2006
DOI: 10.1002/jctb.1525
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Thermodynamics of the encapsulation by cyclodextrins

Abstract: Molecular encapsulation on a molecular basis can be performed by cyclodextrins. The inclusion of organic molecules into the interior changes the properties of these molecules, which may be used for a broad variety of applications. The affinity of guest molecules for the cavities of various cyclodextrins depends on the stereochemistry and on the interaction forces of the molecules involved. Calculations of the thermodynamic parameters show that the reaction entropy is highly important for the inclusion reaction… Show more

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Cited by 35 publications
(17 citation statements)
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“…The most encountered CDs are a-, b-, and g-CDs with six, seven, and eight glucopyranoses, respectively (Bender and Komiyama, 1978;Le Bas and Rysanek, 1987;Charumanee et al, 2006;He et al, 2008). As for their molecular shape, CDs resembles that of cones with a mostly hydrophobic nanocavity having an average diameter of 5 Å (a-CD), 6.2 Å (b-CD), and 7.9 Å (g-CD), respectively, and a thickness of 8 Å. CDs internal nanocavity can accommodate a wide range of guest molecules, ranging from polar ones (e.g., alcohols, acids, and small inorganic anions) to hydrophobic molecules with surface exposed aliphatic and aromatic hydrocarbons.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…The most encountered CDs are a-, b-, and g-CDs with six, seven, and eight glucopyranoses, respectively (Bender and Komiyama, 1978;Le Bas and Rysanek, 1987;Charumanee et al, 2006;He et al, 2008). As for their molecular shape, CDs resembles that of cones with a mostly hydrophobic nanocavity having an average diameter of 5 Å (a-CD), 6.2 Å (b-CD), and 7.9 Å (g-CD), respectively, and a thickness of 8 Å. CDs internal nanocavity can accommodate a wide range of guest molecules, ranging from polar ones (e.g., alcohols, acids, and small inorganic anions) to hydrophobic molecules with surface exposed aliphatic and aromatic hydrocarbons.…”
Section: Introductionmentioning
confidence: 99%
“…As for their molecular shape, CDs resembles that of cones with a mostly hydrophobic nanocavity having an average diameter of 5 Å (a-CD), 6.2 Å (b-CD), and 7.9 Å (g-CD), respectively, and a thickness of 8 Å. CDs internal nanocavity can accommodate a wide range of guest molecules, ranging from polar ones (e.g., alcohols, acids, and small inorganic anions) to hydrophobic molecules with surface exposed aliphatic and aromatic hydrocarbons. Importantly, the driving force for the formation of inclusion complex comes from non-covalent interactions such as van der Waals forces, hydrophobic interactions, and steric factors; nevertheless, the affinity of compounds to interact with the interior of various CDs depends on other several factors, such as stereochemistry, polarity, electrostatic potentials as well as on the propensity to form hydrogen bonds (Chen et al, 2004;Charumanee et al, 2006). As we will show here, some of these properties may prove advantageous in discriminating between similar organic compounds of interest in pharmacology.…”
Section: Introductionmentioning
confidence: 99%
“…A formação do complexo envolvendo sildenafil e β-CD é dirigida principalmente pelo fator entálpico, sendo que a força motriz dominante para a complexação é do tipo de van der Waals com uma contribuição eletrostática muito pequena 44 . Em um trabalho bastante recente, Viernstein e colaboradores 45 demonstraram que, dependendo da estrutura da CD empregada e da natureza do substrato que irá se ligar a ela, mecanismos de interação completamente diferentes são observados, podendo estes processos apresentar compensação entálpica/entrópica ou serem controlados entropicamente. Demonstraram ainda que processos de protonação e desprotonação do substrato influenciam significativamente a reação de inclusão 45 .…”
Section: Mecanismos Responsáveis Pela Inclusãounclassified
“…Em um trabalho bastante recente, Viernstein e colaboradores 45 demonstraram que, dependendo da estrutura da CD empregada e da natureza do substrato que irá se ligar a ela, mecanismos de interação completamente diferentes são observados, podendo estes processos apresentar compensação entálpica/entrópica ou serem controlados entropicamente. Demonstraram ainda que processos de protonação e desprotonação do substrato influenciam significativamente a reação de inclusão 45 . Buvári-Barcza e colaboradores 46 estudaram a interação de ácidos dicarboxílicos alifáticos com CDs.…”
Section: Mecanismos Responsáveis Pela Inclusãounclassified
“…They are non-toxic commodity chemicals, and are prepared by the action of bacteria on starch [1]. Practical applications include solubility enhancement of hydrophobic solutes such as pharmaceuticals [2], the stabilization of volatile compounds for odour control [3,4] the controlled release of pesticides [5] and the detackification of adhesive contaminants in recycle paper mills [6].…”
Section: Introductionmentioning
confidence: 99%