Kinetics of Inclusion Reactions of β-Cyclodextrin with Several Dihydroxycholate Ions Studied by NMR Spectroscopy

Yim, C. T.; Zhu, Xiaoxia; Brown, G. R.

doi:10.1021/jp9833909

Cited by 51 publications

(43 citation statements)

References 31 publications

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“…They differ in the number and position of hydroxy groups at C3, C7, and C12. The thermodynamics [25] and kinetics [26] of the inclusion of some bile acid salts into native b-cyclodextrin have been studied by NMR spectroscopy. The thermodynamics of inclusion [30] and the effect of the presence of cyclodextrins on the thermodynamics of micelle formation [27] have been studied by microcalorimetry.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

et al. 2000

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The dansyl-modified dimer 9 complexes strongly with the steroidal bile salts. Relative to native beta-cyclodextrin, the binding of cholate (1a) and deoxycholate (1b) salts is especially enhanced. These steroids bind exclusively in a 1:1 fashion. For other bile salts (1c-1e) both 1:1 and 1:2 complexes were observed with stabilities similar to those of native beta-cyclodextrin. This indicates that only one cavity is used, with a small contribution from the second. The difference is attributed to the absence of a 12-hydroxy group in the second group of steroids. Comparison with a dimer that lacks the dansyl moiety (6) shows that this group especially hinders the cooperative binding of la and 1b. The smaller interference in the binding of the other steroids indicates that self-inclusion of the dansyl moiety hardly occurs. This weak self-inclusion is supported by fluorescence studies. The dansyl fluorescence of dimer 9 is less blue-shifted than that of other known dansyl-appended cyclodextrin derivatives; this is indicative of a more polar micro-environment. Addition of guests causes a change in fluorescence intensity.

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Section: Introductionmentioning

confidence: 99%

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

et al. 2000

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“…When the charged part penetrated the extended cavity of an empty SBE‐β‐cyclodextrin, the part might interact with a hydroxyl group in the SBE‐β‐cyclodextrin to form a hydrogen bond. Furthermore, the van der Waals interaction between most of the hydrophobic part of CDC and the extended cavity of the SBE‐β‐cyclodextrin might be stronger 22. Therefore, the large inclusion‐binding value of 33.245 mM −1 should be reasonable 21,24…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, for the binding of CDC anion to β‐cyclodextrin, the binding affinity was quantified to be approximately 22.908 mM −1 15. Because of the absence of a 12‐hydroxyl group, researchers strongly believed that the CDC anion deeply penetrates the β‐cyclodextrin cavity via the hydrophilic end 17,22,23. Obviously, the negatively charged part of the CDC molecule is the hydrophilic end.…”

Section: Resultsmentioning

confidence: 99%

Determination of Binding Affinity for Chenodeoxycholate in Equilibrium with Sulfobutylether-β-Cyclodextrin

Liu

Chang

Jhou

et al. 2012

Journal of Pharmaceutical Sciences

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“…[45][46][47][48][49] Bile acids have the property of associating with ␤-cyclodextrin (␤-CD), due to the compatibility of the size and shape of bile acids with the cavity of ␤-CD. [50][51][52][53][54][55] This reversible association allows the tuning of the thermoresponsive properties via the addition of a supramolecular host. Jia and Zhu showed that the block copolymer of N-isopropylacrylamide (iPA), N,N=-dimethylacrylamide (DMA), and a CA-based methacrylate monomer had thermoresponsive properties with a CP at 22°C depending on the monomer ratio (Fig.…”

Section: Thermoresponsive Polymers and Hydrogelsmentioning

confidence: 99%

Polymers made of bile acids: from soft to hard biomaterials

Cunningham

Zhu

2016

Can. J. Chem.

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Bile acids are gaining increasing importance as building blocks in the development of novel polymeric materials. This is evidenced by the growing number of publications advocating the advantages of their incorporation in the design and construction of materials. Composed of a rigid steroid backbone, functional groups with potential towards diverse reactions, and a biocompatible framework, there are various ways in which these molecules can be utilized to afford biomaterials via distinct architectures. Soft materials utilize the intrinsic capacity of bile acids to self-assemble and have seen a range of applications, most notably in the field of drug delivery. On the other hand, there is also the possibility of including bile acids in the polymer backbone, which has been used in the preparation of elastomers. This review discusses a selection of materials that can be prepared using bile acids and the advantages afforded by these molecules. Focus will be on the development of soft and hard materials, where soft materials are described as being held by weak intermolecular interactions, whereas hard materials are mechanically stronger with bile acids covalently incorporated in the polymer network.Key words: bile acids, polymers, biomaterials, drug delivery, dental composites. Résumé :Les acides biliaires sont des synthons de plus en plus importants dans la mise au point de nouveaux matériaux à base de polymères, comme en témoigne le nombre croissant de publications préconisant leur incorporation dans la conception et la fabrication de ces matériaux. Composées d'un squelette stéroïdien rigide, de groupes fonctionnels au potentiel réactionnel diversifié, et d'une structure biocompatible, ces molécules, de par leurs différentes architectures, présentent diverses possibilités d'application dans le domaine des biomatériaux. La capacité intrinsèque des acides biliaires à s'autoassembler permet de produire des matériaux souples dont les applications sont variées, notamment dans le domaine de la libération des médica-ments. Par ailleurs, la possibilité d'intégrer des acides biliaires dans le squelette de polymères a aussi été explorée dans le cadre de la fabrication d'élastomères. Le présent article de synthèse porte sur une sélection de matériaux pouvant être préparés à partir d'acides biliaires et sur les avantages que comportent ces molécules. Une attention particulière est accordée à la mise au point de matériaux souples et de matériaux rigides. On y décrit les matériaux souples comme étant maintenus par des interactions intermoléculaires faibles, tandis que les matériaux rigides, dans lesquels les acides biliaires sont incorporés dans le réseau polymérique par des liaisons covalentes, sont mécaniquement plus solides. [Traduit par la Rédaction]

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Kinetics of Inclusion Reactions of β-Cyclodextrin with Several Dihydroxycholate Ions Studied by NMR Spectroscopy

Cited by 51 publications

References 31 publications

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

Determination of Binding Affinity for Chenodeoxycholate in Equilibrium with Sulfobutylether-β-Cyclodextrin

Polymers made of bile acids: from soft to hard biomaterials

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