Enzymatic reduction of 3-nitrotyrosine generates superoxide

Chemical Research in Toxicology

Volumn 11, Issue 5, 1998, Pages 495-502

  Krainev, Arkadi G ^a   Williams, Todd D ^a   Bigelow, Diana J ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 NITROTYROSINE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; CYTOCHROME C; DEFEROXAMINE; ENKEPHALIN; PENTETIC ACID; REACTIVE OXYGEN METABOLITE; SUPEROXIDE;

ACETYLATION; ARTICLE; ENZYME ACTIVATION; ENZYME INHIBITION; MICHAELIS CONSTANT; OXIDATION REDUCTION REACTION; SPECIES DIFFERENTIATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME C GROUP; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENKEPHALIN, LEUCINE; KINETICS; MASS SPECTROMETRY; OXIDATION-REDUCTION; PEPTIDE FRAGMENTS; SUPEROXIDES; TRYPSIN; TYROSINE;

EID: 0031801147     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970201p     Document Type: Article

References (44)

1. Bagasra, O., Michaels, F. H., Zheng, Y. M., Bobroski, L. E., Spitsin, S. V., Fu, Z. F., Tawadros, R., and Koprowski, H. (1995) Activation of the inducible form of nitric oxide synthase in the brains of patients with multiple sclerosis. Proc. Natl. Acad. Sci. U.S.A. 93, 12041-12045.
2. Ryan, J., Jennings, G., Dudley, F., and Chin-Dusting, J. (1996) Smooth muscle-derived nitric oxide is elevated in isolated forearm veins in human alcoholic cirrhosis. Clin. Sci. 91, 23-28.
3. Viner, R. I., Ferrington, D. A., Hühmer, A. F. R., Bigelow, D. J., and Schöneich, C. (1996) Accumulation of nitrotyrosine on the SERCA2a isoform of SR Ca-ATPase of rat skeletal muscle during aging: a peroxynitrite-mediated process? FEBS Lett. 379, 286-290.
4. Crow, J. P., and Beckman, J. S. (1995) Quantification of protein tyrosine, 3-nitrotyrosine, and 3-aminotyrosine utilizing HPLC and intrinsic ultraviolet absorbance. Methods Enzymol. 7, 116-120.
5. Ischiropoulos, H., and Al-Mehdi, A. B. (1995) Peroxynitrite-mediated oxidative protein modifications. FEBS Lett. 364, 279-282.
6. Lymar, S. V., Jiang, Q., and Hurst, J. K. (1996) Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35, 7855-7861.
7. MacMillan-Crow, L. A., Crow, J. P., Kerby, J. D., Beckman, J. S., and Thompson, J. A. (1996) Nitration and inactivation of manganese Superoxide dismutase in chronic rejection of human renal allografts. Proc. Natl. Acad. Sci. U.S.A. 93, 11853-11858.
8. Greis, K. D., Zhu, S., and Matalon, S. (1996) Identification of nitration sites on surfactant protein A by tandem electrospray mass spectrometry. Arch. Biochem. Biophys. 335, 396-402.
9. 15N]-tetranitromethane, a new NMR reporter for nitrotyrosines. Biochim. Biophys. Acta 1162, 297-308.
10. Kong, S. K., Yim, M. B., Stadtman, E. R., and Chock, P. B. (1996) Peroxynitrite disables the tyrosine phosphorylation regulatory mechanism: Lymphocyte-specific tyrosine kinase fails to phosphorylate nitrated cdc2(6-20)NH2 peptide. Proc. Natl. Acad. Sci. U.S.A. 93, 3373-3382.
11. Berlett, B. S., Friguet, B., Yim, M. B., Chock, P. B., and Stadtman, E. R. (1996) Peroxynitrite-mediated nitration of tyrosine residues in Escherichia coli glutamine synthetase mimics adenylylation: relevance to signal transduction. Proc. Natl. Acad. Sci. U.S.A. 93, 1776-1780.
12. Ye, Y. Z., Strong, M., Huang, Z. Q., and Beckman, J. S. (1996) Antibodies that recognize nitrotyrosine. Methods Enzymol. 269, 201-209.
13. Gow, A. J., Duran, D., Malcolm, S., and Ischiropoulos, H. (1996) Effects of peroxynitrite-induced protein modifications on tyrosine phosphorylation and degradation. FEBS Lett. 385, 63-66.
14. Prutz, W. A. (1986) Nitro-tyrosine as promoter of free radical damage in a DNA model system. Free Radical Res. Commun. 2, 77-83.
15. Orna, M. V., and Mason, R. P. (1989) Correlation of kinetic parameters of nitroreductase enzymes with redox properties of nitroaromatic compounds. J. Biol. Chem. 264, 12379-12384.
16. Yao, Y., Schöneich, C., and Squier, T. C. (1994) Resolution of structural changes associated with calcium activation of calmodulin using frequency domain fluorescence spectroscopy. Biochemistry 33, 7797-7810.
17. Richman, P. G., and Klee, C. B. (1978) Conformation-dependent nitration of the protein activator of cyclic adenosine 3′,5′-monophosphate phosphodiesterase. Biochemistry 17, 928-935.
18. Beyer, W. F., Jr., and Fridovich, I. (1987) Assaying for Superoxide dismutase activity: some large consequences of minor changes in conditions. Anal. Biochem. 161, 559-566.
19. Azzi, A., Montecucco, C., and Richter, C. (1975) The use of acetylated ferricytochrome c for the detection of Superoxide radicals produced in biological membranes. Biochem. Biophys. Res. Commun. 65, 597-603.
20. Habeeb, A. F. S. A. (1966) Determination of free amino groups in proteins by trinitrobenzenesulfonic acid. Anal. Biochem. 14, 328-336.
21. Krainev, A. G., and Bigelow, D. J. (1996) Comparison of 2,2′-azobis(2-amidinopropane) hydrochloride (AAPH) and 2,2′-azobis-(2,4-dimethylvaleronitrile) (AMVN) as free radical initiators: a spin-trapping study. J. Chem. Soc., Perkin Trans. 2 4, 747-754.
22. Krainev, A. G., Williams, T. D., and Bigelow, D. J. (1996) Oxygen-centered spin adducts of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and 2H-imidazole 1-oxides. J. Magn. Reson. B 111, 272-280.
23. Finkelstein, E., Rosen, G. M., Rauckman, E. J., and Paxton, J. (1979) Spin trapping of Superoxide. Mol. Pharmacol. 16, 676-685.
24. Sushkov, D. G., Gritsan, N. P., and Weiner, L. M. (1987) Generation of OH radical during enzymatic reduction of 9,10-anthraquinone-2-sulphonate. Can semiquinone decompose hydrogen peroxide? FEBS Lett. 225, 139-144.
25. Buettner, G. R. (1987) Spin trapping: ESR parameters of spin adducts. Free Radical Biol. Med. 3, 259-303.
26. Finkelstein, E., Rosen, G. M., and Rauckman, E. J. (1982) Production of hydroxyl radical by decomposition of Superoxide spin-trapped adducts. Mol. Pharmacol. 21, 262-265.
27. Yelinova, V., Krainev, A., Savelov, A., and Grigor'ev, I. (1993) Comparative study of the reduction rates of various types of imidazoline radicals in tissues. J. Chem. Soc., Perkin Trans. 2 11, 2053-2055.
28. Finkelstein, E., Rosen, G. M., and Rauckman, E. J. (1980) Spin trapping. Kinetics of the reaction of Superoxide and hydroxyl radicals with nitrones. J. Am. Chem. Soc. 102, 4994-4999.
29. Lloyd, R. V., and Mason, R. P. (1990) Evidence against transition metal-independent hydroxyl radical generation by xanthine oxidase. J. Biol. Chem. 265, 16733-16736.
30. Richards, P. G., Walton, D. J., and Heptinstall, J. (1996) The effects of tyrosine nitration on the structure and function of hen egg-white lysozyme. Biochem. J. 315, 473-479.
31. Gaskell, S. J., Reilly, M. H., and Porter, C. J. (1988) Collisionally activated decomposition of leucine-enkephalin and analogues using a hybrid tandem mass spectrometer. Rapid Commun. Mass Spectrom. 2, 142-145.
32. Roepstorff, P., and Fohlman, J. (1984) Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed. Mass Spectrom. 11, 601.
33. Berndt, K. D., Guntert, P., Orbons, L. P., and Wüthrich, K. (1992) Determination of a high-quality nuclear magnetic resonance solution structure of the bovine pancreatic trypsin inhibitor and comparison with three crystal structures. J. Mol. Biol. 227, 757-775.
34. Meites, L., and Zuman, P., Eds. (1976) Handbook Series in Organic Electrochemistry, Vol. I, CRC Press, Boca Raton, FL.
35. + oxidoreductase. J. Biol. Chem. 263, 1204-1211.
36. 5 reductase and the other flavin-dependent reductases: pyridine nucleotide-binding and interaction with an electron-transfer partner. Proteins 26, 32-41.
37. Bielski, B. H., and Cabelli, D. E. (1991) Highlights of current research involving Superoxide and perhydroxyl radicals in aqueous solutions. Int. J. Radiat. Biol. 59, 291-319.
38. Stadtman, E. R. (1993) Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu. Rev. Biochem. 62, 797-821.
39. Kaur, H., and Halliwell, B. (1994) Evidence for nitric oxidemediated oxidative damage in chronic inflammation. Nitrotyrosine in serum and synovial fluid from rheumatoid patients. FEBS Lett. 350, 9-12.
40. Bolscher, B. G., Denis, S. W., Verhoeven, A. J., and Roos, D. (1990) The activity of one soluble component of the cell-free NADPH:02 oxidoreductase of human neutrophils depends on guanosine 5′-O-(3-thio)triphosphate. J. Biol. Chem. 265, 15782-15787.
41. Leeuwenburgh, C., Hardy, M. M., Hazen, S. L., Wagner, P., Ohishi, S., Steinbrecher, U. P., and Heinecke, J. W. (1997) Reactive nitrogen intermediates promote low-density lipoprotein oxidation in human atherosclerotic intima. J. Biol. Chem. 272, 1433-1436.
42. Huges, J., Smith, T. W., Kosterlitz, H. W., Fothergill, L. A., Morgan, B. A., and Morris, H. R. (1975) Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 258, 577-579.
43. Radcliffe, B. C., and Nikolas, D. J. (1968) Some properties of a nitrite reductase from Pseudomonas denitrificans. Biochim. Biophys. Acta 153, 545-554.
44. Wessels, J. S. (1965) Mechanism of the reduction of organic nitro compounds by chloroplasts. Biochim. Biophys. Acta 109, 357-371.