Lipocarbazole, an efficient lipid peroxidation inhibitor anchored in the membrane

Gabin Fabre; A. Hänchen; Claude-Alain Calliste; Karel Berka; S Banala; Michal Otyepka; Roderich Süssmuth; Patrick Trouillas

doi:10.1016/j.bmc.2015.05.031

Lipocarbazole, an efficient lipid peroxidation inhibitor anchored in the membrane

Gabin Fabre ^{1, 2} A. Hänchen ³ Claude-Alain Calliste ¹ Karel Berka ² S Banala ^{2, 4} Michal Otyepka ² Roderich Süssmuth ³ Patrick Trouillas ^{5, 4, *}

* Auteur correspondant

1 LCSN - Laboratoire de Chimie des Substances Naturelles

2 Department of Physical Chemistry

3 Institut für Chemie

4 Institute for Experimental Molecular Imaging (ExMI)

5 PIST - Pharmacologie des Immunosuppresseurs et de la Transplantation

Abstract : Lipid peroxidation is a major deleterious effect caused by oxidative stress. It is involved in various diseases such as atherosclerosis, rheumatoid arthritis and neurodegenerative diseases. In order to inhibit lipid peroxidation, antioxidants must efficiently scavenge free radicals and penetrate inside biological membranes. Lipocarbazole has recently been shown to be a powerful antioxidant in solution. Here, we show its powerful capacity as lipid peroxidation inhibitor. Its mechanism of action is rationalized based on molecular dynamics simulations on a biomembrane model, quantum calculations and experimental evaluation. The role of the lipocarbazole side chain is particularly highlighted as a critical chemical feature responsible for its antioxidant activity.

Keywords : Antioxidant Lipid bilayer membrane Lipid peroxidation Molecular dynamics

Type de document :

Article dans une revue

Bioorganic and Medicinal Chemistry, 2015, 23 (15), pp.4866-4870. 〈10.1016/j.bmc.2015.05.031〉

Domaine :

Chimie / Chimie théorique et/ou physique

Chimie / Chimie thérapeutique

Chimie / Chimie analytique

Chimie / Chimie organique

Liste complète des métadonnées

https://hal-unilim.archives-ouvertes.fr/hal-01257158
Contributeur : Vincent Sol <>
Soumis le : vendredi 15 janvier 2016 - 18:13:17
Dernière modification le : mardi 20 mars 2018 - 16:36:27

Lipocarbazole, an efficient lipid peroxidation inhibitor anchored in the membrane

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