Xanthine oxidase-mediated denitrosation of N-nitroso-tryptophan by superoxide and uric acid

Nitric Oxide - Biology and Chemistry

Volumn 28, Issue , 2013, Pages 57-64

  Viles, Kimberley ^a   Mathai, Clinton ^a   Jourd'Heuil, Frances L ^a   Jourd'Heuil, David ^a  

^a ALBANY MEDICAL COLLEGE   (United States)

Author keywords

Nitric oxide; Nitrosation; Nitrosylation; Superoxide; Tryptophan; Xanthine oxidase

Indexed keywords

HYPOXANTHINE; MYOGLOBIN; NITRITE; S NITROSOGLUTATHIONE; SUPEROXIDE; TRYPTOPHAN DERIVATIVE; URIC ACID; XANTHINE OXIDASE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMOLUMINESCENCE; CONCENTRATION (PARAMETERS); DECOMPOSITION; DENITROSATION; NITROSYLATION; PRIORITY JOURNAL; PROTEIN DEGRADATION;

NITRIC OXIDE; NITROSAMINES; SUPEROXIDES; TRYPTOPHAN; URIC ACID; XANTHINE OXIDASE;

EID: 84868517738     PISSN: 10898603     EISSN: 10898611     Source Type: Journal    
DOI: 10.1016/j.niox.2012.10.004     Document Type: Article

References (33)

1. J.S. Beckman, and W.H Koppenol Nitric oxide, superoxide, and peroxynitrite; the good, the bad, and the ugly Am. J. Physiol. 271 1996 C1424 C1437
2. M.W. Foster, D.T. Hess, and J.S. Stamler Protein S-nitrosylation in health and disease: a current perspective Trends Mol. Med. 15 2009 391 404
3. F.L. Jourd'heuil, A.M. Lowery, E.M. Meton, S. Mnaimneh, N.S. Bryan, B.O. Fernandez, J.H. Park, C.E. Ha, N.V. Bhagavan, M. Feelisch, and D. Jourd'heuil Redox-sensitivity and site-specificity of S- and N- denitrosation in proteins PLoS One 5 2010 e14400
4. D.L.H. Williams Nitrosation 1988 Press Syndicate of the University of Cambridge Cambridge
5. T. Suzuki, H.F. Mower, M.D. Friesen, I. Gilibert, T. Sawa, and H. Ohshima Nitration and nitrosation of N-acetyl-tryptophan and tryptophan residues in proteins by various reactive nitrogen species Free Radical Biol. Med. 37 2004 671 681 (Pubitemid 38993513)
6. T. Rassaf, N.S. Bryan, M. Kelm, and M. Feelisch Concomitant presence of N-nitroso and S-nitroso proteins in human plasma Free Radical Biol. Med. 33 2002 1590 1596 (Pubitemid 35355729)
7. N.S. Bryan, T. Rassaf, R.E. Maloney, C.M. Rodriguez, F. Saijo, J.R. Rodriguez, and M. Feelisch Cellular targets and mechanisms of nitros(yl)ation: An insight into their nature and kinetics in vivo Proc. Natl. Acad. Sci. USA 101 2004 4308 4313 (Pubitemid 38405925)
8. Y.Y. Zhang, A.M. Xu, M. Nomen, M. Walsh, J.F. Keaney Jr., and J. Loscalzo Nitrosation of tryptophan residue(s) in serum albumin and model dipeptides. Biochemical characterization and bioactivity. J. Biol. Chem. 271 1996 14271 14279
9. B. Blanchard-Fillion, C. Servy, and C. Ducrocq 1-Nitrosomelatonin is a spontaneous NO-releasing compound Free Radical Res. 35 2001 857 866 (Pubitemid 34065674)
10. U. Berchner-Pfannschmidt, S. Tug, B. Trinidad, M. Becker, F. Oehme, I. Flamme, J. Fandrey, and M. Kirsch The impact of N-nitrosomelatonin as nitric oxide donor in cell culture experiments J. Pineal Res. 45 2008 489 496
11. U. Berchner-Pfannschmidt, S. Tug, J. Hu, B.D. Reyes, J. Fandrey, and M. Kirsch Role of N-acetyl-N-nitroso-tryptophan as nitric oxide donor in the modulation of HIF-1-dependent signaling Biol. Chem. 391 2010 533 540
12. K. Sonnenschein, G.H. de, and M. Kirsch Formation of S-nitrosothiols from regiospecific reaction of thiols with N-nitrosotryptophan derivatives J. Biol. Chem. 279 2004 45433 45440 (Pubitemid 39491527)
13. M. Kirsch, and H.G. Korth Generation, basic chemistry, and detection of N-nitrosotryptophan derivatives Org. Biomol. Chem. 5 2007 3889 3894 (Pubitemid 350205982)
14. S.R. Jaffrey, H. Erdjument-Bromage, C.D. Ferris, P. Tempst, and S.H. Snyder Protein S-nitrosylation: a physiological signal for neuronal nitric oxide Nat. Cell Biol. 3 2001 193 197 (Pubitemid 32118373)
15. M. Feelisch, T. Rassaf, S. Mnaimneh, N. Singh, N.S. Bryan, D. Jourd'heuil, and M. Kelm Concomitant S-, N-, and heme-nitros(yl)ation in biological tissues and fluids: implications for the fate of NO in vivo FASEB J. 16 2002 1775 1785 (Pubitemid 35340358)
16. K. Muller, H.G. Korth, G.H. de, and M. Kirsch Reaction of vitamin E compounds with N-nitrosated tryptophan derivatives and its analytical use Chemistry 13 2007 7532 7542 (Pubitemid 47425851)
17. T.A. Meyer, and D.L.H. Williams Denitrosation of N-acetyl-N- nitrosotryptophan in acid solution J. Chem. Soc., Perkin Trans.2 1982 1383 1387
18. A. Kytzia, H.G. Korth, R. Sustmann, G.H. de, and M. Kirsch On the mechanism of the ascorbic acid-induced release of nitric oxide from N-nitrosated tryptophan derivatives: scavenging of NO by ascorbyl radicals Chemistry 12 2006 8786 8797 (Pubitemid 44852464)
19. M. Trujillo, M.N. Alvarez, G. Peluffo, B.A. Freeman, and R. Radi Xanthine oxidase-mediated decomposition of S-nitrosthiols J. Biol. Chem. 273 1999 7828 7834
20. D. Jourd'heuil, C.T. Mai, S.F. Laroux, D.A. Wink, and M.B. Grisham The reaction of S-nitrosoglutathione with superoxide Biochem. Biophys. Res. Commun. 244 1998 525 530 (Pubitemid 28414115)
21. S. Aleryani, E. Milo, Y. Rose, and P. Kostka Superoxide-mediated decomposition of biological S-nitrosothiols J. Biol. Chem. 273 1998 6041 6045 (Pubitemid 28144681)
22. M. Kirsch, A. Fuchs, and H. de Groot Regiospecific nitrosation of N-terminal-blocked tryptophan derivatives by N2O3 at physiological pH J. Biol. Chem. 278 2003 11931 11936 (Pubitemid 36800166)
23. G.R. Buettner The pecking order of free radicals and antioxidants: lipid peroxidation, α-tocopherol, and ascorbate Arch. Biochem. Biophys. 300 1993 535 543 (Pubitemid 23232908)
24. C.C. Winterbourn Production of hydroxyl radicals from paraquat radicals and H2O2 FEBS Lett. 128 1981 339 342
25. M. Kirsch, and M. Lehnig Generation of peroxynitrite from reaction of N-acetyl-N-nitrosotryptophan with hydrogen peroxide over a wide range of pH values Org. Biomol. Chem. 3 2005 2085 2090 (Pubitemid 40859883)
26. K. Harohalli, C.E. Petersen, C.E. Ha, J.B. Feix, and N.V. Bhagavan 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 (Pubitemid 34124207)
27. E. Ford, M.N. Hughes, and P. Wardman The reaction of superoxide radicals with S-nitrosoglutathione and the products of its reductive heterolysis J. Biol. Chem. 277 2002 2430 2436 (Pubitemid 34953264)
28. X.Q. Zhu, J.Q. He, Q. Li, M. Xian, J. Lu, and J.P. Cheng N-NO bond dissociation energies of N-nitroso diphenylamine derivatives (or analogues) and their radical anions: implications for the effect of reductive electron transfer on N-NO bond activation and for the mechanisms of NO transfer to nitranions J. Org. Chem. 65 2000 6729 6735
29. T. Suzuki, A. Naka, and H. Kimura Effects of uric acid on nitrosation of N-acetylcysteine by diethylamine NONOate and N-acetyl-N-nitrosotryptophan Chem. Pharm. Bull. (Tokyo) 57 2009 736 739
30. T. Suzuki Nitrosation of uric acid induced by nitric oxide under aerobic conditions Nitric Oxide 16 2007 266 273 (Pubitemid 46149396)
31. E.E. Kelley, N.K. Khoo, N.J. Hundley, U.Z. Malik, B.A. Freeman, and M.M. Tarpey Hydrogen peroxide is the major oxidant product of xanthine oxidase Free Radical Biol. Med. 48 2010 493 498
32. Y. Zhang, and N. Hogg The Formation Stability of S-Nitrosothiols in RAW 264.7 Cells Am. J. Physiol. Lung Cell Mol. Physiol. 2003 00350
33. X. Wang, N.S. Bryan, P.H. MacArthur, J. Rodriguez, M.T. Gladwin, and M. Feelisch Measurement of nitric oxide levels in the red cell: validation of tri-iodide-based chemiluminescence with acid-sulfanilamide pretreatment J. Biol. Chem. 281 2006 26994 27002 (Pubitemid 44401728)