Publication: Effects of a Semisynthetic Catechin on Phosphatidylglycerol Membranes: A Mixed Experimental and Simulation Study
Authors
Aranda, Elisa ; Teruel, José A. ; Ortiz, Antonio ; Pérez-Cárceles, María Dolores ; Rodríguez-López, José N. ; Aranda, Francisco J.
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Publisher
MDPI
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Description
©2023. 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/molecules28010422
Abstract
Catechins have been shown to display a great variety of biological activities, prominent
among them are their chemo preventive and chemotherapeutic properties against several types
of cancer. The amphiphilic nature of catechins points to the membrane as a potential target for
their actions. 3,4,5-Trimethoxybenzoate of catechin (TMBC) is a modified structural analog of
catechin that shows significant antiproliferative activity against melanoma and breast cancer cells.
Phosphatidylglycerol is an anionic membrane phospholipid with important physical and biochemical
characteristics that make it biologically relevant. In addition, phosphatidylglycerol is a preeminent
component of bacterial membranes. Using biomimetic membranes, we examined the effects of
TMBC on the structural and dynamic properties of phosphatidylglycerol bilayers by means of
biophysical techniques such as differential scanning calorimetry, X-ray diffraction and infrared
spectroscopy, together with an analysis through molecular dynamics simulation. We found that
TMBC perturbs the thermotropic gel to liquid-crystalline phase transition and promotes immiscibility
in both phospholipid phases. The modified catechin decreases the thickness of the bilayer and is
able to form hydrogen bonds with the carbonyl groups of the phospholipid. Experimental data
support the simulated data that locate TMBC as mostly forming clusters in the middle region of each
monolayer approaching the carbonyl moiety of the phospholipid. The presence of TMBC modifies
the structural and dynamic properties of the phosphatidylglycerol bilayer. The decrease in membrane
thickness and the change of the hydrogen bonding pattern in the interfacial region of the bilayer
elicited by the catechin might contribute to the alteration of the events taking place in the membrane
and might help to understand the mechanism of action of the diverse effects displayed by catechins.
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