Kinetic and mechanistic considerations to assess the biological fate of peroxynitrite

Biochimica et Biophysica Acta - General Subjects

Volumn 1840, Issue 2, 2014, Pages 768-780

  Carballal, Sebastián ^a   Bartesaghi, Silvina ^a   Radi, Rafael ^a  

^a DEPARTAMENTO DE BIOQUÍMICA   (Uruguay)

Author keywords

Free radical; Nitric oxide; Nitrotyrosine; Oxidative stress; Peroxynitrite; Superoxide radical

Indexed keywords

3 NITROTYROSINE; CARBON DIOXIDE; CARBONIC ACID; FREE RADICAL; GLUTATHIONE; METALLOPROTEIN; NITROGEN DIOXIDE; PEROXYNITRITE; SCAVENGER; THIOL; PEROXIREDOXIN; THIOL DERIVATIVE;

ANTIOXIDANT ACTIVITY; BIOSYNTHESIS; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CONCENTRATION RESPONSE; CORRELATIONAL STUDY; DECOMPOSITION; DETOXIFICATION; ELECTRON SPIN RESONANCE; HALF LIFE TIME; HUMAN; MOLECULAR MODEL; NITRATION; NONHUMAN; OXIDATION KINETICS; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; STEADY STATE; TOXICOKINETICS; ARTICLE; IN VIVO STUDY; MATHEMATICAL MODEL; QUANTITATIVE ANALYSIS;

2,2′-AZINOBIS (3-ETHYLBENZTHIAZOLINE-6-SULFONIC ACID); 3-NITROTYROSINE; 5,5-DIMETHYL-1-PYRROLINE-N-OXIDE; ABTS(2-); DIETHYLENETRIAMINEPENTAACETIC ACID; DMPO; DTPA; EOSINOPHIL PEROXIDASE; EPO; FREE RADICAL; GLUTATHIONE; GSH; MPO; MYELOPEROXIDASE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITROTYROSINE; NOS; NT; OXIDATIVE STRESS; PEROXIREDOXIN; PEROXYNITRITE; PRX; SOD; SUPEROXIDE DISMUTASE; SUPEROXIDE RADICAL;

ANIMALS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; KINETICS; PEROXYNITROUS ACID;

EID: 84890124303     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.07.005     Document Type: Review

References (174)

1. C. Szabo, H. Ischiropoulos, and R. Radi Peroxynitrite: biochemistry, pathophysiology and development of therapeutics Nat. Rev. Drug Discov. 6 2007 662 680 (Pubitemid 47207751)
2. L.J. Ignarro Endothelium-derived nitric oxide: actions and properties FASEB J. 3 1989 31 36 (Pubitemid 19042562)
3. L.J. Ignarro Biosynthesis and metabolism of endothelium-derived nitric oxide Annu. Rev. Pharmacol. Toxicol. 30 1990 535 560
4. S. Moncada, R.M. Palmer, and E.A. Higgs Nitric oxide: physiology, pathophysiology, and pharmacology Pharmacol. Rev. 43 1991 109 142
5. X. Liu, M.J. Miller, M.S. Joshi, H. Sadowska-Krowicka, D.A. Clark, and J.R. Lancaster Jr. Diffusion-limited reaction of free nitric oxide with erythrocytes J. Biol. Chem. 273 1998 18709 18713 (Pubitemid 28366253)
6. N.M. Tsoukias, M. Kavdia, and A.S. Popel A theoretical model of nitric oxide transport in arterioles: frequency- vs. amplitude-dependent control of cGMP formation Am. J. Physiol. Heart Circ. Physiol. 286 2004 H1043 H1056
7. J.S. Beckman, T.W. Beckman, J. Chen, P.A. Marshall, and B.A. Freeman Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide Proc. Natl. Acad. Sci. U. S. A. 87 1990 1620 1624
8. R. Radi, J.S. Beckman, K.M. Bush, and B.A. Freeman Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide J. Biol. Chem. 266 1991 4244 4250 (Pubitemid 21909347)
9. E.M. Fielden, P.B. Roberts, R.C. Bray, D.J. Lowe, G.N. Mautner, G. Rotilio, and L. Calabrese Mechanism of action of superoxide dismutase from pulse radiolysis and electron paramagnetic resonance. Evidence that only half the active sites function in catalysis Biochem. J. 139 1974 49 60
10. J.L. Hsu, Y. Hsieh, C. Tu, D. O'Connor, H.S. Nick, and D.N. Silverman Catalytic properties of human manganese superoxide dismutase J. Biol. Chem. 271 1996 17687 17691 (Pubitemid 26250738)
11. D. Klug-Roth, I. Fridovich, and J. Rabani Pulse radiolytic investigations of superoxide catalyzed disproportionation. Mechanism for bovine superoxide dismutase J. Am. Chem. Soc. 95 1973 2786 2790
12. B. Halliwell, and J. Gutteridge Antioxidant defences Free Radicals in Biology and Medicine Fourth Ed. 1999 Oxford University Press Oxford 79 185
13. L.Y. Chang, J.W. Slot, H.J. Geuze, and J.D. Crapo Molecular immunocytochemistry of the CuZn superoxide dismutase in rat hepatocytes J. Cell Biol. 107 1988 2169 2179 (Pubitemid 19015096)
14. C. Quijano, D. Hernandez-Saavedra, L. Castro, J.M. McCord, B.A. Freeman, and R. Radi Reaction of peroxynitrite with Mn-superoxide dismutase. Role of the metal center in decomposition kinetics and nitration J. Biol. Chem. 276 2001 11631 11638
15. R.J. Gryglewski, R.M. Palmer, and S. Moncada Superoxide anion is involved in the breakdown of endothelium-derived vascular relaxing factor Nature 320 1986 454 456 (Pubitemid 16097810)
16. G.M. Rubanyi, and P.M. Vanhoutte Superoxide anions and hyperoxia inactivate endothelium-derived relaxing factor Am. J. Physiol. 250 1986 H822 H827
17. - and HO2: A pulse radiolysis study Free Radic. Biol. Med. 19 1995 505 510
18. R.E. Huie, and S. Padmaja The reaction of no with superoxide Free Radic. Res. Commun. 18 1993 195 199
19. R. Kissner, T. Nauser, P. Bugnon, P.G. Lye, and W.H. Koppenol Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis Chem. Res. Toxicol. 10 1997 1285 1292 (Pubitemid 27524836)
20. - at chemical equilibrium with ONOO J. Phys. Chem. B 114 2010 16584 16593
21. G. Ferrer-Sueta, and R. Radi Chemical biology of peroxynitrite: kinetics, diffusion, and radicals ACS Chem. Biol. 4 2009 161 177
22. C. Quijano, L. Castro, G. Peluffo, V. Valez, and R. Radi Enhanced mitochondrial superoxide in hyperglycemic endothelial cells: direct measurements and formation of hydrogen peroxide and peroxynitrite Am. J. Physiol. Heart Circ. Physiol. 293 2007 H3404 H3414
23. C.H. Lim, P.C. Dedon, and W.M. Deen Kinetic analysis of intracellular concentrations of reactive nitrogen species Chem. Res. Toxicol. 21 2008 2134 2147
24. M.N. Alvarez, M. Trujillo, and R. Radi Peroxynitrite formation from biochemical and cellular fluxes of nitric oxide and superoxide Methods Enzymol. 359 2002 353 366 (Pubitemid 35387036)
25. W.H. Koppenol, and R. Kissner Can ONOOH undergo homolysis? Chem. Res. Toxicol. 11 1998 87 90
26. -) system Chem. Res. Toxicol. 11 1998 243 246
27. S.S. Marla, J. Lee, and J.T. Groves Peroxynitrite rapidly permeates phospholipid membranes Proc. Natl. Acad. Sci. U. S. A. 94 1997 14243 14248 (Pubitemid 28041358)
28. A. Denicola, J.M. Souza, and R. Radi Diffusion of peroxynitrite across erythrocyte membranes Proc. Natl. Acad. Sci. U. S. A. 95 1998 3566 3571 (Pubitemid 28173168)
29. N. Romero, A. Denicola, J.M. Souza, and R. Radi Diffusion of peroxynitrite in the presence of carbon dioxide Arch. Biochem. Biophys. 368 1999 23 30 (Pubitemid 29372300)
30. M.N. Hughes, and H.G. Nicklin The chemistry of pernitrites. Part I. Kinetics of decomposition of pernitrous acid J. Chem. Soc. A 1968 450 456
31. O. Augusto, R.M. Gatti, and R. Radi Spin-trapping studies of peroxynitrite decomposition and of 3-morpholinosydnonimine N-ethylcarbamide autooxidation: direct evidence for metal-independent formation of free radical intermediates Arch. Biochem. Biophys. 310 1994 118 125
32. O.V. Gerasimov, and S.V. Lymar The yield of hydroxyl radical from the decomposition of peroxynitrous acid Inorg. Chem. 38 1999 4317 4321
33. S. Goldstein, and G. Czapski Direct and indirect oxidations by peroxynitrite Inorg. Chem. 34 1995 4041 4048
34. R. Radi Peroxynitrite reactions and diffusion in biology Chem. Res. Toxicol. 11 1998 720 721 (Pubitemid 28350720)
35. S. Bartesaghi, G. Ferrer-Sueta, G. Peluffo, V. Valez, H. Zhang, B. Kalyanaraman, and R. Radi Protein tyrosine nitration in hydrophilic and hydrophobic environments Amino Acids 32 2007 501 515 (Pubitemid 46790931)
36. S. Bartesaghi, V. Valez, M. Trujillo, G. Peluffo, N. Romero, H. Zhang, B. Kalyanaraman, and R. Radi Mechanistic studies of peroxynitrite-mediated tyrosine nitration in membranes using the hydrophobic probe N-t-BOC-l-tyrosine tert-butyl ester Biochemistry 45 2006 6813 6825 (Pubitemid 43856667)
37. V.B. O'Donnell, J.P. Eiserich, A. Bloodsworth, P.H. Chumley, M. Kirk, S. Barnes, V.M. Darley-Usmar, and B.A. Freeman Nitration of unsaturated fatty acids by nitric oxide-derived reactive species Methods Enzymol. 301 1999 454 470 (Pubitemid 28489807)
38. R. Radi, J.S. Beckman, K.M. Bush, and B.A. Freeman Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide Arch. Biochem. Biophys. 288 1991 481 487
39. H. Rubbo, A. Trostchansky, and V.B. O'Donnell Peroxynitrite-mediated lipid oxidation and nitration: mechanisms and consequences Arch. Biochem. Biophys. 484 2009 167 172
40. R. Radi, A. Denicola, B. Alvarez, G. Ferrer, and H. Rubbo The biological chemistry of peroxynitrite L.J. Ignarro, Nitric Oxide Biology and Pathobiology 2000 Academic Press San Diego 57 82
41. M. Trujillo, B. Alvarez, J.M. Souza, N. Romero, L. Castro, L. Thomson, and R. Radi Mechanisms and biological consequences of peroxynitrite-dependent protein oxidation and nitration J.L. Ignarro, Nitric Oxide Biology and Pathobiology 2010 Academic Press San Diego 61 102
42. M.G. Bonini, R. Radi, G. Ferrer-Sueta, A.M. Ferreira, and O. Augusto Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide J. Biol. Chem. 274 1999 10802 10806
43. A. Denicola, B.A. Freeman, M. Trujillo, and R. Radi Peroxynitrite reaction with carbon dioxide/bicarbonate: kinetics and influence on peroxynitrite-mediated oxidations Arch. Biochem. Biophys. 333 1996 49 58 (Pubitemid 26276973)
44. S. Goldstein, and G. Czapski The effect of bicarbonate on oxidation by peroxynitrite: implication for its biological activity Inorg. Chem. 36 1997 5113 5117 (Pubitemid 127490034)
45. 2-catalyzed one-electron oxidations by peroxynitrite: properties of the reactive intermediate Inorg. Chem. 37 1998 294 301 (Pubitemid 128483312)
46. M.G. Bonini, and O. Augusto Carbon dioxide stimulates the production of thiyl, sulfinil and disulfide radical anion from thiol oxidation by peroxynitrite J. Biol. Chem. 276 2001 9749 9754
47. W.H. Koppenol, J.J. Moreno, W.A. Pryor, H. Ischiropoulos, and J.S. Beckman Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide Chem. Res. Toxicol. 5 1992 834 842 (Pubitemid 23004874)
48. S.V. Lymar, H.A. Schwarz, and G. Czapski Medium effects on reactions of the carbonate radicals with thiocyanate, iodide and ferrocyanide ions Radiat. Phys. Chem. 59 2000 387 392 (Pubitemid 30616433)
49. R.E. Huie, C.L. Clifton, and P. Neta Electron-transfer reaction rates and equilibria of the carbonate and sulfate radical anions Radiat. Phys. Chem. 38 1991 477 481
50. O. Augusto, M.G. Bonini, A.M. Amanso, E. Linares, C.C. Santos, and S.L. De Menezes Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology Free Radic. Biol. Med. 32 2002 841 859 (Pubitemid 34439255)
51. M. Trujillo, and R. Radi Peroxynitrite reaction with the reduced and the oxidized forms of lipoic acid: new insights into the reaction of peroxynitrite with thiols Arch. Biochem. Biophys. 397 2002 91 98 (Pubitemid 34848253)
52. M. Dubuisson, D. Vander Stricht, A. Clippe, F. Etienne, T. Nauser, R. Kissner, W.H. Koppenol, J.F. Rees, and B. Knoops Human peroxiredoxin 5 is a peroxynitrite reductase FEBS Lett. 571 2004 161 165 (Pubitemid 38992941)
53. M. Trujillo, A. Clippe, B. Manta, G. Ferrer-Sueta, A. Smeets, J.P. Declercq, B. Knoops, and R. Radi Pre-steady state kinetic characterization of human peroxiredoxin 5: taking advantage of Trp84 fluorescence increase upon oxidation Arch. Biochem. Biophys. 467 2007 95 106 (Pubitemid 47625297)
54. G. Ferrer-Sueta, B. Manta, H. Botti, R. Radi, M. Trujillo, and A. Denicola Factors affecting protein thiol reactivity and specificity in peroxide reduction Chem. Res. Toxicol. 24 2011 434 450
55. C. Quijano, B. Alvarez, R.M. Gatti, O. Augusto, and R. Radi Pathways of peroxynitrite oxidation of thiol groups Biochem. J. 322 1997 167 173 (Pubitemid 27095537)
56. P. Wardman, and C. von Sonntag Kinetic factors that control the fate of thiyl radicals in cells Methods Enzymol. 251 1995 31 45
57. H. Karoui, N. Hogg, C. Frejaville, P. Tordo, and B. Kalyanaraman 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 1996 6000 6009 (Pubitemid 26095401)
58. A.B. Ross, W.G. Mallard, W.P. Helman, G.V. Buxton, R.T. Huie, and P. Neta NDRLNIST Solution Kinetics Database, Version 3, Notre Dame Radiation Laboratory, Notre Dame, IN, and NIST Standard Reference Data 1998
59. A. Daiber, S. Herold, C. Schoneich, D. Namgaladze, J.A. Peterson, and V. Ullrich Nitration and inactivation of cytochrome P450BM-3 by peroxynitrite. Stopped-flow measurements prove ferryl intermediates Eur. J. Biochem. 267 2000 6729 6739
60. R. Floris, S.R. Piersma, G. Yang, P. Jones, and R. Wever Interaction of myeloperoxidase with peroxynitrite. A comparison with lactoperoxidase, horseradish peroxidase and catalase Eur. J. Biochem. 215 1993 767 775 (Pubitemid 23246850)
61. P.G. Furtmuller, W. Jantschko, M. Zederbauer, M. Schwanninger, C. Jakopitsch, S. Herold, W.H. Koppenol, and C. Obinger Peroxynitrite efficiently mediates the interconversion of redox intermediates of myeloperoxidase Biochem. Biophys. Res. Commun. 337 2005 944 954 (Pubitemid 41447005)
62. B. Alvarez, V. Demicheli, R. Duran, M. Trujillo, C. Cervenansky, B.A. Freeman, and R. Radi Inactivation of human Cu,Zn superoxide dismutase by peroxynitrite and formation of histidinyl radical Free Radic. Biol. Med. 37 2004 813 822 (Pubitemid 39078553)
63. L.A. MacMillan-Crow, J.P. Crow, J.D. Kerby, J.S. Beckman, and J.A. Thompson Nitration and inactivation of manganese superoxide dismutase in chronic rejection of human renal allografts Proc. Natl. Acad. Sci. U. S. A. 93 1996 11853 11858 (Pubitemid 26347213)
64. B. Alvarez, G. Ferrer-Sueta, B.A. Freeman, and R. Radi Kinetics of peroxynitrite reaction with amino acids and human serum albumin J. Biol. Chem. 274 1999 842 848
65. A. Denicola, J.M. Souza, R.M. Gatti, O. Augusto, and R. Radi Desferrioxamine inhibition of the hydroxyl radical-like reactivity of peroxynitrite: role of the hydroxamic groups Free Radic. Biol. Med. 19 1995 11 19
66. S. Bartesaghi, M. Trujillo, A. Denicola, L. Folkes, P. Wardman, and R. Radi Reactions of desferrioxamine with peroxynitrite-derived carbonate and nitrogen dioxide radicals Free Radic. Biol. Med. 36 2004 471 483 (Pubitemid 38224519)
67. M.A. Adgent, G.L. Squadrito, C.A. Ballinger, D.M. Krzywanski, J.R. Lancaster, and E.M. Postlethwait Desferrioxamine inhibits protein tyrosine nitration: mechanisms and implications Free Radic. Biol. Med. 53 2012 951 961
68. R. Radi Kinetic analysis of reactivity of peroxynitrite with biomolecules Methods Enzymol. 269 1996 354 366 (Pubitemid 26295723)
69. G. Ferrer-Sueta, C. Quijano, B. Alvarez, and R. Radi Reactions of manganese porphyrins and manganese-superoxide dismutase with peroxynitrite Methods Enzymol. 349 2002 23 37 (Pubitemid 34229490)
70. M. Trujillo, H. Budde, M.D. Pineyro, M. Stehr, C. Robello, L. Flohe, and R. Radi Trypanosoma brucei and Trypanosoma cruzi tryparedoxin peroxidases catalytically detoxify peroxynitrite via oxidation of fast reacting thiols J. Biol. Chem. 279 2004 34175 34182 (Pubitemid 39318040)
71. J.H. Espenson Chemical Kinetics and Reaction Mechanisms Second ed. 1995 McGraw-Hill
72. T. Jaeger, H. Budde, L. Flohe, U. Menge, M. Singh, M. Trujillo, and R. Radi Multiple thioredoxin-mediated routes to detoxify hydroperoxides in Mycobacterium tuberculosis Arch. Biochem. Biophys. 423 2004 182 191 (Pubitemid 38198227)
73. G. Ferrer-Sueta, D. Vitturi, I. Batinic-Haberle, I. Fridovich, S. Goldstein, G. Czapski, and R. Radi Reactions of manganese porphyrins with peroxynitrite and carbonate radical anion J. Biol. Chem. 278 2003 27432 27438 (Pubitemid 36899925)
74. R. Ogusucu, D. Rettori, D.C. Munhoz, L.E. Netto, and O. Augusto Reactions of yeast thioredoxin peroxidases I and II with hydrogen peroxide and peroxynitrite: rate constants by competitive kinetics Free Radic. Biol. Med. 42 2007 326 334 (Pubitemid 46038040)
75. E. Ford, M.N. Hughes, and P. Wardman Kinetics of the reactions of nitrogen dioxide with glutathione, cysteine, and uric acid at physiological pH Free Radic. Biol. Med. 32 2002 1314 1323 (Pubitemid 34607635)
76. P. Wardman, and A.B. Ross "Radiation chemistry" literature compilations: their wider value in free radical research Free Radic. Biol. Med. 10 1991 243 247 (Pubitemid 121003233)
77. K.D. Asmus Pulse radiolysis methodology Methods Enzymol. 105 1984 167 178
78. G.V. Buxton, and A.J. Elliot Rate-constant for reaction of hydroxyl radical with bicarbonate ions Radiat. Phys. Chem. 27 1986 241 243
79. D. Behar, G. Czapski, and I. Duchovny Carbonate radical in flash photolysis and pulse radiolysis of aqueous carbonate solutions J. Phys. Chem. 74 1970 2206 2210
80. - ions in aqueous solutions J. Phys. Chem. 71 1967 1472 1477
81. S.N. Chen, and M.Z. Hoffman Rate constants for the reaction of the carbonate radical with compounds of biochemical interest in neutral aqueous solution Radiat. Res. 56 1973 40 47
82. O. Augusto, and S. Muntz Vaz EPR spin-trapping of protein radicals to investigate biological oxidative mechanisms Amino Acids 32 2007 535 542 (Pubitemid 46790935)
83. M.J. Davies, and C.L. Hawkins EPR spin trapping of protein radicals Free Radic. Biol. Med. 36 2004 1072 1086 (Pubitemid 38479861)
84. J. Stubbe, and W.A. van der Donk Protein radicals in enzyme catalysis Chem. Rev. 98 1998 705 762 (Pubitemid 128631440)
85. G.M. Rosen, and E.J. Rauckman Spin trapping of superoxide and hydroxyl radicals Methods Enzymol. 105 1984 198 209
86. M.N. Alvarez, G. Peluffo, L. Folkes, P. Wardman, and R. Radi Reaction of the carbonate radical with the spin-trap 5,5-dimethyl-1-pyrroline-N-oxide in chemical and cellular systems: pulse radiolysis, electron paramagnetic resonance, and kinetic-competition studies Free Radic. Biol. Med. 43 2007 1523 1533 (Pubitemid 47615394)
87. C.D. Detweiler, L.J. Deterding, K.B. Tomer, C.F. Chignell, D. Germolec, and R.P. Mason Immunological identification of the heart myoglobin radical formed by hydrogen peroxide Free Radic. Biol. Med. 33 2002 364 369 (Pubitemid 34786275)
88. C.D. Detweiler, O.M. Lardinois, L.J. Deterding, P.R. de Montellano, K.B. Tomer, and R.P. Mason Identification of the myoglobin tyrosyl radical by immuno-spin trapping and its dimerization Free Radic. Biol. Med. 38 2005 969 976 (Pubitemid 40321088)
89. D.C. Ramirez, Y.R. Chen, and R.P. Mason Immunochemical detection of hemoglobin-derived radicals formed by reaction with hydrogen peroxide: involvement of a protein-tyrosyl radical Free Radic. Biol. Med. 34 2003 830 839 (Pubitemid 36316067)
90. N. Romero, R. Radi, E. Linares, O. Augusto, C.D. Detweiler, R.P. Mason, and A. Denicola Reaction of human hemoglobin with peroxynitrite. Isomerization to nitrate and secondary formation of protein radicals J. Biol. Chem. 278 2003 44049 44057 (Pubitemid 37377145)
91. P. Cassina, A. Cassina, M. Pehar, R. Castellanos, M. Gandelman, A. de Leon, K.M. Robinson, R.P. Mason, J.S. Beckman, L. Barbeito, and R. Radi Mitochondrial dysfunction in SOD1G93A-bearing astrocytes promotes motor neuron degeneration: prevention by mitochondrial-targeted antioxidants J. Neurosci. 28 2008 4115 4122
92. R. Radi Nitric oxide, oxidants, and protein tyrosine nitration Proc. Natl. Acad. Sci. U. S. A. 101 2004 4003 4008 (Pubitemid 38405874)
93. R. Radi Protein tyrosine nitration: biochemical mechanisms and structural basis of its functional effects Acc. Chem. Res. 46 2013 550 559
94. M. Sokolovsky, J.F. Riordan, and B.L. Vallee Tetranitromethane. A reagent for the nitration of tyrosyl residues in proteins Biochemistry 5 1966 3582 3589
95. J.M. Souza, G. Peluffo, and R. Radi Protein tyrosine nitration - functional alteration or just a biomarker? Free Radic. Biol. Med. 15 2008 357 366
96. H. Ischiropoulos, L. Zhu, and J.S. Beckman Peroxynitrite formation from macrophage-derived nitric oxide Arch. Biochem. Biophys. 298 1992 446 451
97. J.S. Beckman, Y.Z. Ye, P.G. Anderson, J. Chen, M.A. Accavitti, M.M. Tarpey, and C.R. White Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry Biol. Chem. Hoppe Seyler 375 1994 81 88
98. R. Radi, G. Peluffo, M.N. Alvarez, M. Naviliat, and A. Cayota Unraveling peroxynitrite formation in biological systems Free Radic. Biol. Med. 30 2001 463 488 (Pubitemid 32162954)
99. J.M. Souza, S. Bartesaghi, G. Peluffo, and R. Radi Nitrotyrosine: quantitative analysis, mapping in proteins and biological significance G. Aldini, K. Yeum, E. Niki, R.M. Russel, Biomarkers for Antioxidant Defense and Oxidative Damage 2010 Wiley-Blackwell Ames, Iowa, USA 199 218
100. M.H. Shishehbor, R.J. Aviles, M.L. Brennan, X. Fu, M. Goormastic, G.L. Pearce, N. Gokce, J.F. Keaney Jr., M.S. Penn, D.L. Sprecher, J.A. Vita, and S.L. Hazen Association of nitrotyrosine levels with cardiovascular disease and modulation by statin therapy JAMA 289 2003 1675 1680 (Pubitemid 37430273)
101. C. Isobe, T. Abe, and Y. Terayama Remarkable increase in 3-nitrotyrosine in the cerebrospinal fluid in patients with lacunar stroke Brain Res. 1305 2009 132 136
102. B. Liu, A.K. Tewari, L. Zhang, K.B. Green-Church, J.L. Zweier, Y.R. Chen, and G. He Proteomic analysis of protein tyrosine nitration after ischemia reperfusion injury: mitochondria as the major target Biochim. Biophys. Acta 1794 2009 476 485
103. I.V. Turko, L. Li, K.S. Aulak, D.J. Stuehr, J.Y. Chang, and F. Murad Protein tyrosine nitration in the mitochondria from diabetic mouse heart. Implications to dysfunctional mitochondria in diabetes J. Biol. Chem. 278 2003 33972 33977 (Pubitemid 37553232)
104. R. Zhang, M.L. Brennan, X. Fu, R.J. Aviles, G.L. Pearce, M.S. Penn, E.J. Topol, D.L. Sprecher, and S.L. Hazen Association between myeloperoxidase levels and risk of coronary artery disease JAMA 286 2001 2136 2142 (Pubitemid 34041599)
105. D.A. Butterfield, T.T. Reed, M. Perluigi, C. De Marco, R. Coccia, J.N. Keller, W.R. Markesbery, and R. Sultana Elevated levels of 3-nitrotyrosine in brain from subjects with amnestic mild cognitive impairment: implications for the role of nitration in the progression of Alzheimer's disease Brain Res. 1148 2007 243 248 (Pubitemid 46602178)
106. P. Pacher, J.S. Beckman, and L. Liaudet Nitric oxide and peroxynitrite in health and disease Physiol. Rev. 87 2007 315 424 (Pubitemid 46217686)
107. M.R. Reynolds, R.W. Berry, and L.I. Binder Site-specific nitration differentially influences tau assembly in vitro Biochemistry 44 2005 13997 14009 (Pubitemid 41507480)
108. M.R. Reynolds, R.W. Berry, and L.I. Binder Site-specific nitration and oxidative dityrosine bridging of the tau protein by peroxynitrite: implications for Alzheimer's disease Biochemistry 44 2005 1690 1700 (Pubitemid 40204410)
109. B. Alvarez, and R. Radi Peroxynitrite reactivity with amino acids and proteins Amino Acids 25 2003 295 311 (Pubitemid 38041267)
110. W.A. Prutz, H. Monig, J. Butler, and E.J. Land Reactions of nitrogen dioxide in aqueous model systems: oxidation of tyrosine units in peptides and proteins Arch. Biochem. Biophys. 243 1985 125 134
111. S. Solar, W. Solar, and N. Getoff Reactivity of OH with tyrosine in aqueous solution studied by pulse radiolysis J. Phys. Chem. 88 1984 2091 2095
112. M. Tien Myeloperoxidase-catalyzed oxidation of tyrosine Arch. Biochem. Biophys. 367 1999 61 66 (Pubitemid 29394193)
113. L.A. Marquez, and H.B. Dunford Kinetics of oxidation of tyrosine and dityrosine by myeloperoxidase compounds I and II. Implications for lipoprotein peroxidation studies J. Biol. Chem. 270 1995 30434 30440
114. L.K. Folkes, S. Bartesaghi, M. Trujillo, R. Radi, and P. Wardman Kinetics of oxidation of tyrosine by a model alkoxyl radical Free Radic. Res. 46 2012 1150 1156
115. S. Bartesaghi, J. Wenzel, M. Trujillo, M. Lopez, J. Joseph, B. Kalyanaraman, and R. Radi Lipid peroxyl radicals mediate tyrosine dimerization and nitration in membranes Chem. Res. Toxicol. 19 2010 821 835
116. C.C. Winterbourn, H.N. Parsons-Mair, S. Gebicki, J.M. Gebicki, and M.J. Davies Requirements for superoxide-dependent tyrosine hydroperoxide formation in peptides Biochem. J. 381 2004 241 248 (Pubitemid 38932230)
117. C.X. Santos, M.G. Bonini, and O. Augusto Role of the carbonate radical anion in tyrosine nitration and hydroxylation by peroxynitrite Arch. Biochem. Biophys. 377 2000 146 152 (Pubitemid 30257299)
118. Y.R. Chen, C.L. Chen, W. Chen, J.L. Zweier, O. Augusto, R. Radi, and R.P. Mason Formation of protein tyrosine ortho-semiquinone radical and nitrotyrosine from cytochrome c-derived tyrosyl radical J. Biol. Chem. 279 2004 18054 18062 (Pubitemid 38560575)
119. M.L. Brennan, W. Wu, X. Fu, Z. Shen, W. Song, H. Frost, C. Vadseth, L. Narine, E. Lenkiewicz, M.T. Borchers, A.J. Lusis, J.J. Lee, N.A. Lee, H.M. Abu-Soud, H. Ischiropoulos, and S.L. Hazen A tale of two controversies: defining both the role of peroxidases in nitrotyrosine formation in vivo using eosinophil peroxidase and myeloperoxidase-deficient mice, and the nature of peroxidase-generated reactive nitrogen species J. Biol. Chem. 277 2002 17415 17427 (Pubitemid 34967541)
120. J.P. Eiserich, M. Hristova, C.E. Cross, A.D. Jones, B.A. Freeman, B. Halliwell, and A. van der Vliet Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils Nature 391 1998 393 397 (Pubitemid 28093514)
121. J. Soubhye, I. Aldib, B. Elfving, M. Gelbcke, P.G. Furtmuller, M. Podrecca, R. Conotte, J.M. Colet, A. Rousseau, F. Reye, A. Sarakbi, M. Vanhaeverbeek, J.M. Kauffmann, C. Obinger, J. Neve, M. Prevost, K. Zouaoui Boudjeltia, F.M. Dufrasne, and P.G. Van Antwerpen Design, synthesis, and structure-activity relationship studies of Novel 3-alkylindole derivatives as selective and highly potent myeloperoxidase inhibitors J. Med. Chem. 56 2013 3943 3958
122. L.K. Folkes, M. Trujillo, S. Bartesaghi, R. Radi, and P. Wardman Kinetics of reduction of tyrosine phenoxyl radicals by glutathione Arch. Biochem. Biophys. 506 2011 242 249
123. A.A. Petruk, S. Bartesaghi, M. Trujillo, D.A. Estrin, D. Murgida, B. Kalyanaraman, M.A. Marti, and R. Radi Molecular basis of intramolecular electron transfer in proteins during radical-mediated oxidations: computer simulation studies in model tyrosine-cysteine peptides in solution Arch. Biochem. Biophys. 525 2012 82 91
124. F. Yamakura, H. Taka, T. Fujimura, and K. Murayama Inactivation of human manganese-superoxide dismutase by peroxynitrite is caused by exclusive nitration of tyrosine 34 to 3-nitrotyrosine J. Biol. Chem. 273 1998 14085 14089 (Pubitemid 28319114)
125. M.C. Franco, Y. Ye, C.A. Refakis, J.L. Feldman, A.L. Stokes, M. Basso, R.M. Melero Fernandez de Mera, N.A. Sparrow, N.Y. Calingasan, M. Kiaei, T.W. Rhoads, T.C. Ma, M. Grumet, S. Barnes, M.F. Beal, J.S. Beckman, R. Mehl, and A.G. Estevez Nitration of Hsp90 induces cell death Proc. Natl. Acad. Sci. U. S. A. 110 2013 E1102 E1111
126. C. Quijano, N. Romero, and R. Radi Tyrosine nitration by superoxide and nitric oxide fluxes in biological systems: modeling the impact of superoxide dismutase and nitric oxide diffusion Free Radic. Biol. Med. 39 2005 728 741 (Pubitemid 41139888)
127. S. Bharath, and J.K. Andersen Glutathione depletion in a midbrain-derived immortalized dopaminergic cell line results in limited tyrosine nitration of mitochondrial complex I subunits: implications for Parkinson's disease Antioxid. Redox Signal. 7 2005 900 910 (Pubitemid 40967141)
128. L.A. Castro, R.L. Robalinho, A. Cayota, R. Meneghini, and R. Radi Nitric oxide and peroxynitrite-dependent aconitase inactivation and iron-regulatory protein-1 activation in mammalian fibroblasts Arch. Biochem. Biophys. 359 1998 215 224 (Pubitemid 28525236)
129. K.A. Marshall, M. Reist, P. Jenner, and B. Halliwell The neuronal toxicity of sulfite plus peroxynitrite is enhanced by glutathione depletion: implications for Parkinson's disease Free Radic. Biol. Med. 27 1999 515 520 (Pubitemid 29408636)
130. H. Muyderman, M. Nilsson, and N.R. Sims Highly selective and prolonged depletion of mitochondrial glutathione in astrocytes markedly increases sensitivity to peroxynitrite J. Neurosci. 24 2004 8019 8028 (Pubitemid 39280821)
131. B. Manta, M. Hugo, C. Ortiz, G. Ferrer-Sueta, M. Trujillo, and A. Denicola The peroxidase and peroxynitrite reductase activity of human erythrocyte peroxiredoxin 2 Arch. Biochem. Biophys. 484 2009 146 154
132. D. Bartlett, D.F. Church, P.L. Bounds, and W.H. Koppenol The kinetics of the oxidation of l-ascorbic acid by peroxynitrite Free Radic. Biol. Med. 18 1995 85 92
133. C.X. Santos, E.I. Anjos, and O. Augusto Uric acid oxidation by peroxynitrite: multiple reactions, free radical formation, and amplification of lipid oxidation Arch. Biochem. Biophys. 372 1999 285 294 (Pubitemid 30026778)
134. G.L. Squadrito, R. Cueto, A.E. Splenser, A. Valavanidis, H. Zhang, R.M. Uppu, and W.A. Pryor Reaction of uric acid with peroxynitrite and implications for the mechanism of neuroprotection by uric acid Arch. Biochem. Biophys. 376 2000 333 337 (Pubitemid 30210881)
135. R.J. Teng, Y.Z. Ye, D.A. Parks, and J.S. Beckman Urate produced during hypoxia protects heart proteins from peroxynitrite-mediated protein nitration Free Radic. Biol. Med. 33 2002 1243 1249 (Pubitemid 35246592)
136. M. Simic, and S. Jovanovic Antioxidation mechanisms of uric acid J. Am. Chem. Soc. 111 1989 5718-5182
137. T. Massuda, H. Shinohara, and M. Kondo Reactions of hydroxyl radicals with nucleic acid bases and the related compounds in gamma-irradiated aqueous solution J. Radiat. Res. (Tokyo) 16 1975 153 161
138. I. Batinic-Haberle, J.S. Reboucas, and I. Spasojevic Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential Antioxid. Redox Signal. 13 2010 877 918
139. R. Kachadourian, C.A. Johnson, E. Min, I. Spasojevic, and B.J. Day Flavin-dependent antioxidant properties of a new series of meso-N,N′- dialkyl-imidazolium substituted manganese(III) porphyrins Biochem. Pharmacol. 67 2004 77 85 (Pubitemid 37518536)
140. V. Valez, A. Cassina, I. Batinic-Haberle, B. Kalyanaraman, G. Ferrer-Sueta, and R. Radi Peroxynitrite formation in nitric oxide-exposed submitochondrial particles: detection, oxidative damage and catalytic removal by Mn-porphyrins Arch. Biochem. Biophys. 529 2013 45 54
141. G. Ferrer-Sueta, L. Hannibal, I. Batinic-Haberle, and R. Radi Reduction of manganese porphyrins by flavoenzymes and submitochondrial particles: a catalytic cycle for the reduction of peroxynitrite Free Radic. Biol. Med. 41 2006 503 512 (Pubitemid 44037285)
142. 5 +, targets mouse heart mitochondria Free Radic. Biol. Med. 42 2007 1193 1200 (Pubitemid 46437360)
143. H. Masumoto, R. Kissner, W.H. Koppenol, and H. Sies Kinetic study of the reaction of ebselen with peroxynitrite FEBS Lett. 398 1996 179 182 (Pubitemid 26414305)
144. A.H. Bubolz, Q. Wu, B.T. Larsen, D.D. Gutterman, and Y. Liu Ebselen reduces nitration and restores voltage-gated potassium channel function in small coronary arteries of diabetic rats Am. J. Physiol. Heart Circ. Physiol. 293 2007 H2231 H2237
145. E. Noiri, A. Nakao, K. Uchida, H. Tsukahara, M. Ohno, T. Fujita, S. Brodsky, and M.S. Goligorsky Oxidative and nitrosative stress in acute renal ischemia Am. J. Physiol. Renal Physiol. 281 2001 F948 F957
146. T. Takase, T. Ohta, R. Ogawa, M. Tsuji, Y. Tamura, S. Kazuki, and T. Miyamoto Effect of ebselen on contractile responses in perfused rabbit basilar artery Neurosurgery 44 1999 370 377 (discussion 377-378)
147. A.F. Bem, B. Fiuza, P. Calcerrada, P.M. Brito, G. Peluffo, T.C. Dinis, M. Trujillo, J.B. Rocha, R. Radi, and L.M. Almeida Protective effect of diphenyl diselenide against peroxynitrite-mediated endothelial cell death: a comparison with ebselen Nitric Oxide 31C 2013 20 30
148. J. Zielonka, A. Sikora, J. Joseph, and B. Kalyanaraman Peroxynitrite is the major species formed from different flux ratios of co-generated nitric oxide and superoxide: direct reaction with boronate-based fluorescent probe J. Biol. Chem. 285 2010 14210 14216
149. H.H. Szeto, and P.W. Schiller Novel therapies targeting inner mitochondrial membrane - from discovery to clinical development Pharm. Res. 28 2011 2669 2679
150. Y. Ye, C. Quijano, K.M. Robinson, K.C. Ricart, A.L. Strayer, M.A. Sahawneh, J.J. Shacka, M. Kirk, S. Barnes, M.A. Accavitti-Loper, R. Radi, J.S. Beckman, and A.G. Estevez Prevention of peroxynitrite-induced apoptosis of motor neurons and PC12 cells by tyrosine-containing peptides J. Biol. Chem. 282 2007 6324 6337 (Pubitemid 47100881)
151. D.C. Fernandes, D.B. Medinas, M.J. Alves, and O. Augusto Tempol diverts peroxynitrite/carbon dioxide reactivity toward albumin and cells from protein-tyrosine nitration to protein-cysteine nitrosation Free Radic. Biol. Med. 38 2005 189 200 (Pubitemid 39656130)
152. A.M. James, H.M. Cocheme, R.A. Smith, and M.P. Murphy Interactions of mitochondria-targeted and untargeted ubiquinones with the mitochondrial respiratory chain and reactive oxygen species. Implications for the use of exogenous ubiquinones as therapies and experimental tools J. Biol. Chem. 280 2005 21295 21312 (Pubitemid 40805692)
153. B.R. Babu, and O.W. Griffith Design of isoform-selective inhibitors of nitric oxide synthase Curr. Opin. Chem. Biol. 2 1998 491 500 (Pubitemid 128645702)
154. O.W. Griffith, and R.G. Kilbourn Nitric oxide synthase inhibitors: amino acids Methods Enzymol. 268 1996 375 392 (Pubitemid 26286380)
155. D.J. Stuehr, O.A. Fasehun, N.S. Kwon, S.S. Gross, J.A. Gonzalez, R. Levi, and C.F. Nathan Inhibition of macrophage and endothelial cell nitric oxide synthase by diphenyleneiodonium and its analogs FASEB J. 5 1991 98 103 (Pubitemid 21892842)
156. D.C. Hooper, O. Bagasra, J.C. Marini, A. Zborek, S.T. Ohnishi, R. Kean, J.M. Champion, A.B. Sarker, L. Bobroski, J.L. Farber, T. Akaike, H. Maeda, and H. Koprowski Prevention of experimental allergic encephalomyelitis by targeting nitric oxide and peroxynitrite: implications for the treatment of multiple sclerosis Proc. Natl. Acad. Sci. U. S. A. 94 1997 2528 2533 (Pubitemid 27136909)
157. I. Batinic-Haberle, L. Benov, I. Spasojevic, and I. Fridovich The ortho effect makes manganese(III) meso-tetrakis(N-methylpyridinium-2-yl)porphyrin a powerful and potentially useful superoxide dismutase mimic J. Biol. Chem. 273 1998 24521 24528 (Pubitemid 28454947)
158. D. Obal, S. Dai, R. Keith, N. Dimova, J. Kingery, Y.T. Zheng, J. Zweier, M. Velayutham, S.D. Prabhu, Q. Li, D. Conklin, D. Yang, A. Bhatnagar, R. Bolli, and G. Rokosh Cardiomyocyte-restricted overexpression of extracellular superoxide dismutase increases nitric oxide bioavailability and reduces infarct size after ischemia/reperfusion Basic Res. Cardiol. 107 2012 305
159. W. Ying, C.M. Anderson, Y. Chen, B.A. Stein, C.S. Fahlman, J.C. Copin, P.H. Chan, and R.A. Swanson Differing effects of copper, zinc superoxide dismutase overexpression on neurotoxicity elicited by nitric oxide, reactive oxygen species, and excitotoxins J. Cereb. Blood Flow Metab. 20 2000 359 368 (Pubitemid 30108455)
160. M.N. Alvarez, G. Peluffo, L. Piacenza, and R. Radi Intraphagosomal peroxynitrite as a macrophage-derived cytotoxin against internalized Trypanosoma cruzi: consequences for oxidative killing and role of microbial peroxiredoxins in infectivity J. Biol. Chem. 286 2011 6627 6640
161. P. Mendes Biochemistry by numbers: simulation of biochemical pathways with Gepasi 3 Trends Biochem. Sci. 22 1997 361 363 (Pubitemid 27376273)
162. - under physiological conditions. How the radicals do the job J. Biol. Chem. 275 2000 3031 3036 (Pubitemid 30082996)
163. T. Logager, and K. Sehested Formation and decay of peroxynitrous acid: a pulse radiolysis study J. Phys. Chem. 97 1993 6664 6669
164. I. Fridovich Superoxide dismutases. An adaptation to a paramagnetic gas J. Biol. Chem. 264 1989 7761 7764 (Pubitemid 19137245)
165. P. Nagy, and M.T. Ashby Reactive sulfur species: kinetics and mechanisms of the oxidation of cysteine by hypohalous acid to give cysteine sulfenic acid J. Am. Chem. Soc. 129 2007 14082 14091 (Pubitemid 350106102)
166. C.C. Winterbourn, and D. Metodiewa Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide Free Radic. Biol. Med. 27 1999 322 328 (Pubitemid 29395424)
167. C.M. Jones, A. Lawrence, P. Wardman, and M.J. Burkitt Electron paramagnetic resonance spin trapping investigation into the kinetics of glutathione oxidation by the superoxide radical: re-evaluation of the rate constant Free Radic. Biol. Med. 32 2002 982 990 (Pubitemid 34465650)
168. M. Hoffman, and E. Hayon Pulse radiolysis study of sulfhydryl compounds in aqueous solution J. Phys. Chem. 77 1973 990 996
169. S. Mezyk Rate constant determination for the reaction of hydroxyl radical and glutathione thyil radicals with glutathione in aqueous solution J. Phys. Chem. 100 1996 8861 8866 (Pubitemid 126834590)
170. M. Tamba, G. Simone, and M. Quintiliani Interactions of thiyl freeradicals with oxygen: a pulse radiolysis study Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 50 1986 595 600 (Pubitemid 16026696)
171. M. Kirsch, M. Lehnig, H.G. Korth, R. Sustmann, and H. de Groot Inhibition of peroxynitrite-induced nitration of tyrosine by glutathione in the presence of carbon dioxide through both radical repair and peroxynitrate formation Chemistry 7 2001 3313 3320 (Pubitemid 32777233)
172. M. Quintiliani, R. Badiello, M. Tamba, A. Esfandi, and G. Gorin Radiolysis of glutathione in oxygen-containing solutions of pH 7 Int. J. Radiat. Biol. 32 1977 195 202
173. P. Wardman Evaluation of the 'radical sink' hypothesis from a chemical-kinetic viewpoint J. Radioanal. Nucl. Chem. 232 1998 23 27
174. 2: evidence for carbonate radical production J. Am. Chem. Soc. 120 1998 3458 3463 (Pubitemid 28289084)