Determination of association constants of inclusion complexes of steroid hormones and cyclodextrins from their electrophoretic mobility

Shakalisava, Yuliya; Regan, Fiona

doi:10.1002/elps.200500842

Cited by 17 publications

(16 citation statements)

References 30 publications

(43 reference statements)

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“…However, there are only few papers where these calculation methods are compared. Shakalisava and Regan utilized three linearization plots (x‐reciprocal, y‐reciprocal and double reciprocal) and although they found all of them acceptable for determination of K b of inclusion complexes of steroid hormones with βCD andγCD and their hydroxypropyl derivatives, relatively different K b values were obtained from different plots. The differences were attributed to the fact that these plotting methods are not quite equivalent due to the difference in relative uncertainties in the x and y variables before and after transformation for plotting.…”

Section: Introductionmentioning

confidence: 99%

Estimation of apparent binding constant of complexes of selected acyclic nucleoside phosphonates with β‐cyclodextrin by affinity capillary electrophoresis

et al. 2015

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Affinity capillary electrophoresis (ACE) has been applied to estimation of apparent binding constant of complexes of (R,S)-enantiomers of selected acyclic nucleoside phosphonates (ANPs) with chiral selector β-cyclodextrin (βCD) in aqueous alkaline medium. The noncovalent interactions of five pairs of (R,S)-enantiomers of ANPs-based antiviral drugs and their derivatives with βCD were investigated in the background electrolyte (BGE) composed of 35 or 50 mM sodium tetraborate, pH 10.0, and containing variable concentration (0-25 mM) of βCD. The apparent binding constants of the complexes of (R,S)-enantiomers of ANPs with βCD were estimated from the dependence of effective electrophoretic mobilities of (R,S)-enantiomers of ANPs (measured simultaneously by ACE at constant reference temperature 25°C inside the capillary) on the concentration of βCD in the BGE using different nonlinear and linear calculation methodologies. Nonlinear regression analysis provided more precise and accurate values of the binding constants and a higher correlation coefficient as compared to the regression analysis of the three linearized plots of the effective mobility dependence on βCD concentration in the BGE. The complexes of (R,S)-enantiomers of ANPs with βCD have been found to be relatively weak - their apparent binding constants determined by the nonlinear regression analysis were in the range 13.3-46.4 L/mol whereas the values from the linearized plots spanned the interval 12.3-55.2 L/mol.

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Section: Introductionmentioning

confidence: 99%

Estimation of apparent binding constant of complexes of selected acyclic nucleoside phosphonates with β‐cyclodextrin by affinity capillary electrophoresis

et al. 2015

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“…There is no reason to expect that inclusion of EE 2 would be an important factor for either 7EACD or 7EqCD, because EE 2 has low reported affinity for β-CD ( K d = 8 mM),45,46 and a more polar CD annulus is known to reduce the affinity for hydrophobic aromatic guests further 18,21. The presence of EE 2 in the 7EqCD product was tested in the same Ishikawa cell cultures used for assessment of classical estrogenic activity.…”

Section: Resultsmentioning

confidence: 99%

Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

Kim

Sohn

Wijewickrama

et al. 2010

Bioorganic & Medicinal Chemistry

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Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E 2 ) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E 2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer -E 2 conjugates, CD-E 2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm.

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“…providing fundamental information on the analyte-ligand affinity and understanding the molecular interactions [8,18]). Wren and Rowe [19,20] developed a theoretical model relating the mobility to the CD concentration.…”

Section: Determination Of Binding Constantsmentioning

confidence: 99%

Determination of the binding constants of modafinil enantiomers with sulfated β‐cyclodextrin chiral selector by capillary electrophoresis using three different linear plotting methods

2010

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Binding constants for the enantiomers of modafinil with the negatively charged chiral selector sulfated-β-CD (S-β-CD) using CE technique is presented. The calculations of the binding constants employing three different linearization plots (double reciprocal, X-reciprocal and Y-reciprocal) were performed from the electrophoretic mobility values of modafinil enantiomers at different concentrations of S-β-CD in the BGE. The highest inclusion affinity of the modafinil enantiomers were observed for the S-enantiomer-S-β-CD complex, in agreement with the computational calculations performed previously. Binding constants for each enantiomer-S-β-CD complex at different temperatures, as well as thermodynamic parameters for binding, were calculated. Host-guest binding constants using the double reciprocal fit showed better linearity (r(2)>0.99) at all temperatures studied (15-30°C) and compared with the other two fit methods. The linear van't Hoff (15-30°C) plot obtained indicated that the thermodynamic parameters of complexation were temperature dependent for the enantiomers.

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Determination of association constants of inclusion complexes of steroid hormones and cyclodextrins from their electrophoretic mobility

Cited by 17 publications

References 30 publications

Estimation of apparent binding constant of complexes of selected acyclic nucleoside phosphonates with β‐cyclodextrin by affinity capillary electrophoresis

Estimation of apparent binding constant of complexes of selected acyclic nucleoside phosphonates with β‐cyclodextrin by affinity capillary electrophoresis

Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

Determination of the binding constants of modafinil enantiomers with sulfated β‐cyclodextrin chiral selector by capillary electrophoresis using three different linear plotting methods

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