Publication: 3,4,5-Trimethoxybenzoate of Catechin, an Anticarcinogenic Semisynthetic Catechin, Modulates the Physical Properties of Anionic Phospholipid Membranes
Authors
Aranda, Elisa ; Pérez-Cárceles, María Dolores ; Aranda Martínez, Francisco José ; Ortiz López, Antonio ; Rodríguez López, José Neptuno ; Teruel Puche, José Antonio
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Publisher
MDPI
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DOI
https://doi.org/10.3390/molecules27092910
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info:eu-repo/semantics/article
Description
©2022. This manuscript version is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by /4.0/
This document is the Published, version of a Published Work that appeared in final form in Molecules. To access the final edited and published work see https://doi.org/10.3390/molecules27092910
Abstract
3,4,5-Trimethoxybenzoate of catechin (TMBC) is a semisynthetic catechin which shows
strong antiproliferative activity against malignant melanoma cells. The amphiphilic nature of the
molecule suggests that the membrane could be a potential site of action, hence the study of its inter action with lipid bilayers is mandatory in order to gain information on the effect of the catechin on
the membrane properties and dynamics. Anionic phospholipids, though being minor components of
the membrane, possess singular physical and biochemical properties that make them physiologically
essential. Utilizing phosphatidylserine biomimetic membranes, we study the interaction between the
catechin and anionic bilayers, bringing together a variety of experimental techniques and molecular
dynamics simulation. The experimental data suggest that the molecule is embedded into the phos phatidylserine bilayers, where it perturbs the thermotropic gel to liquid crystalline phase transition.
In the gel phase, the catechin promotes the formation of interdigitation, and in the liquid crystalline
phase, it decreases the bilayer thickness and increases the hydrogen bonding pattern of the interfacial
region of the bilayer. The simulation data agree with the experimental ones and indicate that the
molecule is located in the interior of the anionic bilayer as monomer and small clusters reaching the
carbonyl region of the phospholipid, where it also disturbs the intermolecular hydrogen bonding
between neighboring lipids. Our observations suggest that the catechin incorporates well into phos phatidylserine bilayers, where it produces structural changes that could affect the functioning of
the membrane
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Citation
Molecules 2022, 27, 2910
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