Lipocarbazole, an efficient lipid peroxidation inhibitor anchored in the membrane

Bioorg Med Chem. 2015 Aug 1;23(15):4866-4870. doi: 10.1016/j.bmc.2015.05.031. Epub 2015 May 27.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Antioxidants / metabolism
  • Carbazoles / chemistry*
  • Carbazoles / metabolism
  • Fatty Acids / chemistry*
  • Fatty Acids / metabolism
  • Molecular Dynamics Simulation
  • Quantum Theory
  • Thermodynamics
  • Unilamellar Liposomes / chemistry*
  • Unilamellar Liposomes / metabolism

Substances

  • Antioxidants
  • Carbazoles
  • Fatty Acids
  • Unilamellar Liposomes
  • lipid peroxidation inhibitor
  • carbazole