4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 2. Computational and experimental approach of the radical scavenging mechanism.

Details

Serval ID
serval:BIB_7ECDB53DBDCB
Type
Article: article from journal or magazin.
Collection
Publications
Title
4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 2. Computational and experimental approach of the radical scavenging mechanism.
Journal
Free radical research
Author(s)
Zoete V., Vezin H., Bailly F., Vergoten G., 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
525-533
Language
english
Notes
Publication types: Journal Article
Publication Status: ppublish
Abstract
The radical-scavenging mechanism of fourteen 4-mercaptoimidazoles, derived from the natural family of ovothiols, was studied via a QSAR approach, cyclic voltammetry, ESR and NMR spectroscopy. A significant correlation was found between the DPPH scavenging abilities of test compounds and thermodynamic parameters like overall ease of disulphide formation. The production of a disulphide compound via thiyl radical formation is proposed. Upon DPPH scavenging, hydrogen abstraction from thiols yields transient short-lived thiyl radicals, which were characterised by ESR and rapidly dimerise to form a disulphide compound. Cyclic voltammetry showed that the best DPPH scavengers exhibit low oxidation potentials for their oxidation to disulphides.
Keywords
Antioxidants/chemistry, Bepridil/analogs & derivatives, Bepridil/chemistry, Biphenyl Compounds, Electrochemistry, Electron Spin Resonance Spectroscopy, Free Radical Scavengers, Free Radicals, Hydroxyl Radical/chemistry, Imidazoles/chemistry, Imidazoles/pharmacology, Methylhistidines/chemistry, Molecular Structure, Picrates, Structure-Activity Relationship, Sulfhydryl Compounds/chemistry, Thermodynamics
Pubmed
Web of science
Create date
22/01/2019 10:29
Last modification date
21/08/2019 5:37
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