Host-Guest Interactions of Plumbagin with β-Cyclodextrin, Dimethyl-β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin: Semi-Empirical Quantum Mechanical PM6 and PM7 Methods

Scientia pharmaceutica
Ornin SrihakulungAnd Luckhana Lawtrakul

Abstract

Molecular interactions of plumbagin inclusion complexes with β-cyclodextrin (BCD), dimethyl--cyclodextrin (MBCD), and hydroxypropyl-β-cyclodextrin (HPBCD) were investigated by semi-empirical, Parameterization Method 6 and 7 (PM6, and PM7) in the aqueous phase using polarizable continuum calculations. The results revealed two different binding modes of the plumbagin molecule inside the BCD cavity with a negative value of the complexation energy. In conformation-I, the hydroxyl phenolic group of plumbagin was placed in the BCD cavity near the narrow-side of the host molecule. In the other model, conformation-II, the methyl quinone group of plumbagin was placed in the cavity of BCD near the narrow-side of the host molecule. The higher the negative value of the complexation energy, the more favorable is the pathway of inclusion-complex formation.

References

Dec 30, 1991·Carbohydrate Research·K HarataK Uekama
Aug 5, 1997·Chemical Reviews·Kenneth A. Connors
Feb 6, 2004·Memórias do Instituto Oswaldo Cruz·Selma Ribeiro de PaivaMaria Auxiliadora Coelho Kaplan
Dec 2, 2006·International Journal of Pharmaceutics·Thorsteinn Loftsson, Dominique Duchêne
Apr 29, 2009·Journal of Computational Chemistry·Garrett M MorrisArthur J Olson

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