Publication:
3,4,5-Trimethoxybenzoate of Catechin, an Anticarcinogenic Semisynthetic Catechin, Modulates the Physical Properties of Anionic Phospholipid Membranes

dc.contributor.authorAranda, Elisa
dc.contributor.authorPérez-Cárceles, María Dolores
dc.contributor.authorAranda Martínez, Francisco José
dc.contributor.authorOrtiz López, Antonio
dc.contributor.authorRodríguez López, José Neptuno
dc.contributor.authorTeruel Puche, José Antonio
dc.contributor.departmentBioquímica y Biología Molecular Aes
dc.date.accessioned2024-12-16T12:30:43Z
dc.date.available2024-12-16T12:30:43Z
dc.date.issued2022-05-03
dc.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/molecules27092910es
dc.description.abstract3,4,5-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 membranees
dc.formatapplication/pdfes
dc.format.extent16es
dc.identifier.citationMolecules 2022, 27, 2910
dc.identifier.doihttps://doi.org/10.3390/molecules27092910
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10201/147512
dc.languageenges
dc.publisherMDPIes
dc.relationSin financiación externa a la Universidades
dc.relation.publisherversionhttps://www.mdpi.com/journal/moleculeses
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAtribución 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectCatechines
dc.subjectDimyristoylphosphatidylserinees
dc.subjectPhospholipid membraneses
dc.title3,4,5-Trimethoxybenzoate of Catechin, an Anticarcinogenic Semisynthetic Catechin, Modulates the Physical Properties of Anionic Phospholipid Membraneses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
relation.isAuthorOfPublication90cfeea8-d683-4572-a187-13fe27a83750
relation.isAuthorOfPublicatione5a9bd2b-1205-406b-ae4f-7e90a2d0adca
relation.isAuthorOfPublication36d7ac7e-b9a7-477c-8f7e-f03d4cc834c1
relation.isAuthorOfPublicationbd0ae640-4c40-439e-bf79-a87fea6c8898
relation.isAuthorOfPublication.latestForDiscovery90cfeea8-d683-4572-a187-13fe27a83750
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