Determination of formation constants of cyclodextrin inclusion complexes using affinity capillary electrophoresis

Plätzer, Manuela; Schwarz, Maria A.; Neubert, Reinhard H.H.

doi:10.1002/(sici)1520-667x(1999)11:3<215::aid-mcs7>3.0.co;2-o

Cited by 29 publications

(11 citation statements)

References 11 publications

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“…2 In several studies, the stability constant of the complex has been calculated to quantify the supramolecular interaction in solution between the organic guest and the cyclodextrin host. To obtain such information, several approaches have been described, such as isothermal titration calorimetry, 4 solubility diagrams 5 and multivariate analysis, 6 as well as Scott/Scatchard plots, which were applied to data obtained from UV absorption spectroscopy, 7 capillary electrophoresis (CE) 8 and high performance liquid chromatography (HPLC). 9 The stability constants could also be calculated from diffusion coefficient data obtained by diffusion ordered spectroscopy (DOSY) experiments.…”

Section: Introductionmentioning

confidence: 99%

Recognition mechanism of d- and l-tryptophan enantiomers using 2-hydroxypropyl-α- or β-cyclodextrins as chiral selectors

Malta

Cordeiro

Tinoco

et al. 2008

Tetrahedron: Asymmetry

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Section: Introductionmentioning

confidence: 99%

Recognition mechanism of d- and l-tryptophan enantiomers using 2-hydroxypropyl-α- or β-cyclodextrins as chiral selectors

Malta

Cordeiro

Tinoco

et al. 2008

Tetrahedron: Asymmetry

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“…The electrophoretic mobilities are corrected for viscosity changes by multiplying the mobilities by the ratio 0 /. The three linear equations are used since differences due to relative uncertainties of the variables before and after transformation for plotting can occur [34,35]. Moreover, deviations from linearity can be more easily observed using x-or double-reciprocal plot than the y-reciprocal plot [36].…”

Section: Determination Of Apparent Binding Constantsmentioning

confidence: 99%

Evaluation of three neutral capillary coatings for the determination of analyte-cyclodextrin binding constants by affinity capillary electrophoresis. Application to N , N ⿲-disubstituted piperazine derivatives.

Danel

Melnyk

Azaroual

et al. 2016

Journal of Chromatography A

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The performances of three neutral static coatings (hydroxypropyl cellulose, polyethylene oxide and poly(N,N-dimethylacrylamide) have been evaluated in order to determine the binding constants of the complexes formed between four polycationic compounds (piperazine derivatives) and four cyclodextrins of pharmaceutical interest (β-CD, HP-β-CD, Me-β-CD and sulfobutyl ether-β-CD) by affinity capillary electrophoresis. The physically-adsorbed poly(N,N-dimethylacrylamide) coating proves to be the more efficient to mask the silanol groups of the capillary wall since the lowest electroosmotic flow was measured for this coating. Moreover, it drastically reduces the adsorption of the compounds since it allows a correct repeatability of their migration time, higher efficiencies of the peaks and no baseline shift. Then, it was verified for four complexes that this coating allows a correct determination of the binding constants avoiding the CD adsorption which is responsible of an undervaluation of binding constants. The highest binding constants are obtained using the anionic sulfobutyl ether-β-CD (SBE-β-CD). The structure of the complex formed between the tacrine derivative and the SBE-β-CD was further investigated through 2D ROESY NMR experiments and structure-binding constant relationships. Results suggest that the inclusion in the SBE-β-CD cavity occurs through the aliphatic ring portion of the tacrine moiety.

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“…ACE has been used to study different interactions (examples: CD–drug complex, drug–anion complex) and to quantify their formation constants ( K f ) depending on the migration behavior of the interacting molecules . So first , this study developed an ACE technique to investigate the IPF between the cationic drug (GLB) and different anionic molecules and to evaluate their formation strength ( K f ).…”

Section: Introductionmentioning

confidence: 99%

Optimization of ion‐pair formation between glycopyrronium bromide and different ion‐pair agents using ACE

2015

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Glycopyrronium bromide (GLB) is an anticholinergic drug. Its highly polar quaternary ammonium group could limit the skin permeation of the topical hydrophilic drug. The ion pair formation with suitable anionic molecules was suggested to play a role in enhancing the cationic drug transport to the target site. The interactions between GLB and different ion‐pair agents (IPAs) were investigated using ACE. The changes in the effective mobility of 0.05 mM GLB were correlated with the increasing concentrations of IPAs in 20 mM BGE of pH 6.2, and successfully fitted into a nonlinear binding isotherm equation assuming 1:1 stoichiometric interaction. The formation constants (Kf) were 74.33, 28.5, 18.17, 8.2, 7.6, 5.69, 4.76, and 3.96 M−1 for sodium salts of dodecyl sulfate, taurodeoxycholate, taurocholate, glycodeoxycholate, glycocholate, salicylate, quinolone sulfonate, and p‐toluene sulfonate; respectively. Surfactant's and bile salts’ concentrations were below CMCs. The partition coefficient of GLB between buffer phase and n‐octanol was determined successfully in the absence and presence of different IPAs. The study confirmed the linear correlation (R2 = 0.907) between the affinity strength of ion pair and the partition behavior of GLB in the presence of anionic molecules at 1:1 molar ratio.

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Determination of formation constants of cyclodextrin inclusion complexes using affinity capillary electrophoresis

Cited by 29 publications

References 11 publications

Recognition mechanism of d- and l-tryptophan enantiomers using 2-hydroxypropyl-α- or β-cyclodextrins as chiral selectors

Recognition mechanism of d- and l-tryptophan enantiomers using 2-hydroxypropyl-α- or β-cyclodextrins as chiral selectors

Evaluation of three neutral capillary coatings for the determination of analyte-cyclodextrin binding constants by affinity capillary electrophoresis. Application to N , N ⿲-disubstituted piperazine derivatives.

Optimization of ion‐pair formation between glycopyrronium bromide and different ion‐pair agents using ACE

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