Efficient detection and evaluation of cyclodextrin multiple complex formation

Armstrong, Daniel W.; Nome, Faruk; Spino, Larry A.; Golden, Teresa D.

doi:10.1021/ja00267a010

Cited by 116 publications

(60 citation statements)

References 2 publications

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“…However, as concluded by Cabrer et al [13], the stability constant K 1:2 is low relative to K 1:1 . Hence, the 1:1 stoichiometry model may be descriptive in the b-CD concentration range investigated here, but 1:2 binding cannot be ruled out since complexation stoichiometries may be strongly concentration dependent [59]. The R 2 values for the nonlinear regression analysis were 0.987 and 0.988 for GDC-b-CD and TDC-b-CD complexation, respectively.…”

Section: Complex Formation With Natural â-Cdmentioning

confidence: 79%

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: 79%

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

et al. 2007

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“…More recently, a number of 2: 1 cyclodextrin-substrate complexes have been characterized (2). With surfactants, a 1:l stoichiometry is usually presumed (3-5) but Hersey and co-workers (6) have demonstrated that a-cyclodextrin binds with alkylsulphate anions in a 2: 1 ratio.…”

Section: Introductionmentioning

confidence: 99%

Surfactant–cyclodextrin interactions by conductance measurements

Palepu¹,

Reinsborough²

1988

Can. J. Chem.

141

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PALEPU and VINCENT C . REINSBOROUGH. Can. J. Chem. 66, 325 (1988). Conductance measurements were used to identify and to obtain association constants for the complexes formed between cyclodextrins (CD) with emphasis on P-cyclodextrin (PCD), and surfactants such as sodium dodecylsulfate (SDS) and tetradecyltrimethyl ammonium bromide. With both anionic and cationic surfactants, a C D forms predominantly a 2:l CD/surfactant complex while with both PCD and y C D the main species is I: 1. y C D binds much less strongly with surfactants than both a C D and PCD. Cyclodextrins destroy micelles by complexing the surfactant monomers more strongly than they are bound in self-association.RAMAMURTHY PALEPU et VINCENT C. REINSBOROUGH. Can. J. Chem. 66, 325 (1988) On a utilisk des mesures de conductance pour identifier et pour obtenir les constantes d'association des complexes qui se forment entre des cyclodextrines (CD) et des agents de surface, principalement entre la P-CD et le dodCcylsulfate de sodium (DSS), tant au-dessous qu'au-dessus de la concentration micellaire critique. Tant avec les agents de surface anioniques que cationiques, la a-CD forme principalement un complexe 2:l de CD:agent de surface; par ailleurs, les P-et y-CD forment principalement des complexes 1:l. La -y-CD se lie moins fortement que les a-et P-CD avec les agents de surface. Par comparaison avec leurs propres auto-associations, les cyclodextrines complexent avec les agents de surface monomkres plus fortement que les monomkres se complexent avec lui-m&mes et elles dCtruisent ainsi les micelles.[Traduit par la revue]

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“…For the 1:1 stoichiometry inclusion complex between rutin and the host molecule, two equilibria on the plate are expressed as follows (Armstrong et al, 1986;Armstrong and Stine, 1983):…”

Section: Resultsmentioning

confidence: 99%

Comparative study on the inclusion behaviour of cyclodextrin derivatives with venoruton and rutin by thin layer chromatography

Guo

Shuang²,

Wang

et al. 2004

Biomedical Chromatography

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The interaction of rutin and venoruton (troxerutin), with alpha-, beta- and gamma-cyclodextrin (CD), hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and methyl-beta-cyclodextrin (M-beta-CD) was investigated by reversed-phase thin layer chromatography on polyamide plates. A mobile phase consisted of NH(4)OH; NH(4)Cl buffer solution containing various CD concentrations (pH = 9.7, 20 degrees C) was used as mobile phase. The equilibrium constants (K(f)) and the retention factor (R(f)) were determined and used to study the inclusion process. The in fluence of CDs on the solubility of rutin and venoruton was characterized by R(M) values and the increasing hydrophilicity of drugs. The results show that the inclusion capacity of cyclodextrins follows the order HP-beta-CD > M-beta-CD > beta-CD > gamma-CD, and rutin is more easily included by the studied cyclodextrins than venoruton. In addition, the thermodynamic parameters (Delta H, Delta S) for the formation of complexes were obtained from the van't Hoff equation, displaying the enthalpy-entropy compensation effect.

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Efficient detection and evaluation of cyclodextrin multiple complex formation

Cited by 116 publications

References 2 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

Surfactant–cyclodextrin interactions by conductance measurements

Comparative study on the inclusion behaviour of cyclodextrin derivatives with venoruton and rutin by thin layer chromatography

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