Thiolation and nitrosation of cysteines in biological fluids and cells

Amino Acids

Volumn 25, Issue 3-4, 2003, Pages 323-339

  Di Simplicio, P ^a   Franconi, F ^b   Frosali S ^a   Di Giuseppe, D ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

Nitrosothiols; NO; Protein SH groups; S Nitrosylation; S Thiolation; Thiols

Indexed keywords

ALBUMIN; ANTIOXIDANT; CYSTEINE DERIVATIVE; DISULFIDE; HEMOGLOBIN; OXIDIZING AGENT; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; SULFENIC ACID DERIVATIVE; THIOL DERIVATIVE;

ANTIOXIDANT ACTIVITY; BODY FLUID; CONJUGATION; ENZYME MODIFICATION; NITROSATION; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PKA; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN INTERACTION; PROTEIN STRUCTURE; REVIEW; STEREOSPECIFICITY;

ANIMALS; BODY FLUIDS; CELL PHYSIOLOGY; CYSTEINE; ERYTHROCYTES; GLUTATHIONE; HUMANS; NITROSATION; OXIDATION-REDUCTION; PROTEINS; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES; SULFENIC ACIDS; SULFHYDRYL COMPOUNDS;

EID: 0347361494     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-003-0020-1     Document Type: Review

References (217)

1. Abate C, Patel L, Rauscher FJ, Curran T (1990) Redox regulation of Fos and Jun DNA-binding activity in vitro. Science 249: 1157-1161
2. Ahern GP, Klyachko VA, Jackson MB (2002) cGMP and S-nitrosylation: two routes for modulation of neuronal excitability by NO. Trends Neurosci 25: 510-517
3. - donation by nitrosothiols: implication for regulation of physiological function by S-nitrosylation and acceleration of disulfide formation. Arch Biochem Biophys 318: 279-285
4. Arteel GE, Brivida K, Sies H (1999) Protection against peroxynitrite. FEES Lett 445: 226-230
5. Arstall MA, Bailey C, Gross WL, Bak M, Balligand J-L, Kelly RA (1998) Reversible S-nitrosation of creatine kinase by nitric oxide in adult rat ventricular myocytes. J Molec Cell Cardiol 30: 979-988
6. Ascenzi P, Colasanti M, Persichini T, Muolo M, Polticelli F, Venturini G, Bordo D, Bolognesi M (2000) Re-evaluation of amino acid sequence and structural consensus rules for cysteine-nitric oxide reactivity. Biol Chem 381: 623-627
7. Ashok BT, Ali R (1999) The aging paradox: free radical theory of aging. Exp Gerontol 34: 293-303
8. Baker TL, Booden MA, Buss JE (2000) S-nitrosocysteine increases palmitate turnover on H-Ras in NIH 3T3 cells. J Biol Chem 275: 467-473
9. Barret WC, DeGnore JP, Konig S, Fales HM, Keng YF, Zhang ZY, Yim MB, Chock PB (1999) Regulation of PTP1B via glutathionylation of the active site cysteine 215. Biochemistry 38: 6699-6705
10. Becker K, Savvides SN, Keese M, Schirmer RH, Karplus PA (1998) Enzyme inactivation through sulfhydryl oxidation by physiologic NO-carries. Nature Struct Biol 5: 267-271
11. Beckman JS, Koppenol WH (1996) Nitric oxide, superoxide and peroxynitrite: the good, the bad and the ugly. Am J Physiol 271: C1424-C1437
12. Beckman JS, Beckman TW, Chen J, Marshall PA, Freeman BA (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc Natl Acad Sci USA 87: 1620-1624
13. Berlett BS, Stadtman ER (1997) Protein oxidation in aging, disease, and oxidative stress. J Biol Chem 272: 20313-20316
14. Blough NV, Zafiriou OC (1985) Reaction of superoxide with nitric oxide to form peroxynitrite in alkaline aqueous solution. Inorg Chem 24: 3502-3504
15. Bonner FT, Stedman G (1996) The chemistry of nitric oxide and redox-related species. In: Feelisch M, Stamler JS (eds) Methods in nitric oxide research. Wiley, Chichester, pp 341-356
16. Borland C (1991) Endothelium in control. Br Heart J 66: 405
17. Bredt DS (1999) Endogeneous nitric oxide synthesis: biological functions and pathophysiology. Free Rad Res 31: 577-596
18. Brendeford EM, Anderson KB, Gabrielsen OS (1998) Nitric oxide (NO) disrupts specific DNA binding of the transcription factor c-Myb in vitro. FEBS Lett 20: 52-56
19. Brigelius R (1985) Mixed disulfides: biological functions and increase in oxidative stress. In: Sies H (ed) Oxidative stress. Academic Press, New York, pp 242-272
20. Catani MV, Bernassola F, Rossi A, Melino G (1998) Inhibition of clotting factor XIII activity by nitric oxide. Biochem Biophys Res Commun 249: 275-278
21. Chai YC, Jumg CH, Lii CK, Ashraf SS, Hendrich S, Wolf B, Sies H, Thomas JA (1991) Identification of an abundant S-thiolated rat liver protein as carbonic anhydrase III; characterization of S-thiolation and dethiolation reactions. Arch Biochem Biophys 284: 270-278
22. Chai Y-C, Hendrich S, Thomas JA (1994a) Protein S-thiolation in hepatocytes stimulated by t-butyl hydroperoxide, menadione, and neutrophils. Arch Biochem Biophys 310: 264-272
23. Chai Y-C, Ashraf SS, Rokutan K, Johnston RB Jr, Thomas JA (1994b) S-thiolation of individual human neutrophil proteins including actin by stimulation of the respiratory burst: evidence against a role for glutathione disulfide. Arch Biochem Biophys 310: 273-281
24. Chandra A, Srivastava S, Petrash JM, Bhatnagar A, Srivastava SK (1997) Modification of aldose reductase by S-nitrosoglutathione. Biochemistry 36: 15801-15809
25. Christodoulou J, Sadler P, Tucker A (1995) 1H NMR of albumin in human blood plasma: drug binding and redox reactions at Cys34. FEBS Lett 376: 1-5
26. Claiborne A, Miller H, Parsonage D, Ross RP (1993) Protein-sulfenic acid stabilization and function in enzyme catalysis and gene regulation. FASEB J 7: 1483-1490
27. Claiborne A, Yeh JI, Mallett C, Luba J, Crane EJ III, Charrier V, Parsonage D (1999) Protein-sulfenic acids: diverse roles for an unlikely player in enzyme catalysis and redox regulation. Biochemistry 38: 15407-15416
28. Clancy R, Levartosvsky D, Leszczynska-Pyziak J, Yegudin J, Abramson SB (1994) Nitric oxide reacts with intracellular glutathione and activates the hexose monophosphate shunt in human neutrophils: evidence for S-nitrosoglutathione as a bioactive intermediary. Proc Natl Acad Sci USA 91: 3680-3684
29. Clark AG, Debnam P (1988) Inhibition of glutathione S-transferases from rat liver by S-nitroso-L-glutathione. Biochem Pharmacol 37: 3199-3201
30. Collison M, Thomas JA (1987) S-thiolation of cytoplasmic cardiac creatine kinase in heart cells treated with diamide. Biochim Biophys Acta 928: 121-129
31. Cooper CE (1999) Nitric oxide and iron proteins. Biochim Biophys Acta 1411: 290-309
32. Cotgreaves IA, Jerdes RG (1998) Recent trends in glutathione biochemistry - Glutathione-protein interactions: a molecular link between oxidative stress and cell proliferation? Biochem Biophys Res Commun 242: 1-9
33. Crow JP, Beckman JS (1996) The importance of superoxide in nitric oxide-dependent toxicity: evidence for peroxynitrite-mediated injury. Adv Exp Med Biol 387: 147-161
34. DelaTorre A, Schroeder RA, Kuo PC (1997) Alteration of NF-kappa B p50 DNA binding kinetics by S-nitrosylation. Biochem Biophys Res Commun 238: 703-706
35. DeMaster EG, Quast BJ, Redfern B, Nagasawa HT (1995) Reaction of nitric oxide with the free sulfhydryl group of human serum albumin yields a sulfenic acid and nitrous oxide. Biochemistry 34: 11494-11499
36. Denu JM, Tanner KG (1998) Specific and reversible inactivation of protein tyrosine phosphatases by hydrogen peroxide: evidence for a sulfenic acid intermediate and implications for redox regulation. Biochemistry 37: 5633-5642
37. Dimmeler S, Haendeler J, Sause A, Zeiher AM (1998) Nitric oxide inhibits APO-1/Fas-mediated cell death. Cell Growth Differ 9: 415-422
38. Di Simplicio P, Rossi R (1994) The time-course of mixed disulfide formation between GSH and proteins in rat blood after oxidative stress with tert-butyl hydroperoxide. Biochim Biophys Acta 1199: 245-252
39. Di Simplicio P, Ignesti G, Pirisino R (1985) Relationship between the SH group reactivity and concentration of bovine serum albumin and rat plasma. Pharmacol Res Commun 17: 913-925
40. Di Simplicio P, Cacace M, Lusini L, Giannerini F, Giustarini D, Rossi R (1998a) Role of protein -SH grouops in redox homeostasis- The erythrocytes as a model system. Arch Biochem Biophys 355: 145-152
41. Di Simplicio P, Lusini L, Giannerini F, Giustarini D, Bellelli A, Boumis G, Amiconi G, Rossi R (1998b) In: Moncada S, Higgs HA, Bagetta G (eds) Nitric oxide and Cell: proliferation and death. Portland Press, London, pp 47-59
42. Di Simplicio P, Giannerini F, Giustarini D, Lusini L, Rossi R (1998c) The role of cysteine in the regulation of blood glutathione-protein mixed disulfides in rats treated with diamide. Toxicol Appl Pharmacol 148: 56-64
43. Di Giuseppe D, Di Simplicio P, Capecchi PL, Lazzerini PE, Laghi Pasini F (2003) Alteration in the redox state of plasma in heart transplanted patients with moderate hyperhocysteinemia. J Lab Clin Med 141 (in press)
44. Do K, Benz B, Grima G, Gutteck-Amsler U, Kluge I, Salt T (1996) Nitric oxide precursor arginine and S-nitrosoglutathione in synaptic and glial function. Neurochem Int 29: 213-224
45. Duhé RJ, Evans GA, Erwin RA, Akirken R, Cox GW, Farrar WL (1998) Nitric oxide and thiol redox regulation of Janus kinase activity. Proc Natl Acad Sci USA 95: 126-131
46. Eu JP, Liu L, Zeng M, Stamler JS (2000) An apoptotic model for nitrosative stress. Biochemistry 39: 1040-1047
47. Feldman PL, Griffith OW, Stuehr DJ (1993) The surprising life of nitric oxide. Chem Engin New 71: 26-38
48. Figueiredo-Pereira ME, Yakushin S, Cohen G (1998) Disruption of the intracellular sulfhydryl homeostasis by cadmium-induced oxidative stress leads to protein thiolation and ubiquitination in neuronal cells. J Biol Chem 273: 12703-12709
49. Flohe L, Brigelius-Flohe R, Saliou C, Traber MG, Packer L (1997) Redox regulation of NF-kappa β activation. Free Radic Biol Med 22: 1115-1126
50. Floyd RA (1990) Role of oxygen free radicals in carcinogenesis and brain ischemia. FASEB J 4: 2587-2597
51. Floyd RA (1999) Antioxidants, oxidative stress, and degenerative neurological disorders. Proc Soc Exp Biol Med 222: 236-245
52. Fratelli M, Demol H, Puype M, Casagrande S, Eberini I, Salmona M, Sonetto V, Mengozzi M, Duffieux F, Miclet E, Bachi A, Vandekerckhove, Giannazza E, Ghezzi P (2002) Identification by redox proteomics of glutathionylated proteins in oxidatively stressed human T lymphocytes. Proc Natl Acad Sci USA 99: 3505-3510
53. -) play a major role in cytotoxicity? Acc Chem Res 30: 149-152
54. Galli F, Rossi R, Di Simplicio P, Floridi A, Canestrari F (2002) Protein thiols and glutathione influence the nitric oxide-dependent regulation of the red blood cell metabolism. Nitric Oxide 6: 186-199
55. Gaston B, Reilly J, Drazen JM, Fackler J, Ramden P, Arnelle D, Mullins ME, Sugarbaker D, Chee C, Singel D, Loscalzo J, Stamler JS (1993) Endogeneous nitrogen oxides and bronchodilator S-nitrosothiols in human airways. Proc Natl Acad Sci USA 90: 10957-10961
56. Gaston B, Sears S, Woods J, Hunt J, Ponaman T, McMahon T, Stamler JS (1998) Bronchodilator S-nitrosothiol deficiency in asthmatic respiratory failure. Lancet 351: 1317-1319
57. Gatti RM, Radi R, Augusto O (1994) Peroxynitrite-mediated oxidation of albumin to the protein-thyil free radical. FEBS Lett 348: 287-290
58. Gergel D, Cederbaum AI (1996) Inhibition of the catalytic activity of alcohol dehydrogenase by nitric oxide is associated with S-nitrosylation and the release of zinc. Biochemistry 35: 16186-16194
59. Gilbert HF (1984) Redox control of enzyme activities by thiol/disulfides exchange. Methods Enzymol 107: 330-351
60. Gilbert HF (1995) Thiol/disulfide exchange equilibria and disulfide bond stability. Methods Enzymol 251: 8-28
61. Giovannoni G, Land J, Keir G, Thompson E, Heales S (1997) Adaptation of the nitrate reductase and Griess reaction methods for the measurement of serum nitrate plus nitrite. Ann Clin Biochem 34: 193-198
62. Giustarini D, Campoccia G, Fanetti G, Rossi R, Giannerini F, Lusini L, Di Simplicio P (2000) Minor thiols cysteine and cysteinylglycine regulate the competition between GSH and protein SH groups in human platelets subjected to oxidative stress. Arch Biochem Biophys 380: 1-10
63. Gordge MP, Hothersall J, Neild GH, Dutra AAN (1996) Role of copper (I)-dependent enzyme in the anti-platelet action of S-nitrosoglutathione. Br J Pharmacol 119: 533-538
64. Gordge MP, Addis P, Noronha-Dutra A, Hothersall J (1998) Cell-mediated biotransformation of S-nitrosoglutathione. Biochem Pharmacol 55: 657-665
65. 2 and peroxynitrite in membranes: physiological implication. Free Rad Res 31: 597-606
66. Gow AJ, Buerk DG, Ischiropoulos H (1997) A novel reaction mechanism for the formation of S-nitrosothiol in vivo. J Biol Chem 272: 2841-2845
67. Groves JT (1999) Peroxynitrite: reactive, invasive and enigmatic. Curr Opin Chem Biol 3: 226-235
68. Halliwell B, Zhao K, Whiteman M (1999) Nitric oxide and peroxynitrite. The ugly, the uglier and the not so good. A personal view of recent controversies. Free Rad Res 31: 651-669
69. Hegesh E, Shiloah J (1982) Blood nitrates and infantile methemoglobinemia. Clin Chim Acta 125: 107-115
70. Hausladen A, Stamler JS (1999) Nitrosative stress. Methods Enzymol 300: 389-395
71. Heslop RP, Jones K (1976) Inorganic chemistry, Elsevier, Amsterdam, pp 424-432
72. Hirayama A, Norona-Dutra AA, Gordge MP, Neild GH, Hothersall JS (1999) S-nitrosothiols are stored by platelets and released during platelet-neutrophil interactions. Nitric Oxide Biol Chem 3: 95-104
73. Hogg DR (1990) Chemistry of sulphenic acids and esters. In: Patai S (ed) The chemistry of sulphenic acid and their derivatives. John Wiley & Sons, New York, pp 361-402
74. Hogg N (1999) The kinetics of S-transnitrosation - A reversibile second-order reaction. Anal Biochem 272: 257-262
75. Hogg N (2000) Biological chemistry and clinical potential of S-nitrosothiols. Free Radic Biol Med 28: 1478-1486
76. Hogg N (2002) The biochemistry and physiology of S-nitrosothiols. Ann Rev Pharmacol Toxicol 42: 585-600
77. Hogg N, Kalyanaraman B (1999) Nitric oxide and lipid peroxidation. Biochim Biophys Acta 1411: 378-384
78. Hogg N, Singh RJ, Kalyanaraman B (1996) The role of glutathione in the transport and catabolism of nitric oxide. FEBS Lett 382: 223-228
79. 2+ -dependent stimulation of L-arginine transport in human platelets. Thromb Res 91: 113-120
80. Hughes MH (1999) Relationship between nitric oxide, nitroxyl ion, nitrosocation and peroxynitrite. Biochem Biophys Acta 1411: 263-272
81. Huie RE, Padmaja S (1993) The reaction of NO with superoxide. Free Rad Commun 18: 195-199
82. Ignarro L, Lippton H, Edwards J, Baricos W, Hyman A, Kadowitz P, Gruetter C (1981) Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: evidence for the involvement of S-nitrosothiols as active intermediates. J Pharmacol Exp Ther 218: 739-749
83. Ischiropoulos H, Zhu L, Beckman JS (1992) Peroxynitrite formation from macrophage derived nitric oxide. Arch Biochem Biophys 298: 446-451
84. Jia L, Bonaventura C, Bonaventura J, Stamler JS (1996) S-nitrosohaemoglobin: a dynamic activity of blood involved in vascular control. Nature 380: 221-226
85. Ji Y, Akerboom TPM, Sies H, Thomas JA (1999) S-nitrosylation and S-glutathiolation of protein sulfhydryls by S-nitroso glutathione. Arch Biochem Biophys 362: 67-78
86. Joshi MS, Ponthier JL, Lancaster JR (1999) Cellular antioxidant and pro-oxidant actions of nitric oxide. Free Radic Biol Med 27: 1357-1366
87. Jung C-H, Thomas JA (1996) S-glutathiolated hepatocyte proteins and insulin disulfides as substrates for reduction by glutaredoxin, thioredoxin, protein disulfide isomerase, and glutathione. Arch Biochem Biophys 335: 61-72
88. Kamisaki Y, Wada K, Bian K, Balabanli B, Davis K, Martin E, Behbod F, Lee YC, Murad F (1998) An activity in rat tissues that modifies nitrotyrosine-containing proteins. Proc Natl Acad Sci USA 95: 11584-11589
89. Karinotov VG, Sundquist AR, Sharma VS (1995) Kinetics of nitrosation of thiols by nitric oxide in the presence of oxygen. J Biol Chem 270: 28158-28164
90. Karoui H, Hogg N, Frejaville C, Tordo P, Kalyanaraman B (1996) 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: 6000-6009
91. Kelm M (1999) Nitric oxide metabolism and breakdown. Biochim Biophys Acta 1411: 273-289
92. Kelm M, Schrader J (1990) Control of coronary vascular tone by nitric oxide. Circ Res 66: 1561-1575
93. Kelm M, Feelisch M, Deussen A, Schrader J, Strauer BE (1991) The role of nitric oxide in the control of coronary vascular tone in relation to partial oxygen pressure, perfusion pressure and flow. J Cardiovasc Pharmacol 17: 95-99
94. Kelm M, Feelisch M, Krebber T, Deussen A, Motz W, Strauer BE (1995) Role of nitric oxide in the regulation of coronary vascular tone in hearts from hypertensive rats. Maintenance of nitric oxide-forming capacity and increased basal production of nitric oxide. Hypertension 25: 186-193
95. Kelm M, Schäfer S, Feelisch, Dahmann R, Dolu B, Perings S, Decking U, Schrader J, Strauer, BE (1997a) Nitric oxide induced contractile dysfunction is related to a reduction in myocardial energy generation. Cardiovasc Res 36: 185-194
96. 2/NO interaction. J Biol Chem 272: 9922-9932
97. Kice JL (1980) Mechanisms and reactivity in reactions of organic oxyacids of sulfur and their anhydrides. Adv Phys Org Chem 17: 65-181
98. Klatt P, Pineda Molina E, Lacoba MG, Padilla CA, Martinez Galisteo E, Barcena JA, Lamas S (1999a) Redox regulation of c-Jun DNA binding by reversible S-glutathiolation. FASEB J 13: 1481-1490
99. Klatt P, Pineda Molina E, Lamas S (1999b) Nitric oxide inhibits c-Jun DNA binding by specifically targeted S-glutathionylation. J Biol Chem 274: 15857-15864
100. Klatt P, Pineda Molina E, Perez-Sala D, Lamas S (2000) Novel application of S-nitrosoglutathione sepharose to identify proteins that are potential targets for S-nitrosoglutathione-induced mixed disulfide formation. Biochem J 349: 567-578
101. Kluge I, Gutteck-Amsler U, Zollinger M, Do KQ (1997) 5- nitrosoglutathione in rat cerebellum: identification and quantification by liquid chromatography-mass spectrometry. J Neurochem 69: 2599-2607
102. Knowles RG, Palacios M, Palmer RM, Moncada S (1989) Formation of nitric oxide from L-arginine in the central nervous system: a transduction mechanism for stimulation of the soluble guanylate cyclase. Proc Natl Acad Sci 86: 5159-5162
103. Kondo T, Higashiyama Y, Goto S, Iida T, Cho S, Iwanaga M, Mori K, Tani M, Urata Y (1999) Regulation of gamma-glutamylcysteine synthetase expression in response to oxidative stress. Free Rad Res 31: 325-334
104. Konorev EA, Hogg N, Kalyanaraman B (1998) Rapid and irreversible inhibition of creatine kinase by eproxynitrite. FEBS Lett 427: 171-174
105. Konorev EA, Kalyanaraman B, Hogg N (2000) Modification of creatine kinase by S-nitrosothiols: S-nitrosation vs. S-thiolation. Free Radic Biol Med 28: 1671-1678
106. Kovaluck EA, Fung HL (1990) Spontaneous liberation of nitric oxide cannot account for in vitro vascular relaxation by S-nitrosothiols. J Pharmacol Exp Ther 255: 1256-1264
107. Kuo WN, Kanadia RN, Shanbahg VP (1999) Denitration of peroxynitrite-treated proteins by 'protein nitratases' from dog prostate. Biochem Mol Biol Int 47: 1061-1067
108. Lancaster J (1998) Simulation of the diffusion and reaction of endogenously produced nitric oxide. Proc Natl Acad Sci 91: 8137-8141
109. ras. J Biol Chem 270: 7010-7020
110. ras. J Biol Chem 272: 4323-4326
111. Lee SR, Kwon KS, Kim SR, Rhee SG (1998) Reversible inactivation of protein-tyrosine phosphatase 1B in A431 cells stimulated with epidermal growth factor. J Biol Chem 273: 15366-15372
112. Li J, Billiar TR, Talanian RV, Kim YM (1997) Nitric oxide reversibly inhibits seven members of the caspase family via S-nitrosylation. Biochem Biophys Res Commun 240: 419-424
113. Lii C-K, Chai Y-C, Zhao W, Thomas JA, Hendrich S (1994) S-thiolation and irreversible oxidation of sulfhydryl on carbonic anhydrase III during oxidative stress: A method for studying protein modification in intact cells and tissues. Arch Biochem Biophys 308: 231-239
114. Lin LH, Emson PC, Talman WT (2000) Apposition of neuronal elements containing nitric oxide synthase and glutamate in the nucleus tractus solitarii of rat: a confocal microscopic analysis. Neuroscience 96: 341-350
115. Lind C, Gerdes R, Schuppe-Koistinen, Cotgreave IA (1998) Studies on the mechanism of oxidative modification of human glyceraldehydes-3-phosphate dehydrogenase by glutathione: catalysis by glutaredoxin. Biochem Biophys Res Commun 247: 481-486
116. Lipton SA, Rayudu PV, Choi YB, Sucher NJ, Chen HS (1998) Redox modulation of the NMDA receptor by NO-related species. Prog Brain Res 118: 73-82
117. 2 within the hydrophobic interior of biological membranes. Proc Natl Acad Sci 95: 2175-2179
118. Liu L, Hausladen A, Zeng M, Que L, Heitman J, Stamler JS (2001) A metabolic enzyme for S-nitrosothiol conserved from bacteria to humans. Nature 410: 490-494
119. Lo Bello M, Nuccetelli M, Caccuri AM, Stella L, Parker MW, Rossjohn J, McKinstry WJ, Mozzi AF, Federici G, Polizio F, Pedersen JZ, Ricci G (2001) Human glutathione transferase Pl-1 and nitric oxide carrier. J Biol Chem 276: 42138-42145
120. Lohse DL, Denu JM, Santoro N, Dixon JE (1997) Roles of aspartic acid-181 and serine-222 in intermediate formation and hydrolysis of the mammalian protein-tyrosine-phosphatase PTP1. Biochemistry 36: 4568-4575
121. Lou MF, Dickerson JE, Tung WH, Wolfe JK, Chylack LT (1999) Correlation of nuclear color and opalescence with protein S-thiolation in human lenses. Exp Eye Res 68: 547-522
122. Lusini L, Rossi R, Giustarini D, Di Simplicio P (2002) The pro-oxidant role of protein SH groups of hemoglobin in rat erythrocytes exposed to menadione. Chem Biol Interact 139: 97-114
123. Mallis RJ, Thomas JA (2000) Effect of S-nitrosothiols on cellular glutathione and reactive protein sulfhydryls. Arch Biochem Biophys 383: 60-69
124. Mannervik B, Axelsson K (1980) Role of cytoplasmic thiol-transferase in cellular regulation by thiol-disulfide interchange. Biochem J 190: 125-130
125. Mannick JB, Hausladen A, Liu L, Hess DZ, Zeng M, Miao QX, Kane LS, Gow AJ, Stamler JS (1999) Fas-induced caspase denitrosylation. Science 284: 651-654
126. Mansoor MA, Svardal AM, Ueland PM (1992) Determination of the in vivo status of cysteine, cysteinylglycine, homocysteine, and glutathione in human plasma. Anal Biochem 200: 218-229
127. Mayer B, Schrammel A, Klatt P, Koesling D, Schmidt K (1995) Peroxynitrite-induced accumulation of cyclic GMP in endothelial cells and stimulation of purified soluble role of S-nitrosation. J Biol Chem 270: 17355-17360
128. Maxwell AJ, Cooke JP (2001) In: Loscalzo J, Vita JA (eds) Nitric oxide and the cardiovascular system. Humana, Totowa, NJ, pp 547-585
129. Mc Bride AA, Klausner RD, Howley PM (1992) Conserved cysteine residue in the DNA-binding domain of the bovine papillomavirus type 1 E2 protein confers redox regulation of the DNA-binding activity in vitro. Proc Natl Acad Sci USA 89: 7531-7535
130. McCall MR, Frei B (1999) Can antioxidant vitamins materially reduce oxidative damage in humans? Free Radic Biol Med 26: 1034-1053
131. Merkesbery WR, Carney JM (1999) Oxidative alterations in Alzheimer's disease. Brain Pathol 9: 133-146
132. Meyer DJ, Kramer H, Ozer N, Coles B, Ketterer B (1994) Kinetics and equilibria of S-nitrosothiol-thiol exchange between glutathione, cysteine, penicillamine and serum albumin. FEBS Lett 345: 177-180
133. Miles AM, Bohle DS, Glassbrenner PA, Hansert B, Wink DA, Grisham MB (1996) Modulation of superoxide-dependent oxidation and hydroxylation reactions by nitric oxide. J Biol Chem 271: 40-47
134. Miller RM, Sies H, Park E-M, Thomas JA (1990) Phosphorylase and creatine kinase modification by thiol-disulfide exchange and by xanthine oxidase-initiated S-thiolation. Arch Biochem Biophys 276: 355-363
135. Mirza UA, Chait BT, Lander HM (1995) Monitoring reactions of nitric oxide with peptides and proteins by electrospray ionization-mass spectrometry. J Biol Chem 270: 17185-17188
136. Moellering D, McAndrew J, Patel RP, Forman HJ, Mulcahy RT, Jo H, Darley-Usmar VM (1999) The induction of GSH synthesis by nanomolar concentrations of NO in endothelial cells: a role for gamma- glutamylcysteinesynthetase and gamma-glutamyltranspeptidase. FEBS Lett 448: 292-296
137. Mohr S, Hallack H, de Boitte A, Lapetina EG, Brüne B (1999) Nitric oxide-induced S-glutathionylation and inactivation of glyceraldehyde-3- phosphate dehydrogenase. J Biol Chem 274: 9427-9430
138. Moncada S, Palmer RMJ, Higgs EA (1991) Nitric oxide: physiology, and pharmacology. Pharmacol Rev 43: 109-142
139. Morel Y, Barouki R (1999) Repression of gene expression by oxidative stress. Biochem J 342: 481-496
140. Moro MA, Darley-Usmar VM, Goodwin DA, Read NG, Zamora-Pino R, Feelisch M, Radomski MW, Moncada S (1994) Paradoxical fate and biological action of peroxynitrite on human platelets. Proc Natl Acad Sci USA 91: 6702-6706
141. Murphy ME, Sies H (1991) Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase. Proc Natl Acad Sci USA 88: 10860-10864
142. Murphy MP, Packer MA, Scarlett JL, Martin SW (1998) Peroxynitrite: a biologically significant oxidant. Gen Pharmacol 31: 179-186
143. Nathan C, Xie QW (1994) Nitric oxide synthases: role, tolls, and controls. Cell 78: 915-918
144. Oae S, Shinama K (1983) Organic thionitrite and related substances. Org Prep Proced Int 15: 165-198
145. Okamoto T, Akaike T, Sawa T, Miyamoto Y, van der Vliet A, Maeda H (2001) Activation of matrix metalloproteinase by peroxynitrite-induced via disulfide S-oxide formation. J Biol Chem 276: 29596-29602
146. Padgett CM, Whorton AR (1998) cellular responses to nitric oxide - Role of protein S-thiolation/dethiolation. Arch Biochem Biophys 358: 232-242
147. Park JW (1988) reaction of S-nitrosoglutathione with sulfhydryl groups in proteins. Biochem Biophys Res Commun 152: 916-920
148. Park E-M, Thomas JA (1988) S-thiolation of creatine kinase and glycogen phosphorylase b initiated by partially reduced oxygen species. Biochim Biophys Acta 964: 151-160
149. Park JW, Billman GE, Means GE (1993) Transnitrosation as a predominant mechanism in the hypotensive effects of S-nitrosoglutathione. Biochem Mol Biol Int 30: 885-891
150. Park E-M, Park YM, Gwak YS (1998) Oxidative damage in tissues of rats exposed to cigarette smoke. Free Radic Biol Med 25: 79-86
151. Patel RP, Hogg N, Spencer NY, Kalyanaraman B, Matalanon S, Darley-Usmar VM (1999) Biochemical characterization of human S-nitrosohemoglobin: effects on oxygen binding and transnitrosation. J Biol Chem 274: 15487-15492
152. Percival MD, Ouellet M, Campagnolo C, Claveau D, Li C (1999) Inhibition of cathepsin K by nitric oxide donors: evidence for the formation of mixed disulfides and a sulfenic acid. Biochemistry 38: 13574-13583
153. Peshenko IV, Shichi H (2001) Oxidation of active center cysteine of bovine 1-cys peroxiredoxin to the cysteine sulfenic acid form by peroxide and peroxynitrite. Free Radic Biol Med 31: 292-303
154. Powis G, Gasdaska JR, Baker A (1997) Redox signaling and the control of cell growth and death. Adv Pharmacol 38: 329-359
155. Quijano C, Alvarez B, Gatti RM, Augusto O, Radi R (1997) Pathways of peroxynitrite oxidation of thiol groups. Biochem J 322: 167-173
156. Radi R, Beckman JS, Bush KM, Freeman BA (1991) Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. J Biol Chem 266: 4244-4250
157. Ravichandran V, Seres R, Moriguchi T, Thomas JA, Johnston RB Jr (1994) S-thiolation of glyceraldehydes-3-phosphate dehydrogenase induced by the phagocytosis-associated respiratory burst in blood monocytes. J Biol Chem 269: 25010-25015
158. Reddy S, Jones AD, Cross CE, Wong PS-Y, van der Vliet A (2000) Inactivation of creatine kinase by S-glutathionylation of the active-site cysteine residue. Biochem J 347: 821-827
159. Rigacci S, Iantomasi T, Marracini P, Berti A, Vincenzini MT, Ramponi G (1997) Evidence for glutathione involvement in platelet-derived growth-factor-mediated signal transduction. Biochem J 324: 791-796
160. Rossi R, Barra D, Bellelli A, Boumis G, Canofeni S, Di Simplicio P, Lusini L, Pascarella S, Amiconi G (1998) Fast-reacting thiols in rat hemoglobins can intercept damaging species in erythrocytes more efficiently than glutathione. J Biol Chem 273: 19198-19206
161. Rossi R, Milzani A, Dalle-Donne I, Giannerini F, Giustarini D, Lusini L, Colombo R, Di Simplicio P (2001a) Different metabolizing ability of thiol reactants in human and rat blood. Biochemical and pharmacological implication. J Biol Chem 276: 7004-7010
162. Rossi R, Giustarini D, Milzani A, Colombo R, Dalle-Donne T, Di Simplicio P (2001b) Physiological levels of S-nitrosothiols in human plasma. Cir Res 89: 1
163. Rubanyi GM, Ho EH, Cantor EH, Lumma WC, Botelho LH (1991) Cytoprotective function of nitric oxide: inactivation of superoxide radicals produced by human leucocytes. Biochem Biophys Res Commun 181: 1392-1397
164. Ruiz F, Corrales FJ, Miqueo C, Mato JM (1998) Nitric oxide inactivates rat hepatic methionine adenosyl transferase in vivo by S-nitrosylation. Hepathology 28: 1051-1057
165. Saugstad OD (1998) Oxygen radical disease in neonatology. Semin Neonatol 3: 229-238
166. Schafer FQ, Buettner GR (2001a) Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radic Biol Med 30: 1191-1212
167. Schafer FQ, Buettner GR (2001b) Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radic Biol Med 30: 1191-1212
168. Schmid E, Hotz-Wagenblatt A, Hacj V, Dröge W (1999) Phosphorylation of the insulin receptor kinase by phosphocreatine in combination with hydrogen peroxide: the structural basis of redox priming. FASEB J 13: 1491-1500
169. Schmidt HH, Hofmann H, Schlinder U, Shutenko ZS, Cunningham DD, Feelisch M (1996) No NO from NO synthase. Proc Natl Acad Sci USA 93: 14492-14497
170. Schreck R, Rieber P, Bauerle PA (1991) Reactive oxygen intermediates as apparently widely used messengers in the activation of the NF-κB transcription factor and HIV-1. EMBO J 10: 2247-2258
171. Schuppe-Koistinen I, Moldeus P, Bergman T, Cotgreave IA (1994a) S-thiolation of human endothelial cell glyceraldehydes-3-phosphate dehydrogenase after hydrogen peroxide treatment. Eur J Biochem 221: 1033-1037
172. Schuppe-Koistinen I, Gerdes R, Moldeus P, Cotgreave IA (1994b) Studies on the reversibility of protein S-thiolation in human endothelial cells. Arch Biochem Biophys 315: 226-234
173. Sen CK, Packer L (1996) Antioxidant and gene regulation of gene transcription. FASEB J 10: 709-720
174. Sengupta S, Chen H, Togawa T, DiBello PM, Majors AK, Budy B, Ketterer ME, Jacobsen DW (2001) Albumin thiolate is an intermediate in the formation of albumin-S-S-homocysteine. J Biol Chem 276: 30111-30117
175. Sies H (1993) Strategies of oxidant defense. Eur J Biochem 215: 213-219
176. Simon DI, Mullins ME, Jia L, Gaston B, Singel DJ, Stamler JS (1996) Polynitrosylated proteins: characterization, bioactivity, and functional consequences. Proc Natl Acad Sci USA 93: 4736-4741
177. Sing RJ, Hogg N, Joseph J, Kalyanaraman B (1996) Mechanism of nitric oxide release from nitrosothiols. J Biol Chem 271: 18596-18603
178. Sing RJ, Hogg N, Joseph J, Konorev E, Kalyanaraman B (1999) Peroxynitrite generator, SIN-1, becomes a nitric oxide donor in the presence of electron acceptors. Arch Biochem Biophys 361: 331-339
179. Singh SP, Wishnok JS, Keshive M, Deen WM, Tannenbaum SR (1996) The chemistry of the S-nitrosoglutathione glutathione system. Proc Natl Acad Sci USA 93: 14428-14433
180. Sharpe MA, Cooper CE (1998) Reactions of nitric oxide with mithocondrial cytochrome c: a novel mechanism for the formation of nitroxyl anion and peroxynitrite. Biochem J 332: 9-19
181. Snyder GH, Cennerazzo MJ, Karalis AJ, Field D (1981) Electrostatic influence of local cysteine environments on disulfide exchange kinetics. Biochemistry 20: 6509-6519
182. Speziale MV, Detwiler TC (1990) Free thiols of platelet thrombospondin. J Biol Chem 265: 17859-17867
183. Stamler JS (1994) Redox signaling: nitrosylation and related target interactions of nitric oxide. Cell 78: 931-936
184. Stamler JS (1995) S-nitrosothiols and the bioregulatory actions of nitrogen nitrogen oxides through reactions with thiol groups. Curr Topics Microbiol Immunol 196: 19-36
185. Stamler JS (1999) Nitric oxide in the cardiovascular system. A review in depth. In: Nitric oxide in the cardiovascular system. Williams & Wilkins, Baltimore MD, p 273
186. Stamler JS, Hauslanden A (1998) Oxidative modification in nitrosative stress. Nature Struct Biol 5: 247-249
187. Stamler JS, Singel DL, Loscalzo J (1992a) Biochemistry of nitric oxide and its redox-activated forms. Science 258: 1898-1902
188. Stamler JS, Jaraki O, Osborne JA, Simon DI, Keany J, Vita J, Singel D, Valeri CR, Loscalzo J (1992b) Nitric oxide circulates in mammalian plasma primarily as a S-nitroso adduct of serum albumin. Proc Natl Acad Sci USA 89: 7674-7677
189. Stamler JS, Simon DI, Osborne JA, Mullins ME, Jaraki O, Michel T, Singel DJ, Loscalzo J (1992e) S-nitrosylation of proteins with nitric oxide: Synthesis and characterization of biologically active compounds. Proc Natl Acad Sci USA 89: 444-448
190. Stamler JS, Toone EJ, Lipton SA, Sucher NJ (1997) (S)NO signals: translocation, regulation, and a consensus motif. Neuron 18: 691-696
191. Stuehr DJ (1999) Mammalian nitric oxide synthase. Biochim Biophys Acta 1411: 217-230
192. Stuehr DJ, Marletta MA (1985) Mammalian nitrate biosynthesis: mouse macrophages produce nitrite and nitrate in response to Escherichia coli lipopolysaccaride. Proc Natl Acad Sci USA 82: 7738-7742
193. Suzuki YJ, Forman HJ, Sevanian A (1997) Oxidants as stimulators of signal transduction. Free Rad Biol Med 22: 269-285
194. Tenneti L, D'Emilian DM, Lipton SA (1997) Suppression of neuronal apoptosis by S-nitrosylation of caspases. Neurosci Lett 236: 139-142
195. Terada T, Maeda H, Okamoto K-I, Nishinaka T, Mizoguchi T, Nishihara T (1993) Modulation of glutathione S-transferase activity by a thiol/disulfide exchange reaction and involvement of thiolatransferase. Arch Biochem Biophys 300: 495-500
196. Thomas JA, Poland B, Honzatko R (1995) Protein sulfhydryls and their role in the antioxidant function of protein S-thiolation. Arch Biochem Biophys 319: 1-9
197. Torchinsky YM (1981) Sulfur in proteins. Pergamon Press, New York
198. Tsukahara T, Kominani E, Katunuma N (1987) Formation of mixed disulfide of cystatin-beta in culturad macrophages treated with various oxidants. J Biochem (Tokyo) 101: 1447-1456
199. Uppu RM, Squadrito GL, Pryor WA (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch Biochem Biophys 327: 335-343
200. van Asbeck BS, Hoidal J, Vercellotti GM, Schwartz BA, Moldow CF, Jacob HS (1985) Protection against lethal hyperoxia by tracheal insufflation of erythrocytes: role of red cell glutathione. Science 277: 756-759
201. van der Vliet A, Chr't Hoen PA, Wong PSY, Bast A, Cross CE (1998) Formation of S-nitrosothiols via direct nucleophilic nitrosation of thiols by peroxynitrite with elimination of hydrogen peroxide. J Biol Chem 273: 30255-30262
202. Venturini G, Fioravanti, Colasanti M, Persichini T, Ascenzi P (1998) Cys25-nitrosylation inactivates papain. Biochem Mol Biol Int 46: 425-428
203. 3 into nitrate is enhanced by endotoxin treatment. Proc Natl Acad Sci 80: 4518-4521
204. Wink DA, Mitchell JB (1998) Chemical biology of nitric oxide: insights into regulatory, cytotoxic, and cytoprotective mechanisms of nitric oxide. Free Radic Biol Med 25: 434-456
205. 2 reaction. Chem Res Toxicol 7: 519-525
206. Wink DA, Miranda KM, Espey MG (2000) Effects of oxidative and nitrosative stress in cytotoxicity. Semin Perinatol 24: 20-23
207. Whiteman M, Halliwell B (1997) Thiols and disulfides can aggravate peroxynitrite-dependent inactivation of alpha1-anti-proteinase. FEBS Lett 414: 497-500
208. Wolokser H, Panizzutti R, Engelender S (1996) Inhibition of creatine kinase by S-nitrosoglutathione. FEBS Lett 392: 274-276
209. Wong PS-Y, Hyun J, Fukuto JM, Shirota FN, DeMaster EG, Shoeman DW, Nagasawa HT (1998) Reaction between S-nitrosothiols anf thiols: generation of nitroxyl (HNO) and subsequent chemistry. Biochemistry 37: 5362-5371
210. Xanthoudakis S, Miao G, Wang F, Pan Y-CE, Curran T (1992) Redox activation of Fos-Jun DNA binding activity is mediated by a DNA repair enzyme. EMBO J 11: 3323-3335
211. Xian M, Chen XC, Liu ZY, Wang K, Wang PG (2000) Inhibition of papain by S-nitrosothiols: formation of mixed disulfides. J Biol Chem 275: 467-473
212. Xu L, Eu JP, Meissner G, Stamler JS (1998) Activation of the cardiac calcium release channel (ryanodine receptor) by poly-S-nitrosylation. Science 279: 234-237
213. Yang ES, Richter C, Chun JS, Huh TL, Kang SS, Park JW (2002) Inactivation of NADP(+)-dependent isocitrate dehydrogenase by nitric oxide. Free Radic Biol Med 33: 927-937
214. Zech B, Wilm M, van Eldik R, Brune B (1999) Mass spectrometric analysis of nitric oxide-modified caspase-3. J Biol Chem 274: 20931-20936
215. Zeng H, Spencer NY, Hogg N (2001) Metabolism of S-nitrosoglutathione by endothelial cells. Am J Physiol Heart Circ Physiol 281: H432-H439
216. Ziegler DM (1985) Role of reversible oxidation-reduction of enzyme thiols-disulfides in metabolic regulation. Ann Rev Biochem 54: 305-329
217. Zweier JL, Samouilov A, Kuppusamy P (1999) Non-enzymatic nitric oxide synthesis in biological systems. Biochim Biophys Acta 1411: 250-262