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

Carolina Jullian, Sebastián Miranda, Gerald Zapata-Torres, Fernando Mendizábal, Claudio Olea-Azar

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

98 Citas (Scopus)

Resumen

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.

Idioma originalInglés
Páginas (desde-hasta)3217-3224
Número de páginas8
PublicaciónBioorganic and Medicinal Chemistry
Volumen15
N.º9
DOI
EstadoPublicada - 1 may 2007

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Medicina molecular
  • Biología molecular
  • Ciencias farmacéuticas
  • Descubrimiento de medicamentos
  • Bioquímica clínica
  • Química orgánica

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