Interference of carboxy-PTIO with nitric oxide-and peroxynitrite- mediated reactions

Free Radical Biology and Medicine

Volumn 22, Issue 5, 1997, Pages 787-794

  Pfeiffer, Silvia ^a   Leopold, Eva ^a   Hemmens, Benjamin ^a   Schmidt, Kurt ^a   Werner, Ernst R ^b   Mayer, Bernd ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b Institute for Ion Physics and Applied Physics   (Austria)

Author keywords

3 Nitrotyrosine; Carboxy PTIO; Nitric oxide; Peroxynitrite; S Nitrosogluthatione; SIN 1

Indexed keywords

NITRIC OXIDE; PEROXYNITRITE; SCAVENGER;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD VESSEL REACTIVITY; NONHUMAN; OXIDATIVE STRESS; PATHOPHYSIOLOGY; PRIORITY JOURNAL; SWINE;

ANIMALS; BENZOATES; CATTLE; CELLS, CULTURED; CYCLIC GMP; ENDOTHELIUM, VASCULAR; FREE RADICAL SCAVENGERS; IMIDAZOLES; KINETICS; MOLSIDOMINE; NITRATES; NITRIC OXIDE; NITRITES; SERUM ALBUMIN, BOVINE; SWINE; TYROSINE;

EID: 0031020378     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00407-8     Document Type: Article

References (43)

1. Moncada S., Palmer R. M. J., Higgs E. A. Nitric oxidePhysiology, pathophysiology, and pharmacology. Pharmacol. Rev. 43:1991;109-142.
2. Miles A. M., Bohle D. S., Glassbrenner P. A., Hansert B., Wink D. A., Grisham M. B. Modulation of superoxide-dependent oxidation and hydroxylation reactions by nitric oxide. J. Biol. Chem. 271:1996;40-47.
3. Henry Y., Lepoivre M., Drapier J.-C., Ducrocq C., Boucher J.-L., Guissani A. EPR characterization of molecular targets for NO in mammalian cells and organelles. FASEB J. 7:1993;1124-1134.
4. 2 reaction. Chem. Res. Toxicol. 6:1993;23-27.
5. Kharitonov V. G., Sundquist A. R., Sharma V. S. Kinetics of nitric oxide autoxidation in aqueous solution. J. Biol. Chem. 269:1994;5881-5883.
6. Mayer B., Klatt P., Werner E. R., Schmidt K. Kinetics and mechanism of tetrahydrobiopterin-induced oxidation of nitric oxide. J. Biol. Chem. 270:1995;655-659.
7. Wink D. A., Kasprzak K. S., Maragos C. M., Elespuru R. K., Misra M., Dunams T. M., Cebula T. A., Koch W. H., Andrews A. W., Allen J. S., Keefer L. K. DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science. 254:1991;1001-1003.
8. Nguyen T., Brunson D., Crespi C. L., Penman B. W., Wishnok J. S., Tannenbaum S. R. DNA damage and mutation in human cells exposed to nitric oxide invitro. Proc. Natl. Acad. Sci. USA. 89:1992;3030-3034.
9. Lewis R. S., Deen W. M. Kinetics of the reaction of nitric oxide with oxygen in aqueous solutions. Chem. Res. Toxicol. 7:1994;568-574.
10. 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.
11. Huie R. E., Padmaja S. The reaction of NO with superoxide. Free Radic. Res. Commun. 18:1993;195-199.
12. Pryor W. A., Squadrito G. L. The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 12:1995;L699-L722.
13. Ischiropoulos H., Zhu L., Chen J., Tsai M., Martin J. C., Smith C. D., Beckman J. S. Peroxynitrite-mediated tyrosine nitration catalysed by superoxide dismutase. Arch. Biochem. Biophys. 298:1992;431-437.
14. Beckman J. S., Ischiropoulos H., Zhu L., van der Woerd M., Smith C., Chen J., Harrison J., Martin J. C., Tsai M. Kinetics of superoxide dismutase- and iron-catalyzed nitration of phenolics by peroxynitrite. Arch. Biochem. Biophys. 298:1992;438-445.
15. Ramezanian M. S., Padmaja S., Koppenol W. H. Nitration and hydroxylation of phenolic compounds by peroxynitrite. Chem. Res. Toxicol. 9:1996;232-240.
16. Liu S., Beckman J. S., Ku D. D. Peroxynitrite, a product of superoxide and nitric oxide, produces coronary vasorelaxation in dogs. J. Pharmacol. Exp. Ther. 268:1994;1114-1121.
17. Moro M. A., Darley-Usmar V. M., Goodwin D. A., Read N. G., Zamorapino R., Feelisch M., Radomski M. W., Moncada S. Paradoxical fate and biological action of peroxynitrite on human platelets. Proc. Natl. Acad. Sci. USA. 91:1994;6702-6706.
18. Mayer B., Schrammel A., Klatt P., Koesling D, Schmidt K. Peroxynitrite-induced accumulation of cyclic GMP in endothelial cells and stimulation of purified soluble guanylyl cyclase. Dependence on glutathione and possible role of S-nitrosation. J. Biol. Chem. 270:1995;17355-17360.
19. Gorren A. C. F., Schrammel A., Schmidt K., Mayer B. Decomposition of S-Nitrosoglutathione in the presence of copper and glutathione. Arch. Biochem. Biophys. 330:1996;219-228.
20. Feelisch M., Noack E. A. Correlation between nitric oxide formation during degradation of organic nitrates and activation of guanylate cyclase. Eur. J. Pharmacol. 139:1987;19-30.
21. Schmidt K., Klatt P., Mayer B. Reaction of peroxynitrite with oxyhaemoglobin: Interference with photometrical determination of nitric oxide. Biochem. J. 301:1994;645-647.
22. Ullman E. F., Call L., Osiecki J. H. New imino, amidino, and carbamoyl nitroxides. J. Org. Chem. 35:1970;3623-3629.
23. Akaike T., Yoshida M., Miyamoto Y., Sato K., Kohno M., Sasamoto K., Miyazaki K., Ueda S., Maeda H. Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor/NO through a radical reaction. Biochemistry. 32:1993;827-832.
24. Rand M. J., Li C. G. Discrimination by the NO-trapping agent, carboxy-PTIO, between NO and the nitrergic transmitter but not between NO and EDRF. Br. J. Pharmacol. 116:1995;1906-1910.
25. Mayer B., Brunner F., Schmidt K. Inhibition of nitric oxide synthesis by methylene blue. Biochem. Pharmacol. 45:1993;367-374.
26. Green L. C., Wagner D. A., Glogowski J., Skipper P. L., Wishnok J. S., Tannenbaum S. R. Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal. Biochem. 126:1982;131-138.
27. Werner-Felmayer G., Prast H., Werner E. R., Philippu A., Wachter H. Induction of GTP cyclohydrolase I by bacterial lipopolysaccharide in the rat. FEBS Lett. 322:1993;223-226.
28. Beckman J. S., Ye Y. Z., Anderson P. G., Chen J., Accavitti M. A., Tarpey M. M., White C. R. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler. 375:1994;81-88.
29. Ford P. C., Wink D. A., Stanbury D. M. Autoxidation kinetics of aqueous nitric oxide. FEBS Lett. 326:1993;1-3.
30. Doyle M. P., Hoeksta J. W. Oxidation of nitrogen oxides by bound dioxygen in hemoproteins. J. Inorg. Biochem. 14:1981;351-358.
31. Prütz W. A., Mönig H., Butler J., Land E. J. Reactions of nitrogen dioxide in aqueous model systems: Oxidation of tyrosine units in peptides and proteins. Arch. Biochem. Biophys. 243:1985;125-134.
32. Schmidt K., Mayer B., Kukovetz W. R. Effect of calcium on endothelium-derived relaxing factor formation and cGMP levels in endothelial cells. Eur. J. Pharmacol. 170:1989;157-166.
33. 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.
34. 2 reaction. Chem. Res. Toxicol. 7:1994;519-525.
35. Kharitonov V. G., Sundquist A. R., Sharma V. S. Kinetics of nitrosation of thiols by nitric oxide in the presence of oxygen. J. Biol. Chem. 270:1995;28158-28164.
36. Feelisch M., Ostrowski J., Noack E. On the mechanism of NO release from sydnonimines. J. Cardiovasc. Pharmacol. 14:1989;13-22.
37. Pryor W. A., Church D. F., Govindan C. K., Crank G. Oxidation of thiols by nitric oxide and nitrogen dioxide: synthetic utility and toxicological implications. J. Org. Chem. 47:1982;156-159.
38. Ignarro L. J., Fukuto J. M., Griscavage J. M., Rogers N. E. Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate: Comparison with enzymatically formed nitric oxide. Proc. Natl. Acad. Sci. USA. 90:1993;8103-8107.
39. Goldstein S., Czapski G. Kinetics of nitric oxide autoxidation in aqueous solution in the absence and presence of various reductants. The nature of the oxidizing intermediates. Free Radic. Biol. Med. 117:1995;12078-12084.
40. Lewis R. S., Tannenbaum S. R., Deen W. M. Kinetics of N-nitrosation in oxygenated nitric oxide solutions at physiological pH: Role of nitrous anhydride and effects of phosphate and chloride. J. Am. Chem. Soc. 117:1995;3933-3939.
41. Goldstein S., Czapski G. Mechanism of the nitrosation of thiols and amines by oxygenated NO solutions: The nature of the nitrosating intermediates. J. Am. Chem. Soc. 118:1996;3419-3425.
42. Hogg N., Singh R. J., Joseph J., Neese F., Kalyanaraman B. Reactions of nitric oxide with nitronyl nitroxides and oxygen: Prediction of nitrite and nitrate formation by kinetic simulation. Free Radic. Res. 22:1995;47-56.
43. Maragos C. M., Morley D., Wink D. A., Dunams T. M., Saavedra J. E., Hoffman A., Bove A. A., Isaac L., Hrabie J. A., Keefer L. K. Complexes of NO with nucleophiles as agents for the controlled biological release of nitric oxide-vasorelaxant effects. J. Med. Chem. 34:1991;3242-3247.