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Molecules 2016, 21(7), 829; doi:10.3390/molecules21070829

Location and Effects of an Antitumoral Catechin on the Structural Properties of Phosphatidylethanolamine Membranes

1
Departamento de Bioquímica y Biología Molecular-A, Universidad de Murcia, Campus de Espinardo, Murcia E-30100, Spain
2
IMDEA-Nanoscience, Campus de Cantoblanco, Madrid E-28049, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 9 May 2016 / Revised: 21 June 2016 / Accepted: 22 June 2016 / Published: 24 June 2016
(This article belongs to the Special Issue Catechins and Human Health: Current State of the Science)
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Abstract

Green tea catechins exhibit high diversity of biological effects including antioncogenic properties, and there is enormous interest in their potential use in the treatment of a number of pathologies. It is recognized that the mechanism underlying the activity of catechins relay in part in processes related to the membrane, and many studies revealed that the ability of catechins to interact with lipids plays a probably necessary role in their mechanism of action. We present in this work the characterization of the interaction between an antitumoral synthetically modified catechin (3-O-(3,4,5-trimethoxybenzoyl)-(−)-catechin, TMCG) and dimiristoylphosphatidyl-ethanolamine (DMPE) membranes using an array of biophysical techniques which include differential scanning calorimetry, X-ray diffraction, infrared spectroscopy, atomic force microscopy, and molecular dynamics simulations. We found that TMCG incorporate into DMPE bilayers perturbing the thermotropic transition from the gel to the fluid state forming enriched domains which separated into different gel phases. TMCG does not influence the overall bilayer assembly of phosphatidylethanolamine systems but it manages to influence the interfacial region of the membrane and slightly decrease the interlamellar repeat distance of the bilayer. TMCG seems to be located in the interior of the phosphatidylethanolamine bilayer with the methoxy groups being in the deepest position and some portion of the molecule interacting with the water interface. We believe that the reported interactions are significant not only from the point of view of the known antitumoral effect of TMCG, but also might contribute to understanding the basic molecular mechanism of the biological effects of the catechins found at the membrane level. View Full-Text
Keywords: catechins; TMCG; phosphatidylethanolamine; DSC; X-ray diffraction; AFM; FT-IR; molecular dynamics catechins; TMCG; phosphatidylethanolamine; DSC; X-ray diffraction; AFM; FT-IR; molecular dynamics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Casado, F.; Teruel, J.A.; Casado, S.; Ortiz, A.; Rodríguez-López, J.N.; Aranda, F.J. Location and Effects of an Antitumoral Catechin on the Structural Properties of Phosphatidylethanolamine Membranes. Molecules 2016, 21, 829.

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