Glutathiyl radical as an intermediate in glutathione nitrosation

Free Radical Biology and Medicine

Volumn 53, Issue 10, 2012, Pages 1968-1976

  Madrasi, Kumpal ^a   Joshi, Mahesh S ^a   Gadkari, Tushar ^a   Kavallieratos, Konstantinos ^b   Tsoukias, Nikolaos M ^a  

^a Florida International University   (United States)

^b FLORIDA INTERNATIONAL UNIVERSITY   (United States)

Author keywords

Free radicals; Glutathione; Kinetics; Nitric oxide; Thiyl radical

Indexed keywords

BUFFER; GLUTATHIONE; GLUTATHIYL RADICAL; NITROGEN DIOXIDE; S NITROSOGLUTATHIONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMOLUMINESCENCE; NITROSATION; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY;

CATALYSIS; GLUTATHIONE; KINETICS; NITRIC OXIDE; NITROGEN DIOXIDE; NITROSATION; S-NITROSOGLUTATHIONE; SULFHYDRYL COMPOUNDS;

EID: 84868568935     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2012.08.013     Document Type: Article

References (55)

1. L.J. Ignarro, G.M. Buga, K.S. Wood, and R.E. Byrns Endothelial-derived relaxing factor produced and released from artery and vein is nitric oxide Proc. Natl. Acad. Sci. USA 84 1987 9265 9269
2. D.S. Bredt, and S.H. Snyder Nitric oxide mediates glutamate-linked enhancement of cGMP levels in the cerebellum Proc. Natl. Acad. Sci. USA 86 1989 9030 9033
3. D.J. Stuehr, and M.A. Marletta Mammalian nitrate biosynthesis: mouse macrophages produce nitrite and nitrate in response to Escherichia coli lipopolysaccharide Proc. Natl. Acad. Sci. USA 82 1985 7738 7742
4. J.R. Lancaster Jr. Simulation of the diffusion and reaction of endogenously produced nitric oxide Proc. Natl. Acad. Sci. USA 91 1994 8137 8141
5. L. Jia, C. Bonaventura, J. Bonaventura, and J.S. Stamler S-nitrosohaemoglobin: a dynamic activity of blood involved in vascular control Nature 380 1996 221 226
6. L.J. Ignarro, H. Lipton, J.C. Edwards, W.H. Baricos, A.L. Hyman, P.J. Kadowitz, and C.A. Gruetter Mechanism of vascular smooth muscle cell relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: evidence for the involvement of S-nitrosothiols as active intermediates J. Pharmacol. Exp. Ther. 218 1981 739 749
7. 2 reaction Chem. Res. Toxicol. 6 1993 23 27
8. - Free Radic. Biol. Med. 34 2003 1078 1088
9. L. Field, R.V. Dilts, R. Ravichandran, P.G. Lenhert, and G.F. Carnahan An unusually stable thionitrite from N-acetyl-D,L-penicillamine: X-ray crystal and molecular structure of 2-(acetylamino)-2-carboxy-1,1-dimethylethyl thionitrite J. Chem. Soc. Chem. Commun. 6 1978 249 250
10. D.L.H. Williams S-nitrosothiols and role of metal ions in decomposition to nitric oxide Methods Enzymol 268 1996 299 308
11. K. Fang, N.V. Ragsdale, R.M. Carey, T. MacDonald, and B. Gaston Reductive assays for S-nitrosothiols: implications for measurements in biological systems Biochem. Biophys. Res. Commun. 252 1998 535 540
12. A.C. Gorren, A. Schrammel, K. Schmidt, and B. Mayer Decomposition of S-nitrosoglutathione in the presence of copper ions and glutathione Arch. Biochem. Biophys. 330 1996 219 228
13. B. Saville A scheme for the colorimetric determination of microgram amounts of thiols Analyst 83 1958 670 672
14. L.K. Keefer, R.W. Nims, K.M. Davies, and D.A. Wink NONOates (1-substituted diazen-1-ium-1,2-diolates) as nitric oxide donors: convenient nitric oxide dosage forms Methods Enzymol. 268 1996 281 293
15. C.M. Maragos, D. Morley, D.A. Wink, T.M. Dunams, J.E. Saavedra, A. Hoffman, A. Bove, L. Isaac, J.A. Hrabie, and L.K. Keefer Complexes of NO with nucleophiles as agents for the controlled biological release of nitric oxide vasorelaxant effects J. Med. Chem. 34 1991 3242 3247
16. 3 the main nitrosating intermediate in aerated nitric oxide (NO) solutions in vivo? If so, where, when, and which one? J Biochem. Mol. Toxicol 16 2002 109 120
17. V.G. Kharitonov, A.R. Sundquist, and V.S. Sharma Kinetics of nitrosation of thiols by nitric oxide in the presence of oxygen J. Biol. Chem. 269 1995 28158 28164
18. S. Goldstein, and G. Czapski Mechanism of the nitrosation of thiols and amines by oxygenated radical NO solutions, the nature of the nitrosating intermediates J. Am. Chem. Soc 118 1996 3419 3425
19. V.A. Gordin, and A.A. Nedospasov NO catastrophes in vivo as a result of micellar catalysis FEBS Lett 424 1998 239 242
20. A.A. Nedospasov Competition involving biogenic NO Biochemistry (Moscow) 63 1998 744 765
21. 2 within the hydrophobic interior of biological membranes Proc. Natl. Acad. Sci. USA 95 1998 2175 2179
22. A. Keszler, Y. Zhang, and N. Hogg The reaction between nitric oxide, glutathione and oxygen in the presence and absence of protein: how are S-nitrosothiols formed? Free Radic. Biol. Med 48 2010 55 64
23. A. Samouilov, and J.L. Zweier Development of chemiluminescence based methods for specific quantitation of nitrosylated thiols Anal. Biochem. 258 1998 322 330
24. O. Rafikova, R. Rafikov, and E. Nudler Catalysis of S-nitrosothiols formation by serum albumin: the mechanism and implication in vascular control Proc. Natl. Acad. Sci. USA 99 2002 5913 5918
25. J.R.Nitroxidative Lancaster nitrosative, and nitrative stress: kinetic predictions of reactive species chemistry under biological conditions Chem. Res. Toxicol. 19 2006 1160 1174
26. D.D. Thomas, K.M. Miranda, and C.A. Colton Citrin, D.; Espey, M.G.; Wink, D.A. Heme proteins and nitric oxide (NO): the neglected eloquent chemistry in NO redox signaling and regulation Antioxid. Redox Signaling 5 2003 307 317
27. 2 and peroxynitrite in membranes: physiological implications Free Radic. Res. 31 1999 597 606
28. D.C. Hooper, S. Spitsin, R.B. Kean, J.M. Chapion, G.M. Dickson, and I. Chaudry Uric acid, a natural scavenger of peroxynitrite, in experimental allergic encephalomyelitis and multiple sclerosis Proc. Natl. Acad. Sci. USA 95 1998 675 680
29. H. Rubbo, S. Parthasarathy, S. Barnes, M. Kirk., B. Kalyanaraman, and B.A. Freeman Nitric oxide inhibition of lipoxygenase-dependent liposome and low density lipoprotein oxidation: termination of radical chain propagation reactions and formation of nitrogen containing oxidized lipid derivatives Arch. Biochem. Biophys. 324 1995 15 25
30. E. Ford, M.N. Hughes, and P. Wardman Kinetics of the reactions of nitrogen dioxide with glutathione, cysteine and uric acid at physiological pH Free Radic. Biol. Med. 32 2002 1314 1323
31. M. Keshive, S. Singh, J.S. Wishnok, S.R. Tannenbaum, and W.M. Deen Kinetics of S-nitrosation of thiols in nitric oxide solutions Chem. Res. Toxicol. 9 1996 988 993
32. 2 reaction Chem. Res. Toxicol. 7 1994 519 525
33. A. Meister, and M.E. Anderson Glutathione Annu. Rev. Biochem. 52 1983 711 760
34. D. Jourd'heuil, F.L. Jourd'heuil, and M. Feelisch Oxidation and nitrosation of thiols at low micromolar exposure to nitric oxide: evidence for a free radical mechanism J. Biol. Chem 278 2003 15720 15726
35. N. Hogg, R.J. Singh, and B. Kalyanaraman The role of glutathione in the transport and catabolism of nitric oxide FEBS Lett 82 1996 223 228
36. R.T. Carroll, P. Galatsis, S. Borosky, K.K. Kopec, V. Kumar, J.S. Althaus, and E.D. Hall 4-Hydroxy-2,2,6,6,-tetramethylpiperidine-1-oxyl (Tempol) inhibits peroxynitrite mediated phenol nitration Chem. Res. Toxicol. 13 2000 294 300
37. C.H. Lim, P.C. Dedon, and W.M. Deen Kinetic analysis of intracellular concentrations of reactive nitrogen species Chem. Res. Toxicol. 21 2008 2134 2147
38. S. Goldstein, and G. Czapski Kinetics of nitric oxide autoxidation in aqueous solution in the absence and presence of various reductants: the nature of the oxidized intermediates J. Am. Chem. Soc 117 1995 12078 12084
39. Schwartz, S.E. Trace atmospheric constituents: properties, transformations and fates. In Advances in Environmental Science and Technology. New York: Wiley; 1969:1-115.
40. P. Wardman Evaluation of the radical sink hypothesis from a chemical-kinetic viewpoint J. Radioanal. Nucl. Chem. 232 1998 23 27
41. P. Wardman, and C. von Sontag Kinetic factors that control the fate of thiyl radicals in cells Methods Enzymol 251 1995 31 45
42. P.D. Wood, B. Mutus, and R.W. Redmond The mechanism of photochemical release of nitric oxide from S-nitrosoglutathione Photochem. Photobiol. 64 1996 518 524
43. G. Czapski, and S. Goldstein The role of the reactions of NO with superoxide and oxygen in biological systems: a kinetic approach Free Radic. Biol. Med 19 1995 785 794
44. C. Griffiths, V. Wykes, T.C. Bellamy, and J. Garthwaite A new and simple method for delivering clamped nitric oxide concentrations in the physiological range: application to activation of guanylyl cyclase coupled nitric oxide receptors Mol. Pharmacol 64 2003 1349 1356
45. D.D. Thomas, K.M. Miranda, M.G. Espey, D. Citrin, D. Jourd'heuil, N. Paolocci, S.J. Hewett, C.A. Colton, M.B. Grisham, M. Feelisch, and D.A. Wink Guide for the use of nitric oxide (NO) donors as probes of the chemistry of NO and related redox species in biological systems Methods Enzymol. 359 2002 84 105
46. Q. Li, and J.R. Lancaster Jr. Calibration of nitric oxide flux generation from diazeniumdiolate (*)NO donors Nitric Oxide 21 2009 69 75
47. I. Koshiishi, T. Takajo, and K. Tsuchida Regulation of S-thiolation and S-nitrosylation in the thiol/nitric oxide system by radical scavengers Nitric Oxide 16 2007 356 361
48. E. Madej, L.K. Folkes, P. Wardman, G. Czapski, and S. Goldstein Thiyl radicals react with nitric oxide to form S-nitrosothiols with rate constants near the diffusion controlled limit Free Radic. Biol. Med 44 2008 2013 2018
49. S. Basu, A. Keszler, N.A. Azarova, N. Nwanze, A. Perlegas, S. Shiva, K.A. Broniowska, N. Hogg, and D.B. Kim-Shapiro A novel role for cytochrome c: efficient catalysis of S-nitrosothiol formation Free Radic. Biol. Med. 48 2010 255 263
50. K.A. Broniowska, A. Keszler, S. Basu, D.B. Kim-Shapiro, and N. Hogg Cytochrome c-mediated formation of S-nitrosothiol in cells Biochem. J. 441 2012 191 197
51. C.A. Bosworth, J.C. Toledo, J.W. Zmijewski, Q. Li, and J.R. Lancaster Dinitrosyliron complexes and the mechanism(s) of cellular protein nitrosothiol formation from nitric oxide Proc. Natl. Acad. Sci. USA 106 2009 4671 4676
52. K. Inoue, T. Akaike, Y. Miyamoto, T. Okamoto, T. Sawa, M. Otaqiri, S. Suzuki, T. Yoshimura, and H. Maeda Nitrosothiol formation catalyzed by ceruloplasmin: implication for cytoprotective mechanism in vivo J. Biol. Chem. 274 1999 27069 27075
53. A. Weischel, E.M. Maes, J.F. Andersen, J.G. Valenzuela, T.K. Shokhireva, F.A. Walker, and W.R. Montfort Heme-assisted S-nitrosation of a proximal thiolate in a nitric oxide transport protein Proc. Natl. Acad. Sci. USA 102 2005 594 599
54. B.P. Luchsinger, E.N. Rich, A.J. Gow, E.M. Williams, J.S. Stamler, and D.J. Singel Routes to S-nitroso-hemoglobin formation with heme redox and preferential reactivity in the beta subunits Proc. Natl. Acad. Sci. USA 100 2003 461 466
55. B. Gaston, S. Sears, J. Woods, J. Hunt, M. Ponaman, T. McMahon, and J.S. Stamler Bronchodilator S-nitrosothiol deficiency in asthmatic respiratory failure Lancet 351 1998 1317 1319