Studies on complexation between β-cyclodextrin and bile salts

Tan, Xinyi; Lindenbaum, Siegfried

doi:10.1016/0378-5173(91)90229-h

Cited by 66 publications

(77 citation statements)

References 21 publications

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“…The assigned complex stoichiometry is supported by the studies of Abadie et al [15]. In contrast, Tan and Lindenbaum [16], and Cabrer et al [13] have reported 1:2 complexes (BS:CD) for the interaction between the dihydroxy BS TDC and GDC and b-CD. However, as concluded by Cabrer et al [13], the stability constant K 1:2 is low relative to K 1:1 .…”

Section: Complex Formation With Natural â-Cdmentioning

confidence: 83%

“…The propensity for such displacement reactions to occur in the species man, rat, and canine may, as a first approximation, be evaluated by the stability constants of the relevant glyco-and tauro-conjugated BS to CDs. The interaction between a number of BS and CDs has previously been determined by NMR [13,14,23] and calorimetry [16,20,21,25,26]. ACE may be an interesting alternative to these methods since it requires only small amounts of sample and is relatively fast and easily automated.…”

Section: Resultsmentioning

confidence: 99%

“…Consequently, it is generally recommended that a) Stability constants determined by a phase solubility technique (displacement assay) [15]. b) Stability constants determined by flow microcalorimetry [16]. c) Stability constants determined by NMR [13].…”

Section: Estimation Of Stability Constantsmentioning

confidence: 99%

“…Most of the studies investigating the interaction between BS and CDs have used NMR [13,14,23,24] or calorimetry [16,20,21,25,26]. As BS are negatively charged at neutral pH, techniques exploiting the conductive properties of the involved species should also be applicable.…”

Section: Introductionmentioning

confidence: 99%

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Complexation of tauro‐ and glyco‐conjugated bile salts with three neutral β‐CDs studied by ACE

et al. 2007

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Complexation of the bile salts (BS) taurocholate, tauro-beta-muricholate, taurodeoxycholate, taurochenodeoxycholate, glycocholate, glycodeoxycholate, and glycochenodeoxycholate common in rat, dog, and man with natural beta-CD and the chemically modified beta-CDs 2-hydroxypropyl-beta-CD and 2-O-methyl-beta-CD was studied using mobility shift ACE. The CDs were selected due to their frequent use in preformulation and drug formulation as oral excipients for the solubilization of drug substances with low aqueous solubility. ACE was demonstrated to be a feasible and efficient technique for investigation of the interactions between BS and beta-CDs. All the investigated BS possessed affinity for the three CDs with stability constants ranging from 2x10(3) to 4x10(5) M(-) (1). The requirements and assumptions related to the use of ACE for estimating high affinity stability constants were discussed. The extent and pattern of hydroxylation significantly influenced the affinity of the glyco- and tauro-conjugated BS toward the beta-CDs (chenodeoxycholates >> deoxycholates > cholates) whereas the nature of the beta-CD derivatization and BS conjugation played a minor role only. The results indicate that displacement of drug substances from beta-CD inclusion complexes is likely to occur in the small intestine where BS are present potentially influencing drug bioavailability.

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Section: Complex Formation With Natural â-Cdmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Estimation Of Stability Constantsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Complexation of tauro‐ and glyco‐conjugated bile salts with three neutral β‐CDs studied by ACE

et al. 2007

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“…Autores que estudaram o comportamento da HP-β-CD administrada por via IV concluem que esta se mantém em circulação e que não atravessa membranas lipídicas em razão da sua polaridade, podendo, quando em contato com elas, extrair componentes lipídicos, preferencialmente o colesterol, atuando, assim, também como transportadores de moléculas lipídicas existentes na corrente sanguínea (Irie et al, 1992a(Irie et al, e 1992b. Os complexos de colesterol:HP-β-CD dissociam-se no filtrado glomerular, a HP-β-CD passa através do glomérulo sem provocar obstrução e ocorre deposição de colesterol no rim (Fini et al, 1995;Flourié et al, 1993;Frijlink et al, 1990a;Gerloczy et al, 1994;Nakanishi et al, 1992;Shamat, 1993;Tan, Lindenbaum, 1991).…”

Section: Mecanismo De Complexação Conseqüências E Limitações Dos Comunclassified

Aspectos biofarmacêuticos da formulação de medicamentos para neonatos: fundamentos da complexação de indometacina com hidroxipropil-beta-ciclodextrina para tratamento oral do fechamento do canal arterial

Rama¹,

Veiga²,

Figueiredo³

et al. 2005

Rev. Bras. Cienc. Farm.

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INTRODUÇÃOA investigação farmacêutica tem como intuito o desenvolvimento de novos agentes terapêuticos direcionados à resolução de situações clínicas, integrando conhecimentos pluridisciplinares.A prática de cuidados farmacêuticos possibilita a identificação de situações clínicas para as quais os recursos terapêuticos existentes não são os adequados. Fazer parte da equipe de saúde de uma unidade de cuidados intensivos de neonatologia é um desafio para o farmacêu-tico clínico, confrontado com a necessidade de dar resposta aos problemas biofarmacêuticos decorrentes da anatomofisiologia e das patologias inerentes àquele gru- Unitermos• Indometacina• Hidroxipropil-β-ciclodextrina• Recém-nascidos• Canal arterial

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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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Studies on complexation between β-cyclodextrin and bile salts

Cited by 66 publications

References 21 publications

Complexation of tauro‐ and glyco‐conjugated bile salts with three neutral β‐CDs studied by ACE

Complexation of tauro‐ and glyco‐conjugated bile salts with three neutral β‐CDs studied by ACE

Aspectos biofarmacêuticos da formulação de medicamentos para neonatos: fundamentos da complexação de indometacina com hidroxipropil-beta-ciclodextrina para tratamento oral do fechamento do canal arterial

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

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