S-Nitrosothiols and the Bioregulatory Actions of Nitrogen Oxides Through Reactions with Thiol Groups

  • J. S. Stamler
Part of the Current Topics in Microbiology and Immunology book series (CT MICROBIOLOGY, volume 196)


Chemists have long been aware of the red color that develops upon treatment of thiols with nitrous acid. Shortly after the turn of the last century, Tasker and Jones (1909) reported on the synthesis of benzene thionitrite, which exhibits a red color. The authors further noted that the compound was highly unstable and rapidly decomposed to (biphenyl) disulfide and nitric oxide (NO) gas. Thermal and photolytic decomposition of thionitrites was later shown to involve homolytic fission, as inferred from these early experiments (Lecher and Siefken 1926; Rao et al. 1967; Josephy et al. 1984). Tasker and Jones (1909) also described the thionitrite (or S-nitrosothiol; RS-NO) formed from ethane-thiol treatment with nitrosyl chloride (NOCI). This compound was shown to be significantly more stable than the corresponding benzene thiol derivative, but also disappeared with evolution of nitric oxide. Thus, the well documented importance of the electron withdrawing effect of the thiyl (RS) group in hastening the homolytic decomposition of RS-NO had been appreciated well over 50 years ago. In 1969, Mirna and Hofman provided additional insight into the physical properties of biological RS-NOs. These studies demonstrated the trend for greater stability of thionitrites at low pH. At the same time, differences in the stability of thionitrites derived from cysteine and glutathione were noted. While S nitroso-cysteine rapidly decomposes through homolytic fission, the S-nitroso adduct of glutathione remains stable over a wide (physiological) pH range (Mirna and Hofmann 1969). Shortly thereafter, Field and colleagues, isolated the highly stable thionitrite derivative of N-acetylpenicillamine (Field et al. 1978). More importantly, this work also demonstrated that disappearance of RS-NO can follow heterolytic pathways, specifically, reactions in which IRS-NO formally transfers NO+ (or NO). Additional reactions, persumed to be heterolytic in mechanism, were subsequently reported by Massey and colleagues (1978) and Oae and coworkers (1978) and supported the growing use of thionitrites in organic synthesis as effective nitrosating agents. The notable stability of protein thionitrites has been appreciated most recently, and heterolytic fission of the S-N bond appears to predominate in many biological systems (Stamler et al. 1992a,b,c; Lipton et al. 1993; Stamler 1994).


Nitric Oxide Nitric Oxide Nitrogen Oxide Guanylate Cyclase Homolytic Fission 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Al-Kaabi SS, Williams DLH, Bonnet R, Ooi S (1982) A kinetic investigation of the thionitrite from (±)-2acetylamino-2-carboxy-1,1-dimethylethanethiol as a possible nitrosating agent. J Chem Soc Perkins IL 227–230Google Scholar
  2. Aldred SE, Williams LH (1982) Kinetics and mechanisms of the nitrosation of alcohols, carbohydrates, and a thiol. J Chem Soc Perkin Trans II: 777–782Google Scholar
  3. Beckman JS, Beckman TW, Chen J, Marshell PA, Freeman BA (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc nati Acad Sci USA 87: 1620–1624CrossRefGoogle Scholar
  4. Bolotina VM, Najibi S, palacio JJ, Pagano PJ, Cohen RA (1994) Nitric oxide directly activates calcium-dependent potassium channels in vascular smooth muscle. Nature 368: 850–853PubMedCrossRefGoogle Scholar
  5. Bonnett R, Holleyhead R, Johnson BI, Randall EW (1975) Reactions of acidified nitrite solutions with peptide derivatives: evidence for nitrosamine and thionitrite formation from 15N N.M.R. studies. J Chem Soc Perkin I: 2261–2264CrossRefGoogle Scholar
  6. Butler AR, Askew SC (1993) The vascular action of S-nitroglutathione: evidence for NO transfer. Endothelium 1: 144AGoogle Scholar
  7. Byler DM, Gosser DK, Susi H (1983) Spectroscopic estimation of the extent of S-nitrosothiol formation by nitrite action on sulfhydryl groups. J Agric Food Chem 31: 523–527CrossRefGoogle Scholar
  8. Castellani AG, Niven CF (1985) Factors affecting the bacteriostatic action of sodium nitrite. Appl Microbiol 3: 154–159Google Scholar
  9. Clancy RM, Piziak-Leszcynska J, Abramson SB (1993) Nitric oxide stimulates ADP-ribosylation of action in human neutrophils. Biochem Biophys Res Commun 191: 847–852PubMedCrossRefGoogle Scholar
  10. Clancy RM, Yegudin J, Levartovsky D, Piziak-Leszcynska 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. Pro Natl Acad Sci USA 91: 3680–3684CrossRefGoogle Scholar
  11. Chong S, Fung HI (1990) Thiol-mediated catalysis of nitroglycerin degradation by serum proteins. Drug Metab Dispos 18: 61–67PubMedGoogle Scholar
  12. Chong S, Fung H (1991) Biochemical and pharmacological interactions between nitroglycerin and thiols. Biochem Pharmacol 42: 1433–1439PubMedCrossRefGoogle Scholar
  13. Cook JP, Stamler JS, Andon N, Davies PF, McKinley G, Loscalzo J (1990) Flow Stimulation endothelial cells to release a nitrosovasodilator that is potentiated by reduced thiol. Am J Physiol 28: H804 — H812Google Scholar
  14. Dimmler S, Brune B (1992) Characterization of a nitric oxide catalysed ADP ribosylation of glyceraldehyde-3-phosphate dehydrogenase. Eur J Biochem 1202: 305–310CrossRefGoogle Scholar
  15. Feelisch M (1991) The biochemical pathways of nitric oxide formation from nitrosovasodilators; Appropriate choice of exogenous NO donors and aspects of preparation and handling of aqueous NO solutions. J Cardiovasc Pharmacol 17 Suppl 3: S25 — S33CrossRefGoogle Scholar
  16. Feelisch M, Noack E (1987) Nitric oxide formation from nitrovasodilators occurs independently of hemoglobin or non-heme iron. Eur J Pharmacol 142: 465–469PubMedCrossRefGoogle Scholar
  17. Field L. Dilts RV, Ravichandran R, Lenhert PG, Carnahan GE (1978) An unusually stable thionitrite from N-acetyl-D, L-penicillamine; X-ray crystal and molecular structure of 2-(acetylamino)-2-carboxy-1, 1dimethylethyl thionitrite. J Chem Soc Chem Comm: 249–250Google Scholar
  18. Fung HL, Chong S, Kowaluk E, Hough K, Kakemi M (1988) Mechanisms for the pharmacologic interaction of organic nitrates with thiols. Existence of an extracellular pathway for the reversal of nitrate vascular tolerance by N-acetylcysteine. J Pharmacol Exp Ther 245: 524–530PubMedGoogle Scholar
  19. Chong S, Fung H (1991) Biochemical and pharmacological interactions between nitroglycerin and thiols. Biochem Pharmacol 42: 1433–1439PubMedCrossRefGoogle Scholar
  20. Gaston B, Drazen JM, Loscalzo J, Stamler JS (1994a) The biology of nitrogen oxides in the airways. State-of-the-Art. Am Rev Respir Dis 149: 538–551Google Scholar
  21. Gaston B, Drazen JM, Jansen A, Sugarbaker DJ, Loscalzo J, Richards W, Stamler JS (1994b) Relaxation of human bronchial smooth muscle by S-nitrosothiols in vitro. J Pharmacol Exp Ther 268: 978–984PubMedGoogle Scholar
  22. Gruetter CA, Gruetter DY, Lyon JE, Kadowitz PJ, Ignarro LJ (1981) Relationship between cyclic guanosine 3’:5’-monophosphate formation and relaxation of coronary arterial smooth muscle by glycerol trinitrate, nitroprusside, nitrite and nitric oxide: effects of methylene blue and methemoglobin. J Pharmacol Exp Ther 219: 181–186PubMedGoogle Scholar
  23. Han J, Stamler JS, Griffith O (1994) Inhibition of y-glutamylcysteine synthetase by nitirc oxide donors. FASEB J 8: Al288Google Scholar
  24. Hibbs JB (1991) Overview of cytotoxic mechanisms and defense of the intracellular environment against microbes. The biology of Nitric oxide II. Portland, Chapel Hills, pp 201–206Google Scholar
  25. Incze K, Parkes J, Mihalyi V, Zukal E (1974) Antibacterial effect of cysteine-nitrosothiol and possible precursors thereof. Appl Microbiol 27: 202–205PubMedGoogle Scholar
  26. Ignarro LJ (1989) Biological actions and properties of endothelium-derived nitric oxide formed and released from artery and vein. Circ Res 65: 1–21PubMedGoogle Scholar
  27. Ignarro L, Gruetter CA (1980) Requirement of thiols for activation of coronary arterial guanylate cyclase by glycerol trinitrate and sodium nitrite. Biochim Biophys Acta 631: 221–231PubMedGoogle Scholar
  28. Ignarro LJ, Edwards JC, Gruetter DY, Barry BK, Gruetter CA (1980) Possible involvement of S-nitrosothiols in the activation of guanylate cyclase by nitroso compounds. FEBS Lett 110: 275–278PubMedCrossRefGoogle Scholar
  29. Iganarro LJ, Lippton H, Edwards JC, Bancos WH, Hyman AL, Kadowitz PH, Gruetter CA (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: 739–749Google Scholar
  30. Jansen A, Drazen J, Osborne JA, Brown R, Loscalzo J, Stamler JS (1992) The relaxant properties in guinea pig airways of S-nitrosothiols. J Pharmacol Exp Ther 261: 154–160PubMedGoogle Scholar
  31. Jocelyn PC (1972) In: Biochemistry of the SH group. Academic, LondonGoogle Scholar
  32. Johnson MA, Loynes R (1971) Inhibition of Clostridium botulinum by sodium nitrite in a bacteriologic medium and in meat. Can Inst Food Technol J 4: 179–184Google Scholar
  33. Josephy PD, Rehorek D, Janzen EG (1984) Electron spin resonance spin trapping of thiyl radicals from the decomposition of thionitrites.Tetrahedron Lett 25: 1685–1688CrossRefGoogle Scholar
  34. Kamisaki Y, Waldman SA, Murad F (1986) The involvement of catalytic site thiol groups in the activation of soluble guanylate cyclase by sodium nitroprusside. Arch Biochem Biophys 251: 709–714PubMedCrossRefGoogle Scholar
  35. Kanner J (1979) S-nitrosocysteine (RSNO), and effective antioxidant in cured meat. J Am Oil Chem Soc 56: 74–76CrossRefGoogle Scholar
  36. Keaney JF, Simon DI, Stamler JS, Jaraki 0, Scharfstein J, Vita JA, Loscalzo J (1993) NO forms an adduct with serum albumin that has endothelium-derived relaxing factro-like properties. J Clin Invest 91: 1582–1589PubMedCrossRefGoogle Scholar
  37. Kerr SW, Buchanan LV, Bunting S, Mathews WR (1992) Evidence that S-nitrosothiols are responsible for the smooth muscle relaxing activity of the bovine retractor penis inhibitory factor. J Pharmacol Exp Ther 263: 285–263PubMedGoogle Scholar
  38. Kowaluk EA, Fung HL (1990) Spontaneous liberation of nitric oxide cannot account for in vitro vascular relaxation by S-nitrosothiols. J Pharmacol Exp Ther 255: 1256–1264PubMedGoogle Scholar
  39. Lecher H, Siefken W (1926) Nitrosyl-derivate des zweiwertigen Schwefels, I: Das Nitrosylethylmercaptid. Ber Dtsch Chem Ges 59B: 1314–1326Google Scholar
  40. Lei SZ, Pan ZH, Aggarwal SK, Chen HSV, Hartman J, Sucher NJ, Lipton SA (1992) Effect of nitric oxide production on the redox modulatory site of the NMDA receptor-channel complex. Neuron 8: 1087–1099PubMedCrossRefGoogle Scholar
  41. Lipton SA, Choi YB, Pan ZH, Lei SZ, Vincent Chen HS, Sucher NJ, Loscalzo J, Singel DJ, Stamler JS (1993) A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. Nature 364: 626–632PubMedCrossRefGoogle Scholar
  42. Loscalzo J (1985) N-acetylcysteine potentiates inhibition of platelet aggregation by nitroglycerin. J Clin Invest 76: 703–708PubMedCrossRefGoogle Scholar
  43. Manzoni O, Prezeau L, Marin P, Deshager S, Bockaert J, Fagni L (1992) Nitric oxide-induced blockade of NMDA receptors. Neuron 8: 653–662PubMedCrossRefGoogle Scholar
  44. Mason J (1969) Trithioromethyl thionitrite. J Chem Soc A 1587–1592Google Scholar
  45. Massey RC, Crews C, Davies R, McWeeny DJ (1978) A study of the competitive nitrosations of pyrrolidine, ascorbic acid, cysteine and p-Cresol in a protein-based model system. J Sci Food Agric 29: 815–821CrossRefGoogle Scholar
  46. McNainly J, Williams DLH (1993) Fate of nitric oxide from the decomposition of S-nitrosothiols. Endothelium 1: 141AGoogle Scholar
  47. Mima A, Hofmann K (1969) Uber den verbleib von Nitrit in fleischwaren. 1. Umsetzung von Nitrit mit sulhydryl verbindungen. Fleischwirtschaft 10: 1361–1364Google Scholar
  48. Molina Y Vedia L, Mcdonald B, Reep B, Brune B, DiSilvio M, BilliarTR, Lapentina EG (1992) Nitric-oxideinduced S-nitrosylation of glyceraldehyde-3-phosphate dehydrogenase inhibits enzymatic activity and increases endogenous ADP ribosylation. J Biol Chem. 267: 24929–24932Google Scholar
  49. Mohr S, Stamler JS, Brune B (1994) Mechanism of covalent modification of glyceraldehyde-3phosphate dehydrogenase at its active site thiol by nitric oxide, peroxynitrite and related nitrosating agents. FEBS Letters 348: 223–227PubMedCrossRefGoogle Scholar
  50. Morris SL, Hansen JN (1981) Inhibition of Bacillus cereus spore outgrowth by covalent modifications of a sulfhydryl group by nitrosothiol and iodoacetate. J Bacteriol 148: 465–471PubMedGoogle Scholar
  51. Morris SL, Walsh RC, Hansen JN (1984) Identification and characterization of some bacterial membrane sulfhydryl groups which are targets of bacteriostatic and antibiotic action. J Biol Chem 259: 13590–13594PubMedGoogle Scholar
  52. Myers PR, Minor RL, Guerra R, Bates JN, Harrison DG (1990) Vasorelaxant properties of the endothelium-derived relaxing factor more closely resemble S-nitrosocysteine than nitric oxide. Nature 345: 161–163PubMedCrossRefGoogle Scholar
  53. Niroomand F, Rossle R, Mulsch A, Bohme A (1989) Under anaerobic conditions, soluble guanylate cyclase is specifically stimulated by glutathione. Biochem Biophys Res Commun 161: 75–80.PubMedCrossRefGoogle Scholar
  54. Oae S, Shinhama K (1983) Organic thionitrites and related substances. In: Organic preparations and procedures. Organic Prep Proced 15: 165–198CrossRefGoogle Scholar
  55. Oae S, Fukushima D, Kim YH (1977) Novel method of activating thiols by their conversion into thionitries with dinitrogen tetroxide. J Chem Soc Chem Comm: 407–408Google Scholar
  56. Oae S, Kim YH, Fukushima D, Shinhama K (1978) New syntheses of thionitrites and their chemical reactivities. J Chem Soc Perkin 1: 913–917CrossRefGoogle Scholar
  57. O’Leary V, Solberg M (1976) Effect of sodium nitrite on inhibition of intracellular thiol groups and on the activity of certain glycolytic enzymes in Clostridium porringers. Appl Environ Microbiol 31: 208–212PubMedGoogle Scholar
  58. Park JW (1988) Reaction of 5-nitrosoglutathione with sulfhydryl groups in protein. Biochem Biophys Res Commun 152: 916–920PubMedCrossRefGoogle Scholar
  59. Pryor WA, Church DF, Govinden CK, Crank G (1982) Oxidation of thiols by nitric oxide and nitrogen dioxide: synthetic utility and toxicological implications. J Org Chem 47: 156–159.CrossRefGoogle Scholar
  60. Radomski MW, Rees DD, Durta A, Moncada S (1993) S-nitroso-glutathione inhibits platelet activation in vitro and in vivo. Br J Pharmacol, 107: 745–749Google Scholar
  61. Ramdev P, Loscalzo J, Feelisch M, Stamler JS (1993) Biochemical properties and bioactivity of a physiologic NO reservoir. Circulation 88: 1–522Google Scholar
  62. Rao PM, Copeck JA, Knight AR (1967) Reactions of thiyl radicals II. The photolysis of methyl disulfide vapor. Can J Chem 45: 1369–1374CrossRefGoogle Scholar
  63. Ribeiro JM, Hazzard JMH, Nussenzveig RH, Champagne DE, Walker FA (1993) Reversible binding of nitric oxide by a salivary heure protein from a bloodsucking insect. Science 260: 539–541PubMedCrossRefGoogle Scholar
  64. Ridd J (1978) Diffusion control and pre-association in nitrosation, nitration and halogenation. Adv Phys Organ Chem 16: 1–49CrossRefGoogle Scholar
  65. Rinden E, Maricq MM, Grabowski JJ (1989) Gas-phase ion-molecule reactions of the nitric oxide anion. J Am Chem Soc II: 1203–1210CrossRefGoogle Scholar
  66. Rockett KA, Auburn MM, Lowden WB, Clark IA (1991) Killing of Plasmodium falciparum in vivo by nitric oxide derivatives. Infect Immun 59: 3280–3283PubMedGoogle Scholar
  67. Schafer JE, Lee F, Thomson S, Han BJ, Cooke JR, Loscalzo J (1991) The hemodynamic effects of S-nitrosocaptopril in anesthetized dogs. J Pharmacol Exp Ther 256: 704–709Google Scholar
  68. Scharfstein JS, Keaney J, Stamler JS, Vita J, Loscalzo (1993a) Low molecular weight thiols transfer nitric oxide from an endogenous plasma reservoir to vascular smooth muscle. Clin Res 41: 232AGoogle Scholar
  69. Scharfstein JS, Slivka A, Stamler JS, Loscalzo J (1993b) In vivo transfer of nitric oxide from a plasma reservoir to cysteine. Circulation 88: 1–523Google Scholar
  70. Simon DI, Stamler JS, Jaraki O, Keaney J, Osborne JA, Francis SA, Singel DJ, Loscalzo J (1993) Antiplatelet properties of protein S-nitrosothiols derived from nitric oxide and endothelium-derived relaxing factor. Arterioscler Thromb 13: 791–799PubMedCrossRefGoogle Scholar
  71. Simon DI, Stamler JS, Jaraki O, Keaney J, Osborne JA, Francis SA, Singel DJ, Loscalzo J (1993) Antiplatelet properties of protein S-nitrosothiols derived from nitric oxide and endothelium-derived relaxing factor. Arterioscler Thromb 13: 791–799PubMedCrossRefGoogle Scholar
  72. Snyder SH (1993) Janus faces of nitric oxide. Nature 364: 577PubMedCrossRefGoogle Scholar
  73. Stamler JS, Loscalzo J (1991) The antithrombotic effects of organic nitrates. Trends Cardiovasc Med 1: 346–353PubMedCrossRefGoogle Scholar
  74. Stamler JS (1994) Redox Signaling: Nitrosylation and related target interactions of nitric oxide. Cell 78: 931–936PubMedCrossRefGoogle Scholar
  75. Stamler JS, Loscalzo J (1992) Capillary electrophoretic detection of thiols and their 5-nitrosated derivatives. Anal Chem 64: 779–785PubMedCrossRefGoogle Scholar
  76. Stamler JS, Cunningham M, Loscalzo J (1988) Reduced thiols and the effect of nitroglycerin on platelet function. Am J Cardiol 62: 377–380PubMedCrossRefGoogle Scholar
  77. Stamler JS, Mendelsohn M, Amarante P, Davies PF, Cooke JP, Loscalzo J (1989) N-acetylcysteine potentiates platelet inhibition by endothelium derived relaxing factor. Circ Res 65: 789–795PubMedGoogle Scholar
  78. Stamler JS, Simon DI, Osborne JA, Mullins ME, Jaraki O, Michel T, Singel DJ, Loscalzo J (1992a) 5-nitrosylation of proteins with nitric oxide: synthesis and characterization of biologically active compounds. Proc Natl Acad Sci USA 89: 444–448PubMedCrossRefGoogle Scholar
  79. Stamler JS, Jaraki 0, Osborne J, Simon DI, Keaney J, Vita J, Singel D, Valeria RC (1992b) Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin. Proc Natl Acad Sci USA 89: 7674–7677PubMedCrossRefGoogle Scholar
  80. Stamler JS, Singel D, Loscalzo J (1992c) Biochemistry of nitric oxide and its redox activated forms. Science 258: 1898–1902PubMedCrossRefGoogle Scholar
  81. Stamler JS, Simon DI, Jaraki O, Osborne JA, Francis J, Mullins M, Singel D, Loscalzo (1992d) Snitrosylation of tissue-type plasminogen activator confers vasodilatory and antiplatelet properties on the enzyme. Proc Natl Acad Sci USA 89: 8087–8091Google Scholar
  82. Stamler JS, Simon DI, Osborne JA, Mullins M, Jaraki 0, Michel T, Singel D, Loscalzo J (1992e) Exposure of sulfhydryl containing proteins to nitric oxide and endothelium-derived relaxing factor confers novel bioactivity and modulates their intrinsic functional properties. In: Moncada S, Marietta MA, Higgs A, Hibbs JB (eds) Biology of nitric oxide I. Portland Chapel Hill, pp 20–23Google Scholar
  83. Stamler JS, Osborne JA, Jaraki O, Rabbani LE, Mullins M, Singel D, Loscalzo J (1993) Adverse effects of homocysteine are modulated by endothelium-derived relaxing factor and related oxides of nitrogen. J Clin Invest 1: 308–318CrossRefGoogle Scholar
  84. Starkebaum G, Harlan JM (1986) Endothelial cell injury due to copper-catalyzed hydrogen peroxide generation from homocysteine. J Clin Invest 77: 1370–1376PubMedCrossRefGoogle Scholar
  85. Tasker HS, Jones HQ (1909) The action of mercaptans on acid chlorides, part II. The acid chlorides of phosphorous, sulfur and nitrogen. J Chem Soc 95: 1910Google Scholar
  86. Turk T, Hollocher TC (1992) Oxidation of dithiothreitol during turnover of nitric oxide reductase: evidence for generation of nitroxyl with the enzyme from paracoccus denitrificans. Biochem Biophys Res Commun 183: 983–988PubMedCrossRefGoogle Scholar
  87. Williams DHL (1988) Nitrosation. Cambridge University Press, CambridgeGoogle Scholar
  88. Wink DA, Kasprzak KS, Maragos CM, Elespuru RK, Misra M, Dunams TM, Cebula TA, Koch WH, Andrews AW, Allen S, Keefer LK (1991) DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science 254: 1001–1003PubMedCrossRefGoogle Scholar
  89. Wink DA, Darbyshire JF, Nims RW, Saavedra JE, Ford PC (1993) Reactions of bioregulatory agent nitric oxide in oxygenated aqueous media: determination of the kinetics of oxidation and nitrosation by intermediates generated in the NO/O2 reaction. Chem Res Toxicol 6: 23–27PubMedCrossRefGoogle Scholar
  90. World Health Organization (1977) Environmental health criteria 4 oxides of nitrogen. World Health Organization, GenevaGoogle Scholar
  91. Wu M, Kaminski PM, Fayngersh RP, Groszek LL, Pritchard KA, Hintze TH, Stemerman MB, Wolin MS (1994) Involvement of nitric oxide and nitrosothiols in relaxation of pulmonary arteries to peroxynitrite. Am J Physiol 266: H2108 — H2113PubMedGoogle Scholar
  92. Yeates RA, Laufen H, Leitold M (1985) The reaction between organic nitrates and sulfhydryl compounds: a possible model system for the activation of organic nitrates. Mol Pharmacol 28: 555–559PubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1995

Authors and Affiliations

  • J. S. Stamler
    • 1
  1. 1.Divisions of Respiratory Medicine and Cardiovascular MedicineDuke University Medical CenterDurhamUSA

Personalised recommendations