Advanced search
Publication Cover
Free Radical Research Volume 32, 2000 - Issue 6
Submit an article Journal homepage
55
Views
23
CrossRef citations to date
0
Altmetric
Original Article

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

Vincent Zoete Laboratoire de Chimie Organique Physique associée à l'Ecole Nationale Supérieure de Chimie de Lille, ESA CNRS 8009, Bâtiment C3, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Herve Vezin Centre de Recherche et d'Etudes en Simulations et Modélisation Moléculaire, Bâtiment C5, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Fabrice Bailly Laboratoire de Chimie Organique Physique associée à l'Ecole Nationale Supérieure de Chimie de Lille, ESA CNRS 8009, Bâtiment C3, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Gerard Vergoten Centre de Recherche et d'Etudes en Simulations et Modélisation Moléculaire, Bâtiment C5, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Jean-Pierre Catteau Laboratoire de Chimie Organique Physique associée à l'Ecole Nationale Supérieure de Chimie de Lille, ESA CNRS 8009, Bâtiment C3, UST Lille I, 59655, Villeneuve d'Ascq, France
&
Jean-Luc Bernier Centre de Recherche et d'Etudes en Simulations et Modélisation Moléculaire, Bâtiment C5, UST Lille I, 59655, Villeneuve d'Ascq, France
Pages 525-533 | Received 05 Jul 1999, Published online: 07 Jul 2009

References

  • Zoete V., Bailly F., Catteau J.P., Bernier J.L. Design, synthesis and antioxidant properties of ovothiolderived 4-mercaptoimidazoles. Journal of the Chemical Society, Perkin Trans. 1997; 1: 2983–2988
  • Ruiz J., Pérez A., Pouplana R. QSAR study of phenols: relation between the phenoxyl radical formation and the antiinflammatory activity via an antioxidant mechanism. Quantitative Structure-Activity Relationship 1996; 15: 219–223
  • Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. AM1: a new general purpose quantum mechanical molecular model. Journal of the American Chemical Society 1985; 107: 3902–3909
  • Holler T.P., Hopkins P.B. Ovothiols as free radical scavengers and the mechanism of ovothiolpromoted NAD(P)H-O2 oxidoreductase activity. Biochemistry 1990; 29: 1953–1961
  • So S.-S., Karplus M. Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 1. Method and validations. Journal of Medicinal Chemistry 1997; 40: 4347–4359
  • Bradbury J.R., Masters A.F., McDonell A.C., Brunette A.A., Bond A.M., Wedd A.G. Redox properties of thiolate compounds of oxomolybdenum (V) and their tungsten and selenium analogues. Journal of the American Chemical Society 1981; 103: 1959–1964
  • Josephy P.D., Rehorek D., Janzen E.G. Electron spin resonance spin trapping of thiyl radicals from the decomposition of thionitrites. Tetrahedron Letters 1984; 25: 1685–1688
  • Ito O., Matsuda M. Flash photolysis study for substituent and solvent effects on spin-trapping rates of phenylthiyl radicals with nitrones. Bulletin of the Chemical Society of Japan 1984; 57: 1745–1749
  • Holler T.P., Hopkins P.B. Ovothiols as biological antioxidants. The thiol groups of ovothiol and glutathione are chemically distinct. Journal of the American Chemical Society 1988; 110: 4837–4840
  • Marjanovic B., Simic M.G., Jovanovic S.V. Heterocyclic thiols as antioxidants: why ovothiol C is a better antioxidant than ergothioneine. Free Radical Biology and Medicine 1995; 18: 679–685
  • Weaver K.H., Rabenstein D.L. Thiol/disulfide exchange reactions of ovothiol A with glutathione. Journal of Organic Chemistry 1995; 60: 1904–1907

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.