Nitration and nitrosation of N-acetyl-L-tryptophan and tryptophan residues in proteins by various reactive nitrogen species

Free Radical Biology and Medicine

Volumn 37, Issue 5, 2004, Pages 671-681

  Suzuki, Toshinori ^a   Mower, Howard F ^b   Friesen, Marlin D ^a   Gilibert, Isabelle ^a   Sawa, Tomohiro ^a   Ohshima, Hiroshi ^a  

^a INTERNATIONAL AGENCY FOR RESEARCH ON CANCER   (France)

^b UNIVERSITY OF HAWAII   (United States)

Author keywords

1 nitro N acetyl L tryptophan; 1 nitroso N acetyl L tryptophan; 1NO N AcTrp; 1NO 2 N AcTrp; Free radicals; N Ac fKyn; N acetyl N formyl L kynurenine; Nitration; Nitrosation; Peroxynitrite; Reactive nitrogen species; Tryptophan

Indexed keywords

1 NITRO N ACETYLTRYPTOPHAN; 1 NITROSO N ACETYLTRYPTOPHAN; 3 NITROTYROSINE; 6 NITRO N ACETYLTRYPTOPHAN; BIOLOGICAL MARKER; BOVINE SERUM ALBUMIN; HYDROGEN PEROXIDE; LINSIDOMINE; MYELOPEROXIDASE; N ACETYL N' FORMYLKYNURENINE; N ACETYLTRYPTOPHAN; NITROGEN DERIVATIVE; NITROSO DERIVATIVE; PEROXYNITRITE; REACTIVE NITROGEN SPECIES; SPERMINE DERIVATIVE; TRYPTOPHAN; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; ELECTROCHEMICAL DETECTION; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; NITRATION; NITROSATION; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; NITRATES; NITROSATION; NITROSO COMPOUNDS; PEROXYNITROUS ACID; PROTEINS; REACTIVE NITROGEN SPECIES; TRYPTOPHAN;

BOVINAE;

EID: 3342945275     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.05.030     Document Type: Article

References (55)

1. Ohshima H., Tatemichi M., Sawa T. Chemical basis of inflammation-induced carcinogenesis. Arch. Biochem. Biophys. 417:2003;3-11
2. Szabo C. Multiple pathways of peroxynitrite cytotoxicity. Toxicol. Lett. 140-141:2003;105-112
3. Miranda K.M., Espey M.G., Ludwick N., Kim S., Jourd'heuil D., Grisham M.B., Feelisch M., Fukuto J.M., Wink D.A. Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion. J. Biol. Chem. 276:2001;1720-1727
4. Ohshima H. Genetic and epigenetic damage induced by reactive nitrogen species: implications in carcinogenesis. Toxicol. Lett. 140-141:2003;99-104
5. Davis K.L., Martin E., Turko I.V., Murad F. Novel effects of nitric oxide. Annu. Rev. Pharmacol. Toxicol. 41:2001;203-236
6. Ischiropoulos H., Zhu L., Chen J., Tsai M., Martin J.C., Smith C.D., Beckman J.S. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298:1992;431-437
7. van der Vliet A., Eiserich J.P., O'Neill C.A., Halliwell B., Cross C.E. Tyrosine modification by reactive nitrogen species: a closer look. Arch. Biochem. Biophys. 319:1995;341-349
8. + Helicobacter pylori infection and inflammation. Dig. Dis. Sci. 46:2001;836-844
9. Pignatelli B., Li C.Q., Boffetta P., Chen Q., Ahrens W., Nyberg F., Mukeria A., Bruske-Hohlfeld I., Fortes C., Constantinescu V., Ischiropoulos H., Ohshima H. Nitrated and oxidized plasma proteins in smokers and lung cancer patients. Cancer Res. 61:2001;778-784
10. Ischiropoulos H. Biological tyrosine nitration: a pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356:1998;1-11
11. Alvarez B., Ferrer-Sueta G., Freeman B.A., Radi R. Kinetics of peroxynitrite reaction with amino acids and human serum albumin. J. Biol. Chem. 274:1999;842-848
12. Ischiropoulos H., al Mehdi A.B. Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 364:1995;279-282
13. Eiserich J.P., Butler J., van der Vliet A., Cross C.E., Halliwell B. Nitric oxide rapidly scavenges tyrosine and tryptophan radicals. Biochem. J. 310:1995;745-749
14. Haddad I.Y., Zhu S., Ischiropoulos H., Matalon S. Nitration of surfactant protein A results in decreased ability to aggregate lipids. Am. J. Physiol. 270:1996;L281-L288
15. Kato Y., Kawakishi S., Aoki T., Itakura K., Osawa T. Oxidative modification of tryptophan residues exposed to peroxynitrite. Biochem. Biophys. Res. Commun. 234:1997;82-84
16. Minetti M., Mallozzi C., Di Stasi A.M., Pietraforte D. Bilirubin is an effective antioxidant of peroxynitrite-mediated protein oxidation in human blood plasma. Arch. Biochem. Biophys. 352:1998;165-174
17. Di Mascio P., Dewez B., Garcia C.R. Ghost protein damage by peroxynitrite and its protection by melatonin. Braz. J. Med. Biol. Res. 33:2000;11-17
18. Kikugawa K., Kato T., Okamoto Y. Damage of amino acids and proteins induced by nitrogen dioxide, a free radical toxin, in air. Free Radic. Biol. Med. 16:1994;373-382
19. Yamakura F., Matsumoto T., Fujimura T., Taka H., Murayama K., Imai T., Uchida K. Modification of a single tryptophan residue in human Cu,Zn-superoxide dismutase by peroxynitrite in the presence of bicarbonate. Biochim. Biophys. Acta. 1548:2001;38-46
20. Alvarez B., Rubbo H., Kirk M., Barnes S., Freeman B.A., Radi R. Peroxynitrite-dependent tryptophan nitration. Chem. Res. Toxicol. 9:1996;390-396
21. Blanchard B., Pompon D., Ducrocq C. Nitrosation of melatonin by nitric oxide and peroxynitrite. J. Pineal Res. 29:2000;184-192
22. Blanchard B., Servy C., Ducrocq C. Chemical evaluation of compounds as nitric oxide or peroxynitrite donors using the reactions with serotonin. Free Radic. Res. 34:2001;189-191
23. Zhang Y.Y., Xu A.M., Nomen M., Walsh M., Keaney J.F. Jr., Loscalzo J. Nitrosation of tryptophan residue(s) in serum albumin and model dipeptides: biochemical characterization and bioactivity. J. Biol. Chem. 271:1996;14271-14279
24. Harohalli K., Petersen C.E., Ha C.E., Feix J.B., Bhagavan N.V. Site-directed mutagenesis studies of human serum albumin define tryptophan at amino acid position 214 as the principal site for nitrosation. J. Biomed. Sci. 9:2002;47-58
25. 3 at physiological pH. J. Biol. Chem. 278:2003;11931-11936
26. Herold S. Nitrotyrosine, dityrosine, and nitrotryptophan formation from metmyoglobin, hydrogen peroxide, and nitrite. Free Radic. Biol. Med. 36:2004;565-579
27. Reed J.W., Ho H.H., Jolly W.L. Chemical syntheses with a quenched flow reactor: hydroxytrihydroborate and peroxynitrite. J. Am. Chem. Soc. 96:1974;1248-1249
28. Beckman J.S., Chen J., Ischiropoulos H., Crow J.P. Oxidative chemistry of peroxynitrite. Methods Enzymol. 233:1994;229-240
29. Bonnett R., Holleyhead R. Reaction of tryptophan derivatives with nitrite. J. Chem. Soc. Perkin Trans. 1:1974;962-964
30. Moriya T., Hagio K., Yoneda N. A facile synthesis of 6-chloro-D- tryptophan. Bull. Chem. Soc. Jpn. 48:1975;2217-2218
31. Auerbach V.H., Knox W.E. L-Kynurenine and N1-formyl-L-kynurenine. Methods Enzymol. 3:1957;620-623
32. Ohshima H., Celan I., Chazotte L., Pignatelli B., Mower H.F. Analysis of 3-nitrotyrosine in biological fluids and protein hydrolysates by high-performance liquid chromatography using a postseparation, on-line reduction column and electrochemical detection: results with various nitrating agents. Nitric Oxide. 3:1999;132-141
33. Phillips R.S., Marmorstein R.Q. 6-Nitro-L-tryptophan: a novel spectroscopic probe of Trp aporepressor and human serum albumin. Arch. Biochem. Biophys. 262:1988;337-344
34. Bonnett R., Nicolaidou P. Nitrite and the environment: the nitrosation of α-amino acid derivatives. Heterocycles. 7:1977;637-659
35. 2 and evidence for common intermediates. J. Am. Chem. Soc. 122:2000;6911-6916
36. Masuda M., Mower H.F., Pignatelli B., Celan I., Friesen M., Nishino H., Ohshima H. Formation of N-nitrosamines and N-nitramines by the reaction of secondary amines with peroxynitrite and other reactive nitrogen species: comparison with nitrotyrosine formation. Chem. Res. Toxicol. 13:2000;301-308
37. Koppenol W.H. Thermodynamics of reactions involving nitrogen-oxygen compounds. Methods Enzymol. 268:1996;7-12
38. Lymar S.V., Jiang Q., Hurst J.K. Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry. 35:1996;7855-7861
39. 2: evidence for carbonate radical production. J. Am. Chem. Soc. 120:1998;3458-3463
40. Czapski G., Holcman J., Bielski B.H.J. Reactivity of nitric oxide with short-lived radicals in aqueous solutions. J. Am. Chem. Soc. 116:1994;11465-11469
41. Caulfield J.L., Singh S.P., Wishnok J.S., Deen W.M., Tannenbaum S.R. Bicarbonate inhibits N-nitrosation in oxygenated nitric oxide solutions. J. Biol. Chem. 271:1996;25859-25863
42. Hodges G.R., Marwaha J., Paul T., Ingold K.U. A novel procedure for generating both nitric oxide and superoxide in situ from chemical sources at any chosen mole ratio. First application: tyrosine oxidation and a comparison with preformed peroxynitrite. Chem. Res. Toxicol. 13:2000;1287-1293
43. Daiber A., Frein D., Namgaladze D., Ullrich V. Oxidation and nitrosation in the nitrogen monoxide/superoxide system. J. Biol. Chem. 277:2002;11882-11888
44. Hogg N., Darley Usmar V.M., Wilson M.T., Moncada S. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. Biochem. J. 281:1992;419-424
45. Haddad I.Y., Crow J.P., Hu P., Ye Y., Beckman J., Matalon S. Concurrent generation of nitric oxide and superoxide damages surfactant protein A. Am. J. Physiol. 267:1994;L242-L249
46. Shafirovich V., Lymar S.V. Nitroxyl and its anion in aqueous solutions: spin states, protic equilibria, and reactivities toward oxygen and nitric oxide. Proc. Natl. Acad. Sci. USA. 99:2002;7340-7345
47. Kirsch M., de Groot H. Formation of peroxynitrite from reaction of nitroxyl anion with molecular oxygen. J. Biol. Chem. 277:2002;13379-13388
48. ·NO solutions: the nature of the nitrosating intermediates. J. Am. Chem. Soc. 118:1996;3419-3425
49. van der Vliet A., Eiserich J.P., Halliwell B., Cross C.E. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite: a potential additional mechanism of nitric oxide-dependent toxicity. J. Biol. Chem. 272:1997;7617-7625
50. Venitt S., Crofton-Sleigh C., Ooi S.L., Bonnett R. Mutagenicity of nitrosated alpha-amino acid derivatives N-acetyl-N′-nitrosotryptophan and its methyl ester in bacteria. Carcinogenesis. 1:1980;523-532
51. Herold S., Shivashankar K., Mehl M. Myoglobin scavenges peroxynitrite without being significantly nitrated. Biochemistry. 41:2002;13460-13472
52. - reaction. Proc. Natl. Acad. Sci. USA. 99:2002;12691-12696
53. Bian K., Gao Z., Weisbrodt N., Murad F. The nature of heme/iron-induced protein tyrosine nitration. Proc. Natl. Acad. Sci. USA. 100:2003;5712-5717
54. Kooy N.W., Royall J.A., Ischiropoulos H., Beckman J.S. Peroxynitrite-mediated oxidation of dihydrorhodamine 123. Free Radic. Biol. Med. 16:1994;149-156
55. Crow J.P. Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: implications for intracellular measurement of reactive nitrogen and oxygen species. Nitric Oxide. 1:1997;145-157