Peroxynitrite-mediated decarboxylation of pyruvate to both carbon dioxide and carbon dioxide radical anion

Chemical Research in Toxicology

Volumn 10, Issue 7, 1997, Pages 786-794

  Vásquez Vivar, Jeannette ^a   Denicola, Ana ^b   Radi, Rafael ^b   Augusto, Ohara ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b DEPARTAMENTO DE BIOQUÍMICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBON DIOXIDE; GLUTATHIONE; PEROXYNITRITE; PYRUVIC ACID;

ANTIOXIDANT ACTIVITY; ARTICLE; DECARBOXYLATION; REACTION ANALYSIS;

ANIONS; CARBON DIOXIDE; CHROMATOGRAPHY, ION EXCHANGE; DECARBOXYLATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; KINETICS; NITRATES; OXIDANTS; OXYGEN CONSUMPTION; PYRUVIC ACID;

EID: 0343580474     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970031g     Document Type: Article

References (55)

1. Stanko, R. T., Mitrakou, A., Greenwalt, K., and Gerich, J. (1990) The effect of dihydroxyacetone and pyruvate on plasma glucose concentration and turnover in noninsulin-dependent diabetes mellitus. Clin. Physiol. Biochem. 8, 283-288.
2. Stanko, R. T., Mullick, P., Clarke, M. R., Contis, L. C., Janosky, J. E., and Ramasastry, S. S. (1994) Pyruvate inhibits grow of mammary carcinoma 13762 in rats. Cancer Res. 54, 1004-1007.
3. 2 in vitro and in vivo and reduce menadione-induced DNA injury and cytotoxicity. Am. J. Physiol. 268, C227-C236.
4. Varma, S. D., and Devamanoharan, P. S. (1995) Oxidative denaturation of lens protein: prevention by pyruvate. Ophthal. Res. 27, 18-22.
5. Yanagida, S., Luo, C. S., Doyle, M., Pohost, G. M., and Pike, M. M. (1995) Nuclear magnetic resonance studies of cationic and energetic alterations with oxidant stress in perfused heart. Modulation with pyruvate and lactate. Circ. Res. 77, 773-783.
6. de Groot, M. J. M., van Helden, M. A. B., de Jong, Y. F., Coumans, W. A., and van der Vusse, G. J. (1995) The influence of lactate, pyruvate and glucose as exogenous substrates on free radical defense mechanisms in isolated rat hearts during ischaemia and reperfusion. Mol. Cell. Biochem. 146, 147-155.
7. O'Donnell-Tormey, J., Nathan, C. F., Lanks, K., DeBoer, C. J., and Harpe, J. (1987) Secretion of pyruvate. An antioxidant defense of mammalian cells. J. Exp. Med. 165, 500-514.
8. Stanko, R. T., Sekas, G., Isaacson, I. A., Clarke, M. R., Billiar, T. R., and Paul, H. S. (1995) Pyruvate inhibits clofibrate-induced hepatic peroxisomal proliferation and free radical production in rats. Metabolism 44, 166-171.
9. Holleman, M. A. F. (1904) Notice sur l'action de léau oxigénée sur les acides acétoniques et sur les dicétones 1.2. Recl. Trav. Chim. Pays-Bas Belg. 23, 169-171.
10. Huie, R. E., and Padmaja, S. (1993) The reaction of NO with superoxide. Free Radical Res. Commun. 18, 195-199.
11. •: A pulse radiolysis study. Free Radical Biol. Med. 19, 505-510.
12. Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. M., and Freeman, B. A. (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. U.S.A. 87, 1620-1624.
13. Beckman, J. S., Ye, Y. Z., Anderson, P., Chen, J., Accavitti, M. A., Tarpey, M. M., and White, C. R. (1994) Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler 375, 81-88.
14. Kooy, N. W., Royall, J. A., Ye, Y. Z., Kelly, D. R., and Beckman, J. S. (1995) Evidence for in vivo peroxynitrite production in human acute lung injury. Am. J. Resp. Crit. Care Med. 151, 1250-1254.
15. Giorgio, S., Linares, E., Capurro, M. de L., de Bianchi, A. G., and Augusto, O. (1996) Formation of nitrosyl hemoglobin and nitrotyrosine during murine leishmaniasis. Photochem. Photobiol. 63, 750-754.
16. 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, 834-841.
17. 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. (Lung Cell Mol. Physiol.) 268, 699-722.
18. Goldstein, S., Squadrito, G. L., Pryor, W. A., and Czapski, G. (1996) Direct and indirect oxidations by peroxynitrite, neither involving the hydroxyl radical. Free Radical Biol. Med. 21, 965-974.
19. Pryor, W. A., Jin, X., and Squadrito, G. L. (1994) One- and two-electron oxidations of methionine by peroxynitrite. Proc. Natl. Acad. Sci. U.S.A. 91, 11173-11177.
20. Augusto, O., Gatti, R. M., and Radi, R. (1994) Spin-trapping studies of peroxynitrite decomposition and of 3-morpholinosydnonimine N-ethylcarbamide autoxidation: direct evidence for metal-independent formation of free radical intermediates. Arch. Biochem. Biophys. 310, 118-125.
21. Vásquez-Vivar, J., Santos, A. M., Junqueira, V. B. C., and Augusto, O. (1996) Peroxynitrite-mediated formation of free radicals in human plasma: EPR detection of ascorbyl, albuminthiyl and uric acid-derived free radicals. Biochem. J. 314, 869-876.
22. Quijano, C., Alvarez, B., Gatti, R. M., Augusto, O., and Radi, R. (1997) Pathways of peroxynitrite oxidation of thiol groups. Biochem. J. 322, 167-173.
23. Lymar, S. V., and Hurst, J. K. (1995) Rapid reaction between peroxynitrite ion and carbon dioxide: implications for biological activity. J. Am. Chem. Soc. 117, 8867-8868.
24. Uppu, R. M., Squadrito, G. L., and Pryor, W. A. (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 372, 335-343.
25. Lymar, S. V., Jiang, Q., and Hurst, J. K. (1996) Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35, 7855-7861.
26. Denicola, A., Freeman, B. A., Trujillo, M., and Radi, R. (1996) Peroxynitrite reaction with carbon dioxide/bicarbonate: kinetics and influence on peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 333, 49-58.
27. Edwards, J. O., and Plumb, R. C. (1994) The chemistry of peroxonitrites. Prog. Inorg. Chem. 41, 599-635.
28. Augusto, O., Radi, R., Gatti, R. M., and Vásquez-Vivar, J. (1996) Detection of secondary radicals from peroxynitrite-mediated oxidations by electron spin resonance. Methods Enzymol. 269 (Part B), 346-354.
29. Beckman, J. S., Chen, J., Ischiropoulos, H., and Crow, J. P. (1994) Oxidative chemistry of peroxynitrite. Methods Enzymol. 233, 229-250.
30. Pryor, W. A., Cueto, R., Jin, X., Koppenol, W. H., Ngu-Schwemlein, M., Squadrito, G. L., Uppu, P. L., and Uppu, R. M. (1995) A practical method for preparing peroxynitrite solutions of low ionic strength and free of hydrogen peroxide. Free Radical Biol. Med. 18, 75-83.
31. Radi, R., Turrens, J. F., Chang, L. Y., Bush, K. M., Crapo, J. D., and Freeman, B. A. (1991) Detection of catalase in rat heart mitochondria. J. Biol. Chem. 266, 22028-22034.
32. Robinson, J., and Cooper, J. M. (1970) Method of determining oxygen concentration in biological media, suitable for calibrations of the oxygen electrode. Anal. Biochem. 33, 390-399.
33. Alvarez, B., Denicola, A., and Radi, R. (1995) Reaction between peroxynitrite and hydrogen peroxide: formation of oxygen and slowing of peroxynitrite decomposition. Chem. Res. Toxicol. 8, 859-864.
34. Squadrito, G. L., Jin, X., and Pryor, W. A. (1995) Stopped-flow kinetic study of the reaction of ascorbic acid with peroxynitrite. Arch. Biochem. Biophys. 322, 53-59.
35. Alvarez, B., Rubbo, H., Kirk, M., Barnes, S., Freeman, B. A., and Radi, R. (1996) Peroxynitrite dependent tryptophan nitration. Chem. Res. Toxicol. 9, 390-396.
36. Darley, K. S. (1978) Ph.D. Dissertation, University of Toronto; Dis. Abstr. Int. B93, 3428 (1979).
37. Lemercier, J. N., Squadrito, G. L., and Pryor, W. A. (1995) Spintrap studies on the decomposition of peroxynitrite. Arch. Biochem. Biophys. 321, 31-39.
38. Pou, S., Nguyen, S. Y., Gladwell, T., and Rosen, G. M. (1995) Does peroxynitrite generate hydroxyl radical? Biochim. Biophys. Acta 1244, 62-68.
39. 2+ in the presence of veratryl alcohol, malonic or oxalic acid, and oxygen. Biochemistry 29, 10475-10480.
40. 4 in the perfused rat liver in vivo. J. Biol. Chem. 261, 4542-4548.
41. 2 peroxidizing systems. J. Biol. Chem. 260, 4003-4006.
42. Buettner, G. R., and Mason, R. P. (1990) Spin-trapping methods for detecting superoxide and hydroxyl free radicals in vitro and in vivo. Methods Enzymol. 186, 127-133.
43. Koppenol, W. H. (1994) Chemistry of iron and copper in radical reactions. In Free Radical Damage and Its Control (Rice-Evans, C. A., and Burdon, R. H., Eds.) pp 3-24, Elsevier Science B.V., London.
44. Finkelstein, E., Rosen, G. M., and Rauckman, E. J. (1980) Spin trapping. Kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. J. Am. Chem. Soc. 102, 4994-4999.
45. Kraljic, I. (1967) Kinetics of OH radical reactions in radiolysis, photolysis and the Fenton system. In The Chemistry of Ionization and Excitation (Johnson, G. R. A., and Scholes, G., Eds.) pp 302-309, Taylor B. Francis Ltd., London.
46. Adams, G. E., and Wilson, R. L. (1969) Pulse radiolysis studies on the oxidation of organic radicals in aqueous solution. Trans. Faraday Soc. 65, 2981-2987.
47. Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite-induced membrane lipid peroxidation: cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288, 481-487.
48. Steenken, S., Sprague, E. D., and Schulte-Frohlinde, D. (1975) Photofragmentation of α-oxocarboxylic acids in aqueous solution. An EPR study. Formation of semidione radicals by decarboxylative substitution of α-oxocarboxylic acids by acyl radicals-I: glyoxilic, pyruvic, α-oxocarbutyric, α-oxoglutaric and α-oxoisocaproic acids. Photochem. Photobiol. 22, 19-27.
49. 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. J. Biol. Chem. 271, 6000-6009.
50. Karoui, H., Hogg, N., Joseph, J., and Kalyanaraman, B. (1996) Effect of superoxide dismutase mimics on radical adduct formation during the reaction between peroxynitrite and thiols-An ESR-spin trapping study. Arch. Biochem. Biophys. 330, 115-124.
51. 2. Biochem. J. 252, 913-915.
52. Siegel, B., and Lanphear, J. (1979) Kinetics and mechanisms for the acid-catalyzed oxidative decarboxylation of benzoylformic acid. J. Org. Chem. 44, 942-946.
53. Bernardi, R., Caronna, T., Galli, R., Minisci, F., and Perchinunno, M. (1973) Nucleophilic character of carbon free radicals a new convenient, selective carbozylation of heteroaromatic bases. Tetrahedron Lett. 9, 645-648.
54. Hems, D. A., and Brosnan, J. T. (1970) Effect of ischaemia on content of metabolites in rat liver and kidney in vivo. Biochem. J. 120, 105-111.
55. Aw, T. Y., Andersson, B. S., and Jones, D. P. (1987) Mitochondrial transmembrane ion distribution during anoxia. Am. J. Physiol. 252 (Cell Physiol. 21), C356-C361.