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

Free Radical Research

Volumn 32, Issue 6, 2000, Pages 515-524

  Zoete, Vincent ^a   Bailly, Fabrice ^a   Vezin, Hervé ^a   Teissier, Elisabeth ^b   Duriez, Patrick ^b   Fruchart, Jean Charles ^b   Catteau, Jean Pierre ^a   Bernier, Jean Luc ^a  

^a UNIV LILLE   (France)

^b INSTITUT PASTEUR DE LILLE   (France)

Author keywords

4 Mercaptoimidazoles; Hydrogen peroxide; Hydroxyl radical; Hypochlorous acid; Lipid peroxidation

Indexed keywords

ANTIOXIDANT; IMIDAZOLE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; CHELATION; ELECTRON SPIN RESONANCE; LIPID PEROXIDATION; SCAVENGING SYSTEM;

LETHRINIDAE;

EID: 0034012314     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760000300521     Document Type: Article

References (35)

1. A. Palumbo, M. d'Ishia, C. Misuraca and G. Prota (1982) Isolation and structure of a new sulphur-containing aminoacid from sea urchin eggs. Tetrahedron Letters, 23, 3207-3208.
2. A. Palumbo, G. Misuraca, M. d'Ischia, F. Donaudy and G. Prota (1984) Isolation and distribution of 1-methyl-5-thiol-L-histidine disulphide and a related metabolite in eggs from echinoderms. Comprehensive Biochemical Physiology, 78B, 81-83.
3. 2 oxidoreductase activity on ovoperoxidase. Journal of Biological Chemistry, 261, 13 056-13 063.
4. E. Turner, R. Klevit, L.J. Hager and B.M. Shapiro (1987) Ovothiols: a family of redox-active thiohistidine compounds from marine invertebrate eggs. Biochemistry, 26, 4028-4036.
5. E. Turner, C.E. Somers and B.M. Shapiro (1985) The relationship between a novel NAD(P)H oxidase activity of ovoperoxidase and the CN resistant respiratory burst that follows fertilisation of sea urchin eggs. Journal of Biological Chemistry, 260, 13 163-13 171.
6. 2 oxidoreductase activity. Biochemistry, 29, 1953-1961.
7. B.M. Shapiro and P.B. Hopkins (1991) Ovothiols: biological and chemical perspectives. In: Meister, A. (Ed.), Advances in Enzymology and Related Areas of Molecular Biology, New York: John Wiley and Sons Inc., pp. 291-316.
8. 2 scavenger in sea urchin eggs. Science, 242, 939-941.
9. K.H. Weaver and D.L. Rabenstein (1995) Thiol/disulfide exchange reactions of ovothiol A with glutathione. Journal of Organic Chemistry, 60, 1904-1907.
10. B. Marjanovic, M.G. Simic and S.V. Jovanovic (1995) Heterocyclic thiols as antioxidants: why ovothiol C is a better antioxidant than ergothioneine. Free Radical Biology and Medicine, 18, 679-685.
11. T.P. Holler and P.B. Hopkins (1988) Ovothiols as biological antioxidants. The thiol groups of ovothiol and glutathione are chemically distinct. Journal of the American Chemical Society, 110, 4837-4840.
12. V. Zoete, F. Bailly, J.P. Catteau and J.L. Bernier (1997) Design, synthesis and antioxidant properties of ovothiol-derived 4-mercaptoimidazoles. Journal of the Chemical Society, Perkin Transactions 1, 2983-2988.
13. L. Packer, E.H. Witt and H.J. Tritschler (1995) Alpha-lipoic acid as a biological antioxidant. Free Radical Biology and Medicine, 19, 227-250.
14. V. Misik, I.T. Mak, R.E. Stafford and W.B. Weglicki (1993) Reactions of captopril and epicaptopril with transition metal ions and hydroxyl radicals: an EPR spectroscopy study. Free Radical Biology and Medicine, 15, 611-619.
15. S. Mankhetkorn, Z. Abedinzadeh and C. Houee-Levin (1994) Antioxidant action of sodium diethyldithiocarbamate: reaction with hydrogen peroxide and superoxide radical., Free Radical Biology and Medicine, 17, 517-527.
16. C.A. Rice-Evans and A.T. Diplock (1993) Current status of antioxidant therapy. Free Radical Biology and Medicine, 15, 77-96.
17. G.L. Ellman (1959) Tissue sulfhydryl groups. Archives in Biochemistry and Biophysics, 82, 70-77.
18. G.R. Buettner and R.P. Mason (1990) Spin-trapping methods for detecting superoxide and hydroxyl free radicals in vitro and in vivo. Methods in Enzymology, 186, 127-133.
19. E. Finkelstein, G.M. Rosen and E.J. Ruckman (1980) Spin trapping. Kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. Journal of the American Chemical Society, 102, 4994-4999.
20. R.J. Havel, H.A. Eder and J.H. Bragdon (1955) The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. Journal of Clinical Investigation, 34, 1345-1353.
21. G.A. Peterson (1977) Simplification of the protein assay method of Lowry et al. which is more generally applicable. Analytical Biochemistry, 83, 346-356.
22. H. Esterbauer, G. Striegl, H. Puhl and M. Rotheneder (1989) Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Radical Research Communications, 6, 67-75.
23. E. Walters Laporte, C. Furman, S. Fouquet, F. Martin-Nizard, S. Lestavel, A. Gozzo, D. Lesieur, J.C. Fruchart, P. Duriez and E. Teissier (1998) A high concentration of melatonin inhibits in vitro LDL peroxidation but not oxidized LDL toxicity toward cultured endothelial cells. Journal of Cardiovascular Pharmacology, 32, 582-592.
24. S.J. Weiss (1986) Oxygen, ischemia and inflammation. Acta Physiologica Scandinavica, 548 (Suppl.), 9-37.
25. O.I. Aruoma, B. Halliwell, B.M. Hoey and J. Butler (1989) The antioxidant action of N-acetylcysteine: its reaction with hydrogen peroxide, hydroxyl radical, superoxide, and hypochlorous acid. Free Radical Biology and Medicine, 6, 593-597.
26. A.B. Farhataziz, Ross (1977) Selected specific rates of reaction of transients from water in aqueous solution. III. Hydroxyl radical and perhydroxyl radical and their reaction ions. Natl. Stand. Ref. Data Syst. No 59. Washington: US National Bureau of Standards.
27. M. Rougee, R.V. Bensasson, E.J. Land and R. Pariente (1988) Deactivation of singlet molecular oxygen by thiols and related compounds, possible protectors against skin photosensitivity. Photochemistry and Photobiolog, 47, 485-489.
28. B. Kalyanaraman, H. Karoui, R.J. Singh and C.C. Felix (1996) Detection of thiyl radical adducts formed during hydroxyl radical-and peroxynitrite-mediated oxidation of thiols. A high resolution ESR spin-trapping study at Q-band (35GHz). Analytical Biochemistry, 241, 75-81.
29. O. Ito and M. Matsuda (1984) Flash photolysis study for substituent and solvent effects on spin-trapping rates of phenylthiyl radicals with nitrones. Bulletin of the Chemical Society of Japan, 57, 1745-1749.
30. M.J. Davies, L.G. Forni and S.L. Shuter (1987) Electron spin resonance and pulse radiolysis studies on the spin trapping of sulphur-centered radicals. Chemico-biological Interactions, 61, 177-188.
31. 2+ by dihydrolipoic acid prevents human low density lipoprotein peroxidation. Free Radical Biology and Medicine, 25, 287-297.
32. B. Zieden, D.M. Wuttge, B.E. Karlberg and A.G. Olsson (1995) Effects of in vitro addition of captopril on copper-induced low density lipoprotein oxidation. British Journal of Clinical Pharmacology, 89, 201-203.
33. E.G. Godfrey, J. Stewart, H.J. Dargie, J.L. Reid, M. Dominiczak, C.A. Hamilton and J. Mc Murray (1994) Effects of ACE inhibitors on oxidation of human low density lipoprotein. British Journal of Clinical Pharmacology, 37, 63-66.
34. B. Halvorsen, I. Brude, C.A. Drevon, J. Nysom, L. Ose, E.N. Christiansen and M.S. Nenseter (1996) Effect of homocysteine on copper-ion catalyzed, azo compound-initiated, and mononuclear cell-mediated oxidative modification of low density lipoprotein. Journal of Lipid Research, 37, 1591-1600.
35. 2 production by chelating copper. Archives in Biochemistry and Biophysics, 290, 463-467.