The reactivity of hypotaurine and cysteine sulfinic acid with peroxynitrite

Advances in Experimental Medicine and Biology

Volumn 583, Issue , 2006, Pages 15-24

  Fontana, Mario ^a   Duprè, Silvestro ^c   Pecci, Laura ^a,b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CNR   (Italy)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84934434513     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-0-387-33504-9_2     Document Type: Conference Paper

References (33)

1. Alvarez, J. G. and Storey, B. T., 1983, Taurine, hypotaurine, epinephrine and albumin inhibit lipid peroxidation in rabbit spermatozoa and protect against loss of motility, Biol. Reprod. 29:548.
2. Aruoma, O. I., Halliwell, B., Hoey, B. M., and Butler, J., 1988, The antioxidant action of taurine, hypotaurine and their metabolic precursor, Biochem. J. 256:251.
3. Augusto, O., Bonini, M. G., Amanso, A. M., Linares, E., Santos, C. C. X., and De Menezes, S. L., 2002, Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology, Free Radic. Biol. Med. 32:841.
4. Beckman, J. S., Chen, J., Ischiropoulos, H., and Crow, J. P., 1994, Oxidative chemistry of peroxynitrite, Methods Enzymol. 233:229.
5. Eiserich, J. P., Patel, R. P., and O'Donnel, V. B., 1998, Pathophysiology of nitric oxide and related species: free radical reactions and modification of biomolecules, Mol. Aspects Med. 19:221.
6. Fellman, J. H., Green, T. R., and Eicher, A. L., 1987, The oxidation of hypotaurine to taurine: bis-aminoethyl-α-disulfone, a metabolic intermediate in mammalian tissue, Adv. Exp. Med. Biol. 217:39.
7. Fontana, M., Pecci, L., Duprè, S., and Cavallini, D., 2004, Antioxidant properties of sulfinates: protective effect of hypotaurine on peroxynitrite-dependent damage, Neurochem. Res. 29:111.
8. Fontana, M., Amendola, D., Orsini, E., Boffi, A., and Pecci, L., 2005, Oxidation of hypotaurine and cysteine sulphinic acid by peroxynitrite, Biochem. J. 389:233.
9. Giles, G. I., Tasker, K. M., and Jacob, C., 2001, Hypothesis: the role of reactive sulfur species in oxidative stress, Free Radic. Biol. Med. 31:1279.
10. Green, T. R., Fellman, J. H., and Eicher, A. L., 1985, Myeloperoxidase oxidation of sulfur-centered and benzoic acid hydroxyl radical scavengers, FEBS Lett. 192:33.
11. Green, T. R., Fellman, J. H., Eicher, A. L., and Pratt, K. L., 1991, Antioxidant role and subcellular location of hypotaurine and taurine in human neutrophils, Biochim. Biophys. Acta 1073:91.
12. Green, T. R. and Fellman, J. H., 1994, Effect of photolytically generated riboflavin radicals and oxygen on hypotaurine antioxidant free radical scavenging activity, Adv. Exp. Med. Biol. 359:19.
13. Harman, L. S., Mottley, C., and Mason, R. P., 1984, Free radical metabolites of L-cysteine oxidation, J. Biol. Chem. 259:5609.
14. Hirschberger, L. L., De la Rosa, J., and Stipanuk, M., 1985, Determination of cysteinesulfinate, hypotaurine and taurine in physiological samples by reversed-phase high-performance liquid chromatography, J. Chromatogr. B 343:303.
15. Holmes, R. P., Goodman, H. O., Shihabi, Z. K., and Jarow, J. P., 1992, The taurine and hypotaurine content of human semen, J. Androl. 13:289.
16. Huie, R. E. and Padmaja, S., 1993, The reaction of NO with superoxide, Free Rad. Res. Commun. 18:195.
17. Huxtable, R. J., 1992, Physiological actions of taurine, Physiol. Rev. 72:101.
18. Jourd'heuil, D., Jourd'heuil, F. L., and Feelisch, M., 2003, Oxidation and nitrosation of thiols at low micromolar exposure to nitric oxide. Evidence for a free radical mechanism, J. Biol. Chem. 278:15720.
19. Karoui, H., Hogg, N., Fréjaville, C., Tordo, P., and Kalyanaraman, B., 1996 Characterization of sulfur-centered radical intermediates formed during the oxidation of thiols and sulfite by peroxynitrite. ESR-spin trapping and oxygen uptake studies, J. Biol. Chem. 271:6000.
20. Kissner, R., and Koppenol, W. H., 2002, Product distribution of peroxynitrite decay as function of pH, temperature, and concentration, J. Am. Chem. Soc. 124:234.
21. Koppenol, W. H., Moreno J. J., Pryor W. A., Ischiropoulos H., and Beckman, J. S., 1992, Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide, Chem. Res. Toxicol. 5:834.
22. Learn, D. B., Fried, V. A., and Thomas, E. L., 1990, Taurine and hypotaurine content of human leukocytes, J. Leukoc. Biol. 48:174.
23. Mottley, C. and Mason, R. P., 1988, Sulfate anion radical formation by the peroxidation of (bi)sulfite and its reaction with hydroxyl radical scavengers, Arch. Biochem. Biophys. 267:681.
24. Pasantes-Morales, H., Klethi, J., Ledig, M., and Mandel, P., 1972, Free amino acids of chicken and rat retina, Brain Res. 41:494.
25. Pecci, L., Costa, M., Montefoschi, G., Antonucci, A., and Cavallini, D., 1999, Oxidation of hypotaurine to taurine with photochemically generated singlet oxygen: the effect of azide, Biochem. Biophys. Res. Commun. 254:661.
26. Pryor, W. A. and Squadrito, G. L., 1995, The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide, Am. J. Physiol. 268:L699.
27. Radi, R., Peluffo, G., Alvarez, M. N., Naviliat, M., and Cayota, A., 2001, Unraveling peroxynitrite formation in biological system, Free Radic. Biol. Med. 30:463.
28. Ricci, G., Duprè, S., Federici, G., Spoto, G., Matarese, R. M., and Cavallini, D., 1978, Oxidation of hypotaurine to taurine by ultraviolet irradiation, Physiol. Chem. Phys. 10:435.
29. Schöneich, C., Dillinger, U., von Bruchhausen, F., and Asmus, K.-D., 1992, Oxidation of polyunsaturated fatty acids and lipids through thiyl and sulfonyl radicals: reaction kinetics, and influence of oxygen and structure of thiyl radicals, Arch. Biochem. Biophys. 292:456.
30. • from the reaction of cysteine, glutathione and penicillamine thiyl radicals with molecular oxygen, Int. J. Radiat. Biol. 57:65.
31. Stewart, V. C. and Heales, S. J., 2003, Nitric oxide-induced mitochondrial dysfunction: implications for neurodegeneration, Free Radic. Biol. Med. 34:287.
32. Tadolini, B., Pintus, G., Pinna, G. G., Bennardini, F., and Franconi, F., 1995, Effects of taurine and hypotaurine on lipid peroxidation, Biochem. Biophys. Res. Commun. 213:820.
33. Wright, C. E., Tallan, H. H., Lin, Y. Y., and Gaull, G. E., 1986, Taurine: biological update, Annu. Rev. Biochem. 55:427.