Classical QSAR and comparative molecular field analyses of the host-guest interaction of organic molecules with cyclodextrins

Authors: Suzuki, T.1; Ishida, M.1; Fabian, W.M.F.2

Source: Journal of Computer-Aided Molecular Design, Volume 14, Number 7, October 2000 , pp. 669-678(10)

Publisher: Springer

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The application of classical QSAR and molecular modeling analysis using Comparative Molecular Field Analysis (CoMFA) to the complexation of some natural and modified cyclodextrins (CDs) with guest molecules was examined. For 1:1 complexation systems between natural β-CD, modified α-, β-, and γ-CD that bear one p-(dimethylamino)benzoyl (DMAB) moiety (DMAB-α-, β-, and γ-CDs) and guest molecules of widely varying chemical structures and properties, the binding constants of the complexes were successfully fitted using multiple linear regression (MLR) with hydrophobic descriptor log P (the partition coefficient between 1-octanol and water phases) and molecular connectivity indices. A non-linear dependency of binding constants on the zero-th and/or first order molecular connectivity index as a measure of size becomes apparent. The modeling performance of the CoMFA models with steric/electrostatic fields to DMAB-α- and β-CD systems was comparable to those of MLR models. However, statistically significant CoMFA models for γ-CD systems which have higher conformational flexibility of the ring could not be obtained. The CoMFA models obtained for DMAB-α- and β-CD systems showed that the predominant effects were steric for the DMAB-α-CD system and electrostatic for the DMAB-β-CD system, respectively.

Keywords: CoMFA; cyclodextrin complexes; lipophilicity; molecular connectivity; molecular recognition; multivariate analysis

Document Type: Regular Paper

Affiliations: 1: Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan 2: Institut für Chemie, Karl-Franzens-Universität Graz, Heinrichstr. 28, A-8010 Graz, Austria

Publication date: October 1, 2000

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