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Effects of lipid composition on membrane distribution and permeability of natural quinones

Natural quinones are amphiphilic molecules that function as mobile charge carriers in biological energy transduction. Their distribution and permeation across membranes are important for binding to enzymatic complexes and for proton translocation. Here, we employ molecular dynamics simulations and f...

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Detalles Bibliográficos
Autores principales: Teixeira, Murilo Hoias, Arantes, Guilherme Menegon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9064471/
https://www.ncbi.nlm.nih.gov/pubmed/35516391
http://dx.doi.org/10.1039/c9ra01681c
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author Teixeira, Murilo Hoias
Arantes, Guilherme Menegon
author_facet Teixeira, Murilo Hoias
Arantes, Guilherme Menegon
author_sort Teixeira, Murilo Hoias
collection PubMed
description Natural quinones are amphiphilic molecules that function as mobile charge carriers in biological energy transduction. Their distribution and permeation across membranes are important for binding to enzymatic complexes and for proton translocation. Here, we employ molecular dynamics simulations and free energy calculations with a carefully calibrated classical force-field to probe quinone distribution and permeation in a multi-component bilayer trying to mimic the composition of membranes involved in bioenergetic processes. Ubiquinone, ubiquinol, plastoquinone and menaquinone molecules with short and long isoprenoid tails are simulated. We find that penetration of water molecules bound to the polar quinone head increases considerably in the less ordered and porous bilayer formed by di-linoleoyl (18:2) phospholipids, resulting in a lower free energy barrier for quinone permeation and faster transversal diffusion. In equilibrium, quinone and quinol heads localize preferentially near lipid glycerol groups, but do not perform specific contacts with lipid polar heads. Quinone distribution is not altered significantly by the quinone head, tail and lipid composition in comparison to a single-component bilayer. This study highlights the role of lipid acyl chain unsaturation for permeation and transversal diffusion of polar molecules across biological membranes.
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spelling pubmed-90644712022-05-04 Effects of lipid composition on membrane distribution and permeability of natural quinones Teixeira, Murilo Hoias Arantes, Guilherme Menegon RSC Adv Chemistry Natural quinones are amphiphilic molecules that function as mobile charge carriers in biological energy transduction. Their distribution and permeation across membranes are important for binding to enzymatic complexes and for proton translocation. Here, we employ molecular dynamics simulations and free energy calculations with a carefully calibrated classical force-field to probe quinone distribution and permeation in a multi-component bilayer trying to mimic the composition of membranes involved in bioenergetic processes. Ubiquinone, ubiquinol, plastoquinone and menaquinone molecules with short and long isoprenoid tails are simulated. We find that penetration of water molecules bound to the polar quinone head increases considerably in the less ordered and porous bilayer formed by di-linoleoyl (18:2) phospholipids, resulting in a lower free energy barrier for quinone permeation and faster transversal diffusion. In equilibrium, quinone and quinol heads localize preferentially near lipid glycerol groups, but do not perform specific contacts with lipid polar heads. Quinone distribution is not altered significantly by the quinone head, tail and lipid composition in comparison to a single-component bilayer. This study highlights the role of lipid acyl chain unsaturation for permeation and transversal diffusion of polar molecules across biological membranes. The Royal Society of Chemistry 2019-05-29 /pmc/articles/PMC9064471/ /pubmed/35516391 http://dx.doi.org/10.1039/c9ra01681c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Teixeira, Murilo Hoias
Arantes, Guilherme Menegon
Effects of lipid composition on membrane distribution and permeability of natural quinones
title Effects of lipid composition on membrane distribution and permeability of natural quinones
title_full Effects of lipid composition on membrane distribution and permeability of natural quinones
title_fullStr Effects of lipid composition on membrane distribution and permeability of natural quinones
title_full_unstemmed Effects of lipid composition on membrane distribution and permeability of natural quinones
title_short Effects of lipid composition on membrane distribution and permeability of natural quinones
title_sort effects of lipid composition on membrane distribution and permeability of natural quinones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9064471/
https://www.ncbi.nlm.nih.gov/pubmed/35516391
http://dx.doi.org/10.1039/c9ra01681c
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