Prediction of Binding Constants of α-Cyclodextrin Complexes

Proceeding from a phenomenological theory of pairwise interactions (solvent–solvent, solvent–solute, and solute–solute), the binding constant K11 (in M−1) for 1:1 complex formation by α-cyclodextrin at a substrate binding site, at 25°C in water, is given by log K11=−1.74 −[Z] + 0.032(−ΔA), where [Z]...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1996-08, Vol.85 (8), p.796-802
Main Author: Connors, Kenneth A.
Format: Article
Language:English
Subjects:
alpha-Cyclodextrins
Binding Sites
Biological and medical sciences
Cyclodextrins - chemistry
General pharmacology
Isomerism
Medical sciences
Models, Chemical
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
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Summary:Proceeding from a phenomenological theory of pairwise interactions (solvent–solvent, solvent–solute, and solute–solute), the binding constant K11 (in M−1) for 1:1 complex formation by α-cyclodextrin at a substrate binding site, at 25°C in water, is given by log K11=−1.74 −[Z] + 0.032(−ΔA), where [Z] incorporates solvent–solute (solvation) and solute–solute interactions and ΔA is the decrease in nonpolar surface area (in Å2 molecule−1) on the substrate that is exposed to solvent when the binding site enters the cyclodextrin cavity. ΔA is estimated from the structure of the binding site. Three levels of approximation are described for estimating [Z]. At the third (highest) level, the procedure when applied to 569 complex systems generated predicted values of log K11 that agreed within 0.30 unit of the experimental values in 58% of cases, and that agreed within 1.00 unit in 95% of cases.
ISSN:0022-3549
1520-6017
DOI:10.1021/js960167j