Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling

Jullian C.; Miranda, S.; Zapata-Torres, G; Mendizabal, F; Olea Azar C.

Abstract

The aim of this paper is to describe the inclusion properties and the factors affecting the complexation selectivity and stabilization of catechin (CA) into β-cyclodextrin (β-CD) and two of its derivatives, namely Heptakis 2,6-di-O-methyl-β-cyclodextrin (DM-β-CD) and 2 hydroxypropyl-β-cyclodextrin (HP-β-CD). Analysis of the proton shift change using the continuous variation method confirm the formation of a 1:1 stoichiometric complex for catechin and the different CDs in aqueous medium. The formations constant obtained by diffusion-ordered spectroscopy (DOSY) techniques indicated the following trend upon complex formation: β-CD > HP-β-CD > DM-β-CD. The detailed spatial configuration is proposed based on 2D NMR methods. These results are further interpreted using molecular modeling studies. The latter results are in good agreement with the experimental data. The models confirm that when CA-β-CD is formed, the catechol moiety in the complex is oriented toward the primary rim; however when CD is derivatized to HP-β-CD and DM-β-CD this ring is oriented toward the secondary rim. © 2007 Elsevier Ltd. All rights reserved.

Más información

Título según WOS: Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling
Título según SCOPUS: Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling
Título de la Revista: BIOORGANIC & MEDICINAL CHEMISTRY
Volumen: 15
Número: 9
Editorial: PERGAMON-ELSEVIER SCIENCE LTD
Fecha de publicación: 2007
Página de inicio: 3217
Página final: 3224
Idioma: English
DOI:

10.1016/j.bmc.2007.02.035

Notas: ISI, SCOPUS