Homolytic pathways drive peroxynitrite-dependent trolox C oxidation

Chemical Research in Toxicology

Volumn 17, Issue 10, 2004, Pages 1377-1384

  Botti, Horacio ^a   Trujillo, Madia ^a   Batthyány, Carlos ^a   Rubbo, Homero ^a   Ferrer Sueta, Gerardo ^a   Radi, Rafael ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL; ANION; CARBON DIOXIDE; CARBONIC ACID; FREE RADICAL; HYDROXYL GROUP; METHIONINE; METHIONINE SULFOXIDE; NITRIC OXIDE; NITROGEN DIOXIDE; OXIDIZING AGENT; PEROXYNITRITE; PHENOL DERIVATIVE; QUINONE DERIVATIVE; RADICAL; SUPEROXIDE; TROLOX C; TROLOX C QUINONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON SPIN RESONANCE; HOMOLYSIS; HOMOLYTIC PATHWAY; IN VIVO STUDY; KINETICS; OXIDATION; PROTON TRANSPORT; REACTION ANALYSIS; SEQUENTIAL ANALYSIS; SPECTROPHOTOMETRY; STOPPED FLOW SPECTROPHOTOMETRY; TOXICITY;

ALPHA-TOCOPHEROL; ANTIOXIDANTS; CARBON DIOXIDE; CATALYSIS; CHROMANS; HYDROGEN PEROXIDE; KINETICS; NITROGEN OXIDES; OXIDATION-REDUCTION; PEROXYNITROUS ACID; PHENOLS;

EID: 6344265444     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx034269i     Document Type: Article

References (84)

1. Huie, R. E., and Padmaja, S. (1993) The reaction of NO with superoxide. Free Radical Res. Commun. 18, 195-199.
2. .: A pulse radiolysis study. Free Radical Biol. Med. 19, 505-510.
3. Kobayashi, K., Miki, M., and Tagawa, S. (1995) Pulse-radiolysis study of the reaction of nitric oxide with superoxide. J. Chem. Soc. Dalton Trans. 17, 2885-2890.
4. Kissner, R., Nauser, T., Bugnon, P., Lye, P. G., and Koppenol, W. H. (1997) Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis. Chem. Res. Toxicol. 10, 1285-1292.
5. Nauser, T., and Koppenol, W. H. (2002) The rate constant of the reaction of superoxide with nitrogen monoxide: Approaching the diffusion limit. J. Phys. Chem. 106, 4084-4086.
6. Lymar, S. V., and Poskrebyshev, G. A. (2003) Rate of ON-OO - Bond homolysis and the Gibbs energy of formation of peroxynitrite. J. Phys. Chem. A 107, 7991-7996.
7. Radi, R., Denicola, A., Alvarez, B., Ferrer, G., and Rubbo, H. (2000) In Nitric Oxide Biology and Pathobiology (Ignarro, L. J., Ed.) pp 57-82, Academic Press, San Diego.
8. Anbar, M., and Taube, H. (1954) Interaction of nitrous acid with hydrogen peroxide and with water. J. Am. Chem. Soc. 76, 6243.
9. Mahoney, L. R. (1970) Evidence for the formation of hydroxyl radicals in the isomerization of pernitrous acid to nitric acid in aqueous solution. J. Am. Chem. Soc. 92, 5262-5263.
10. Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., 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.
11. 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-L722.
12. 2 radicals. Chem. Res. Toxicol. 11, 712-713.
13. Coddington, J. W., Hurst, J. K., and Lymar, S. V. (1999) Hydroxyl radical formation during peroxynitrous acid decomposition. J. Am. Chem. Soc. 121, 2438-2443.
14. Lehnig, M. (1999) Radical mechanisms of the decomposition of peroxynitrite and the peroxynitrite-CO(2) adduct and of reactions with L-tyrosine and related compounds as studied by (15)N chemically induced dynamic nuclear polarization. Arch. Biochem. Biophys. 368, 303-318.
15. Gerasimov, O. V., and Lymar, S. V. (1999) The yield of hydroxyl radical from the decomposition of peroxynitrous acid. Inorg. Chem. 38, 4317-4321.
16. Hodges, G. R., and Ingold, K. U. (1999) Cage-escape of geminate radical pairs can produce peroxynitrate from peroxynitrite under a wide variety of experimental conditions. J. Am. Chem. Soc. 121, 10695-10701.
17. Coddington, J. W., Wherland, S., and Hurst, J. K. (2001) Pressure dependence of peroxynitrite reactions. Support for a radical mechanism. Inorg. Chem. 40, 528-532.
18. Lymar, S. V., Khairutdinov, R. F., and Hurst, J. K. (2003) Hydroxyl radical formation by O-O bond homolysis in peroxynitrous acid. Inorg. Chem. 42, 5259-5266.
19. Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of Superoxide and nitric oxide. J. Biol. Chem. 266, 4244-4250.
20. Radi, R. (1998) Peroxynitrite reactions and diffusion in biology. Chem. Res. Toxicol. 11, 720-721.
21. 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.
22. Radi, R., Cosgrove, T. P., Beckman, J. S., and Freeman, B. A. (1993) Peroxynitrite-induced luminol chemiluminescence. Biochem. J. 290, 51-57.
23. Lymar, S. V., and Hurst, J. K. (1998) Inorg. Chem. 37, 294-301.
24. Goldstein, S., and Czapski, G. (1998) J. Am. Chem. Soc. 120, 3458-3463.
25. Bonini, M. G., Radi, R., Ferrer-Sueta, G., Ferreira, A. M., and Augusto, O. (1999) Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide. J. Biol. Chem. 274, 10802-10806.
26. Lymar, S. V., Jiang, Q., and Hurst, J. K. (1996) Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry. 35, 7855-7861.
27. 2 adduct. Chem. Res. Toxicol. 10, 1216-1220.
28. Goldstein, S., Czapski, G., Lind, J., and Merényi, G. (2001) Carbonate radical ion is the only observable intermediate in the reaction of peroxynitrite with CO(2). Chem. Res. Toxicol. 14, 1273-1276.
29. Esterbauer, H., Puhl, H., Dieber-Rotheneder, M., Waeg, G., and Rabl, H. (1991) Effect of antioxidants on oxidative modification of LDL. Ann. Med. 23, 573-581.
30. Liebler, D. C. (1993) The role of metabolism in the antioxidant function of vitamin E. Crit. Rev. Toxicol. 23, 147-169.
31. Buettner, G. R. (1993) The pecking order of free radicals and antioxidants: Lipid peroxidation, alpha-tocopherol, and ascorbate. Arch. Biochem. Biophys. 300, 535-543.
32. de Groot, H., Hegi, U., and Sies, H. (1993) Loss of alpha-tocopherol upon exposure to nitric oxide or the sydnonimine SIN-1. FEBS Lett. 315, 139-142.
33. Cooney, R. V., Franke, A. A., Harwood, P. J., Hatch-Pigott, V., Custer, L. J., and Mordan, L. J. (1993) Gamma-tocopherol detoxification of nitrogen dioxide: superiority to alpha-tocopherol. Proc. Natl. Acad. Sci. U.S.A. 90, 1771-1775.
34. Hogg, N., Joseph, J., and Kalyanaraman, B. (1994) The oxidation of alpha-tocopherol and trolox by peroxynitrite. Arch. Biochem. Biophys. 314, 153-158.
35. 2 and their formation in rat insulinoma (RINmSF) cells. Free Radical Biol. Med. 19, 259-269.
36. Christen, S., Woodall, A. A., Shigenaga, M. K., Southwell-Keely, P. T., Duncan, M. W., and Ames, B. N. (1997) Gamma-tocopherol traps mutagenic electrophiles such as NO(X) and complements alpha-tocopherol: Physiological implications. Proc. Natl. Acad. Sci. USA 94, 3217-3222.
37. Hoglen, N. C., Waller, S. C., Sipes, I. G., and Liebler, D. C. (1997) Reactions of peroxynitrite with γ-tocopherol. Chem. Res. Toxicol. 10, 401-407.
38. Priyadarsini, K. I., Kapoor, S., and Naik, D. B. (2001) One- and two-electron oxidation reactions of troloxby peroxynitrite. Chem. Res. Toxicol. 14, 567-571.
39. Ramezanian, M. S., Padmaja, S., and Koppenol, W. H. (1996) Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem. Res. Toxicol. 9, 232-240.
40. Alvarez, B., Ferrer-Sueta, G., Freeman, B. A., and Radi, R. (1999) Kinetics of peroxynitrite reaction with amino acids and human serum albumin. J. Biol. Chem. 274, 842-848.
41. Tibi, S., and Koppenol, W. H. (2000) Reactions of peroxynitrite with phenolic and carbonilic compounds: Flavonoids are not scavengers of peroxynitrite. Helv. Chim. Acta 83, 2412-2424.
42. 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.
43. Schopfer, F., Riobo, N., Carreras, M. C., Alvarez, B., Radi, R., Boveris, A., Cadenas, E., and Poderoso, J. J. (2000) Oxidation of ubiquinol by peroxynitrite: Implications for protection of mitochondria against nitrosative damage. Biochem. J. 349, 35-42.
44. Upston, J. M., Terentis, A. C., and Stocker, R. (1999) Tocopherol-mediated peroxidation of lipoproteins: Implications for vitamin E as a potential antiatherogenic supplement. FASEB J. 13, 977-994.
45. Terentis, A. C., Thomas, S. R., Burr, J. A., Liebler, D. C., and Stocker, R. (2002) Vitamin E oxidation in human atherosclerotic lesions. Circ. Res. 90, 333-339.
46. Botti, H., Batthyany, C., Trostchansky, A., Radi, R., Freeman, B. A., and Rubbo, H. (2004) Peroxynitrite-mediated alpha-tocopherol oxidation in low-density lipoprotein: A mechanistic approach. Free Radical Biol. Med. 36, 152-162.
47. Hughes, M. N., and Nicklin, H. G. (1968) The chemistry of pernitrites. Part I. Kinetics of decomposition of pernitrous acid. J. Chem. Soc. 450-452.
48. Radi, R., Denicola, A., and Freeman, B. A. (1999) Peroxynitrite reactions with carbon dioxide-bicarbonate. Methods Enzymol. 301, 353-367.
49. Davies, M. J., Forni, L. G., and Willson, R. L. (1988) Vitamin E analogue Trolox C. E.s.r. and pulse-radiolysis studies of free-radical reactions. Biochem. J. 255, 513-522.
50. Radi, R. (1996) Kinetic analysis of reactivity of peroxynitrite with biomolecules. Methods Enzymol. 269, 354-366.
51. Thomas, M. J., and Bielski, H. J. (1989) Oxidation and reaction of Trolox C, a tocopherol analogue, in aqueous solution. A pulse radyolisis study. J. Am. Chem. Soc. 111, 3315-3319.
52. Perrin, D., and Koppenol, W. H. (2000) The quantitative oxidation of methionine to methionine sulfoxide by peroxynitrite. Arch. Biochem. Biophys. 377, 266-272.
53. Hong, J., and Schoneich, C. (2001) The metal-catalyzed oxidation of methionine in peptides by Fenton systems involves two consecutive one-electron oxidation processes. Free Radical Biol. Med. 31, 1432-1441.
54. Walker, J. M., Ed. (1994) Basic Protein and Peptide Protocols, Humana Press, Totowa, New Jersey.
55. Lipton, S. H., and Bodwell, C. E. (1976) Specific oxidation of methionine to methionine sulfoxide by dimethyl sulfoxide. J. Agric. Food Chem. 24, 26-31.
56. Gilbert, B. C., Kamp, W. J., Lindsay Smith, J. R., and Oakes, J. (1997) EPR evidence for one-electron oxidation of phenols by a dimeric manganese(IV/IV) triazacyclononane complex in the presence and absence of hydrogen peroxide. J. Chem. Soc. Perkin Trans. 2 11, 2161-2165.
57. -): An EPR and spin trapping study. Free Radical Biol. Med. 26, 669-678.
58. Hoglen, N. C., Waller, S. C., Sipes, I. G., and Liebler, D. C. (1997) Reactions of peroxynitrite with γ-tocopherol. Chem. Res. Toxicol. 10, 401-407.
59. Halfpenny, E., and Robinson, P. L. (1952) The nitration and hydroxylation of aromatic compounds by pernitrous acid. J. Chem. Soc., 939-946.
60. van der Vliet, A., O'Neill, C. A., Halliwell, B., Cross, C. E., and Kaur, H. (1994) Aromatic hydroxylation and nitration of phenylalanine and tyrosine by peroxynitrite. Evidence for hydroxyl radical production from peroxynitrite. FEBS Lett. 339, 89-92.
61. Ross, A. B., Mallard, W. P., Helman, G. V., Huie, R. E., and Neta, P. (1998).
62. Gilbert, B. C., Norman, R. O. C., and Sealy, R. C. (1975) Electron spin resonance studies. Part XLIII. Reaction of dimethyl sulphoxide with the hydroxyl radical. J. Chem. Soc. Perkin Trans. 2 303-308.
63. .OH radicals with sulphoxides. J. Chem. Soc. Perkin Trans. 2 146-153.
64. Goldstein, S., Saha, A., Lymar, S. V., and Czapski, G. (1998) Oxidation of peroxynitrite by inorganic radicals: A pulse radiolysis study. J. Am. Chem. Soc. 120, 5549-5554.
65. 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.
66. Koppenol, W. H. (1998) Peroxynitrite uncloaked? Chem. Res. Toxicol. 11, 716-717.
67. Squadrito, G. L., and Pryor, W. A. (1998) The nature of reactive species in systems that produce peroxynitrite. Chem. Res. Toxicol, 11, 718-719.
68. Romero, N., Denicola, A., Souza, J. M., and Radi, R. (1999) Diffusion of peroxynitrite in the presence of carbon dioxide. Arch. Biochem. Biophys. 368, 23-30.
69. Khairutdinov, R. F., Coddington, J. W., and Hurst, J. K. (2000) Permeation of phospholipid membranes by peroxynitrite. Biochemistry 39, 14238-14249.
70. Zhang, H., Joseph, J., Feix, J., Hogg, N., and Kalyanaraman, B. (2001) Nitration and oxidation of a hydrophobic tyrosine probe by peroxynitrite in membranes: Comparison with nitration and oxidation of tyrosine by peroxynitrite in aqueous solution. Biochemistry 40, 7675-7686.
71. Czapski, G., Lymar, S. V., and Scharz, H. A. (1999) Acidity of the carbonate radical. J. Phys. Chem. A 103, 3447-3450.
72. Yoshida, Y., and Niki, E. (2002) Antioxidant effects of alpha- and gamma-carboxyethyl-6-hydroxychromans. Biofactors 16, 93-103.
73. Betancor-Fernandez, A., Sies, H., Stahl, W., and Polidori, M. C. (2002) In vitro antioxidant activity of 2,5,7,8-tetramethyl-2-(2′-carboxyethyl)- 6-hydroxychroman (alpha-CEHC), a vitamin E metabolite. Free Radical Res. 36, 915-921.
74. Mickle, D. A., Li, R. K, Weisel, R. D., Birnbaum, P. L., Wu, T. W., Jackowski, G., Madonik, M. M., Burton, G. W., and Ingold, K. U. (1989) Myocardial salvage with trolox and ascorbic acid for an acute evolving infarction. Ann Thorac. Surg. 47, 553-557.
75. Tan, S., Liu, Y. Y., Nielsen, V. G., Skinner, K., Kirk, K. A., Baldwin, S. T., and Parks, D. A. (1996) Maternal infusion of antioxidants (Trolox and ascorbic acid) protects the fetal heart in rabbit fetal hypoxia. Pediatr. Res. 39, 499-503.
76. Hosomi, A., Arita, M., Sato, Y., Riyose, C., Ueda, T., Igarashi, O., Arai, H., and Inoue, K. (1997) Affinity for alpha-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogues. FEBS Lett. 409, 105-108.
77. Radi, R. (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl. Acad. Sci. U.S.A. 101, 4003-4008.
78. Briviba, K, Kissner, R., Koppenol, W. H., and Sies, H. (1998) Kinetic study of the reaction of glutathione peroxidase with peroxynitrite. Chem. Res. Toxicol. 11, 1398-1401.
79. Mehl, M., Daiber, A., Herold, S., Shoun, H., and Ullrich, V. (1999) Peroxynitrite reaction with heme proteins. Nitric Oxide 3, 142-152.
80. Bailly, F., Zoete, V., Vamecq, J., Catteau, J. P., and Bernier, J. L. (2000) Antioxidant actions of ovothiol-derived 4-mercaptoimidazoles: Glutathione peroxidase activity and protection against peroxynitrite-induced damage. FEBS Lett. 486, 19-22.
81. Ferrer-Sueta, G., Ruiz-Ramirez, L., and Radi, R. (1997) Ternary copper complexes and manganese (III) tetrakis(4-benzoic acid) porphyrin catalyze peroxynitrite-dependent nitration of aromatics. Chem. Res. Toxicol. 10, 1338-1344.
82. Hunt, J. A., Lee, J., and Groves, J. T. (1997) Amphiphilic peroxynitrite decomposition catalysts in liposomal assemblies. Chem. Biol. 4, 845-858.
83. Ferrer-Sueta, G., Batinic-Haberle, I., Spasojevic, I., Fridovich, I., and Radi, R. (1999) Catalytic scavenging of peroxynitrite by isomeric Mn(III) N-methylpyridylporphyrins in the presence of reductants. Chem. Res. Toxicol. 12, 442-449.
84. Daiber, A., Zou, M. H., Bachschmid, M., and Ullrich, V. (2000) Ebselen as a peroxynitrite scavenger in vitro and ex vivo. Biochem. Pharmacol. 59, 153-160.