviewers, which allows for a level of personal support that enables contributors to fully commit and concentrate on the chapters they are writing, editing, or reviewing. I assist authors in the preparation of their full chapter submissions and track important deadlines and ensure they are met. I help to coordinate internal processes such as linguistic review, and monitor the technical aspects of the process. As an ASM I am also involved in the acquisition of editors. 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This force drives outside hot air to pass through the evaporative pad (expanded paper) and causes reduction of indoor temperature, high humidity and constant enthalpy [1]. The thermal performance of solar chimneys using different configurations has been experimentally investigated by different researchers. The concept of metallic solar wall (MSW) on a full-scale model was studied for a single-room house under tropical climatic conditions in Thailand. It was shown that a MSW with 2 m height and 0.145 m air gap (cavity between glass and aluminum) can produce a mass flow rate up to 0.02 kg/s for a house with a base area of 11.55 m2 and a height of 2.68 m and optimum natural ventilation. Such low-cost solar chimney construction can significantly reduce heat gain in the house by creating adequate flow rate to improve thermal comfort [2]. The thermal performance of a solar chimney was investigated on a full-scale model under Mediterranean daylight and night-time conditions for natural ventilation. A 4.5 m high, 1.0 m wide and 0.15 m thick reinforced concrete wall was used as a solar absorber, whose southern surface was painted matte black with insulation on the side and back surfaces. The absorber wall was covered by glass of 0.1 m thickness to reduce the convection heat. With this configuration, a maximum flow rate of 374 m3/h was reported at a solar intensity of 604 W/m2 occurring at around 13:00 h. Discharge coefficient was experimentally determined to carry out volumetric flow rate calculation. It was concluded that the airflow rate through a solar chimney system is greatly affected by the pressure difference between openings caused by thermal gradients and by wind velocity [3]. An experiment of solar-induced ventilation strategy was conducted. The experiment consisted of two parts, namely, a roof solar collector and a vertical stack. The purpose of the roof solar collector was to capture as much solar radiation as possible, thus maximizing the air temperature inside the channel of the roof solar collector. The heated air inside the channel rose and flowed into the vertical stack due to the pressure difference between the two zones. Meanwhile, the vertical stack was important in providing significant height for sufficient stack pressure. The walls of vertical stack were insulated to minimize the heat loss to the environment. The findings indicated that the proposed strategy was able to enhance the stack ventilation, both in semi-clear sky and overcast sky conditions. The highest air temperature difference between the air inside the stack and the ambient air was achieved in the semi-clear sky condition, which was about 9.9°C (45.8–35.9°C). Besides, in the overcast sky condition, the highest air temperature difference was 6.2°C (39.3–33.1°C) [4]. Also, an experimental study of a vertical channel simulating a solar chimney and a Trombe wall was conducted. The vertical channel had a transparent cover and an absorber plate, painted matte black. The vertical channel was open at both ends, and its dimensions were 1.025 m high, 0.925 m wide and 0.02 m–0.11 m variable depth. Heat input to the absorber plate was supplied by electrical means (200–1000 W) in steps of 200 W. Air temperature and velocity measurements inside the channel were obtained. The results showed that air temperature was increased continuously along the channel height, while the cover and the absorber plate temperatures were not. The cover temperature, as well as the absorber plate temperature, increased continuously to the middle height and then began to decrease. The authors concluded that the mass flow rate is a function of the heat input as well as on the channel depth, while the efficiency of the system is a function of the heat input only [5].
\nIt was concluded that a serious problem of discomfort exists inside houses in projects of new Assiut city based on natural ventilation strategy only [6, 7, 8, 9]. Traditional passive techniques were used in ancient architectures to achieve the desired summer comfort without the need for mechanical cooling systems [10]. This traditional technique was based on natural environmental conditions such as wind, water and vegetation to achieve significant indoor thermal comfort [11]. It was concluded that if passive solar solutions are integrated in existing buildings, building energy demand can be reduced [12]. Many researches have been conducted to examine passive cooling strategies in the buildings. Maerefat and Haghighi studied solar chimney integrated with evaporative cooling cavity. This integrated system was capable of providing good indoor conditions during daytime in the living room [10]. Alemu et al. developed a model using passive cooling technique in earth air tunnel. This model investigated the integration of passive techniques [13]. Developing solar chimney with direct evaporative cooling tower using numerical simulation was done using COMIS-TRNSYS software to provide indoor thermal comfort under the climatic conditions of Assiut, Egypt. The results show that the system generates 130.5 m3/h with indoor thermal comfort of 80% acceptable range [7, 8]. Macias et al. developed a passive cooling system for a residential building. Natural ventilation was enhanced with the aid of a solar chimney, and fresh air was cooled down by circulation within the duct area of the building. It was found that the passive cooling system allowed for ensuring thermal comfort through low conventional energy consumption based on a 2-year monitoring period [14] .
\nNo experimental studies were found for the integration of solar chimney with cooling strategies in residential buildings in Egypt except for the ventilated Trombe wall as a solar heating and cooling for building retrofitting in semiarid climate (Saint Katherine, Egypt) [15]. The purpose of using solar chimney is to generate natural air movement and improve stack-induced ventilation with low CO2 concentration and indoor comfort for low-energy buildings in Egypt. The main aim of this study is to investigate the performance of an (SCPC) integrated within a room as a passive cooling technique to provide sufficient fresh cooled air, indoor comfort, and reduce room cooling loads. This stage is the second phase of a project for developing an integration of solar chimneys with passive cooling technique (SCPC) to reduce energy used in buildings in Assiut, Egypt.
\nA single room was built in Assiut University (El-Gorib site) in Assiut, Egypt. Room dimensions are 3.8 x 3.8 x 2.8 m (L × W × H) based on the previous numerical model of solar chimneys integrated with passive cooling [7, 8]. It is located at a latitude of 27°3’N and a longitude of 31°15′ E. In terms of climatic characteristics, Assiut is located in southern Upper Egypt zone. It is characterized by hot dry summers with a maximum outdoor temperature that ranges from 41–46°C and a minimum temperature that ranges from 16–21°C in the summer months. This zone has a global radiation range of 1000 to 1125 W/m2 in the summer and 650 to 800 W/m2 in the winter. Outdoor climate analysis was done based on field measurements at 2-minute time interval to analyze 1-year data (2015). Figure 1 shows the temperature and humidity patterns of 2015. Selecting 2 months for monitoring (August and September) was done to test indoor environment using passive air conditions. These periods were selected to investigate the effect of different patterns of (high/low) outdoor conditions. Also, solar radiation was measured for outdoor conditions, with a maximum solar radiation of 890 W/m2 reached between 11:00 am and 1:00 pm. Solar radiation creates a temperature gradient inside the chimney air cavity that causes the driving force of air inside the chimney under the effect of stack effect.
\nTemperature and humidity pattern of outdoor condition during the year of 2015.
The average solar brightness in Assiut was 12.125 h/day [16]. This encourages applying the SCPC system in this area. The overall heat transfer coefficient of the building part is calculated based on the physical properties of materials available in the local market with the same properties as the materials used in the numerical model. Table 1 shows the characteristics of building materials. The overall heat transfer coefficients of walls, floors and roofs are 2.60, 0.797 and 0.443, respectively. The window opening is oriented towards the south and the door opening towards the north. Figure 2 shows the outer view of the room with the SCPC system on its roof.
\nBuilding part | \nMaterial | \nConductivity (kJ/h m K) | \nU-Value (W/m2 K) | \nThickness (m) | \n
---|---|---|---|---|
Glass windows | \nSingle glass | \n— | \n5.68 | \n0.004 | \n
External walls | \nCommon plaster + cement (coating) | \n1.26 | \n2.60 | \n0.02 | \n
\n | Brick | \n3.60 | \n0.10 | \n|
\n | Common plaster + cement (coating) | \n1.26 | \n0.02 | \n|
Roof | \nInsulation | \n0.2 | \n0.443 | \n0.05 | \n
\n | Concrete slab | \n4.2 | \n0.12 | \n|
\n | Cement plaster (coating) | \n4.50 | \n0.01 | \n|
Ground | \nFloor | \n— | \n0.797 | \n0.10 | \n
\n | Insulation | \n0.2 | \n0.02 | \n|
\n | Concrete | \n4.2 | \n0.10 | \n
Description of building materials used.
The outer view of the room with SCPC system fixed on its roof.
The walls of the building are made from hollow clay bricks 0.1 m thick and covered with cement from both sides with thicknesses 0.02 m and a U-value of 2.6 (W/m2K) for the wall. The ceiling is made from 0.12 m thick concrete and covered with 0.01 m thick cement on the inner side. The ceiling is covered by insulation and concrete cover with thicknesses 0.15 and 0.07 m, respectively, as shown in Figure 3.
\nThe description of roof layers and their thicknesses.
A thermal insulation, 0.1 m thick, is installed inside the floor layer to examine the performance of the integrated SCPC system for indoor thermal comfort while excluding heat effect from the ground. The SCPC system consists of two components: the solar chimney and the short wind tower. The solar chimney was fixed on the roof of the room facing south. The SCPC system is made from widely available and conventional materials in the Egyptian market. The solar chimney is made from black aluminum with emissivity 0.95 and glass with transmissivity 0.84 and thicknesses of 0.002 m and 0.1 m, respectively, as shown in Figure 4. Performance of the solar chimney was examined in the first phase. The maximum airflow rate in the chimney was 0.69 kg/s during a high solar radiation of 890 W/m2 [17, 18].
\nCross section of the solar chimney cross section.
The passive cooling technique was integrated inside the short wind tower with the opening facing north. The method applied in this study will depend on cooling the interior space envelope using cheap and local cooling materials without consuming much energy. The tower was built with dimensions 1 m x 1 m x 1 m (L × W × H). The wet pad in wind tower is made from 0.1-m thick expanded paper. A water tube was installed on the top of the expanded paper with small nozzles. A water pump is used to recirculate water from the water reservoir in the bottom of the pad. Water is supplied from the water tank to the bottom water reservoir using a concentric floating valve. It opens when the level of water in the bottom reservoir decreases as shown in Figure 5.
\nThe description of evaporative technique in the wind tower made from expanded paper with water droplet from upper side.
In order to understand the actual indoor environment after using the passive cooling system, a sample data will be presented from 2-month data monitoring as an example.
\nComfort ventilation is the important factor that deals directly with the human body and depends on the strategy used. It is based on the theory that high airspeed around the human body accelerates the skin’s evaporation rate and, accordingly, improves the heat dissipation from the human body. This in turn shifts up the comfort upper level by providing such direct physiological cooling effect and decreases human discomfort due to skin wetness and the high humidity level [20]. In comfort ventilation strategy, two different impacts of the air velocity of the human body were determined: first, the heat exchange of the body that happens with convection; second, the evaporative capacity of the air. According to ASHRAE Standard 55 for naturally ventilated buildings, the acceptable thermal environment of indoor operative temperature ranges between 22°C and 28°C, and the comfort indoor air velocity of 1.6 m/s can be beneficial for improving comfort at higher temperatures [19]. So, new residence must have the acceptable thermal environment for all occupants. According to ASHRAE Standard 62–2001, ventilation rates depend upon the floor area, whereas the minimum ACH was 0.35, but no less than 15 CFM/person [21]. Also, passive natural ventilation standards require a minimum of three air changes for residential buildings. Finally, the comfort ventilation can easily be enhanced by appropriate building design and the system used.
\nFigure 6(a) shows the variation of daily solar radiation over time. A maximum solar radiation of 890 W/m2 was reached between 11:00 am and 1:00 pm. Solar radiation creates a temperature gradient inside the chimney air cavity, and the warm air is less dense than cool air so it rises and creates a difference in pressure which in turn induces air movement, causing the driving force of air inside the chimney under the effect of stack effect. The main component of the solar chimney is the absorber plate, which was made of an aluminum plate painted black with 0.95 emissivity. A wind-driven protection was used at the top in order to avoid reverse flow. It is clear that the maximum surface temperature of aluminum was 86°C at 1:30 pm due to high intensity of incident solar radiation in this period. Temperature was recorded in the middle of the aluminum plate. After midday, temperature started to decrease until 65°C at 3:30 pm, followed by a sharp drop of temperature due to decrease of solar intensity and high heat release without any thermal storage integrated with the aluminum plate. Also, glass surface temperature has the same pattern as aluminum temperature with 15°C higher than outdoor temperature. This affects air cavity temperature strongly. This finding is in agreement with [22].
\n(a) The variation of daily solar radiation over to time. (b) The variation of different temperatures with time.
Figure 7 shows the temperature profile of outlet air inside the chimney cavity. It is clear that the temperature of the chimney cavity increases and reaches 48°C for the highest temperature at 12:00 pm with high solar radiation. The temperature of air cavity is higher than outdoor until 4:00 pm. Then, a strong reduction of air temperature inside the cavity was reached. This is due to the decrease of aluminum surface temperature and heat release from the absorber. Figure 4 shows the thermal images of outside chimney glass plate with the highest three temperature points on its surface at 12 pm on 13/8/2015.
\n(a) Temperature profile of outlet air inside the chimney cavity from 10:00 am until 14:45 pm. (b) Temperature profile of outlet air inside the chimney cavity from 14:38 am until 18:30 pm.
Figure 8 shows the temperature distribution of three points on the upper side of the solar chimney (glass surface temperature) with an average temperature of 38°C and 36°C at 1:00 pm and 3:00 pm, respectively, due to high solar intensity. The thermal gradient of chimney surface temperature and aluminum surface temperature strongly affects the airflow through the chimney.
\nThe variation of glass surface temperatures in the solar chimney.
Validation was done for the numerical simulation with the experimental results. The detailed model for the numerical calculation was studied, including boundary condition, geometry and material physical properties [7]. Results of chimney air temperature, cooling tower inlet temperature and aluminum surface temperature with the help of the analytical model were found in good agreement with the corresponding experimental values. The experimental results tend to be higher than analytical model by about 2% and 2.5% in average. However, the airflow at the chimney is higher than analytical model by about 40%. This indicates that the presence of outdoor high wind speed and pressure coefficient on building surfaces and chimney outlets increases airflow rate of the stack effect with a negative effect of reverse flow that occurs in the chimney for some time and decreases performance of the evaporative pad with an average difference of 6% for the indoor temperature.
\nDue to the buoyancy force, the outer hot air passed through the expanded paper with water droplet, and then the outdoor air temperature was reduced inside the wind tower after passing through the wet pad. A graph indicating a typical variation of indoor cooling using a cooling medium is shown in Figure 9. The air temperature inside the room increased gradually due to the presence of occupants inside the room and heat gained by the building. Also, the temperature inside chimney air cavity is decreased gradually due to the absence of thermal storage attaching to the aluminum plate when solar irradiation decreases gradually. Therefore, the air temperature increases in the chimney air cavity, corresponding to the increase of solar radiation.
\n(a) The variation between tower inlet temperature, room temperature and chimney inlet temperature based on the cooling effect. (b) The temperature difference between chimney air cavity and outdoor temperature.
Figure 10 shows that the minimum surface temperature of the expanded paper (cooling pad), with water droplet, was 19.4°C at 3:00 pm with an average wet bulb temperature of 22°C. The decrease of surface temperature of cooling pad strongly affects airflow temperature and causes reduction of outdoor air temperature with constant enthalpy. This demonstrates the concept of evaporative cooling. The average water consumption is 16 l/day. This is because the outdoor air that flows through the pads is cooled to a temperature close to the WBT. Then, the indoor air of the building, cooled by an evaporative cooling system, is further heated by about 1–3°C above the output air from the evaporative cooling system, depending on the airflow rate of evaporative cooling and indoor heat gained by the building. This finding is in agreement with [23, 24]. Energy consumption for this system is 18 W only.
\nThe variation of expanded paper surface temperatures (cooling pad).
It is observed that most of the outlet air temperatures from the wind tower are below the upper limit of the 90% acceptable range, as shown in Figure 11. The temperature of the outside air that passes through the wet medium can be reduced significantly with a difference 6 K ~ 7 K. Only 10% of the measured data exceeded the upper limits. Table 2 shows the statistical analysis for indoor temperatures with a statistically significant difference = 0.024 (p level < 0.05). Therefore, the supplied air is still considered suitable to enhance indoor thermal comfort. The maximum indoor temperature was reached at 6:00 pm with a long time lag between outdoor and indoor temperatures. This is due to the effect of indoor thermal mass that impacts room cooling. This is in agreement with [23]. Reducing indoor temperature is based on the amount of water that passes inside the wet pad and the number of nozzles in the water tube.
\nTemperature profile for indoor environment with a cooling technique compared to outdoor condition on the 90% acceptable range of adaptive comfort standard.
Indoor temperature | \nRange | \nMean ± SD | \nSample distribution | \n|
---|---|---|---|---|
Skewness | \nKurtosis | \n|||
\n | 28.3–31.7 | \n30.1 ± 0.86 | \n−0.63 | \n−1.01 | \n
The statistical analysis of indoor temperature.
Humidity is strongly affected by cooling the wet medium. It is observed that indoor relative humidity after using passive cooling did not rise above 57% during daytime and most of the time was below 50%, indicating that further cooling is needed. Figure 12 shows that room relative humidity is located within the acceptable range of relative humidity 20%~60%, according to ASHRAE Standard 2004 [19]. Arundel concluded that the optimum humidity level for minimizing adverse effects for health is between 40 and 60% [25]. Also, most of the investigated cases were very close to the summer comfort zone. This is because the air outside is so dry, typically below 10% relative humidity during daytime.
\nTemperature and humidity conditions inside the room after using the SCPC system.
The concentration of CO2 inside the experimental room is very low. The average concentration is 550 ppm, with three occupants staying inside the room. The lower concentration inside the room is due to high airflow rate in the chimney and wind speed to a maximum of 0.69 kg/s, which affects CO2 concentration. This helps improve the indoor air quality and achieve a safe environment according to [22]. Figure 13 shows the variation of indoor carbon dioxide concentration.
\nIndoor CO2 concentration inside the room with SCPC system.
Using the SCPC system provides many advantages for indoor environments and achieves energy saving for cooling inside indoor room environments of hot arid regions. It is concluded that the airflow rate through a solar chimney system is greatly affected by the pressure difference between openings caused by temperature across the chimney surface. The results indicate that using the SCPC system reduced indoor temperature to be within the 90% acceptable comfort range. The SCPC system is considered a passive cooling air conditioning system that achieves a significant reduction of indoor temperature between 6 and 7 K based on the condition of the wet pad. The findings from the experimental and numerical calculations were in good agreement. Installation of the solar chimney parts and building the short wind tower are based on the available and conventional materials in the Egyptian market. The results of this research will be used to develop a new cooling system for low energy consumption (only 18 W for the water pump). The new cooling system is made of local materials and provides fresh cooled air with good indoor air quality. The materials of the system have high durability and made from normal glass, aluminum plate and standard brick for the tower. These materials are available at the local market and need simple modification in the ceiling structure of the upper flat. The system structure and materials need no specific manufacturing technology. The operation cost for the system is very low as it depends on solar radiation only. The 0.1-m thick evaporation pad in the tower can be changed nearly every 5 years with simple cleaning required every summer. This new cooling system can be integrated in the housing projects (National Housing Authority) of low-income people in new and existing cities. Adopting this system makes a significant improvement in building energy conservation.
\nThe research leading to these results has received funding from Science and Technology Development Fund (Ministry of Higher Education and Scientific Research), project no. 10255—National Challenges Program. The author gives special thanks to the engineers in the ITT unit of Assiut University for their help and using thermal camera.
\nIn 1932 in the UK, Chadwick discovered neutrons, and for his contribution, he was awarded in 1935 with the Nobel Prize in Physics [1]. One year later in the USA, Gordon Locher introduced the concept of boron neutron capture therapy (BNCT) [2]. He hypothesized that if boron could be selectively concentrated in a tumoral tissue and then exposed to a neutrons beam, a higher radiation dose to the tumor relative to surrounding normal cells would result. A mere 2 years later, Goldhaber, Hall, and Kruger performed the first radiobiological studies using boric acid and slow neutrons in a murine tumoral model [3]. However, the first clinical trials against human brain tumors (glioblastoma multiforme (GBM)) that used BNCT could not be initiated until 1951 at the Brookhaven National Laboratory in collaboration with the Massachusetts General Hospital and the Massachusetts Institute of Technology (MIT) [4, 5]. In this case, ten patients were treated with borax (disodium tetraborate decahydrate, Na2B4O7·10H2O; Figure 1) and thermal neutrons without much success. While there were no serious side effects of BNCT in the patients, the large doses of borax (10B-enriched) infused 200 mg/kg, inducing slight toxicity symptoms. In order to improve this, a second approach was developed comprising nine glioma patients but now with a less toxic compound, sodium pentaborate (NaB5O8; Figure 1) in combination with D-glucose. Unlike the first one, a higher dose of 10B was used, and a higher fluency of incident thermal neutron was applied [6]. Unfortunately, again, serious side effects such as radio-dermatoses of the scalp and deep ulcerations were observed [6, 7]. Simultaneously, in 1963, Sweet and co-workers, from the MIT, treated 18 patients using boron-rich disodium decahydrodecaborate (Na2B10H10; Figure 1) [8], which was considered to be less toxic and with the ability to deposit more boron atoms per cell. Symptoms of brain necrosis in patients undergoing BNCT were again observed [9]. Due to these disappointing events, the USA halted the progress of research on BNCT in 1961.
First and current available boron-based drugs for BNCT.
On the other hand, in 1968 at Hitachi training reactor, the Japanese neurosurgeon Hiroshi Hatanaka, who in previous years had worked with Sweet in Boston, began treating patients with high-grade malignant gliomas using disodium mercaptoundecahydro-closo-dodecaborate (Na2B12H11SH, named as BSH; Figure 1) which originally had been synthesized by Soloway in 1967 [10]. The results reported by Hatanaka and co-workers were extraordinary with a 5-year survival rate of 58% [11, 12, 13].
From the 1990s to the present day with the development of new boron compounds and the improvement in radiation source, the boron neutron capture therapy has been expanded to several centers worldwide, among them in the USA at Brookhaven and Cambridge, in the Netherlands at high flux reactor in collaboration with the Department of Radiotherapy of the University of Essen in Germany, in Finland at FiR-1 Otaniemi reactor, in Sweden at R2–R0 reactor, in the Czech Republic at LVR-15 reactor, in Italy at TRIGA reactor, in Japan at Kyoto University Research Reactor Institute, in Argentina at RA-6 and RA-3 reactors, and in Taiwan at THOR reactor, just to name a few [14].
BNCT is considered as a rationale and promising binary therapy modality for treatment of several cancers in particular malignant gliomas. The cell-killing effect of BNCT is based on the nuclear reaction 10B(n,α)7Li (Figure 2) that occurs when the nuclide 10B, which is a nonradioactive constituent of natural elemental boron (approximately 20% abundance), is irradiated with neutrons of the appropriate energy, thermal neutrons. The nuclear reaction yields excited boron-11 (11B*) that after instantaneous nuclear fission produces two high-linear energy transfer entities, i.e., α-particle (4He2+) and recoiling lithium-7 nucleus (7Li3+). Because of the very short track length of these heavy particles (<10 μm; roughly one cell diameter), radiation damage is confined to those cells loaded with 10B.
The two parallel nuclear fission reactions that occur upon capture of a slow (thermal) neutron by a 10B nucleus.
The probability that a nuclide captures a neutron is measured by the neutron capture cross section, σth, having 10B a value of σth = 3838 barns [15]. However, other abundant endogenous nuclei present in the healthy tissue, such as 1H and 14N, could also capture neutrons yielding after nuclear reactions of a gamma ray in the first case, 1H(n,γ)2H, and a proton in the second one, 14N(n,p)14C. However, the σth of these nuclei is smaller than the value for 10B, i.e., σth,1H = 0.332 and σth,14N = 1.82 barns, and the amount of radiation produced by these nuclear reactions is lesser than the produced by the particle and recoiling nucleus in the case of boron [15].
On the other hand, for brain tumor such as GBM, usually higher energy epithermal neutron beams which have a greater depth penetration being thermal neutrons unable to act on tumors located below the tissue surface because of scattering effects have been used. Epithermal neutrons do not suffer from the disadvantages of H-recoil processes and, consequently, allow capture reactions to occur at some distance within the tissue; then, epithermal neutrons are progressively slowed into thermal neutrons through heat-releasing interactions with the hydrogen atom and constituents of biological system, that do not cause damage to the tissue [16].
In order for BNCT to be successful, the 10B-loaded agent must completely fulfill some overriding conditions, namely, (a) selective uptake by tumor tissue relative to normal tissue (preferably accumulating within specific tumoral cell substructure) with ideal tumor:normal tissues and tumor:blood ratios of 3:1 and 5:1, respectively, and (b) appropriate amount of 10B delivered to the tumor tissue, i.e., at least 20 μg 10B/g tumor, corresponding to about 109 atoms of 10B/cell. However, this amount could be lower if the boron delivery system is concentrated in or near the cell nucleus; (c) retention of 10B in tumor during the BNCT process; (d) rapid clearance from blood and healthy tissues; (e) and adequate lipophilicity especially for glioma treatment where the drug should be able to cross blood-brain barrier (BBB) [17]. Furthermore, like any drug in medicinal chemistry, the 10B-loaded agent must meet the following requirements: (f) absence of systemic toxicity, (g) chemical and metabolic stability, and (h) appropriate water solubility.
After the first efforts, during the 1940s and 1950s (see Section 1.1.), the lack of selectivity and low boron tumor accumulation observed for the simplest boron salts (Figure 1) used until the moment prevented their application in BNCT clinical trials. However, around the 1960s, the first studies of the two compounds currently in clinical began, both 10B-enriched, the polyhedral borane BSH (Figure 1) and L-4-dihydroxyborylphenylalanine, known as L-boronophenylalanine (L-BPA; Figure 3) [18], which could be accumulated into desired tissues for its structural analogy to some biomolecules.
(A) Currently, available boronic acid for treatment of GBM trough BNCT. (B) L-BPA-F complex. (C) Esterification of L-BPA with ethylene glycol.
Due to BSH is a small hydrophilic molecule (Figure 1), it does not cross the intact BBB. It only penetrates into the brain passively when the BBB is disrupted [10], as it is observed in the GBM. Although BSH has been applied for the treatment of GBM in infusions with no toxic effects, the efficacy has been limited due to low observed tumor:brain (3:1) and tumor:blood (0.9–2.5:1) ratios [19]. The main structural advantage of BSH compared to L-BPA is that BSH contains 12 times more B per molecule yielding a higher number of events after neutron capture than in L-BPA. BSH has been studied in different therapeutic schedules, combined or not with other small molecules, like L-BPA, or vehicles looking for the improvement of the efficacy and the delivery into the glioma [20]. Medicinal chemistry on BSH, structural modifications, has also been done (see below) seeking better biological behavior.
Nowadays, L-BPA (Figure 3) is the standard therapeutic drug used in BNCT [21, 22, 23]. Since the L-amino acid transport system is highly expressed in tumor cells compared with normal cells in most organs including the brain, some natural amino acid boron derivatives have been studied [24]. L-BPA has very limited water solubility (1.6 g/L), and searching to circumvent this problem, the standard strategy used for clinical BNCT treatment, it is as a soluble fructose complex, known as L-BPA-F (Figure 3), which leads to a pharmaceutical product with favorable biodistribution in human GBM, ratios tumor:blood of 3–4:1 [25], low toxicity, and good capability to cross BBB. Other two strategies include (a) the transformation into the corresponding hydrochloride salt and (b) the esterification of the boronic acid moiety with 1,2- and 1,3-diol producing 1,3,2-dioxaborolanes or 1,3,2-dioxaborinanes, respectively, which is then easily hydrolysable in an aqueous environment (Figure 3) [26, 27]. On the other hand, L-BPA is actively transported across the tumor cell membrane, by the L-amino acid transporter system. It is highly expressed in tumor cells, including the brain, compared with normal tissues and can be stimulated by the previous accumulation of the L-DOPA resulting in a substrate-coupled antiport (exchange) mechanism [28]. At this point, L-BPA is considered to be a better B delivery agent than BSH.
From a medicinal chemistry point of view, different strategies have been studied in order to identify new and more selective molecules to glioma cells, with adequate ability to cross the BBB, with higher tumor concentration in the path of the neutron beam and drug-like properties. The third-generation products, which potentially may accumulate into glioma for its structural analogy to some biomolecules, could be classified [15] in (a) macromolecular species and (b) low molecular weight molecules. In reference to the first group, we could mention monoclonal and bispecific antibodies, epidermal growth factor, and encapsulating agents such as boron-containing nanovehicles (liposomes). Here, we will discuss compounds belonging to the second group, like polyhedral boron cluster derivatives, boronic acid derivatives, and other boron-containing small molecules (e.g., oxaborolanes, dioxaborolanes, and azaboro-heterocycles, among others).
The most known and commonly used class of polyhedral boron compounds in the medicinal chemistry field are the icosahedral dicarba-closo-dodecaborane (C2B10H12) commonly referred to as carboranes which exist in three isomeric forms named with respect to the positioning of the two CH vertices (Figure 4): 1,2- or ortho- (1); 1,7- or meta- (2); and 1,12- or para-carborane (3); to a lesser extent, their mono-anionic derivatives resulting from the loss of a B vertex, commonly known as nido-carborane (4 [C2B9H12]−); and their metal complexes known as metallacarborane (5 [M(C2B9H11)2]−, where M is a metal) that are generated after removal of the bridge hydrogen from the nido-carborane (Figure 4) [29, 30].
(A) Numbering and nomenclature of the closo-carborane systems. Synthesis of meta and para-carborane derivatives from the ortho-carborane isomer through thermal isomerization. (B) Partial degradation of ortho-, meta-, and para-carborane and numbering of nido-carborane system according to IUPAC. (C) Synthesis of metallacarborane from nido-carborane.
Among the outstanding and widely explored properties of carboranes and metallacarboranes for medicinal chemistry research are (a) the geometry and the electron-deficient nature of the boron atoms, which generate a strong hydride character in the BH shell, which are some of the main features that determine the intermolecular interactions with the biological targets because they make the B-clusters extremely hydrophobic; (b) both the pharmacokinetics and the bioavailability can be modulated according to the chemotype of boron cluster selected, so the hydrophilicity and lipophilicity, or both, could be tuned; (c) the globular architecture and rigid geometry allow for molecular construction in three dimensions improving the docking, or not, with bio-targets; (d) high boron content per molecule and stability to catabolism are important criteria for the development of agent for BNCT; and (e) the well-established chemistry that makes boron clusters attractive synthons to construct novel pharmaceuticals [31].
Nevertheless, some problems persist today that delay the application of boron clusters in the development of new drugs: (a) the relatively high cost of carboranes and their derivatives even more if they will be used in BNCT because 10B-enriched compound will be needed; (b) the difficulty of in silico drug design and screening of boron cluster drugs, due to the lack of appropriate descriptors for the interaction potentials of boron and the attached hydrogen atoms; and (c) the lack of libraries of boron cluster compounds for high-throughput screening.
In the past decade, saccharides have been widely studied due to their low toxicities, generally having high water solubility, high expression of specific receptor on the tumor cell surface (specifically in the brain capillary endothelial cells that form the brain barriers, resulting in optimal BBB penetration), and an increased rate of glycolysis in cancer cells. According to this and in order to improve boron uptake, carbohydrates such as ribose, mannose, maltose, and galactose have been chosen to generate carbohydrate-based boron delivery platforms for successful BNCT approach [32, 33]. Since the first description by Hawthorne’s group [34], there have been numerous works on the synthesis and biological evaluation of carboranyl-carbohydrate conjugates. Later, Tietze and co-workers developed and evaluated both in vitro and in vivo, against rat glioma cells (C6) and melanoma cell line (B16), a series of carboranyl glycosides including glucoside, lactoside, and maltoside conjugates (6–8; Figure 5) [35, 36, 37]. Although in the in vitro assays significant killing effect was observed because the three derivatives showed an optimum cellular uptake in the C6 glioma cell line, with maltoside 8 being the derivative that exhibited the highest uptake (65.7 ppm at 12 h), the in vivo performance in rat model bearing brain tumor revealed that the concentration of all carboranyl-appended carbohydrate in blood was maintained at levels that were unacceptably high for meaningful use in BNCT. In order to overcome this drawback, Tietze and Yamamoto designed a new type of mixed carboranyl bisglicoside derivatives as prodrugs (9–12; Figure 5) [38]. Initially, selective uptake of these compounds was not expected due to the hydrophilic sugar moieties at both ends of the carborane preventing cell internalization. The authors demonstrated that the activation of the prodrug could be performed using monoclonal antibodies conjugated to glycohydrolases, which bind to tumor-associated antigens, through the glucosidic bond cleavage and concomitant release of carboranyl moiety in the tumor cell surface.
(A) Compound 6 corresponds to carboranyl derivative of D-glucose, and compounds 7 and 8 are derivatives of lactose and maltose, respectively. (B) Ortho-carboranyl bisglycosides 9–12 containing lactose, glucose, mannose, and galactose in their structures.
On the other hand, in the last few years, boron-bearing purines, pyrimidines, thymidines, nucleosides, and nucleotides have been widely explored as a novel approach to improve boron uptake in glioma tumor cells. This strategy is based on the fact that tumor cells have higher metabolic activity and an increased requirement for DNA and RNA precursors [39, 40]. Although in recent years several strategies have been addressed, the main focus has been on thymidine analogs substituted with ortho-carbonyl cluster at the N-3 positions (13 and 14, named as 3CTAs; Figure 6). Both analogs are potential substrates for human thymidine kinase 1 (hTK1), a cytosolic deoxynucleoside kinase of the DNA synthesis salvage pathway that is predominantly found in proliferating cancer cells. The selective accumulation and retention of 3CTAs in tumor cells via a mechanism known as kinase-mediated trapping (KMT) render these molecules as potential BNCT delivery agents against high-grade brain glioma, such as GBM [41, 42, 43]. Another considerable attention has also been to metallacarborane, mainly the bis-(dicarbollyl)-cobalt and bis-(dicarbollyl)-iron derivatives (15–17, Figure 6). They can also be selectively accumulated in rapidly multiplying neoplastic cells; following their conversion to the corresponding nucleotides, trapped within the cell; or, ideally, incorporated into nuclear DNA of tumors [44]. Despite this, these compounds still have not studied in gliomas.
Chemical structure of the main carborane-bearing nucleoside delivery agents.
Barth and co-workers evaluated 10B-enriched derivative 14, using the RG2 model as in vivo brain tumor model [45]. First, they demonstrated that derivative 14 efficiently delivers boron atoms in cancer cell, which allowed tumor reduction after BNCT in nude mice bearing tumor induced with TK1 positive cell. In addition, based on these favorable results, BNCT studies carried out in the RG2 rat model lead to an increased in life span (ILS) 2.4× in comparison with L-BPA as control therapy. Nevertheless, the greatest percent ILS (122%) was seen in RG2 glioma-bearing rats that received the combination of derivative 14 and L-BPA, and this correlated with the fact that the tumor in these animals received the highest physical radiation doses. These biological studies clearly revealed the therapeutic potential of derivative 14 although some problems and limitation appeared. Among these, derivative 14 showed clear solubility problems under physiological conditions, possibly due to the presence of the carboranyl hydrophobic core and the absence of any functional groups that can be ionized.
Since the first description by Haushalter and Rudolph in 1978 (18 and 19; Figure 7) [46, 47], the potential for medical application of several boron cluster-containing fluorescent dyes, including porphyrins and related macrocyclic, have been highly explored and scrutinized for several reasons, among them: (a) well-known ability to selective accumulate into tumor cells in high amounts, (b) subsequent persistence within tumors, (c) general low dark cytotoxicity, (d) capability to bind to DNA due to their plane aromatic structure, and (e) highly fluorescence, thus enabling tumor diagnosis and facilitating treatment planning. Nonetheless, without any doubt, the most exploited feature of these molecules is the ability to act in photodynamic therapy (PDT). PDT combines a photosensitizer (porphyrin), light, and tissue oxygen, to generate reactive oxygen species, including singlet oxygen, triggering subsequently cell death mechanisms by necrosis and/or apoptosis. The combination of this therapy with BNCT has been of particular interest to control local recurrence of high-grade gliomas such as GBM, because they target different mechanisms of tumor cell death and, thus, increase the therapeutic effect. Both are bimodal therapies, the individual components of which are nontoxic in isolation, but which are tumoricidal in combination.
First boron-containing porphyrins developed by Haushalter and Rudolph for catalysis application.
In the last few years, a large number of boron-containing natural porphyrins have been synthesized and evaluated both in cellular and animal models (20–23; Figure 8) [48]. To date, the tetrakis-carborane carboxylate ester of 2,4-bis(α,β-dihydroxyethyl)deuteroporphyrin IX (22, known as BOPP) was the only compound to be employed in a phase I clinical study against GBM [49, 50]. Pharmacological studies showed its ability to selectively incorporate in tumor cells, in xenograft models of glioma, relative to the surrounding normal brain cells (tumor:brain ratio as high as 400) and situated preferentially in tumor cell mitochondria. Nevertheless, these results could not be replicated in humans.
(A) Structures of some relevant boron-containing porphyrins. (B) Some relevant polyhedron boron cluster water-soluble porphyrins.
The success of derivative 22 was interrupted in a phase I clinical trial for several reasons: (a) it could not deliver to the tumor a therapeutic amount of boron in patients with GBM; (b) thrombocytopenia was observed in patients due to the direct toxic effect of derivative 22 or its metabolites (probably of carboxylic carborane) on platelets; and (c) the pharmacokinetic behavior of derivative 22 in humans was characterized by a prolonged clearance phase, giving rise to potentially toxic metabolites and cutaneous photosensitivity [51].
In order to overcome this drawback, several researchers designed and synthesized a highly boron water-soluble porphyrins as a possible BNCT agents. In this sense, Vicente and co-workers described nido-carborane cluster-linked porphyrins via aromatic linkage (e.g., 24; Figure 8). These amphiphilic derivatives showed very low toxicity, were taken up by 9 L and U-373MG cells in both time- and concentration-dependent manners, and were localized preferentially in cell lysosomes [52]. On the other hand, Deen and co-workers developed the polyboronated ionic porphyrin 25, known as TABP-1, which was administrated by convection-enhanced delivery (CED) to nude rats bearing intracerebral implant of human glioblastoma cell line U-87MG [53]. In contrast to diffusion, CED uses a pressure gradient established at the tip of an infusion catheter to establish bulk flow and distribute drug and solvent throughout the extracellular space. This demonstrated high tumor and low blood boron concentration through intracerebral administration by CED related to systemic administration.
Carborane-containing nucleosides and analogues as the means to concentrate boron within the tumor cell nucleus were described. However, another class of derivatives, which could interact directly to chromosomal DNA, has been developed and widely explored for boron neutron capture therapy. Among this the following could be mentioned (Figure 9): (a) alkylating agents (i.e., 26 and 27), (b) DNA intercalators (i.e., 28 and 29), (c) minor groove binders (i.e., 30 and 31), and (d) cationic polyamines (i.e., 32 and 33) [54]. Regarding the last group of compounds, it should be stated that natural polyamines such as spermidine, spermine, and putrescine, found in both prokaryotic and eukaryotic cell types, are a class of biologically active compounds known to be essential for every cell to support their function such as growth and differentiation. In addition, because they have a specific transportation system, they have been found in high concentration in rapidly proliferating tumor cells. This characteristic was used by Zhuo and co-workers, synthesizing and evaluating derivatives 32 and 33 [55]. These compounds proved to be highly water-soluble, in vitro they have the ability to interact to calf thymus DNA, and they are rapidly taken up by F98 rat glioma cells at levels which match that of clinically used agents. Unfortunately, in vivo biodistribution studies of these derivatives, performed in mice-bearing intracerebral implants of the GL21 glioma and subcutaneous implants of the B16 melanoma, suggested that they were unable to deliver adequate amounts of boron to tumor.
Carborane-containing DNA-interacting agents. (A) Alkylators. (B) Intercalators. (C) Minor-groove binders. (D) Polyamines.
More recently, Vicente’s group proposed other interesting strategies that involved the use of porphyrins bearing p-carboranylmethylthiol moiety conjugated to polyamines (34–41; Figure 10) [56]. In vitro, the polyamines displayed low dark cytotoxicity, low phototoxicity, preferential localization in the endoplasmic reticulum, Golgi and the lysosomes, and, except derivative 34, higher uptake into human glioma T89G cells (up to 12-fold for spermine derivative 39) than the tri-ethyleneoxy conjugate 41. All these results suggested that spermine derivative could serve as an effective carrier of boronated porphyrins for the BNCT of tumor.
Carborane-containing porphyrins porting polyamine framework.
As it is indicated above, BSH inadequate drug-like properties, i.e., lack tumor selectivity and poor BBB crossing ability, have conducted to develop BSH hybrid compounds containing other pharmacophoric moieties seeking improvement biological behavior.
In this sense, some approaches were based on the particular tumoral amino acid requirement and the special ability of some peptides to interact with receptors that, via endocytosis, are internalized into tumoral cells. In the first strategy, hybrid 42 (Figure 11), carrying a fragment derived from an unnatural amino acid that demonstrated a particular uptake by glioblastoma cells [57], was prepared and in vivo evaluated in F98 glioma-bearing animals [58]. The biodistribution studies showed higher tumor boron concentrations for derivative 42 than for BSH but lower than for L-BPA-F i.v. treatments. The CED intracerebral administration of derivative 42 was assayed combined with BNCT reaching better animals’ survival rates than the treatment with L-BPA-F/i.v. On the other hand, in the use of peptides as carrier strategy, the hybrid 43 (Figure 11), derived from Tyr3-octreotate peptide that interacts to somatostatin receptor, was synthesized [59]. This BSH octapeptide still has not study biologically.
Some BSH hybrids attempting to improve BSH biological behavior.
As it was already mentioned, the biochemical peculiarities of the porphyrin system also allowed the delivery of BSH within the tumor. In this sense, hybrid BSH porphyrin 44 (Figure 11) was prepared and evaluated in a 9 L glioma-bearing rat model [60]. Compound 44 displayed higher boron tumor:blood ratio in comparison to BSH 24 h after i.v. treatment and in an in vitro BNCT colony-forming assay higher cytotoxicity than BSH. Another series of BSH porphyrin hybrids consists of compounds like 45 and 46 (Figure 11) that still has not been biologically studied on gliomas [61].
GBM contains areas with different oxygenation levels, and consequently different metabolic patterns, which make difficult the therapeutic strategies [62]. Highly oxygenated regions are close to blood vessels, present high proliferation rate and oxidative metabolism and are susceptible to metabolism-active drugs and radiotherapy. While hypoxic regions present low proliferation rate, reductive metabolism and are resistant to chemo- and radiotherapy. The hypoxic condition in GBM tumors, which induces metastasis and promotes angiogenesis and resistance, has been attributed to contribute to tumor regrowth and, therefore, in a relapse. The troublesome characteristics of hypoxic regions have been exploited to generate cancer therapeutics known as hypoxia-selective bioreductive prodrugs which are compounds able to undergo reduction producing cytotoxic events. Some of the well-known bioreductive pharmacophores, nitroimidazoles, and N-oxide containing heterocycles were used to prepare BSH hybrids for potential use in hypoxia. Thereby, 2-nitroimidazoles 47 and 48 or quinoxaline dioxides 49 and 50 (Figure 12) were prepared and evaluated against some tumoral models using BNCT, but unfortunately they have not yet been studied on glioma models [63, 64, 65].
BSH hybrids with potential use in hypoxic glioma.
Boronic acid (R-B(OH)2) has been utilized as a pharmacophore in the searching of new agents to be employed in BNCT. This functional group has some relevant drug-like properties turning it into a useful moiety for biological applications, for example [66, 67, 68], (a) the sp2-hybridized boron atom possesses a vacant p-orbital which, after biomolecule donor atom attacks, allows the interconversion of boron hybridization, from sp2 to sp3, to generate a new stable anionic compound; (b) the enhanced ability of –B(OH)2 system to interact with biomolecule via (b1) hydrogen bonds, as acceptor and donor through OH groups, and (b2) strong boron Lewis acidity that allows boron-nitrogen, boron-oxygen, or boron-sulfur bonds; (c) the apparent pKa of –B(OH)2 ranging 4.5–8.8, for arylboronic, that allows large acid-base behavior finding the protonated and deprotonated form of the acid according to physiological pH conditions; and (d) apart from the reactivity mentioned above (section a) the particular ability to react with diol-containing compounds, like sugars and sugar-containing biomolecules, yielding the corresponding stable cyclic ester 1,3,2-dioxaborolane. Additionally, the –B(OH)2 group has weak electronic effects being electron donor for induction and electron withdrawing for mesomerism. In reference to the lipophilicity of the –B(OH)2 moiety, it is as lipophilic as –CN group, lesser lipophilic than –CO2CH3 and neutral –CO2H moieties, and more lipophilic than –CONH2, –CH2OH, and –CHO groups (π Hansch constants which are −0.55, −0.57, −0.01, −0.32, −1.49, −1.03, and −0.65, respectively [69]). In vitro boronic acids degrade leading deboronation via hydrolysis/oxidation yielding boric acid (H3BO3). For example, degradation of bortezomib, known as Velcade™ the first boronic acid-containing drug on the market and approved by the US Food and Drug Administration, under acidic and basic conditions seems to be mediated by an initial oxidation producing boric acid and having a plasma half-life of 9–15 h in humans. The end product, boric acid, is not considered especially toxic to humans. For this, it is not expected that boronic acids possess intrinsic toxicity.
The success of the L-BPA in preliminary studies in patients with GBM, followed by PET studies with 1-aminocyclobutane-1-[11C]-carboxylic acid, revealing that cyclic amino acids were located preferentially in this tumor [57], led to the development of series of these cycloalkane-boronic acids (51–54; Figure 13) [70, 71]. They are water-soluble, cross the BBB, and are not metabolized by tumor cells, and while all accumulate into tumor similarly, the cis-isomers (51 and 53) biodistributed four times higher in tumor than in blood that of the trans-ones (52 and 54) and that of L-BPA-F [72, 73, 74]. By secondary ion mass spectrometry, it was proven that nearly 70% of the boron pool from derivative 51 was in the nucleus and cytoplasm of T98G GBM cells [75]. Until now there have been no studies of BNCT with these compounds, and further studies should be done prior to clinical trials.
Some boronic acid derivatives developed as potential BNCT agents. Amino acids 51–54 were studied as a mixture of enantiomers.
As it is mentioned above, polyamines are essential for differentiation and growth of mammalian cell, and their depletion has growth inhibitory effects on tumors. Furthermore, a polyamine-facilitated transport system is present and allows the uptake by malignant cells [76]. For that, boronic acid-containing polyamines have been also studied as potential BNCT agents [77]. Compound 55 (Figure 13) with higher hydrophilicity that of carboranyls 32 and 33 (Figure 9) was designed in order to minimize the carboranyl’s nonspecific binding to biolipids that limits the tumor specificity. This boronic acid derivative was able to bind to calf thymus DNA and rapidly was taken up in vitro by F98 rat glioma cells, but the in vivo biodistribution showed unmeasurable levels of boron in tumor, and for this reason, the authors have considered that derivative 55 is not appropriate for BNCT [55].
Thinking about DNA as target to metabolically incorporate boron atoms to the tumoral cell, boronic acid-containing nucleic acids have been studied. One of the first described compounds was the uracil derivative 56 (Figure 13) [78] which demonstrated unfavorable tumor:blood and brain:blood biodistribution ratios being in all studied times in favor to blood. After that some boronic acid-containing nucleosides, such as 57 (Figure 13), were prepared and studied as potential agents for BNCT; however, no studies with glioma were performed [79]. However, recently nucleoside 58, a boronic cyclic ester (a dioxaborolane derivative; Figure 13), was prepared and evaluated as cytotoxic agent against some tumoral cells [80, 81] including U-118 MG glioblastoma cells [82]. Additionally, the ability of ester 58 to be incorporated into cellular DNA and its selectivity for tumoral cells become its potential usefulness tool in glioma BNCT.
The combination of PDT and BNCT has been also proposed using boronic acid-containing porphyrins, i.e., 59 and 60 (Figure 14) [83]. However, it still has not been conducted studies with these compounds in gliomas.
Some boronic acid derivatives developed as two-target drugs.
As previously stated the particular hypoxic condition of some GBM regions was used as strategy to produce boronic acid derivatives that could be selectively accumulated in this tissue. For example, the well-known 2-nitroimidazolyl hypoxia pharmacophore was employed as structural guide to boron-enriched tumoral cells generating the boronic acid ester 61 (Figure 14) [84]. This dioxaborolane was selectively accumulated in D54 glioma when it was injected intratumorally in a xenograft mouse model reaching 9.5 times the levels of boron into the tumor of L-BPA in the same conditions. However, the pharmacokinetic behavior of derivative 61 should be solved in order to improve the use of this agent in BNCT.
Other boron-containing moieties have been described for BNCT, for example, in compounds 62–68 (Figure 15) [85, 86, 87, 88, 89, 90]. However, in spite of their attractive features as pharmacophores, they have not been applied for glioma treatment. Additionally, they contribute with low number of boron atom per molecule which, as mentioned above, which is a disadvantage respect to boron clusters. However, this could be overcome with a high selective accumulation into the tumor cells. For example, the betaine 68, a boron-containing dipeptide analogue, showed selective accumulation in rat C6 gliosarcomas with 10B tumor:blood and tumor:normal brain ratios of 8.9 and 3.0, respectively [91].
Some other potential boron pharmacophores for glioma BNCT, i.e., boradiazoles, aza-borauracils, 2-boradihydropurines, cyanoboranes, boranophosphates, benzoxaboroles, and trialkylamine-carboxyboranes.
Beyond the strategies of therapy combination mentioned above, such as phototherapy or hypoxia, another hypothesis has been choosing a bio-system overexpressed in tumoral cells, but not in healthy cells, as a way to selectively accumulate boron drugs in the desired tissue to further BNCT. In this sense, Nakamura and colleagues have described the use of protein tyrosine kinases (PTKs), that its uncontrolled activation is often associated with uncontrolled cell growth and tumor progression, to generate boronic acid and esters hybridized with PTK pharmacophores as new drugs (i.e., 69 and 70; Figure 16) [92]. However, they did not bear in mind the glioma treatment nor BNCT with this strategy. Nevertheless, we considered the GBM-PTKs [93] as the target to accumulate a boron-enriched drug to further BNCT procedure. Thereby, we hybridized the 4-anilinoquinazolinyl PTKs and the carboranes as boron delivery pharmacophores, i.e., 71 and 72 (Figure 16) [94]. Especially, hybrid 71 demonstrated 3.3 times higher activity against C6 glioma cells than the parent drug erlotinib (Figure 16), lower cytotoxic effects on normal glia cells, excellent PTK inhibition, capability to accumulate in glioma cells, ability to cross BBB, and stability on simulated biological conditions [94, 95].
Structure of the well-known PTK inhibitor erlotinib and boron-containing compounds derived from 4-anilinoquinazolinyl pharmacophore.
The development of boron-bearing compound for BNCT has been a vast field of research within medicinal chemistry. New and interesting pharmacophores have been described in order to fulfill the BNCT requirements. Despite this, very few reached the stage of clinical studies, being currently L-BPA and BSH, the only two potential therapeutic agents. However, due to the multidisciplinary approach of the BNCT and the emerging novel structures, we expect with optimism the new developments in the years to come.
The authors are SNI-ANII researchers and PEDECIBA members.
The authors declare no conflict of interest.
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I am also a member of the team in charge for the supervision of Ph.D. students in the fields of development of silicon based planar waveguide sensor devices, study of inelastic electron tunnelling in planar tunnelling nanostructures for sensing applications and development of organotellurium(IV) compounds for semiconductor applications. I am a specialist in data analysis techniques and nanosurface structure. 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Today his focus is on defining the growth and development strategy for the company.",institutionString:null,institution:{name:"TU Wien",country:{name:"Austria"}}},{id:"19816",title:"Prof.",name:"Alexander",middleName:null,surname:"Kokorin",slug:"alexander-kokorin",fullName:"Alexander Kokorin",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/19816/images/1607_n.jpg",biography:"Alexander I. Kokorin: born: 1947, Moscow; DSc., PhD; Principal Research Fellow (Research Professor) of Department of Kinetics and Catalysis, N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, Moscow.\r\nArea of research interests: physical chemistry of complex-organized molecular and nanosized systems, including polymer-metal complexes; the surface of doped oxide semiconductors. 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