4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 1. Antioxidant properties.

Details

Serval ID
serval:BIB_EB89FD309B39
Type
Article: article from journal or magazin.
Collection
Publications
Title
4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 1. Antioxidant properties.
Journal
Free radical research
Author(s)
Zoete V., Bailly F., Vezin H., Teissier E., Duriez P., Fruchart J.C., Catteau J.P., Bernier J.L.
ISSN
1071-5762 (Print)
ISSN-L
1029-2470
Publication state
Published
Issued date
06/2000
Peer-reviewed
Oui
Volume
32
Number
6
Pages
515-524
Language
english
Notes
Publication types: Journal Article
Publication Status: ppublish
Abstract
4-Mercaptoimidazoles derived from the naturally occurring family of antioxidants, the ovothiols, were assayed for their antioxidant properties. These compounds are powerful HOCl scavengers, more potent than the aliphatic thiol N-acetylcysteine. They react slowly with hydrogen peroxide with second order rate constants of 0.13-0.89 M(-1)s(-1). Scavenging of hydroxyl radical occurs at a diffusion-controlled rate (k=2.0-5.0 x 10(10)M(-1)s(-1)) for the most active compounds, which are also able to inhibit copper-induced LDL peroxidation. The combination of radical scavenging and copper chelating properties may explain the inhibitory effects on LDL peroxidation. Two molecules of mercaptoimidazole can chelate a copper ion and form a square planar complex detected by EPR. Compounds bearing an electron-withdrawing group on position 2 of the imidazole ring are the most potent antioxidant molecules in this series.
Keywords
Antioxidants/pharmacology, Chelating Agents, Copper/chemistry, Copper/pharmacology, Free Radical Scavengers, Hydrogen Peroxide/chemistry, Hydroxyl Radical/chemistry, Hypochlorous Acid/chemistry, Imidazoles/chemistry, Imidazoles/pharmacology, Lipid Peroxidation, Lipoproteins, LDL/chemistry, Methylhistidines/chemistry, Oxidation-Reduction, Sulfhydryl Compounds/chemistry
Pubmed
Web of science
Create date
22/01/2019 10:27
Last modification date
21/08/2019 5:37
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