Peroxynitrite scavenging by metalloporphyrins and thiolates

Free Radical Biology and Medicine

Volumn 28, Issue 10, 2000, Pages 1487-1494

  Crow, J P ^a  

^a Univ A   (United States)

Author keywords

Carbon dioxide; Free radical; Nitration; Nitric oxide; Nitrotyrosine; Superoxide; Superoxide dismutase

Indexed keywords

FREE RADICAL; NITRIC OXIDE; PEROXYNITRITE; PORPHYRIN DERIVATIVE; SCAVENGER; SUPEROXIDE; SUPEROXIDE DISMUTASE; THIOL DERIVATIVE;

CELL DAMAGE; CELL KILLING; CONFERENCE PAPER; CYTOTOXICITY; HUMAN; INFLAMMATION; NITRATION; OXIDATIVE STRESS; PRIORITY JOURNAL; REACTION ANALYSIS;

ANIMALS; CELL DEATH; FREE RADICAL SCAVENGERS; HUMANS; METALLOPORPHYRINS; NITRATES; OXIDATION-REDUCTION; SULFHYDRYL COMPOUNDS;

EID: 0034656837     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00249-5     Document Type: Conference Paper

References (53)

1. Beckman J.S., Koppenol W.H. Nitric oxide, superoxide, and peroxynitrite the good, the bad, and ugly [review] . Am. J. Physiol. 271:1996;C1424-C1437.
2. Arteel G.E., Briviba K., Sies H. Protection against peroxynitrite [review]. FEBS Lett. 445:1999;226-230.
3. Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. J. Biol. Chem. 266:1991;4244-4250.
4. Radi R., Beckman J.S., Bush K.M., Freeman B.A. Peroxynitrite-induced membrane lipid peroxidation the cytotoxic potential of superoxide and nitric oxide . Arch. Biochem. Biophys. 288:1991;481-487.
5. Yermilov V., Rubio J., Ohshima H. Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Lett. 376:1995;207-210.
6. Ischiropoulos H. Biological tyrosine nitration - a pathophysiological function of nitric oxide and reactive oxygen species [review]. Arch. Biochem. Biophys. 356:1998;1-11.
7. Burney S., Niles J.C., Dedon P.C., Tannenbaum S.R. DNA damage in deoxynucleosides and oligonucleotides treated with peroxynitrite. Chem. Res. Tox. 12:1999;513-520.
8. Estevez A.G., Spear N., Manuel S.M., Radi R., Henderson C.E., Barbeito L., Beckman J.S. Nitric oxide and superoxide contribute to motor neuron apoptosis induced by trophic factor deprivation. J. Neurosci. 18:1998;923-931.
9. Cookson M.R., Ince P.G., Shaw P.J. Peroxynitrite and hydrogen peroxide induced cell death in the Nsc34 neuroblastoma X spinal cord cell line - role of poly(Adp- Ribose) polymerase. J. Neurochem. 70:1998;501-508.
10. Estevez A.G., Spear N., Pelluffo H., Kamaid A., Barbeito L., Beckman J.S. Examining apoptosis in cultured cells after exposure to nitric oxide and peroxynitrite [review]. Nitric Oxide, Pt. C: Biological And Antioxidant Activities. 301:1999;393-402.
11. Forman H.J., Fridovich I. Superoxide dismutase a comparison of rate constants . Arch. Biochem. Biophys. 158:1973;396-400.
12. McCord J.M., Fridovich I. Superoxide dismutase the first twenty years (1968-1988) . Free Radic. Biol. Med. 5:1988;363-369.
13. Beckman J.S., Beckman T.W., Chen J., Marshall P.A., Freeman B.A. Apparent hydroxyl radical production by peroxynitrite implications for endothelial injury from nitric oxide and superoxide . Proc. Natl. Acad. Sci. USA. 87:1990;1620-1624.
14. Crow J.P., Spruell C., Chen J., Gunn C., Ischiropoulos H., Tsai M., Smith C.D., Radi R., Koppenol W.H., Beckman J.S. On the pH-dependent yield of hydroxyl radical products from peroxynitrite. Free Radic. Biol. Med. 16:1994;331-338.
15. Radi R., Denicola A., Freeman B.A. Peroxynitrite reactions with carbon dioxide bicarbonate [review]. Nitric Oxide, Pt. C: Biological And Antioxidant Activities. 301:1999;353-367.
16. Uppu R.M., Squadrito G.L., Pryor W.A. Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 327:1996;335-343.
17. Lymar S.V., Jiang Q., Hurst J.K. Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry. 35:1996;7855-7861.
18. Zhang H., Squadrito G.L., Uppu R.M., Lemercier J.N., Cueto R., Pryor W.A. Inhibition of peroxynitrite-mediated oxidation of glutathione by carbon dioxide. Arch Biochem Biophys. 339:1997;183-189.
19. Lymar S.V., Hurst J.K. Co2-catalyzed one-electron oxidations by peroxynitrite - properties of the reactive intermediate. Inorganic Chemistry. 37:1998;294-301.
20. Meli R., Nauser T., Koppenol W.H. Direct observation of intermediates in the reaction of peroxynitrite with carbon dioxide. Helvetica Chimica Acta. 82:1999;722-725.
21. Tien M., Berlett B.S., Levine R.L., Chock P.B., Stadtman E.R. 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. 96:1999;7809-7814.
22. Souza J.M., Radi R. Glyceraldehyde-3-phosphate dehydrogenase inactivation by peroxynitrite. Arch. Biochem. Biophys. 360:1998;187-194.
23. Ferrer-Sueta G., Batinic-Haberle I., Spasojevic I., Fridovich I., Radi R. Catalytic scavenging of peroxynitrite by isomeric Mn(III) N-methylpyridylporphyrins in the presence of reductants. Chem. Res. Toxicol. 12:1999;442-449.
24. Takakura K., Beckman J.S., MacMillan-Crow L.A., Crow J.P. Rapid and irreversible inactivation of protein tyrosine phosphatases ptp1b, cd45, and lar by peroxynitrite. Arch. Biochem. Biophys. 369:1999;197-207.
25. Konorev E.A., Hogg N., Kalyanaraman B. Rapid and irreversible inhibition of creatine kinase by peroxynitrite. FEBS Lett. 427:1998;171-174.
26. Crow J.P., Beckman J.S., Mccord J.M. Sensitivity of the essential zinc-thiolate moiety of yeast alcohol dehydrogenase to hypochlorite and peroxynitrite. Biochemistry. 34:1995;3544-3552.
27. Castro L., Rodriguez M., Radi R. Aconitase is readily inactivated by peroxynitrite, but not by its precursor, nitric oxide. J. Biol. Chem. 269:1994;29409-29415.
28. Hausladen A., Fridovich I. Superoxide and peroxynitrite inactivate aconitases, but nitric oxide does not. J. Biol. Chem. 269:1994;29405-29408.
29. Groves J.T., Marla S.S. Peroxynitrite-induced DNA strand scission mediated by a manganese porphyrin. J. Am. Chem. Soc. 117:1995;9578-9579.
30. Stern M.K., Jensen M.P., Kramer K. Peroxynitrite decomposition catalysts. J. Am. Chem. Soc. 118:1996;8735-8736.
31. Szabo C., Day B.J., Salzman A.L. Evaluation of the relative contribution of nitric oxide and peroxynitrite to the suppression of mitochondrial respiration in immunostimulated macrophages using a manganese mesoporphyrin superoxide dismutase mimetic and peroxynitrite scavenger. FEBS Lett. 381:1996;82-86.
32. Ferrer-Sueta G., Ruiz-Ramirez L., Radi R. Ternary copper complexes and manganese (III) tetrakis(4-benzoic acid) porphyrin catalyze peroxynitrite-dependent nitration of aromatics. Chem. Res. Toxicol. 10:1997;1338-1344.
33. Marla S.S., Lee J., Groves J.T. Peroxynitrite rapidly permeates phospholipid membranes. Proc. Natl. Acad. Sci. USA. 94:1997;14243-14248.
34. Lee J.B., Hunt J.A., Groves J.T. Rapid decomposition of peroxynitrite by manganese porphyrin- antioxidant redox couples. Bioorg. Med. Chem. Lett. 7:1997;2913-2918.
35. Hunt J.A., Lee J., Groves J.T. Amphiphilic peroxynitrite decomposition catalysts in liposomal assemblies. Chem. Biol. 4:1997;845-858.
36. Salvemini D., Wang Z.Q., Stern M.K., Currie M.G., Misko T.P. Peroxynitrite decomposition catalysts therapeutics for peroxynitrite-mediated pathology . Proc. Natl. Acad. Sci. USA. 95:1998;2659-2663.
37. Misko T.P., Highkin M.K., Veenhuizen A.W., Manning P.T., Stern M.K., Currie M.G., Salvemini D. Characterization of the cytoprotective action of peroxynitrite decomposition catalysts. J. Biol. Chem. 273:1998;15646-15653.
38. Lee J.B., Hunt J.A., Groves J.T. Mechanisms of iron porphyrin reactions with peroxynitrite. J. Am. Chem. Soc. 120:1998;7493-7501.
39. Lee J.B., Hunt J.A., Groves J.T. Manganese porphyrins as redox-coupled peroxynitrite reductases. J. Am. Chem. Soc. 120:1998;6053-6061.
40. Salvemini D., Riley D.P., Lennon P.J., Wang Z.Q., Currie M.G., Macarthur M., Misko T.P. Protective effects of a superoxide dismutase mimetic and peroxynitrite decomposition catalysts in endotoxin-induced intestinal damage. Br. J. Pharmacol. 127:1999;685-692.
41. Crow J.P. Manganese and iron metalloporphyrins catalyze peroxynitrite decomposition and simultaneously increase nitration and oxidant yield implications for their use as peroxynitrite scavengers in vivo . Arch. Biochem. Biophys. 371:1999;41-52.
42. Pryor W.A., Jin X., Squadrito G.L. One- and two-electron oxidations of methionine by peroxynitrite. Proc. Natl. Acad. Sci. USA. 91:1994;11173-11177.
43. Briviba K., Tamler R., Klotz L.O., Engman L., Cotgreave I.A., Sies H. Protection by organotellurium compounds against peroxynitrite-mediated oxidation and nitration reactions. Biochem. Pharmacol. 55:1998;817-823.
44. Masumoto H., Sies H. The reaction of 2-(methylseleno)benzanilide with peroxynitrite. Chem. Res. Toxicol. 9:1996;1057-1062.
45. Sies H., Sharov V.S., Klotz L.O., Briviba K. Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase. J. Biol. Chem. 272:1997;27812-27817.
46. Padmaja S., Squadrito G.L., Lemercier J.N., Cueto R., Pryor W.A. Peroxynitrite-mediated oxidation of D,L-selenomethionine kinetics, mechanism and the role of carbon dioxide . Free Radic. Biol. Med. 23:1997;917-926.
47. Patel M., Day B.J. Metalloporphyrin class of therapeutic catalytic antioxidants [review]. Trends Pharmacol. Sci. 20:1999;359-364.
48. Floris R., Piersma S.R., Yang G., Jones P., Wever R. Interaction of myeloperoxidase with peroxynitrite. A comparison with lactoperoxidase, horseradish peroxidase and catalase. Eur. J. Biochem. 215:1993;767-775.
49. Estevez A.G., Spear N., Manuel S.M., Radi R., Henderson C.E., Barbeito L., Beckman J.S. Nitric oxide and superoxide contribute to motor neuron apoptosis induced by trophic factor deprivation. J. Neurosci. 18:1998;923-931.
50. Pfeiffer S., Schrammel A., Koesling D., Schmidt K., Mayer B. Molecular actions of a Mn(III)Porphyrin superoxide dismutase mimetic and peroxynitrite scavenger reaction with nitric oxide and direct inhibition of NO synthase and soluble guanylyl cyclase . Mol. Pharmacol. 53:1998;795-800.
51. Balavoine, G. G. A.; Geletii, Y. V.; Bejan, D. Nitric Oxide 1:507-521; 1997.
52. Liochev S.I., Fridovich I. A cationic manganic porphyrin inhibits uptake of paraquat by Escherichia coli. Arch. Biochem. Biophys. 321:1995;271-275.
53. Batinic-Haberle I., Liochev S.I., Spasojevic I., Fridovich I. A potent superoxide dismutase mimic manganese beta-octabromo- meso-tetrakis-(N-methylpyridinium-4-yl) porphyrin . Arch. Biochem. Biophys. 343:1997;225-233.