Peroxynitrite and nitrosoperoxycarbonate, a tightly connected oxidizing-nitrating couple in the reactive nitrogen-oxygen species family: New perspectives for protection from radical-promoted injury by flavonoids

Journal of Pharmacy and Pharmacology

Volumn 59, Issue 12, 2007, Pages 1687-1695

  Pavlovic, Radmila ^a   Santaniello, Enzo ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CARBONIC ACID; FLAVONOID; NITROGEN; NITROSOPEROXYCARBONATE; OXYGEN; PEROXYNITRITE; RADICAL; SCAVENGER; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CONFERENCE PAPER; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; OXIDATIVE STRESS; PROTON TRANSPORT;

ANIMALS; CARBONATES; FLAVONOIDS; HUMANS; MODELS, BIOLOGICAL; NITRATES; OXIDANTS; PEROXYNITROUS ACID; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES;

EID: 36849046810     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.59.12.0011     Document Type: Conference Paper

References (123)

1. Alderton, W. K., Cooper, C. E., Knowles, R. G. (2001) Nitric oxide synthases: structure, function and inhibition. Biochem. J. 357: 593-615
2. Alvarez, B., Radi, R. (2003) Peroxynitrite reactivity with amino acids and proteins. Amino Acids 25: 295-311
3. Arteel, G. E., Briviba, K., Sies, H. (1999) Protection against peroxynitrite. FEBS Lett. 445: 226-230
4. 2 impairs peroxynitrite-mediated inhibition of human caspase-3. Biochem. Biophys. Res. Commun. 349: 367-371
5. Auguste, O., Bonini, M. G., Amanso, A. M., Linares, E., Santos, C. C. S., De Menezes, S. L. (2002) Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology. Free Radic. Biol. Med. 32: 841-859
6. Balafanova, Z., Bolli, R., Zhang, J., Zheng, Y., Pass, J. M., Bhatnagar, A., Tang, X. L., Wang, O., Cardwell, E., Ping, P. (2002) Nitric oxide (NO) induces nitration of protein kinase Cε (PKCε), facilitating PKCε translocation via enhanced PKCε-RACK2 interactions. J. Biol. Chem. 277: 15021-15027
7. Bartlett, D., Church, D. F., Baunds, P. L., Koppenol, W. H. (1995) The kinetics of the oxidation of L-ascorbic acid by peroxynitrite. Free Radic. Biol. Med. 18: 85-92
8. Beckman, J. S., Koppenol, W. H. (1996) Nitric oxide, superoxide and peroxynitrite: the good, the bad and the ugly. Am. J. Physiol. 271: C1424-C1437
9. Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., Freeman, B. A. (1990) Apparent hydroxyl radical formation by peroxinitrite: implication in endothelial injury from nitric oxide and superoxide. Proc. Natl Acad. Sci. USA 87: 1620-1624
10. Berlett, B. S., Levine, R. L., 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
11. Bixby, M., Spieler, L., Menini, T., Gugliucci, A. (2005) Ilex paraguariensis extracts are potent inhibitors of nitrosative stress: a comparative study with green tea and wines using a protein nitration model and mammalian cell cytotoxicity. Life Sci. 77: 345-358
12. Boersma, B. J., Patel, R. P., Kirk, M., Jackson, P. L., Muccio, D., Darley-Usmar, V. M., Barnes, S. (1999) Chlorination and nitration of soy isoflavones. Arch. Biochem. Biophys. 368: 265-275
13. Bonini, M. G., Augusto, O. (2001) Carbon dioxide stimulates the production of thiyl, sulfinyl, and disulfide radical anion from thiol oxidation by peroxynitrite. J. Biol. Chem. 276: 9749-9754
14. Bonini, M. G., Radi, R., Ferrer-Sueta, G., Ferreira, A. M., Augusto, O. (1999) Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide. J. Biol. Chem. 274: 10 802-10 806
15. Botti, H., Trujillo, M., Batthyany, C., Rubbo, H., Ferrer-Sueta, G., Radi, R. (2004) Homolytic pathways drive peroxynitrite-dependent Trolox C oxidation. Chem. Res. Toxicol. 17: 1377-1384
16. Boveris, A., Valdez, L., Alvarez, S. (2002) Inhibition by wine polyphenols of peroxynitrite-initiated chemiluminescence and NADH oxidation. Ann. N. Y. Acad. Sci. 957: 90-102
17. Carr, A. C, McCall, M. R., Frei, B. (2000) Oxidation of LDL by myeloperoxidase and reactive nitrogen species: reaction pathways and antioxidant protection. Arterioscler. Thromb. Vasc. Biol. 20: 1716-1723
18. Cassina, A. M., Hodara, R., Souza, J. M., Thomson, L., Castro, L., Ischiropoulos, H., Freeman, B. A., Radi, R. (2000) Cytochrome c nitration by peroxynitrite. J. Biol. Chem. 275: 21409-21415
19. Choi, J. S., Chung, H. Y., Kang, S. S. Jung, M. J., Kim, J. W., No, J. W., Jung, H. A. (2002) The structure-activity relationship of flavonoids as scavengers of peroxynitrite. Phytother. Res. 16: 232-235
20. Chung, H. Y., Yokozawa, T., Soung, D. Y., Kye, I. S., No, J. K., Baek, B. S. (1998) Peroxynitrite-scavenging activity of green tea tannin. J. Agric. Food Chem. 46: 4484-4486
21. Corsaro, M. M., Pietraforte, D., Di Lorenzo, A. S., Minetti, M., Marino, G. (2004) Reaction of peroxynitrite with hyaluronan and related saccharides. Free Radic. Res. 38: 343-353
22. Cotelle, N. (2001) Role of flavonoids in oxidative stress. Curr. Top. Med. Chem. 1: 569-590
23. Crow, J. P, (2000) Peroxynitrite scavenging by metalloporphyrins and thiolates. Free Radic Biol. Med. 28: 1487-1494
24. Cuzzocrea, S., Riley, D. P., Caputi, A. P., Salvemini, D. (2001) Antioxidant therapy: a new pharmacological approach in shock, inflammation, and ischemia/reperfusion injury. Chem. Res. Toxicol. 53: 135-159
25. Dedon, P. C., Tannenbaum, S. R. (2004) Reactive nitrogen species in the chemical biology of inflammation. Arch. Biochem. Biophys. 423: 12-22
26. Eberhardt, M. E. (2000) Reactive oxygen metabolites: chemistry and medical consequences. CRC Press, Boca Raton, USA
27. 9-tetrahydrocannabinol and cannabidiol in N-methyl-D-aspartate-induced retinal neurotoxicity: involvement of peroxynitrite. Am. J. Pathol. 163: 1997-2008
28. Espey, M. G., Miranda, K. M., Thomas, D. D., Xavier, S., Citrin, D., Vitek, M. P., Wink, D. A. (2002) A chemical perspective on the interplay between NO, reactive oxygen species, and reactive nitrogen oxide species. Ann. N. Y. Acad. Sci. 962: 195-206
29. Ferdinandy, P. (2006) Peroxynitrite: just an oxidative/nitrosative stressor or a physiological regulator as well? Br. J. Pharmacol. 148: 1-3
30. Ferdinandy, P., Schulz, R. (2001) Inhibition of peroxynitrite-induced dityrosine formation with oxidized and reduced thiols, nitric oxide donors and purine derivatives. Antiox. Redox. Signal. 3: 165-171
31. 2. J. Agric. Food Chem. 52: 2866-2874
32. Giustarini, D., Milzani, A., Colombo, R., Dalle-Donne, I., Rossi, R. (2003) Nitric oxide and S-nitrosothiols in human blood. Clin. Chim. Acta 330: 85-98
33. 2 - evidence for carbonate radical formation. J. Am. Chem. Soc. 120: 3458-3463
34. Goldstein, S., Saha, A., Lymar, S., Czapski, G. (1998) Oxidation of peroxynitrite by inorganic radicals: a pulse radiolysis study. J. Am. Chem. Soc. 120: 5549-5554
35. Goldstein, S., van Eldik, R., Meyerstein, D., Czapski, G. (1999) Peroxynitrous acid decomposes via homolysis: evidence from high pressure pulse radiolysis. J. Phys. Chem. 103: 6587-6590
36. •- under physiological conditions. How the radicals do the job. J. Biol. Chem. 275: 3031-3036
37. 2 from high-pressure pulse radiolysis. J. Phys. Chem. 104: 9712-9714
38. 2. Chem. Res. Toxicol. 14: 1273-1276
39. Gow, A., Duran, D., Thom, S. R., Ischiropoulos, H. (1996) Carbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Arch. Biochem. Biophys. 333: 42-48
40. Haenen, G. R. M. M., Paquay, J. B. G., Korthouwer, R. E. M., Bast, A. (1997) Peroxynitrite scavenging by flavonoids. Biochem. Biophys. Res. Commun. 236: 591-593
41. Halliwell, B. (1996) Antioxidants in human health and disease. Annu. Rev. Nutr. 16: 33-50
42. Halliwell, B. (1999) Oxygen and nitrogen are pro-carcinogens. Damage to DNA by reactive oxygen, chlorine and nitrogen species: measurement, mechanism and the effects of nutrition. Mutat. Res. 443: 37-52
43. Harborne, J. B., Williams, C. A. (2000) Advances in flavonoid research since 1992. Phytochemistry 55: 481-504
44. Heijnen, C. G. M., Haenen, G. R. M. M, van Acker, F. A. A., van der Vijgh, W. J. F., Bast, A. (2001a) Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups. Toxicol. In Vitro 15: 3-6
45. Heijnen, C. G. M., Haenen, G. R. M. M, Vekemans, J. A. J. M., Bast, A. (2001b) Peroxynitrite scavenging of flavonoids: structure activity relationship. Environ. Toxicol. Pharmacology 10: 199-206
46. Hodges, G. R., 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: 10 695-10 701
47. Hogg, N. (2002) The biochemistry and physiology of S-nitrosothiols. Annu. Rev. Pharmacol. Toxicol. 42: 585-600
48. Hogg, N., Joseph, J., Kalyanaraman, B. (1994) The oxidation of alpha-tocopherol and trolox by peroxynitrite. Arch. Biochem. Biophys. 314: 153-158
49. Hughes, M. N., (1999) Relationships between nitric oxide, nitroxyl ion, nitrosonium cation and peroxynitrite. Biochim. Biophys. Acta 1411: 263-272
50. 2. Toxicology 89: 193-216
51. Huie, R. E., Padmaja, S. (1993) Reaction of nitric oxide with superoxide. Free Radic. Res. Commun. 18: 195-199
52. Imam, S. Z., el-Yazal, J., Newport, G. D., Itzhak, Y., Cadet, J. L., Slikker, W., Jr, Ali, S. F. (2001) Methamphetamine-induced dopaminergic neurotoxicity: role of peroxynitrite and neuroprotective role of antioxidants and peroxynitrite decomposition catalysts. Ann. N. Y Acad. Sci. 939: 366-380
53. Jourd'heuil, D., Miranda, K. M., Kim S. M., Espey, M. G., Vodovotz, Y., Laroux, S., Mai, C. T., Miles, A. M., Grisham, M. B., Wink, D. A. (1999) The oxidative and nitrosative chemistry of the nitric oxide/superoxide reaction in the presence of bicarbonate. Arch. Biochem. Biophys. 365: 92-100
54. Jourd'heuil, D., Jourd'heuil, F., Kutchukian, P. S., Musab, R. A., Wink, D. A., Grisham, M. B. (2001) Reaction of superoxide and nitric oxide with peroxynitrite. J. Biol. Chem. 276: 28 799-28 805
55. Kato, Y., Ogino, Y., Aoki, T., Uchida, K., Kawakishi, S., Osawa, T. (1997) Phenolic antioxidants prevent peroxynitrite-derived collagen modification in vitro. J. Agric. Food Chem. 45: 3004-3009
56. Kerry, N., Rice-Evans, C. (1998) Peroxynitrite oxidises catechols to o-quinones. FEBS Lett. 437: 167-171
57. Ketsawatsakul, U., Whiteman, M., Halliwell, B. (2000) A reevaluation of the peroxynitrite scavenging activity of some dietary phenolics. Biochem. Biophys. Res. Commun. 279: 692-699
58. Kim, J. Y., Jung, K. J., Choi, J. S., Chung, H. Y. (2004) Hesperetin: a potent antioxidant against peroxynitrite. Free Radic. Res. 38: 761-769
59. Kirsch, M., de Groot, H. (2002) Formation of peroxynitrite from reaction of nitroxyl anion with molecular oxygen. J. Biol. Chem. 277: 13 379-13 388
60. Kirsch, M., Lehnig, M., Korth, H. G., Sustmann, R., de Groot, H. (2001) Inhibition of peroxynitrite-induced nitration of tyrosine by glutathione in the presence of carbon dioxide through both radical repair and peroxynitrate formation. Chemistry 7: 3313-3320
61. Klaunig, J. E., Kamendulis, L. M. (2004) The role of oxidative stress in carcinogenesis. Annu. Rev. Pharmacol Toxicol. 44: 239-267
62. Klotz, L. O., Sies, H. (2003) Defenses against peroxynitrite: seleno-compounds and flavonoids. Toxicol. Lett. 140: 125-132
63. Kobayashi, K., Miki, M., Tagawa, S. (1995) Pulse-radiolysis study of the reaction of nitric oxide with superoxide. J. Chem. Soc. Dalton Trans. 17: 2885-2889
64. Kocic, G., Pavlovic, D., Pavlovic, R., Nikolic, G., Cvetkovic, T., Stojanovic, I., Jevtovic, T., Kocic, R., Sokolovic, D. (2004) Sodium nitroprusside and peroxynitrite effect on hepatic DNases: an in vitro and in vivo study. Comp. Hepatol. 3: 6
65. Koppenol, W. H. (1998) The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radic. Biol. Med. 25: 385-391
66. Lee, J., Koo, N., Min, D. B. (2004) Reactive oxygen species, aging, and antioxidative nutraceuticals. Comp. Rev. Food Sci. Food Safety 3: 21-33
67. Lymar, S. V., Hurst, J. K. (1996) Carbon dioxide: physiological catalyst for peroxynitrite-mediated cellular damage or cellular protectant? Chem. Res. Toxicol. 9: 845-850
68. Manach, C., Scalbert, A., Morand, C., Remesy, C., Jimenez, L. (2004) Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr. 79: 727-747
69. Manach, C., Williamson, G., Morand, C., Scalbert, A., Remesy, C. (2005) Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 81: 230S-242S
70. Margolin, Y., Jean-Francois Cloutier, J. F., Shafirovich, V., Geacintov, N. E. Dedon, P. C. (2006) Paradoxical hotspots for guanine oxidation by a chemical mediator of inflammation. Nat. Chem. Biol. 2: 365-366
71. •. J. Biol. Chem. 7: 31-36
72. 2 radicals. Chem. Res. Toxicol. 11: 712-713
73. Miau, J. L., Wang, W. F., Pan, J. X., Lu, C. Y., Li, R. Q., Yao, S. D. (2000) The scavenging reactions of nitrogen dioxide radical and carbonate radical by tea polyphenol derivatives: a pulse radiolysis study. Radiat. Phys. Chem. 60: 163-168
74. Moro, M. A., Darley-Usmar, V. M., Lizasoain, I., Su, Y., Knowles, R. G., Radomski, M. W., Moncada, S. (1995) The formation of nitric oxide donors from peroxynitrite. Br. J. Pharmacol. 116: 1999-2004
75. Ohshima, H., Oshie, Y., Auril, S., Gilbert, I. (1998) Antioxidant and pro-oxidant action of flavonoids: effects on DNA damage induced by nitric oxide, peroxynitrite and nitroxil anion. Free Radic. Biol. Med. 25: 1057-1065
76. Olmos, A., Giner, R. M., Manez, S. (2007) Drugs modulating the biological effects of peroxynitrite and related nitrogen species. Med. Res. Rev. 27: 1-64
77. Ozben, T., Tomasi, A. (2003) Free radicals, nitric oxide and inflammation: molecular, biochemical and clinical aspects. 334 NATO, Science Series IOS Press, Amsterdam, The Netherlands
78. Pannala, A., Rice-Evans, C. A., Halliwell, B., Singh, S. (1997) Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochem. Biophys. Res. Commun. 232: 164-168
79. Pannala, A. S., Raghib, R., Barry, H., Surinder, S., Rice-Evans, C. A. (1998) Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: nitration or electron donation? Free Radic. Biol. Med. 24: 594-606
80. Pannala, A. S., Singh, S., Rice-Evans, C. (1999) Flavonoids as peroxynitrite scavengers in vitro. Methods Enzymol. 299: 207-235
81. 2. Eur. J. Org. Chem. 2003: 172-181
82. Pietraforte, D., Minetti, M. (1997) Direct ESR detection orperoxynitrite-induced tyrosine-centred protein radicals in human blood plasma. Biochem. J. 325: 675-684
83. Pietta, P. G. (2000) Flavonoids as antioxidants. J. Nat. Prod. 63: 1035-1042
84. Pollard, S., Kuhnle, G. G. C., Vauzour, D., Vafeiadou, K., Tzounis, X., Whiteman, M., Rice-Evans, C. A, Spencer, J. P. E. (2006) The reaction of flavonoid metabolites with peroxynitrite. Biochem. Biophys. Res Commun. 350: 960-968
85. Prior, R. L. (2003) Fruits and vegetables in the prevention of cellular oxidative damage. Am. J. Clin. Nutr. 78 (Suppl.): 570-578
86. Pryor, W. A., Squadrito, G. L. (1995) The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 268: L7699-L7622
87. Radi, R., Peluffo, G., Alvarez, M. N., Naviliat, M., Cayota, A. (2001) Unravelling peroxynitrite formation in biological systems. Free Radic. Biol. Med. 30: 463-488
88. Radi, R. (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc. Natl Acad. Sci. USA 101: 4003-4008
89. Rezk, B. M., Haenen, G. R. M. M., van der Vijgh, W. J. F., Bast, A. (2004) Lipoic acid protects efficiently only against a specific form of peroxynitrite-induced damage. J. Biol. Chem. 279: 9693-9697
90. Rhyu, D. Y., Yokozawa, T., Choa, E. J., Park, J. C. (2002) Prevention of peroxynitrite-induced renal injury through modulation of peroxynitrite production by the Chinese prescription Wen-Pi-Tang. Free Radic. Res. 36: 1261-1269
91. Rice-Evans, C. A., Miller, N. J., Paganga, G. (1996) Structure antioxidant relationships of flavonoids and phenylpropanoids. Free Radic. Biol. Med. 20: 933-956
92. Richeson, C. E., Mulder, P., Bowry, V. W., Ingold, K. U. (1998) The complex chemistry of peroxynitrite decomposition: new insights. J. Am. Chem. Soc. 120: 7211-7219
93. Ross, J. A, Kasum, C. M. (2002) Dietary flavonoids: bioavailability, metabolic effects, and safety. Annu Rev. Nutr. 22: 19-34
94. Salvemini, D., Doyle, T. M., Cuzzocrea, S. (2006) Superoxide, peroxynitrite and oxidative/nitrative stress in inflammation. Biochem. Soc. Trans. 34: 965-970
95. Sampson, J. B., Ye, Y. Z., Rosen, H., Beckman, J. S. (1998) Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch. Biochem. Biophys. 356: 207-213
96. Santos, M. R., Mira, L. (2004) Protection by flavonoids against the peroxynitrite-mediated oxidation of dihydrorhodamine. Free Radic. Res. 38: 1011-1018
97. Santos, C. X., Bonini, M. G., Auguste, O. (2000) Role of the carbonate radical anion in tyrosine nitration and hydroxylation by peroxynitrite. Arch. Biochem. Biophys. 377: 146-152
98. Schroeder, P., Klotz, L. O., Buchczyk, D. P., Sadik, C. D., Schewe, T., Sies, H. (2001a) Epicatechin selectively prevents nitration but not oxidation reactions of peroxynitrite. Biochem. Biophys. Res. Commun. 285: 782-787
99. Schroeder, P., Zhang, H., Klotz, L. O., Kalyanaraman, B., Sies, H. (2001b) (-)-Epicatechin inhibits nitration and dimerization of tyrosine in hydrophilic as well as hydrophobic environments. Biochem Biophys Res Commun. 289: 1334-1338
100. Shafirovich, V., Dourandin, A., Huang, W., Geacintov, N. E. (2001) The carbonate radical is a site-selective oxidizing agent of guanine in double-stranded oligonucleotides. J. Biol. Chem. 276: 24 621-24 626
101. Shin, S. G., Kim, J. Y., Chung, H. Y., Jeong, J. C. (2005) Zingerone as an antioxidant against peroxynitrite. J. Agric. Food Chem. 53: 7617-7622
102. Squadrito, G. L., Pryor, W. A. (1998) Oxidative chemistry of nitric oxide: the roles of superoxide, peroxinitrite, and carbon dioxide. Free Radic. Biol. Med. 25: 392-403
103. 2: energetics, reactive species, and biological implications. Chem. Res. Toxicol. 15: 885-895
104. Szabó, C., Mabley, J. G., Moeller, S. M., Shimanovich, R., Pacher, P., Virág, L., Soriano, F. G., VanDuzer, J. H., Williams, W., Salzman, A. L., Groves, J. T. (2002) Part I: pathogenetic role of peroxynitrite in the development of diabetic vascular complications: studies with FP15, a novel potent peroxynitrite decomposition catalyst. Mol. Med. 8: 571-580
105. Tibi, S., Koppenol, W. H. (2000) Reactions of peroxynitrite with phenolic and carbonyl compounds: flavonoids are not scavengers of peroxynitrite. Helv. Chim. Acta 83: 2412-2424
106. Tien, M., Berlett, B. S., Levine, R. L., Chock, P. B., Stadtman, E. R. (1999) Peroxynitrite-mediated modification of proteins at physiological carbon dioxide concentration: pH dependence of carbonyl formation, tyrosine nitration, and methionine oxidation. Proc. Natl Acad. Sci. USA 96: 7809-7814
107. Trujillo, M., Folkes, L., Bartesaghi, S., Kalyanaraman, B., Wardman, P., Radi R. (2005) Peroxynitrite-derived carbonate and nitrogen dioxide radicals readily react with lipoic and dihydrolipoic acid. Free Radic. Biol. Med. 39: 279-288
108. Uppu, R. M., Lemercier, L. J., Squadrito, G. L., Zhang, H., Bolzan, R. M., Pryor, W. A. (1998) Nitrosation of peroxynitrite: use of phenol as a probe. Arch. Biochem. Biophys. 358: 1-16
109. 2 and evidence for common intermediates. J. Am. Chem. Soc. 122: 6911-6916
110. Vadseth, C., Souza, J. M., Thomson, L., Seagraves, A., Nagaswami, C., Scheiner, T., Torbet, J., Vilaire, G., Bennett, J. S., Murciano, J. C., Muzykantov, M., Penn, M. S., Hazen, S. L., Weisel, J. W., Ischiropoulos, H. (2004) Pro-thrombotic state induced by post-translational modification of fibrinogen by reactive nitrogen species. J. Biol. Chem. 279: 8820-8826
111. Valdez, L. B., Alvarez, S., Zaobonski, J. T., Boveris, A. (2004) Polyphenols and red wine as antioxidants against peroxynitrite and other oxidants. Biol. Res. 37: 279-286
112. van der Vliet, A., Smith, D., O'Neill, C. A., Kauer, H., Darley-Usmar, V. M., Cross, C. E., Halliwell, B. (1994) Interactions of peroxynitrite with human plasma and its constituents: oxidative damage and antioxidant depletion. Biochem. J. 303: 295-301
113. Vasela, A., Wilhelm, J. (2002) The role of carbon dioxide in free radical reactions of the organism. Physiol. Res. 51: 335-339
114. Verhagen, J. V., Haenen, G. R. M. M., Bast, A. (1996) Nitric oxide radical scavenging by wines. J. Agric. Food Chem. 44: 3733-3734
115. Virág, L., Szabó, E., Gergely, P., Szabó, C. (2003) Peroxynitrite-induced cytotoxicity: mechanism and opportunities for intervention. Toxicol. Lett. 140-141: 113-124
116. Walker, L. M., Walker, P. D., Imam, S. Z., Ali, S. F., Mayeux, P. R. (2000) Evidence for peroxynitrite formation in renal ischemia-reperfusion injury: studies with the inducible nitric oxide synthase inhibitor L-N6-(1-iminoethyl)lysine. J. Pharmacol. Exp. Ther. 295: 417-422
117. Whiteman, M., Ketsawatsakul, U., Halliwell, B. (2002) A reassessment of the peroxynitrite scavenging activity of uric acid. Ann. N. Y. Acad. Sci. 962: 242-259
118. Wink, D. A., Mitchell, J. B. (1998) Chemical biology of nitric oxide: insights into regulatory, cytotoxic, and cytoprotective mechanism of nitric oxide. Free Radic. Biol. Med. 25: 434-456
119. Wippel, R., Rehn, M., Gorren, A. C. F., Schmidt, K., Mayer, B. (2004) Interference of the polyphenol epicatechin with the biological chemistry of nitric oxide and peroxynitrite-mediated reactions. Biochem. Pharmacol. 67: 1285-1295
120. Wu, G., Meininger, C. J. (2002) Regulation of nitric oxide synthesis by dietary factors. Annu. Rev. Nutr. 22: 61-86
121. Yao, L. H., Jiang, Y. M., Shi, J., Tomas-Barberan, F. A., Datta, N., Singanusong, R., Chen, S. S. (2004) Flavonoids in food and their health benefits. Plant Foods Hum. Nutr. 59: 113-122
122. Yokozawa, T., Rhyu, D. Y., Cho, E. J., Aoyagi, K. (2003) Protective activity of (-)-epicatechin 3-O-gallate against peroxynitrite-mediated renal damage. Free Radic Res. 37: 561-571
123. Yu, H., Venkatarangan, L., Wishnok, J. S., Tannenbaum, S. R. (2005) Quantitation of four guanine oxidation products from reaction of DNA with varying doses of peroxynitrite. Chem. Res. Toxicol. 18: 1849-1857