Inhibition of copper-catalyzed cysteine oxidation by nanomolar concentrations of iron salts

Free Radical Biology and Medicine

Volumn 36, Issue 6, 2004, Pages 757-764

  Munday, Rex ^a   Munday, Christine M ^a   Winterbourn, Christine C ^b  

^a RUAKURA RESEARCH CENTRE   (New Zealand)

^b UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

Assay of iron; Copper catalysis; Cysteine oxidation; Free radicals; Iron inhibition

Indexed keywords

BUFFER; CATALASE; COPPER; CYSTEINE; GLUTATHIONE; GLYCYLGLYCINE; IRON SALT; MERCAPTAMINE; NANOPARTICLE; TRANSITION ELEMENT;

ACCURACY; ACIDITY; ADDITION REACTION; ALKALINITY; ARTICLE; CATALYSIS; CATALYST; CHELATION; CONCENTRATION RESPONSE; CYTOTOXICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; MOLECULE; OXIDATION; PRIORITY JOURNAL; PURIFICATION; REACTION ANALYSIS; REDUCTION KINETICS; TECHNIQUE;

MOPS;

EID: 1342285695     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2003.12.015     Document Type: Article

References (43)

1. Meister A., Anderson M.E. Glutathione. Annu. Rev. Biochem. 52:1983;711-760.
2. Chaudière A., Ferrari-Iliou R. Intracellular antioxidants: from chemical to biochemical mechanisms. Food Chem. Toxicol. 37:1999;949-962.
3. Munday R. Toxicity of thiols and disulphides: involvement of free-radical species. Free Radic. Biol. Med. 7:1989;659-673.
4. Held K.D., Sylvester F.C., Hopcia K.L., Biaglow J.E. Role of Fenton chemistry in thiol-induced toxicity and apoptosis. Radiat. Res. 145:1996;542-553.
5. Nath K.A., Salahudeen A.K. Autoxidation of cysteine generates hydrogen peroxide: cytotoxicity and attenuation by pyruvate. Am. J. Physiol. 264:1993;F306-F314.
6. Jeitner T.M., Lawrence D.A. Mechanisms for the cytotoxicity of cysteamine. Toxicol. Sci. 62:2001;57-64.
7. Stich H.F., Wei L., Lam P. The need for a mammalian test system for mutagens: action of some reducing agents. Cancer Lett. 5:1978;199-201.
8. Reinhardt C.A., Schawalder H., Zbinden G. Cell detachment and cloning efficiency as parameters for cytotoxicity. Toxicology. 25:1982;47-52.
9. Miller D.M., Buettner G.R., Aust S.D. Transition metals as catalysts of "autoxidation" reactions. Free Radic. Biol. Med. 8:1990;95-108.
10. Kachur A.V., Koch C.J., Biaglow J.E. Mechanism of copper-catalyzed autoxidation of cysteine. Free Radic. Res. 31:1999;23-34.
11. Ehrenberg L., Harms-Ringdahl M., Fedorcsák I., Granath F. Kinetics of the copper- and iron-catalysed oxidation of cysteine by dioxygen. Acta Chem. Scand. 43:1989;177-187.
12. Hanaki A., Kamide H. The copper-catalyzed autoxidation of cysteine: the amount of hydrogen peroxide produced under various conditions and the stoichiometry of the reaction. Bull. Chem. Soc. Japan. 56:1983;2065-2068.
13. Hanaki A., Kamide H. Manometric study of the copper-catalyzed oxidation of cysteine. Chem. Pharm. Bull. 19:1971;1006-1010.
14. Nyberg G.K., Granberg G.P.D., Carlsson J. Bovine superoxide dismutase and copper ions potentiate the bactericidal effect of autoxidizing cysteine. Appl. Environ. Microbiol. 38:1979;29-34.
15. Cavallini D., de Marco C., Dupré S., Rotilio G. The copper catalyzed oxidation of cysteine to cystine. Arch. Biochem. Biophys. 130:1969;354-361.
16. Pecci L., Montefoschi G., Musci G., Cavallini D. Novel findings on the copper catalysed oxidation of cysteine. Amino Acids. 13:1997;355-367.
17. Fruton J.S., Clarke H.T. Chemical reactivity of cysteine and its derivatives. J. Biol. Chem. 106:1934;667-691.
18. Elliott K.A.C. On the catalysis of the oxidation of cysteine and thioglycollic acid by iron and copper. Biochem. J. 24:1930;310-326.
19. Biaglow J.E., Issels R.W., Gerweck L.E., Varnes M.E., Jacobson B., Mitchell J.B., Russo A. Factors influencing the oxidation of cysteamine and other thiols: implications for hyperthermic sensitization and radiation protection. Radiat. Res. 100:1984;298-312.
20. Long L.H., Halliwell B. Oxidation and generation of hydrogen peroxide by thiol compounds in commonly used cell culture media. Biochem. Biophys. Res. Commun. 286:2001;991-994.
21. Winterbourn C.C., Peskin A.V., Parsons-Mair H.N. Thiol oxidase activity of copper, zinc superoxide dismutase. J. Biol. Chem. 277:2002;1906-1911.
22. Boeri E., Bonnichsen R.K. Oxidation of thiol groups by catalase. Acta Chem. Scand. 6:1952;968-969.
23. Hanaki A., Kamide H. Acceleration of the copper-catalysed autoxidation of cysteine by ethylenediaminetetraacetic acid and related polyaminopolycarboxylic acids. Chem. Pharm. Bull. 26:1978;325-327.
24. Feldman S.L., Hunter J.S.V., Zgirski A., Chidambaram M.V., Frieden E. Comparison of the catalytic oxidation of cysteine and o-dianisidine by cupric ion and ceruloplasmin. J. Inorg. Biochem. 17:1982;51-60.
25. Sutton H.C., Winterbourn C.C. On the participation of higher oxidation states of iron and copper in Fenton reactions. Free Radic. Biol. Med. 6:1989;53-60.
26. Munday R. Dialuric acid autoxidation: effects of transition metals on the reaction rate and on the generation of "active oxygen" species. Biochem. Pharmacol. 37:1988;409-413.
27. Buettner G.R. In the absence of catalytic metals ascorbate does not autoxidize at pH 7: ascorbate as a test for catalytic metals. J. Biochem. Biophys. Methods. 16:1988;27-40.
28. Ellman G.L. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82:1959;70-77.
29. Hanaki A. An electron spin resonance study of the oxido-reductive interaction of Cu(II)-glycylglycine and cysteine in a neutral aqueous solution. Chem. Lett. 1976;1225-1228.
30. McPhail D.B., Goodman B.A. Tris buffer: a case for caution in its use in copper-containing systems. Biochem. J. 221:1984;559-560.
31. Hanaki A. Kinetic studies on the role of dioxygen in the copper-catalyzed autoxidation of cysteine. Bull. Chem. Soc. Japan. 68:1995;831-837.
32. Kerbele H. The biochemistry of desferrioxamine and its relation to iron metabolism. Ann. NY Acad. Sci. 119:1964;758-768.
33. Winterbourn C.C., Metodiewa D. The reaction of superoxide with reduced glutathione. Arch. Biochem. Biophys. 314:1994;284-290.
34. Blumberg W.E., Peisach J. Bis(thiosemicarbazone) and other nitrogen and sulfur ligated complexes of copper(II). J. Chem. Phys. 49:1968;1793-1802.
35. Vortisch V., Kroneck P., Hemmerich P. Model studies on the coordination of copper in enzymes: IV. Structure and stability of cuprous complexes with sulfur-containing ligands. J. Am. Chem. Soc. 98:1976;2821-2826.
36. Bagiyan G.A., Valeev A.K., Koroleva I.K., Soroka N.V. Complex formation by copper(I) with aminothiols in aqueous solution. Russ. J. Inorg. Chem. 28:1983;1142-1148.
37. 8-chloro-dodeca(D-penicillaminato)-octacuprate(I)hexacuprate(II) n-hydrate. J. Am. Chem. Soc. 99:1977;6890-6899.
38. Issels R.D., Biaglow J.E., Epstein L., Gerweck L.E. Enhancement of cysteamine cytotoxicity by hyperthermia and its modification by catalase and superoxide dismutase in Chinese hamster ovary cells. Cancer Res. 44:1984;3911-3915.
39. Starkebaum G., Harlan J.M. Endothelial cell injury due to copper-catalyzed hydrogen peroxide generation from homocysteine. J. Clin. Invest. 77:1986;1370-1376.
40. White A.R., Multhaup G., Galatis D., McKinstry W.J., Parker M.W., Pipkorn R., Beyreuther K., Masters C.L., Cappai R. Contrasting, species-dependent modulation of copper-mediated neurotoxicity by the Alzheimer's disease amyloid precursor protein. J. Neurosci. 22:2002;365-376.
41. Strausak D., Mercer J.F., Dieter H.H., Stremmel W., Multhaup G. Copper in disorders with neurological symptoms: Alzheimer's, Menkes, and Wilson diseases. Brain Res. Bull. 55:2001;175-185.
42. Munday R. Inhibition of 2,3-dimethyl-1,4-naphthohydroquinone autoxidation by copper and by superoxide dismutase. Free Radic. Biol. Med. 26:1999;1475-1479.
43. Davison A.J., Gee P. Redox state of cytochrome c in the presence of the 6-hydroxydopamine/oxygen couple: oscillations dependent on the presence of hydrogen peroxide or superoxide. Arch. Biochem. Biophys. 233:1984;761-771.