Peroxynitrite: An endogenous oxidizing and nitrating agent

Cellular and Molecular Life Sciences

Volumn 55, Issue 8-9, 1999, Pages 1068-1077

  Ducrocq, C ^a   Blanchard, B ^a   Pignatelli, B ^b   Ohshima, H ^b  

^a CNRS   (France)

^b INTERNATIONAL AGENCY FOR RESEARCH ON CANCER   (France)

Author keywords

Nitric oxide; Oxidative stress; Oxoperoxonitrate; Peroxynitrite; Superoxide

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; CYSTEINE; HEMOPROTEIN; METHIONINE; NITRIC OXIDE; PEROXYNITRITE; SELENIUM; SUPEROXIDE; TRYPTOPHAN; TYROSINE; URATE;

ANIMAL CELL; BIOSYNTHESIS; DNA MODIFICATION; HUMAN; HUMAN CELL; HYDROXYLATION; MEDIATOR; METABOLISM; NITRATION; NONHUMAN; OXIDATION; OXIDATIVE STRESS; REVIEW; TISSUE INJURY;

EID: 0032800690     PISSN: 1420682X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s000180050357     Document Type: Review

References (114)

1. 1 Kanner J., Harel S. and Granit R. (1991) Nitric oxide as an antioxidant. Arch. Biochem. Biophys. 289: 130-136
2. 2 Wink D. A., Hanbauer I., Krishna M. C., DeGraff W., Gamson J. and Mitchell J. B. (1993) Nitric oxide protects against cellular damage and cytotoxicity from reactive oxygen species. Proc. Natl. Acad. Sci. USA 90: 9813-9817
3. 3 Yoshie Y. and Ohshima H. (1997) Nitric oxide synergistically enhances DNA strand breakage induced by polyhydroxyaromatic compounds, but inhibits that induced by the Fenton-reaction. Arch. Biochem. Biophys. 342: 13-21
4. 4 Wink D. A. and Mitchell J. B. (1998) Chemical biology of nitric oxide: insights into regulatory, cytotoxic and cytoprotective mechanisms of nitric oxide. Free Radic. Biol. Med. 25: 434-456
5. 5 Beckman J. S. and Crow J. P. (1993) Pathological implications of NO, superoxide and peroxynitrite formation. Biochem. Soc. Trans. 21: 330-334
6. 6 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
7. 7 Demiryürek A. T., Cakici I. and Kanzik I. (1998) Peroxynitrite: a putative cytotoxine. Pharmacol. Toxicol. 82: 113-117
8. 8 Logager T. and Sehested K. (1993) formation and decay of peroxynitrous acid; a pulse radiolysis study. J. Phys. Chem. 97: 6664-6669
9. 9 Pryor W. A., Cueto R., Jin X., Koppenol W. H., Ngu-Schwemlein M., Squadrito G. L. et al. (1995) A practical method for preparing peroxynitrite solutions of low ionic strength and free of hydrogen peroxide. Free Radic. Biol. Med. 18: 75-83
10. 10 Hughes M. N. and Nicklin H. G. (1971) Autoxidation of hydroxylamine in alkaline solutions. J. Chem. Soc. A: 164-168
11. 11 Uppu R. M. and Pryor W. A. (1996) Synthesis of peroxynitrite in a two-phase system using isoamylnitrite and hydrogen peroxide. Anal. Biochem. 236: 242-249
12. 12 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. 101: 1285-1292
13. 13 Saha A., Goldstein S., Cabelli D. and Czapski G. (1998) Determination of optimal conditions for synthesis of peroxynitrite by mixing acidified hydrogen peroxide with nitrite. Free Radic. Biol. Med. 24: 653-659
14. 14 Beckman J. S. and Koppenol W. H. (1996) Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly. Am. J. Physiol. 271: C1424-C1437
15. 15 Czapski G. and Goldstein S. (1995) The role oft the reactions of NO with superoxide and oxygen in biological systems: a kinetic approach. Free Radic. Biol. Med. 19: 785-794
16. 16 Kelm M., Dahmann R., Wink D. and Feelisch M. (1997) The nitric oxide/superoxide assay. J. Biol. Chem. 272: 9922-9932
17. 17 Koppenol W. H. (1998) The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radic. Biol. Med. 25: 385-391
18. 18 Hobbs A. J., Fukuto J. M. and Ignarro L. J. (1994) Formation of free nitric oxide from L-arginine by nitric oxide synthase: direct enhancement of generation by superoxide dismutase. Proc. Natl. Acad. Sci. USA 91: 10992-10996
19. 19 Mayer B., Klatt P., Werner E. R. and Schmidt K. (1995) Kinetics and mechanism of tetrahydrobiopterin-induced oxidation of nitric oxide. J. Biol. Chem. 270: 655-659
20. 20 Vasquez-Vivar J., Kalyanaraman B., Martasek P., Hogg N., Masters B. S. S., Karoui H. et al. (1998) Superoxide generation by endothelial nitric oxide synthase: the influence of cofactors. Proc. Natl. Acad. Sci. USA 95: 9220-9225
21. 21 Xia Y., Dawson V. L., Dawson T. M., Snyder S. and Zweier J. L. (1996) Nitric oxide synthase generates superoxide and nitric oxide in arginine-depleted cells leading to peroxynitrite-mediated cellular injury. Proc. Natl. Acad. Sci. USA 93: 6770-6774
22. 22 Xia Y. and Zweier J. L. (1997) Superoxide and peroxynitrite generation from inducible nitric oxide synthase in macrophages. Proc. Natl. Acad. Sci. USA 94: 6954-6958
23. 23 Miles A. M., Bohle D. S., Glassbrenner P. A., Hansert B., Wink D. A. and Grisham M. B. (1996) Modulation of superoxide-dependent oxidation and hydroxylation reactions by nitric oxide. J. Biol. Chem. 271: 40-47
24. 24 Ischiropoulos H. (1998) Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356: 1-11
25. 25 Tsai J.-H. M., Harrison J. G., Martin J. C., Hamilton T. P., Woerd M. van der, Jablonsky M. J. et al. (1994) Role of conformation of peroxynitrite anion in its stability and toxicity. J. Am. Chem. Soc. 116: 4115-4116
26. 26 Koppenol W. H., Moreno J. J., Pryor W. A., Ischiropoulos H. and Beckman J. S. (1992) Peroxynitrite, a cloaked oxidant formed by NO and superoxide. Chem. Res. Toxicol. 5: 834-842
27. 27 Pfeiffer S., Gorren A. C. F., Schmidt K., Werner E. R., Hansen B., Bohle D. S. et al. (1997) Metabolic fate of peroxynitrite in aqueous solution. J. Biol. Chem. 272: 3465-3470
28. 28 Kirsch M., Lomonosova E. E., Korth H. G., Sustmann R. and de Groot H. (1998) Hydrogen peroxide formation by reaction of peroxynitrite with HEPES and related tertiary amines: implications for a general mechanism. J. Biol. Chem. 273: 12716-12724
29. 29 Radi R., Cosgrove T. P., Beckman J. S. and Freeman B. A. (1993) Peroxynitrite-induced luminol chemiluminescence. Biochem. J. 290: 51-57
30. 30 Denicola A., Souza J. M. and Radi R. (1998) Diffusion of peroxynitrite across erythrocyte membranes. Proc. Natl. Acad. Sci. USA 95: 3566-3571
31. 31 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
32. 32 Kaur H., Whiteman M. and Halliwell B. (1997) Peroxynitrite-dependent aromatic hydroxylation and nitration of salicylate and phenylalanine: is hydroxyl radical involved? Free Radic. Res. 26: 71-82
33. 33 Koppenol W. H. and Kissner R. (1998) Can O = NOOH undergo homolysis? Chem. Res. Toxicol. 11: 87-90
34. 34 Pryor W. A., Jin X. and Squadrito G. L. (1996) Insensitivity of the rate of decomposition of peroxynitrite to changes in viscosity: evidence against free radical formation. J. Am. Chem. Soc. 118: 3125-3128
35. 2 adduct: density functional theory, transition structures and energetics. J. Am. Chem. Soc. 118: 13002-13006
36. 36 Padmaja S., Kissner R., Bounds P. L. and Koppenol W. H. (1998) Hydrogen isotope effect on the isomerization of peroxynitrous acid. Helv. Chim. Acta 81: 1201-1206
37. 37 Bartberger M. D., Olson L. P. and Houk K. N. (1998) Mechanisms of peroxynitrite oxidation and rearrangements: the theoretical perspective. Chem. Res. Toxicol. 11: 710-711
38. 38 Goldstein S., Squadrito G. L., Pryor W. A. and Czapski G. (1996) Direct and indirect oxidations by peroxynitrite, neither involving the hydroxyl radical. Free Radic. Biol. Med. 21: 965-974
39. 39 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
40. 40 Denicola A., Freeman B. A., Trujillo M. and Radi R. (1996) Peroxynitrite reaction with carbon/ bicarbonate: kinetics and influence on peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 333: 49-58
41. 41 Uppu R. M., Squadrito G. L. and Pryor W. A. (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 327: 335-343
42. 42 Lemercier J.-N., Padmaja S., Cueto R., Squadrito G. L., Uppu R. M. and Pryor W. A. (1997) Carbon dioxide modulation of hydroxylation and nitration of phenol by peroxynitrite. Arch. Biochem. Biophys. 345: 160-170
43. 43 Yermilov V., Yoshie Y., Rubio J. and Ohshima H. (1996) Effects of carbon dioxide/bicarbonate on induction of DNA single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine and base-propenal mediated by peroxynitrite. FEBS Lett. 399: 67-70
44. 2: evidence for carbonate radical production. J. Am. Chem. Soc. 120: 3458-3463
45. 45 Vasquez-Vivar J., Denicola A., Radi R. and Augusto O. (1997) Peroxynitrite-mediated decarboxylation of pyruvate to both carbon dioxide and carbon dioxide radical anion. Chem. Res. Toxicol. 10: 786-794
46. 46 Uppu R. M., Winston G. W. and Pryor W. A. (1997) Reactions of peroxynitrite with aldehydes as probes for the reactive intermediates responsible tor biological nitration. Chem. Res. Toxicol. 10: 1331-1337
47. 47 Radi R., Beckman J. S., Bush K. M. and Freeman B. A. (1991) Peroxynitrite oxidation of sulphhydryls. J. Biol. Chem. 266: 4244-4250
48. 48 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
49. 49 Pietraforte D. and Minetti M. (1997) Direct ESR detection or peroxynitrite-induced tyrosine-centered protein radicals in human blood plasma. Biochem. J. 325: 675-684
50. 50 Pietraforte D. and Minetti M. (1997) One-electron oxidation pathway of peroxynitrite decomposition in human blood plasma: evidence for the formation of protein tryptophan-centered radicals. Biochem. J. 321: 743-750
51. 51 Vasquez-Vivar J., Santos A.M., Junqueira V.B. and Augusto O. (1996) Peroxynitrite-mediated formation of free radicals in human plasma: EPR detection of ascorbyl, albumin-thiyl and uric acid-derived free radicals. Biochem. J. 314: 869-876
52. 52 Zhang H., Squadrito G. L., Uppu R. M., Lemercier J.-N., Cueto R. and Pryor W. A. (1997) Inhibition of peroxynitrite-mediated oxidation of glutathione by carbon dioxide. Arch. Biochem. Biophys. 339: 183-189
53. 53 Scorza G. and Minetti M. (1998) One-electron oxidation pathway of thiols by peroxynitrite in biological fluids: bicarbonate and ascorbate promote the formation of albumindisulphide dimers in human blood plasma. Biochem. J. 329: 405-413
54. 54 Mayer B., Pfeiffer S., Schrammel A., Koesling D., Schmidt K. and Brunner F. (1998) A new pathway of nitric oxide/ cyclic GMP signaling involving S-nitrosoglutathione. J. Biol. Chem. 273: 3264-3270
55. 55 Konorev E. A., Hogg N. and Kalyanaraman B. (1998) Rapid and irreversible inhibition of creatine kinase by peroxynitrite. FEBS Lett. 427: 171-174
56. 56 Whiteman M. and Halliwell B. (1997) Thiols and disulphides can aggravate peroxynitrite-dependent inactivation of α-1-antiproteinase. FEBS Lett. 414: 497-500
57. 57 Rubbo H., Denicola A. and Radi R. (1994) Peroxynitrite inactivates thiol-containing enzymes of Trypanosoma cruzi energetic metabolism and inhibits cell respiration. Arch. Biochem. Biophys. 308: 96-102
58. 58 Pasquet J. P. E. E., Zou M. H. and Ullrich V. (1996) Peroxynitrite inhibition of nitric oxide synthases. Biochimic 78: 785-791
59. 59 Jensen J. L., Miller B. L., Zhang X., Hug G. L. and Schöneich C. (1997) Oxidation of threonylmethionine by peroxynitrite: quantification of the one-electron transfer pathway by comparison to one-electron photooxidation. J. Am. Chem. Soc. 119: 4749-4757
60. 60 Pryor W. A., Jin X. and Squadrito G. L. (1994) One and two-electron oxidations or methionine by peroxynitrite. Proc. Natl. Acad. Sci. USA 91: 11173-11177
61. 61 Berlett B. S., Levine R. L. and Stadtman E. R. (1998) Carbon dioxide stimulates peroxynitrite-mediated nitration of tyrosine residues and inhibits oxidation of methionine residues of glutamine synthetase: both modifications mimic effects of adenylylation. Proc. Natl. Acad. Sci. USA 95: 2784-2789
62. 62 Vogt W. (1995) Oxidation of methionyl residues in proteins: tools, targets, and reversal. Free Radic. Biol. Med. 18: 93-105
63. 63 Moreno J. J. and Pryor W. A. (1992) Inactivation of alpha 1-proteinase inhibitor by peroxynitrite. Chem. Res. Toxicol. 5: 425-431
64. 64 Huhmer A. F., Gerber N. C., de Montellano P. R. and Schoneich C. (1996) Peroxynitrite reduction of calmodulin stimulation of neuronal nitric oxide synthase. Chem. Res. Toxicol. 9: 484-491
65. 65 Lymar S. V., Jiang Q. and Hurst J. K. (1996) Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35: 7855-7861
66. 66 Beckman J. S., Ischiropoulos H., Zhu L., van der Woerd M., Smith C., Chen J. et al. (1992) Kinetics or superoxide dismutase and iron-catalyzed nitration of phenolics by peroxynitrite. Arch. Biochem. Biophys. 298: 438-445
67. 67 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
68. 68 Blanchard B., Dendane M., Gallard J. F., Houee-Levin C., Karim A., Payen D. et al. (1997) Oxidation, nitrosation, and nitration of serotonin by nitric oxide-derived nitrogen oxides: biological implications in the rat vascular system. Nitric Oxide 1: 442-452
69. 69 Crow J. P., Ye Y. Z., Strong M., Kirk M., Barnes S. and Beckman J. S. (1997) Superoxide catalyzes nitration of tyrosines by peroxynitrite in the rod and head domains of neurofilaments-L. J. Neurochem. 69: 1945-1953
70. 70 Kono Y. (1998) Catalase catalyzes of peroxynitrite-mediated phenolic nitration. Biosci. Biotechnol. Biochem. 62: 448-452
71. 71 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
72. 72 Ischiropoulos H. and al Mehdi A. B. (1995) Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 364: 279-282
73. 73 MacMillan-Crow L. A. (1998) Peroxynitrite-mediated inactivation of manganese superoxide dismutase involves nitration and oxidation of critical tyrosine residues. Biochemistry 37: 1613-1622
74. 74 Yamakura F., Taka H., Fujimura T. and Murayama K. (1998) Inactivation of human manganese-superoxide dismutase by peroxynitrite is caused by exclusive nitration of tyrosine 34 to 3-nitrotyrosine. J. Biol. Chem. 273: 14085-14089
75. 75 MacMillan-Crow L. A., Crow J. P., Kerby J. D., Beckman J. S. and Thompson J. A. (1996) Nitration and inactivation of manganese superoxide dismutase in chronic rejection of human renal allografts. Proc. Natl. Acad. Sci. USA 93: 11853-11858
76. 76 Zou M., Martin C. and Ullrich V. (1997) Tyrosine nitration as a mechanism of selective inactivation of prostacyclin synthase by peroxynitrite. Biol. Chem. 378: 707-713
77. 77 Haddad I. Y., Zhu S., Ischiropoulos H. and Matalon S. (1996) Nitration of surfactant protein A results in decreased ability to aggregate lipids. Am. J. Physiol. 270: L281-L288
78. 78 Ara J., Przedborski S., Naini A. B., Jackson-Lewis V., Trifiletti R. R., Horwitz J. et al. (1998) Inactivation of tyrosine hydroxylase by nitration following exposure to peroxynitrite and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Proc. Natl. Acad. Sci. USA 95: 7659-7663
79. 79 Roberts E., S., Lin H., Crowley J. R., Vuletich J. L., Osawa Y. and Hollenberg P. F. (1998) Peroxynitrite-mediated nitration of tyrosine and inactivation of the catalytic activity of cytochrome P450 2B1. Chem. Res. Toxicol. 11: 1067-1074
80. 2 peptide. Proc. Natl. Acad. Sci. USA 93: 3377-3382
81. 81 Kamisaki Y., Wada K., Bian K., Balabanli B., Davis K., Martin E. et al. (1998) An activity in rat tissues that modifies nitrotyrosine-containing proteins. Proc. Natl. Acad. Sci. USA 95: 11584-11589
82. 82 Halliwell B. (1997) What nitrates tyrosine? Is nitrotyrosine specific as a biomarker of peroxynitrite formation in vivo? FEBS Lett. 411: 157-160
83. 83 Ohshima H, Friesen M., Brouet I. and Bartsch H. (1990) Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food. Chem. Toxicol. 28: 647-652
84. 84 Gunther M. R., Hsi L. C., Curtis J. F., Gierse J. K., Marnett L. J., Eling T. E. et al. (1997) Nitric oxide trapping of the tyrosinyl radical of prostaglandin H synthase-2 leads to tyrosine iminoxyl radical and nitrotyrosine formation. J. Biol. Chem. 272: 17086-17090
85. 85 Eiscrich J. P., Hristova M., Cross C. E., Jones A. D., Freeman B. A., Halliwell B. et al. (1998) Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391: 393-397
86. 86 Sampson J. B., Ye Y., Rosen H. and Beckman J. S. (1998) Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch. Biochem. Biophys. 356: 207-213
87. 87 Daveu C., Servy C., Dendane M., Marin P. and Ducrocq C. (1997) Oxidation and nitration of catecholamines by nitrogen oxides derived from nitric oxide. Nitric Oxide 1: 234-243
88. 88 Pannala A. S., Razaq R., Halliwell B., Singh S. and Rice-Evans C. A. (1998) Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: nitration or electron donation? Free Radic. Biol. Med. 24: 594-606
89. 89 Grace S. C., Salgo M. G. and Pryor W. A. (1998) Scavenging of peroxynitrite by a phenolic/peroxidase system prevents oxidative damage to DNA. FEBS Lett 426: 24-28
90. 90 Haenen G. R., Paquay J. B., Korthouwer R. E. and Bast A. (1997) Peroxynitrite scavenging by flavonoids. Biochem. Biophys. Res. Commun. 236: 591-593
91. 91 Ohshima H., Yoshie Y., Auriol S. and Gilibert I. (1998) Anti-oxidant and pro-oxidant actions of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxyl anion. Free Radic. Biol. Med. 25: 1057-1065
92. 92 Vatassery G. T., Smith W. E. and Quach H. T. (1998) Alpha-tocopherol in rat brain subcellular fractions is oxidized rapidly during incubations with low concentrations of peroxynitrite. J. Nutr. 128: 152-157
93. 93 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
94. 94 Masumoto H., Kissner R., Koppenol W. H. and Sies H. (1996) Kinetic study of the reaction of ebsclen with peroxynitrite. FEBS Lett. 398: 179-182
95. 95 Padmaja S., Squadrito G. L., Lemercier J. N., Cueto R. and Pryor W. A. (1997) Peroxynitrite-mediated oxidation of D,L-selenomethionine: kinetics, mechanism and the role of carbon dioxide. Free Radic. Biol. Med. 23: 917-926
96. 96 Arteel G. E., Mostert V., Oubrahim H., Briviba K., Abel J. and Sies H. (1998) Protection by selenoprotein P in human plasma against peroxynitrite-mediated oxidation and nitration. Biol. Chem. 379: 1201-1205
97. 97 Sies H., Sharov V. S., Klotz L. O. and Briviba K. (1997) Glutathione peroxidase protects against peroxynitrite-mediated oxidations: a new function for selenoproteins as peroxynitrite reductase. J. Biol. Chem. 272: 27812-27817
98. 98 Salvemini D., Wang Z. Q., Stern M. K., Currie M. G. and Misko T. P. (1998) Peroxynitrite decomposition catalysts: therapeutics for peroxynitrite-mediated pathology. Proc. Natl. Acad. Sci. USA 95: 2659-2663
99. 99 Bartlett D., Church D. F., Bounds P. L. and Koppenol W. H. (1995) The kinetics of the oxidation of ascorbic acid by peroxynitrite. Free Radic. Biol. Med. 18: 85-92
100. 100 Gow A., Duran D., Thom S. T. and Ischiropoulos H. (1996) Charbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Arch. Biochem. Biophys. 333: 42-48
101. 101 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
102. 102 Kondo H., Takahashi M. and Niki E. (1997) Peroxynitrite-induced hemolysis of human erythrocytes and its inhibition by antioxidants. FEBS Lett. 413: 236-238
103. 103 Minetti M., Mallozzi C., Di Stasi A. M. and Pietraforte D. (1998) Bilirubin is an effective antioxidant of peroxynitrite-mediated protein oxidation in human blood plasma. Arch. Biochem. Biophys. 352: 165-174
104. 104 Kikugawa K., Hiramoto K., Tomiyama S. and Asano Y. (1997) Beta-carotene effectively scavenges toxic nitrogen oxides: nitrogen dioxide and peroxynitrous acid. FEBS Lett. 404: 175-178
105. 105 Gilad E., Cuzzocrea S., Zingarelli B., Salzman A. L. and Szabo C. (1997) Melatonin is a scavenger of peroxynitrite. Life Sci. 60: 169-174
106. 106 Skinner K. A., White C. R., Patel R., Tan S., Barnes S. and Kirk M. (1998) Nitrosation of uric acid by peroxynitrite. J. Biol. Chem. 273: 24491-24497
107. 107 Szabo C. and Ohshima H. (1997) DNA damage induced by peroxynitrite: subsequent biological effects. Nitric Oxide Biol. Chem. 1: 373-385
108. 108 Yermilov V., Rubio J. and Ohshima H. (1995) Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Lett. 376: 207-210
109. 109 Douki T., Cadet J. and Ames B. N. (1996) An adduct between peroxynitrite and 2′-deoxyguanosine: 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2′-decoxyguanosine. Chem. Res. Toxicol. 9: 3-7
110. 110 Rubio J., Yermilov V. and Ohshima H. (1996) DNA damage induced by peroxynitrite: formation of 8-nitroguanine and base propenals. In: The Biology of Nitric Oxide, part 5, p. 34, Moncada S., Stamler J., Gross S. and Higgs E. A., (eds.), Portland press, London
111. 111 Douki T. and Cadet J. (1996) Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA. Free Radic. Res. 24: 369-380
112. 112 Spencer J. P., Wong J., Jenner A., Aruoma O. L., Cross C. E., and Halliwell B. (1996) Base modification and strand breakage in isolated calf thymus DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3-morpholinosydnonimine. Chem. Res. Toxicol. 9: 1152-1158
113. 113 Kennedy L. J., Moore K. Jr., Caulfield J. L., Tannenbaum S. R. and Dedon P. C. (1997) Quantitation of 8-oxoguanine and strand breaks produced by four oxidizing agents. Chem. Res. Toxicol. 10: 386-392
114. 114 Uppu R. M., Cueto R., Squadrito G. L., Salgo M. G. and Pryor W. A. (1996) Competitive reactions of peroxynitrite with 2′-deoxyguanosine and 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-oxodG): relevance to the formation of 8-oxodG in DNA exposed to peroxynitrite. Free Radic. Biol. Med. 21: 407-411.