Reactive sulfur species: Kinetics and mechanism of the oxidation of cystine by hypochlorous acid to give N,N′-dichlorocystine

Chemical Research in Toxicology

Volumn 18, Issue 6, 2005, Pages 919-923

  Nagy, Péter ^a   Ashby, Michael T ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORAMINE DERIVATIVE; CYSTINE; HYPOCHLOROUS ACID; N N' DICHLOROCYSTINE; REACTIVE SULFUR SPECIES; UNCLASSIFIED DRUG;

ARTICLE; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION;

CYSTEINE; CYSTINE; HYPOCHLOROUS ACID; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION;

EID: 21144457596     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050079r     Document Type: Article

References (24)

1. Stocker, R., and Keaney, J. F., Jr. (2004) Role of oxidative modifications in atherosclerosis. Physiol. Rev. 84, 1381-1478.
2. Schwenke, D. C. (1998) Antioxidants and atherogenesis. J. Nutr. Biochem. 9, 424-445.
3. Aviram, M. (2000) Review of human studies on oxidative damage and antioxidant protection related to cardiovascular diseases. Free Radical Res. 33, S85-S97.
4. Heinecke, J. W. (2003) Oxidative stress: New approaches to diagnosis and prognosis in atherosclerosis. Am. J. Cardiol. 91, 12A-16A.
5. Buettner, G. R. (1993) The pecking order of free radicals and antioxidants: Lipid peroxidation, a-tocopherol, and ascorbate. Arch. Biochem. Biophys. 300, 535-543.
6. Ashby, M. T., Carlson, A. C., and Scott, M. J. (2004) Redox buffering of hypochlorous acid by thiocyanate in physiologic fluids. J. Am. Chem. Soc. 126, 15976-15977.
7. Pattison, D. I., and Davies, M. J. (2001) Absolute rate constants for the reaction of hypochlorous acid with protein side chains and peptide bonds. Chem. Res. Toxicol. 14, 1453-1464.
8. Pattison, D. I., Hawkins, C. L., and Davies, M. J. (2003) Hypochlorous acid-mediated oxidation of lipid components and antioxidants present in low-density lipoproteins: Absolute rate constants, product analysis, and computational modeling. Chem. Res. Toxicol. 16, 439-449.
9. Hawkins, C. L., Pattison, D. I., and Davies, M. J. (2003) Hypochlorite-induced oxidation of amino acids, peptides and proteins. Amino Acids 25, 259-274.
10. Irving, H. M. N. H., Miles, M. G., and Pettit, L. D. (1967) A study of some problems in determining the stoichiometric proton dissociation constants of complexes by potentiometric titrations using a glass electrode. Anal. Chim. Acta 38, 475-488.
11. Walti, M., and Hope, D. B. (1971) Synthesis of the isomers of the mono- and di-hydroxy-analogues of cystine and comparison with metabolites excreted in the urine. J. Chem. Soc. Perkin Trans. 1 12, 2326-2328.
12. Kovacic, P., Lowery, M. K., and Field, K. W. (1970) Chemistry of N-bromamines and N-chloramines. Chem. Rev. 70, 639-665.
13. Lacombe, S. M. (1999) Oxysulfur compounds derived from disulfides: stability and reactivity. Rev. Heteroat. Chem. 21, 1-41.
14. Gerritsen, C. M., and Margerum, D. W. (1990) Nonmetal redox kinetics: Hypochlorite and hypochlorous acid reactions with cyanide. Inorg. Chem. 29, 2757-2762.
15. Fogelman, K. D., Walker, D. M., and Margerum, D. W. (1989) Nonmetal redox kinetics: Hypochlorite and hypochlorous acid reactions with sulfite. Inorg. Chem. 28, 986-993.
16. Kumar, K., and Margerum, D. W. (1987) Kinetics and mechanism of general-acid-assisted oxidation of bromide by hypochlorite and hypochlorous acid. Inorg. Chem. 26, 2706-2711.
17. Adam, L. C., Fabian, I., Suzuki, K., and Gordon, G. (1992) Hypochlorous acid decomposition in the pH 5-8 region. Inorg. Chem. 31, 3534-3541.
18. Martell, A. E., and Smith, R. M. (1989) Crit. Stab. Constants 6 (2nd Suppl.).
19. Gray, E. T., Jr., Margerum, D. W., and Huffman, R. P. (1978) Chloramine equilibriums and the kinetics of disproportionation in aqueous solution, ACS Symp. Ser. 82, 264-277.
20. Snyder, M. P., and Margerum, D. W. (1982) Kinetics of chlorine transfer from chloramine to amines, amino acids, and peptides. Inorg. Chem. 21, 2545-2550.
21. Winterbourn, C. C. (1985) Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant to hypochlorite. Biochim. Biophys. Acta 840, 204-210.
22. Ashby, M. T., and Aneetha, H. (2004) Reactive sulfur species: Aqueous chemistry of sulfenyl thiocyanates. J. Am. Chem. Soc. 126, 10216-10217.
23. Winterbourn, C. C. (1995) Free radical toxicology and antioxidant defense. Clin. Exp. Pharmacol. Physiol. 22, 877-880.
24. Armstrong, D., Ed. (2002) Oxidative Stress Biomarkers and Antioxidant Protocols, Methods in Molecular Biology, Vol. 186, Humana Press, Totowa, NJ.