Spin-trapping of free radicals formed during the oxidation of glutathione by tetramethylammonium peroxynitrite

Nitric Oxide - Biology and Chemistry

Volumn 1, Issue 4, 1997, Pages 346-358

  Karoui, Hakim ^a   Hansert, Bernhard ^b   Sand, Patrick J ^b   Tordo, Paul ^c   Bohle, D Scott ^b   Kalyanaraman, B ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

^b UNIVERSITY OF WYOMING   (United States)

^c AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Electron spin resonance; Spin trapping; Tetramethylammonium peroxynitrite; Thiyl radical

Indexed keywords

FREE RADICAL; GLUTATHIONE; PEROXYNITRITE; SUPEROXIDE DISMUTASE; TETRAMETHYLAMMONIUM;

ANION TRANSPORT; ARTICLE; COMPETITIVE INHIBITION; DNA ADDUCT; ELECTRON SPIN RESONANCE; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; OXIDATION REDUCTION REACTION; OXYGEN CONSUMPTION; PRIORITY JOURNAL; REACTION ANALYSIS; SPIN TRAPPING; STOICHIOMETRY;

EID: 0031416665     PISSN: 10898603     EISSN: None     Source Type: Journal    
DOI: 10.1006/niox.1997.0140     Document Type: Article

References (32)

1. ••. 1995;New York Academy of Sciences. p. 69-75.
2. Beckman J. S., Ye Y. Z., Anderson P., Chen J., Accavetti M. A., Tarpey M. M., White C. R. Extensive nitration of protein tyrosines observed in human atheroslerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler. 375:1994;81-88.
3. •. Free Radicals Res. Commun. 18:1993;195-199.
4. 2. Inorg. Chem. 25:1986;2676-2677.
5. Bartlett D., Church D. F., Bounds P. L., Koppenol W. H. The kinetics of the oxidation ofL. Free Radical Biol. Med. 18:1995;85-92.
6. Hogg N., Joseph J., Kalyanaraman B. The oxidation of α-tocopherol and trolox by peroxynitrite. Arch. Biochem. Biophys. 314:1994;153-158.
7. 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.
8. Roussyn I., Briviba K., Masumoto H., Sies H. Selenium-containing compounds protect DNA from single-strand breaks caused by peroxynitrite. Arch. Biochem. Biophys. 330:1996;216-218.
9. Augusto O., Gatti R. M., Radi R. Spin trapping studies of peroxynitrite decomposition and of 3-morpholinosydnonimineN. Arch. Biochem. Biophys. 310:1994;118-125.
10. Shi X., Lenhart A., Mao Y. ESR spin trapping investigation on peroxynitrite decomposition: No evidence for hydroxyl radical production. Biochem. Biophys. Res. Commun. 203:1994;1515-1521.
11. Lemercier J-N., Squadrito G. L., Pryor W. A. Spin trap studies on the decomposition of peroxynitrite. Arch. Biochem. Biophys. 321:1995;31-39.
12. Karoui H., Hogg N., Frejaville C., Tordo P., Kalyanaraman B. 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.
13. Hughes M. N., Nicklin H. G. The chemistry of pernitrites. I. Kinetics of decomposition of pernitrous acid. J. Chem. Soc. A. 1968;450.
14. Pryor W. A., Cueto R., Jin X., Koppenol W. H., Ngu Schwemlein M., Squadrito G. L., Uppu P. L., Uppo R. M. A practical method for preparing peroxynitrite solutions of low ionic strength and free of hydrogen peroxide. Free Radical Biol. Med. 18:1995;75-83.
15. -. J. Am. Chem. Soc. 116:1994;7423-7424.
16. 4. Methods Enzymol. 269:1996;302-311.
17. Anderson M. E., Meister A. Preparation of γ-glutamyl amino acids by chemical and enzymatic methods. Methods Enzymol. 113:1985;555-559.
18. Duling D. R., Motten A. G., Mason R. P. Generation and evaluation of isotropic ESR spectrum simulations. J. Magn. Reson. 77:1988;504-511.
19. Kok S. H., Buckle K. A., Wooton M. Determination of nitrate and nitrite in water using high-performance chromatography. J. Chromatogr. 260:1983;189-192.
20. Dreux M., Lafosee M., Pequignot M. Separation of inorganic anions by ion-pair, reverse phase liquid chromatography monitored by indirect photometry. Chromatographia. 15:1982;653-656.
21. Ischiropoulos H., Zhu L., Chen J., Tsai H. M., Martin J. C., Smith C. D., Beckman J. S. Peroxynitrite-mediated tyrosne nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298:1992;431-437.
22. Liu J., Shigenaga M. K., Yan L-J., Mori A., Ames B. N. Antioxidant activity of diethyldithiocarbamate. Free Radicals Res. 24:1992;461-472.
23. McDonald C. C., Phillips W. D., Mower H. F. C. An electron spin resonance study of some complexes of iron, nitric oxide, and anionic ligands. J. Am. Chem. Soc. 87:1965;3319-3324.
24. 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.
25. Winterbourn C. C. Superoxide as an intracellular radical sink. Free Radical Biol. Med. 14:1993;85-90.
26. Pfeiffer S., Gorren A. C. F., Schmidt K., Werner E. R., Hansert B., Bohle D. S., Mayer B. Metabolic fate of peroxynitrite in aqueous solution. Reaction with nitric oxide and pH-dependent decomposition to nitrite and oxygen in a 2:1 stoichiometry. J. Biol. Chem. 272:1997;3654-3470.
27. Harman L. S., Mottley C., Mason R. P. Free radical metabolites ofL. J. Biol. Chem. 259:1984;5606-5611.
28. Karoui H., Hogg N., Kalyanaraman B. Effect of superoxide dismutase mimics on radical adducts formation during the reaction between peroxynitrite and thiols - An ESR-spin trapping study. Arch. Biochem. Biophys. 330:1996;115-124.
29. Pou S., Hassett D. J., Britigan B. E., Cohen M. J., Rosen G. M. Problems associated with spin trapping oxygen-centered free radicals in biological systems. Anal. Biochem. 177:1989;1-6.
30. 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. J. Biol. Chem. 270:1995;17355-17360.
31. Stern M. K., Jensen M. P., Kramer K. Peroxynitrite decomposition catalysts. J. Am. Chem. Soc. 118:1996;8735-8736.
32. van der Donk W. A., Stubbe J., Gerfen G. J., Bellew B. F., Griffin R. G. EPR investigations of the inactivation ofE. coli. J. Am. Chem. Soc. 117:1995;8908-8916.