Influence of Intramolecular Electron Transfer Mechanism in Biological Nitration, Nitrosation, and Oxidation of Redox-Sensitive Amino Acids

Methods in Enzymology

Volumn 440, Issue , 2008, Pages 65-94

  Zhang, Hao ^a   Xu, Yingkai ^a   Joseph, Joy ^a   Kalyanaraman, B ^a  

^a FREE RADICAL RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; AMINO ACID; CYSTEINE; DISULFIDE; FREE RADICAL; MYELOPEROXIDASE; PEPTIDE DERIVATIVE; TYROSINE; NITRATE;

ANALYTIC METHOD; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NITRATION; NITROSATION; OXIDATION; OXIDATION REDUCTION REACTION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION; PROTEIN STRUCTURE; RESIDUE ANALYSIS; REVIEW; SPIN TRAPPING; ANIMAL; CHEMISTRY; HUMAN; METABOLISM;

AMINO ACIDS; ANIMALS; ELECTRON TRANSPORT; HUMANS; NITRATES; NITROSATION; OXIDATION-REDUCTION;

EID: 44849111614     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(07)00804-X     Document Type: Review

References (80)

1. Arstall M.A., Bailey C., Gross W.L., Bak M., Balligand J.L., and Kelly R.A. Reversible S-nitrosation of creatine kinase by nitric oxide in adult rat ventricular myocytes. J. Mol. Cell Cardiol. 30 (1998) 979-988
2. Aubert C., Vos M.H., Mathis P., Eker A.P., and Brettel K. Intraprotein radical transfer during photoactivation of DNA photolyase. Nature 405 (2000) 586-590
3. Baldus S., Eiserich J., Brennan M., Jackson R., Alexander C., and Freeman B. Spatial mapping of pulmonary and vascular nitrotyrosine reveals the pivotal role of myeloperoxidase as a catalyst for tyrosine nitration in inflammatory diseases. Free Radic. Biol. Med. 33 (2002) 1010
4. Barrett D.M., Black S.M., Todor H., Schmidt-Ullrich R.K., Dawson K.S., and Mikkelsen R.B. Inhibition of protein-tyrosine phosphatases by mild oxidative stresses is dependent on S-nitrosylation. J. Biol. Chem. 280 (2005) 14453-14461
5. Beckman J.S. Oxidative damage and tyrosine nitration from peroxynitrite. Chem. Res. Toxicol. 9 (1996) 836-844
6. Bobrowski K., Wierzchowski K.L., Holcman J., and Ciurak M. Intramolecular electron transfer in peptides containing methionine, tryptophan and tyrosine: A pulse radiolysis study. Int. J. Radiat. Biol. 57 (1990) 919-932
7. Bobrowski K., Wierzchowski K.L., Holcman J., and Ciurak M. Pulse radiolysis studies of intramolecular electron transfer in model peptides and proteins. IV. Met/S:.Br→Tyr/O. radical transformation in aqueous solution of H-Tyr-(Pro)n-Met-OH peptides. Int. J. Radiat. Biol. 62 (1992) 507-516
8. Brennan M.L., Wu W., Fu X., Shen Z., Song W., Frost H., Vadseth C., Narine L., Lenkiewicz E., Borchers M.T., Lusis A.J., Lee J.J., et al. A tale of two controversies: Defining both the role of peroxidases in nitrotyrosine formation in vivo using eosinophil peroxidase and myeloperoxidase-deficient mice, and the nature of peroxidase-generated reactive nitrogen species. J. Biol. Chem. 277 (2002) 17415-17427
9. Bryan N.S., Rassaf T., Maloney R.E., Rodriguez C.M., Saijo F., Rodriguez J.R., and Feelisch M. 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
10. Chen Y.Y., Huang Y.F., Khoo K.H., and Meng T.C. Mass spectrometry-based analyses for identifying and characterizing S-nitrosylation of protein tyrosine phosphatases. Methods 42 (2007) 243-249
11. Chung K.K., Thomas B., Li X., Pletnikova O., Troncoso J.C., Marsh L., Dawson V.L., and Dawson T.M. S-nitrosylation of parkin regulates ubiquitination and compromises parkin's protective function. Science 304 (2004) 1328-13231
12. Denicola A., Batthyany C., Lissi E., Freeman B.A., Rubbo H., and Radi R. Diffusion of nitric oxide into low density lipoprotein. J. Biol. Chem. 277 (2002) 932-936
13. Denicola A., Souza J.M., and Radi R. Diffusion of peroxynitrite across erythrocyte membranes. Proc. Natl. Acad. Sci. USA 95 (1998) 3566-3571
14. Eiserich J.P., Hristova M., Cross C.E., Jones A.D., Freeman B.A., Halliwell B., and van der Vliet A. Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391 (1998) 393-397
15. Espey M.G., Thomas D.D., Miranda K.M., and Wink D.A. Focusing of nitric oxide mediated nitrosation and oxidative nitrosylation as a consequence of reaction with superoxide. Proc. Natl. Acad. Sci. USA 99 (2002) 11127-11132
16. Foster M.W., and Stamler J.S. New insights into protein S-nitrosylation: Mitochondria as a model system. J. Biol. Chem. 279 (2004) 25891-25897
17. Gao C., Guo H., Wei J., Mi Z., Wai P.Y., and Kuo P.C. Identification of S-nitrosylated proteins in endotoxin-stimulated RAW264.7 murine macrophages. Nitric Oxide 12 (2005) 121-126
18. Goss S.P., Hogg N., and Kalyanaraman B. The effect of alpha-tocopherol on the nitration of gamma-tocopherol by peroxynitrite. Arch. Biochem. Biophys. 363 (1999) 333-340
19. Gow A., Duran D., Thom S.R., and Ischiropoulos H. Carbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Arch. Biochem. Biophys. 333 (1996) 42-48
20. Gow A.J., Farkouh C.R., Munson D.A., Posencheg M.A., and Ischiropoulos H. Biological significance of nitric oxide-mediated protein modifications. Am. J. Physiol. Lung Cell Mol. Physiol. 287 (2004) L262-L268
21. Greenacre S.A., and Ischiropoulos H. Tyrosine nitration: Localisation, quantification, consequences for protein function and signal transduction. Free Radic. Res. 34 (2001) 541-581
22. Gunther M.R., Tschirret-Guth R.A., Lardinois O.M., and Ortiz de Montellano P.R. Tryptophan-14 is the preferred site of DBNBS spin trapping in the self-peroxidation reaction of sperm whale metmyoglobin with a single equivalent of hydrogen peroxide. Chem. Res. Toxicol. 16 (2003) 652-660
23. Haddad I.Y., Pataki G., Hu P., Galliani C., Beckman J.S., and Matalon S. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J. Clin. Invest. 94 (1994) 2407-2413
24. Hao G., Derakhshan B., Shi L., Campagne F., and Gross S.S. SNOSID, a proteomic method for identification of cysteine S-nitrosylation sites in complex protein mixtures. Proc. Natl. Acad. Sci. USA 103 (2006) 1012-1017
25. Hao G., Xie L., and Gross S.S. Argininosuccinate synthetase is reversibly inactivated by S-nitrosylation in vitro and in vivo. J. Biol. Chem. 279 (2004) 36192-361200
26. Harman L.S., Mottley C., and Mason R.P. Free radical metabolites of L-cysteine oxidation. J. Biol. Chem. 259 (1984) 5606-5611
27. Huang Y., Man H.Y., Sekine-Aizawa Y., Han Y., Juluri K., Luo H., Cheah J., Lowenstein C., Huganir R.L., and Snyder S.H. S-nitrosylation of N-ethylmaleimide sensitive factor mediates surface expression of AMPA receptors. Neuron 46 (2005) 533-540
28. Ischiropoulos H. Biological tyrosine nitration: A pathophysiological function of nitric oxide and reactive oxygen species. Arch. Biochem. Biophys. 356 (1998) 1-11
29. Ischiropoulos H. Biological selectivity and functional aspects of protein tyrosine nitration. Biochem. Biophys. Res. Commun. 305 (2003) 776-783
30. Ischiropoulos H., Zhu L., Chen J., Tsai M., Martin J.C., Smith C.D., and Beckman J.S. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 298 (1992) 431-437
31. Jia L., Bonaventura C., Bonaventura J., and Stamler J.S. S-nitrosohaemoglobin: A dynamic activity of blood involved in vascular control. Nature 380 (1996) 221-226
32. Jourd'heuil D., Jourd'heuil F.L., Kutchukian P.S., Musah R.A., Wink D.A., and Grisham M.B. Reaction of superoxide and nitric oxide with peroxynitrite: Implications for peroxynitrite-mediated oxidation reactions in vivo. J. Biol. Chem. 276 (2001) 28799-28805
33. Kalyanaraman B., Karoui H., Singh R.J., and Felix C.C. Detection of thiyl radical adducts formed during hydroxyl radical- and peroxynitrite-mediated oxidation of thiols: A high resolution ESR spin-trapping study at Q-band (35 GHz). Anal. Biochem. 241 (1996) 75-81
34. Karoui H., Hogg N., Frejaville C., Tordo P., and 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
35. Khairutdinov R.F., Coddington J.W., and Hurst J.K. Permeation of phospholipid membranes by peroxynitrite. Biochemistry 39 (2000) 14238-14249
36. Kooy N.W., Lewis S.J., Royall J.A., Ye Y.Z., Kelly D.R., and Beckman J.S. Extensive tyrosine nitration in human myocardial inflammation: Evidence for the presence of peroxynitrite. Crit. Care Med. 25 (1997) 812-819
37. Lanone S., Manivet P., Callebert J., Launay J.-M., Payen D., Aubier M., Boczkowski J., and Mebazaa A. Inducible nitric oxide synthase (NOS2) expressed in septic patients is nitrated on selected tyrosine residues: Implications for enzymic activity. Biochem. J. 366 (2002) 399-404
38. Leeuwenburgh C., Hardy M.M., Hazen S.L., Wagner P., Oh-ishi S., Steinbrecher U.P., and Heinecke J.W. Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima. J. Biol. Chem. 272 (1997) 1433-1436
39. Liu X., Miller M.J., Joshi M.S., Thomas D.D., and Lancaster Jr. J.R. Accelerated reaction of nitric oxide with O2 within the hydrophobic interior of biological membranes. Proc. Natl. Acad. Sci. USA 95 (1998) 2175-2179
40. MacPherson J.C., Comhair S.A., Erzurum S.C., Klein D.F., Lipscomb M.F., Kavuru M.S., Samoszuk M.K., and Hazen S.L. Eosinophils are a major source of nitric oxide-derived oxidants in severe asthma: Characterization of pathways available to eosinophils for generating reactive nitrogen species. J. Immunol. 166 (2001) 5763-5772
41. Mallis R.J., Buss J.E., and Thomas J.A. Oxidative modification of H-ras: S-thiolation and S-nitrosylation of reactive cysteines. Biochem. J. 355 (2001) 145-153
42. Marla S.S., Lee J., and Groves J.T. Peroxynitrite rapidly permeates phospholipid membranes. Proc. Natl. Acad. Sci. USA 94 (1997) 14243-14248
43. Marshall H.E., and Stamler J.S. Nitrosative stress-induced apoptosis through inhibition of NF-kappa B. J. Biol. Chem. 277 (2002) 34223-34228
44. McVey M., Hill J., Howlett A., and Klein C. Adenylyl cyclase, a coincidence detector for nitric oxide. J. Biol. Chem. 274 (1999) 18887-18892
45. Newman D.K., Hoffman S., Kotamraju S., Zhao T., Wakim B., Kalyanaraman B., and Newman P.J. Nitration of PECAM-1 ITIM tyrosines abrogates phosphorylation and SHP-2 binding. Biochem. Biophys. Res. Commun. 296 (2002) 1171-1179
46. Pavlick K.P., Laroux F.S., Fuseler J., Wolf R.E., Gray L., Hoffman J., and Grisham M.B. Role of reactive metabolites of oxygen and nitrogen in inflammatory bowel disease. Free Radic. Biol. Med. 33 (2002) 311-322
47. Paxinou E., Chen Q., Weisse M., Giasson B.I., Norris E.H., Rueter S.M., Trojanowski J.Q., Lee V.M.-Y., and Ischiropoulos H. Induction of alpha-synuclein aggregation by intracellular nitrative insult. J. Neurosci. 21 (2001) 8053-8061
48. Pfeiffer S., Lass A., Schmidt K., and Mayer B. Protein tyrosine nitration in mouse peritoneal macrophages activated in vitro and in vivo: Evidence against an essential role of peroxynitrite. FASEB J. 15 (2001) 2355-2364
49. Prutz W.A., Butler J., Land E.J., and Swallow A.J. Direct demonstration of electron transfer between tryptophan and tyrosine in proteins. Biochem. Biophys. Res. Commun. 96 (1980) 408-411
50. Prutz W.A., Butler J., Land E.J., and Swallow A.J. The role of sulphur peptide functions in free radical transfer: A pulse radiolysis study. Int. J. Radiat. Biol. 55 (1989) 539-556
51. Prutz W.A., Moenig H., Butler J., and 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
52. Pryor W.A., and Squadrito G.L. The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 68 (1995) L699-L722
53. Radi R., Denicola A., and Freeman B.A. Peroxynitrite reactions with carbon dioxide-bicarbonate. Methods Enzymol. 301 (1999) 353-367
54. Rassaf T., Bryan N.S., Kelm M., and Feelisch M. Concomitant presence of N-nitroso and S-nitroso proteins in human plasma. Free Radic. Biol. Med. 33 (2002) 1590-1596
55. Rubbo H., Radi R., Trujillo M., Telleri R., Kalyanaraman B., Barnes S., Kirk M., and Freeman B.A. Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation: Formation of novel nitrogen-containing oxidized lipid derivatives. J. Biol. Chem. 269 (1994) 26066-26075
56. Sacksteder C.A., Qian W.J., Knyushko T.V., Wang H., Chin M.H., Lacan G., Melega W.P., Camp II D.G., Smith R.D., Smith D.J., Squier T.C., and Bigelow D.J. Endogenously nitrated proteins in mouse brain: Links to neurodegenerative disease. Biochemistry 45 (2006) 8009-8022
57. Saez G., Thornalley P.J., Hill H.A., Hems R., and Bannister J.V. The production of free radicals during the autoxidation of cysteine and their effect on isolated rat hepatocytes. Biochim. Biophys. Acta 719 (1982) 24-31
58. Satoh T., and Lipton S.A. Redox regulation of neuronal survival mediated by electrophilic compounds. Trends Neurosci. 30 (2007) 37-45
59. Schopfer F.J., Baker P.R., and Freeman B.A. NO-dependent protein nitration: A cell signaling event or an oxidative inflammatory response?. Trends Biochem. Sci. 28 (2003) 646-654
60. Seyedsayamdost M.R., Reece S.Y., Nocera D.G., and Stubbe J. Mono-, di-, tri-, and tetra-substituted fluorotyrosines: New probes for enzymes that use tyrosyl radicals in catalysis. J. Am. Chem. Soc. 128 (2006) 1569-1579
61. Shao B., Bergt C., Fu X., Green P., Voss J.C., Oda M.N., Oram J.F., and Heinecke J.W. Tyrosine 192 in apolipoprotein A-I is the major site of nitration and chlorination by myeloperoxidase, but only chlorination markedly impairs ABCA1-dependent cholesterol transport. J. Biol. Chem. 280 (2005) 5983-5993
62. Sharov V.S., Galeva N.A., Knyushko T.V., Bigelow D.J., Williams T.D., and Schoneich C. Two-dimensional separation of the membrane protein sarcoplasmic reticulum Ca-ATPase for high-performance liquid chromatography-tandem mass spectrometry analysis of posttranslational protein modifications. Anal. Biochem. 308 (2002) 328-335
63. Souza J.M., Daikhin E., Yudkoff M., Raman C.S., and Ischiropoulos H. Factors determining the selectivity of protein tyrosine nitration. Arch. Biochem. Biophys. 371 (1999) 169-178
64. Stamler J.S., Simon D.I., Osborne J.A., Mullins M.E., Jaraki O., Michel T., Singel D.J., and Loscalzo J. S-nitrosylation of proteins with nitric oxide: Synthesis and characterization of biologically active compounds. Proc. Natl. Acad. Sci. USA 89 (1992) 444-448
65. Tanner C., Navaratnam S., and Parsons B.J. Intramolecular electron transfer in the dipeptide, histidyltyrosine: A pulse radiolysis study. Free Radic. Biol. Med. 24 (1998) 671-678
66. Tenneti L., D'Emilia D.M., and Lipton S.A. Suppression of neuronal apoptosis by S-nitrosylation of caspases. Neurosci. Lett. 236 (1997) 139-142
67. Turko I.V., and Murad F. Protein nitration in cardiovascular diseases. Pharmacol. Rev. 54 (2002) 619-634
68. Uehara T., Nakamura T., Yao D., Shi Z.Q., Gu Z., Ma Y., Masliah E., Nomura Y., and Lipton S.A. S-nitrosylated protein-disulphide isomerase links protein misfolding to neurodegeneration. Nature 441 (2006) 513-517
69. van Dalen C.J., Winterbourn C.C., Senthilmohan R., and Kettle A.J. Nitrite as a substrate and inhibitor of myeloperoxidase: Implications for nitration and hypochlorous acid production at sites of inflammation. J. Biol. Chem. 275 (2000) 11638-11644
70. van der Vliet A., Eiserich J.P., Halliwell B., and 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
71. von Freyberg B., and Braun W.J. Efficient search for all low energy conformations of polypeptides by Monte Carlo methods. Comput. Chem. 12 (1991) 1065
72. White C.R., Brock T.A., Chang L.Y., Crapo J., Briscoe P., Ku D., Bradley W.A., Gianturco S.H., Gore J., Freeman B.A., and Tarpey M.M. Superoxide and peroxynitrite in atherosclerosis. Proc. Natl. Acad. Sci. USA 91 (1994) 1044-1048
73. Wu W., Chen Y., and Hazen S.L. Eosinophil peroxidase nitrates protein tyrosyl residues: Implications for oxidative damage by nitrating intermediates in eosinophilic inflammatory disorders. J. Biol. Chem. 274 (1999) 25933-25944
74. Yang Y., and Loscalzo J. S-nitrosoprotein formation and localization in endothelial cells. Proc. Natl. Acad. Sci. USA 102 (2005) 117-122
75. Yao D., Gu Z., Nakamura T., Shi Z.Q., Ma Y., Gaston B., Palmer L.A., Rockenstein E.M., Zhang Z., Masliah E., Uehara T., and Lipton S.A. Nitrosative stress linked to sporadic Parkinson's disease: S-nitrosylation of parkin regulates its E3 ubiquitin ligase activity. Proc. Natl. Acad. Sci. USA 101 (2004) 10810-10814
76. Yasinska I.M., and Sumbayev V.V. S-nitrosation of Cys-800 of HIF-1alpha protein activates its interaction with p300 and stimulates its transcriptional activity. FEBS Lett. 549 (2003) 105-109
77. Zhang H., Bhargava K., Keszler A., Feix J., Hogg N., Joseph J., and Kalyanaraman B. Transmembrane nitration of hydrophobic tyrosyl peptides: Localization, characterization, mechanism of nitration, and biological implications. J. Biol. Chem. 278 (2003) 8969-8978
78. Zhang H., Joseph J., Feix J., Hogg N., and Kalyanaraman B. Nitration and oxidation of a hydrophobic tyrosine probe by peroxynitrite in membranes: Comparison with nitration and oxidation of tyrosine by peroxynitrite in aqueous solution. Biochemistry 40 (2001) 7675-7686
79. -: EPR spin trapping studies. J. Biol. Chem. 280 (2005) 40684-40698
80. Zhang Y.Y., Xu A.M., Nomen M., Walsh M., Keaney Jr. J.F., and Loscalzo J. Nitrosation of tryptophan residue(s) in serum albumin and model dipeptides: Biochemical characterization and bioactivity. J. Biol. Chem. 271 (1996) 14271-14279