Biological chemistry and clinical potential of S-nitrosothiols

Free Radical Biology and Medicine

Volumn 28, Issue 10, 2000, Pages 1478-1486

  Hogg, Neil ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

Free radicals; Nitric oxide; Nitrosation thiolation; S nitrosoglutathione; S nitrosothiols; Thiols

Indexed keywords

FREE RADICAL; S NITROSOGLUTATHIONE;

BLOOD CLOTTING DISORDER; CONFERENCE PAPER; DRUG SYNTHESIS; HUMAN; INFLAMMATION; NEUROTRANSMISSION; NITROSATION; OXIDATIVE STRESS; PRIORITY JOURNAL; THIOLATION;

ANIMALS; DRUG STABILITY; GLUTATHIONE; HUMANS; MERCAPTOETHANOL; NITRIC OXIDE DONORS; NITROSO COMPOUNDS; PENICILLAMINE; PLATELET AGGREGATION INHIBITORS; S-NITROSOGLUTATHIONE; S-NITROSOTHIOLS;

EID: 0034656848     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00248-3     Document Type: Conference Paper

References (104)

1. Oae S., Shinhama K. Organic thionitrites and related substances. Organic Preparations and Procedures International. 15:1983;165-198.
2. Field, L.; Dilts, R. V.; Ravichandran, R.; Lanhert, P. G.; Carnahan, P. G. J. Chem. Soc. Chem. Commun. 249-250;1978.
3. Hart T.W. Some observations concerning the S-nitroso and S-phenylsulphonyl derivatives of L-cysteine and glutathione. Tetrahedron Lett. 26:1985;2013-2026.
4. Oae, S.; Fukushima, D.; Kim, Y. H. Novel method of activating thiols by their conversion into thionitrites with dinitrogen tetraoxide. J. Chem. Soc. Chem. Commun. 407-408; 1977.
5. Kharitonov V.G., Sundquist A.R., Sharma V.S. Kinetics of nitrosation of thiols by nitric oxide in the presence of oxygen. J. Biol. Chem. 270:1995;28158-28164.
6. Wink D.A., Nims R.W., Darbyshire J.F., Christodoulou D., Hanbauer I., Cox G.W., Laval F., Laval J., Cook J.A., Krishna M.C. Reaction kinetics for nitrosation of cysteine and glutathione in aerobic nitric oxide solutions at neutral pH. Insights into the fate and physiological effects of intermediates generated in the NO/O2 reaction. Chem. Res. Toxicol. 7:1994;519-525.
7. Williams D.L. S-nitrosothiols and role of metal ions in decomposition to nitric oxide. Methods Enzymol. 268:1996;299-308.
8. Singh R.J., Hogg N., Joseph J., Kalyanaraman B. Mechanism of nitric oxide release from S-nitrosothiols. J. Biol. Chem. 271:1996;18596-18603.
9. Sexton D.J., Muruganandam A., McKenney D.J., Mutus B. Visible light photochemical release of nitric oxide from S-nitrosoglutathione potential photochemotherapeutic applications . Photochem. Photobiol. 59:1994;463-467.
10. Vanin A.F., Malenkova I.V., Serezhenkov V.A. Iron catalyzes both decomposition and synthesis of S-nitrosothiols optical and electron paramagnetic resonance studies . Nitric Oxide. 1:1997;191-203.
11. 2+ of nitric oxide release from S-nitrosothiols (RSNO). J. Chem. Soc. Perkin Trans. 2 741-745; 1995.
12. 2-mediated nitric oxide release from S-nitrosoglutathione - role of glutamate. Arch. Biochem. Biophys. 372:1999;8-15.
13. Kashiba-Iwatsuki M., Yamaguchi M., Inoue M. Role of ascorbic acid in the metabolism of S-nitroso-glutathione. FEBS Lett. 389:1996;149-152.
14. Scorza G., Pietraforte D., Minetti M. Role of ascorbate and protein thiols in the release of nitric oxide from S-nitroso-albumin and S-nitroso-glutathione in human plasma. Free Radic. Biol. Med. 22:1997;633-642.
15. Butler A.R., Rhodes P. Chemistry, analysis, and biological roles of S-nitrosothiols. Anal. Biochem. 249:1997;1-9.
16. + as the effective reagent in nitric oxide formation from S-nitrosothiols (RSNO). J. Chem. Soc. Perkin Trans. 2 481-487; 1996.
17. Al-Sa'doni H.H., Megson I.L., Bisland S., Butler A.R., Flitney F.W. Neocuproine, a selective Cu(I) chelator, and the relaxation of rat vascular smooth muscle by S-nitrosothiols. Br. J. Pharmacol. 121:1997;1047-1050.
18. Aleryani S., Milo E., Rose Y., Kostka P. Superoxide-mediated decomposition of biological S-nitrosothiols. J. Biol. Chem. 273:1998;6041-6045.
19. Hogg N., Singh R.J., Konorev E., Joseph J., Kalyanaraman B. S-Nitrosoglutathione as a substrate for gamma-glutamyl transpeptidase. Biochem. J. 323:1997;477-481.
20. Jourd'heuil D., Mai C.T., Laroux F.S., Wink D.A., Grisham M.B. The reaction of S-nitrosoglutathione with superoxide. Biochem. Biophys. Res. Commun. 244:1998;525-530.
21. Beckman J.S., Beckman T.W., Chen J., Marshall P.A., Freeman B.A. Apparent hydroxyl radical production by peroxynitrite implications for endothelial injury from nitric oxide and superoxide . Proc. Natl. Acad. Sci. USA. 87:1990;1620-1624.
22. Hogg N. The kinetics of S-Transnitrosation - a reversible second-order reaction. Anal. Biochem. 272:1999;257-262.
23. Patel R.P., Hogg N., Spencer N.Y., Kalyanaraman B., Matalon S., Darley-Usmar V.M. Biochemical characterization of human S-nitrosohemoglobin Effects on oxygen binding and and transnitrosation . J. Biol. Chem. 274:1999;15487-15492.
24. Meyer D.J., Kramer H., Ozer N., Coles B., Ketterer B. Kinetics and equilibria of S-nitrosothiol-thiol exchange between glutathione, cysteine, penicillamines and serum albumin. FEBS Lett. 345:1994;177-180.
25. Stamler J.S. S-nitrosothiols and the bioregulatory actions of nitrogen oxides through reactions with thiol groups. Curr. Topics Microbiol. Immunol. 196:1995;19-36.
26. Mannick J.B., Hausladen A., Liu L., Hess D.T., Zeng M., Miao Q.X., Kane L.S., Gow A.J., Stamler J.S. Fas-induced caspase denitrosylation. Science. 284:1999;651-654.
27. Ruiz F., Corrales F.J., Miqueo C., Mato J.M. Nitric oxide inactivates rat hepatic methionine adenosyltransferase in vivo by s-nitrosylation. Hepatology. 28:1998;1051-1057.
28. Dimmeler S., Haendeler J., Sause A., Zeiher A.M. Nitric oxide inhibits APO-1/Fas-mediated cell death. Cell Growth Differ. 9:1998;415-422.
29. Park J.W. Reaction of S-nitrosoglutathione with sulfhydryl groups in protein. Biochem. Biophys. Res. Commun. 152:1988;916-920.
30. Arnelle D.R., Stamler J.S. NO+, NO, and NO- donation by S-nitrosothiols implications for regulation of physiological functions by S-nitrosylation and acceleration of disulfide formation . Arch. Biochem. Biophys. 318:1995;279-285.
31. Hogg N., Singh R.J., Kalyanaraman B. The role of glutathione in the transport and catabolism of nitric oxide. FEBS Lett. 382:1996;223-228.
32. Wong P.S., Hyun J., Fukuto J.M., Shirota F.N., DeMaster E.G., Shoeman D.W., Nagasawa H.T. Reaction between S-nitrosothiols and thiols generation of nitroxyl (HNO) and subsequent chemistry . Biochemistry. 37:1998;5362-5371.
33. Ji Y., Akerboom T.P., Sies H., Thomas J.A. S-Nitrosylation and S-glutathiolation of protein sulfhydryls by S-nitrosoglutathione. Arch. Biochem. Biophys. 362:1999;67-78.
34. Mohr S., Hallak H., de Boitte A., Lapetina E.G., Brüne B. Nitric oxide-induced S-glutathionylation and inactivation of glyceraldehyde-3-phosphate dehydrogenase. J. Biol. Chem. 274:1999;9427-9430.
35. Konorev, E. A.; Kalyanaraman, B.; Hogg, N. Modification of creatine kinase by S-nitrosothiols: S-Nitrosation vs. S-Thiolation. (In Preparation).
36. Padgett C.M., Whorton A.R. Cellular responses to nitric oxide - role of protein S-thiolation/dethiolation. Arch. Biochem. Biophys. 358:1998;232-242.
37. Fukuto J.M., Hobbs A.J., Ignarro L.J. Conversion of nitroxyl (HNO) to nitric oxide (NO) in biological systems the role of physiological oxidants and relevence to the biological activity of HNO . Biochem. Biophys. Res. Commun. 196:1993;707-713.
38. Turk T., Hollacher T.C. Oxidation of dithiothreitol during turnover of nitric oxide reductase evidence for generation of nitroxyl with the enzyme from paracoccus denitrificans . Biochem. Biophys. Res. Commun. 183:1992;983-988.
39. Haj-Yehia A.I., Benet L.Z. In vivo depletion of free thiols does not account for nitroglycerin-induced tolerance a thiol-nitrate interaction hypothesis as an alternative explanation for nitroglycerin activity and tolerance . J. Pharmacol. Exp. Ther. 278:1996;1296-1305.
40. Askew S.C., Butler A.R., Flitney F.W., Kemp G.D., Megson I.L. Chemical mechanisms underlying the vasodilator and platelet anti-aggregating properties of S-nitroso-N-acetyl-DL-penicillamine and S-nitrosoglutathione. Bioorg. Med. Chem. 3:1995;1-9.
41. Jourd'heuil D., Laroux F.S., Miles A.M., Wink D.A., Grisham M.B. Effect of superoxide dismutase on the stability of S-nitrosothiols. Arch. Biochem. Biophys. 361:1999;323-330.
42. Ignarro L.J., Edwards J.C., Gruetter D.Y., Barry B.K., Gruetter C.A. Possible involvement of S-nitrosothiols in the activation of guanylate cyclase by nitroso compounds. FEBS Lett. 110:1980;275-278.
43. Ignarro L.J., Lippton H., Edwards J.C., Baricos W.H., Hyman A.L., Kadowitz P.J., Gruetter C.A. 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. 218:1981;739-749.
44. Edwards J.C., Ignarro L.J., Hyman A.L., Kadowitz P.J. Relaxation of intrapulmonary artery and vein by nitrogen oxide-containing vasodilators and cyclic GMP. J. Pharmacol. Exp. Ther. 228:1984;33-42.
45. Schrammel A., Pfeiffer S., Schmidt K., Koesling D., Mayer B. Activation of soluble guanylyl cyclase by the nitrovasodilator 3-morpholinosydnonimine involves formation of S-nitrosoglutathione. Mol. Pharmacol. 54:1998;207-212.
46. Kowaluk E.A., Fung H.L. Spontaneous liberation of nitric oxide cannot account for in vitro vascular relaxation by S-nitrosothiols. J. Pharmacol. Exp. Ther. 255:1990;1256-1264.
47. Mathews W.R., Kerr S.W. Biological activity of S-nitrosothiols the role of nitric oxide . J. Pharmacol. Exp. Ther. 267:1993;1529-1537.
48. De Man J.G., Boeckxstaens G.E., De Winter B.Y., Moreels T.G., Misset M.E., Herman A.G., Pelckmans P.A. Comparison of the pharmacological profile of S-nitrosothiols, nitric oxide and the nitrergic neurotransmitter in the canine ileocolonic junction. Br. J. Pharmacol. 114:1995;1179-1184.
49. De Man J.G., De Winter B.Y., Boeckxstaens G.E., Herman A.G., Pelckmans P.A. Effect of Cu2+ on relaxations to the nitrergic neurotransmitter, NO and S-nitrosothiols in the rat gastric fundus. Br. J. Pharmacol. 119:1996;990-996.
50. De Man J.G., De Winter B.Y., Moreels T.G., Herman A.G., Pelckmans P.A. S-nitrosothiols and the nitrergic neurotransmitter in the rat gastric fundus effect of antioxidants and metal chelation . Br. J. Pharmacol. 123:1998;1039-1046.
51. Lipton S.A., Choi Y.B., Pan Z.H., Lei S.Z., Chen H.S., Sucher N.J., Loscalzo J., Singel D.J., Stamler J.S. A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. Nature. 364:1993;626-632.
52. Davisson R.L., Travis M.D., Bates J.N., Johnson A.K., Lewis S.J. Stereoselective actions of S-nitrosocysteine in central nervous system of conscious rats. Am. J. Physiol. 272:1997;H2361-H2368.
53. Brendeford E.M., Andersson K.B., Gabrielsen O.S. Nitric oxide (NO) disrupts specific DNA binding of the transcription factor c-Myb in vitro. FEBS Lett. 425:1998;52-56.
54. Hu H., Chiamvimonvat N., Yamagishi T., Marban E. Direct inhibition of expressed cardiac L-type Ca2+ channels by S-nitrosothiol nitric oxide donors. Circ. Res. 81:1997;742-752.
55. Campbell D.L., Stamler J.S., Strauss H.C. Redox modulation of L-type calcium channels in ferret ventricular myocytes. Dual mechanism regulation by nitric oxide and S-nitrosothiols. J. Gen. Physiol. 108:1996;277-293.
56. Catani M.V., Bernassola F., Rossi A., Melino G. Inhibition of clotting factor xiii activity by nitric oxide. Biochem. Biophys. Res. Commun. 249:1998;275-278.
57. Clark A.G., Debnam P. Inhibition of glutathione S-transferases from rat liver by S-nitroso-L-glutathione. Biochem. Pharmacol. 37:1988;3199-3201.
58. Li J., Billiar T.R., Talanian R.V., Kim Y.M. Nitric oxide reversibly inhibits seven members of the caspase family via S-nitrosylation. Biochem. Biophys. Res. Commun. 240:1997;419-424.
59. Hausladen A., Privalle C.T., Keng T., DeAngelo J., Stamler J.S. Nitrosative stress activation of the transcription factor OxyR . Cell. 86:1996;719-729.
60. Rauhala P., Mohanakumar K.P., Sziraki I., Lin A.M., Chiueh C.C. S-nitrosothiols and nitric oxide, but not sodium nitroprusside, protect nigrostriatal dopamine neurons against iron-induced oxidative stress in vivo. Synapse. 23:1996;58-60.
61. Hogg N., Kalyanaraman B., Joseph J., Struck A., Parthasarathy S. Inhibition of low-density lipoprotein oxidation by nitric oxide. Potential role in atherogenesis. FEBS Lett. 334:1993;170-174.
62. Rubbo H., Radi R., Trujillo M., Telleri R., Kalyanaraman B., Barnes S., Kirk, 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.
63. Chamulitrat W. Nitric oxide inhibited peroxyl and alkoxyl radical formation with concomitant protection against oxidant injury in intestinal epithelial cells. Arch. Biochem. Biophys. 355:1998;206-214.
64. Gutierrez H.H., Nieves B., Chumley P., Rivera A., Freeman B.A. Nitric oxide regulation of superoxide-dependent lung injury oxidant-protective actions of endogenously produced and exogenously administered nitric oxide . Free Radic. Biol. Med. 21:1996;43-52.
65. Struck A.T., Hogg N., Thomas J.P., Kalyanaraman B. Nitric oxide donor compounds inhibit the toxicity of oxidized low-density lipoprotein to endothelial cells. FEBS Lett. 361:1995;291-294.
66. Bouton C., Raveau M., Drapier J.C. Modulation of iron regulatory protein functions. Further insights into the role of nitrogen- and oxygen-derived reactive species. J. Biol. Chem. 271:1996;2300-2306.
67. Kaye D.M., Wiviott S.D., Kobzik L., Kelly R.A., Smith T.W. S-nitrosothiols inhibit neuronal norepinephrine transport. Am. J. Physiol. 272:1997;H875-H883.
68. Stamler J.S., Jaraki O., Osborne J., Simon D.I., Keaney J., Vita J., Singel D., Valeri C.R., Loscalzo J. Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin. Proc. Natl. Acad. Sci. USA. 89:1992;7674-7677.
69. Marley R., Feelisch M., Holt S., Moore K. A chemiluminescence based assay for S-nitrosoalbumin and other plasma S-nitrosothiols. Free Radic. Res. 32:2000;1-9.
70. DelaTorre A., Schroeder R.A., Punzalan C., Kuo P.C. Endotoxin-mediated S-nitrosylation of p50 alters NF-κ B-dependent gene transcription in ANA-1 murine macrophages. J. Immunol. 162:1999;4101-4108.
71. Kluge I., Gutteck-Amsler U., Zollinger M., Do K.Q. S-nitrosoglutathione in rat cerebellum identification and quantification by liquid chromatography-mass spectrometry . J. Neurochem. 69:1997;2599-2607.
72. Park J.K., Kostka P. Fluorometric detection of biological S-nitrosothiols. Anal. Biochem. 249:1997;61-66.
73. Pfeiffer S., Schrammel A., Schmidt K., Mayer B. Electrochemical determination of s-nitrosothiols with a clark-type nitric oxide electrode. Anal. Biochem. 258:1998;68-73.
74. Jia L., Bonaventura C., Bonaventura J., Stamler J.S. S-nitrosohaemoglobin a dynamic activity of blood involved in vascular control . Nature. 380:1996;221-226.
75. Ferranti P., Malorni A., Mamone G., Sannolo N., Marino G. Characterisation of S-nitrosohaemoglobin by mass spectrometry. FEBS Lett. 400:1997;19-24.
76. Stamler J.S., Jia L., Eu J.P., McMahon T.J., Demchenko I.T., Bonaventura J., Gernert K., Piantadosi C.A. Blood flow regulation by S-nitrosohemoglobin in the physiological oxygen gradient. Science. 276:1997;2034-2037.
77. Mellion B.T., Ignarro L.J., Myers C.B., Ohlstein E.H., Ballot B.A., Hyman A.L., Kadowitz P.J. Inhibition of human platelet aggregation by S-nitrosothiols. Heme-dependent activation of soluble guanylate cyclase and stimulation of cyclic GMP accumulation. Mol. Pharmacol. 23:1983;653-664.
78. Gordge M.P., Meyer D.J., Hothersall J., Neild G.H., Payne N.N., Noronha-Dutra A. Copper chelation-induced reduction of the biological activity of S-nitrosothiols. Br. J. Pharmacol. 114:1995;1083-1089.
79. Hirayama A., Noronha-Dutra A., Gordge M.P., Neild G.H., Hothersall J.S. S-nitrosothiols are stored by platelets and released during platelet-neutrophil interactions. Nitric Oxide. 3:1999;95-104.
80. Howard C.M., Sexton D.J., Mutus B. S-nitrosoglutathione/glutathione disulphide/Cu2+-dependent stimulation of L-arginine transport in human platelets. Thromb. Res. 91:1998;113-120.
81. Molloy J., Martin J.F., Baskerville P.A., Fraser S.C.A., Markus H.S. S-nitrosoglutathione reduces the rate of embolization in humans. Circulation. 98:1998;1372-1375.
82. Salas E., Langford E.J., Marrinan M.T., Martin J.F., Moncada S., Debelder A.J. S-nitrosoglutathione inhibits platelet activation and deposition in coronary artery saphenous vein grafts in vitro and in vivo. Heart. 80:1998;146-150.
83. de Belder A., Lees C., Martin J., Moncada S., Campbell S. Treatment of HELLP syndrome with nitric oxide donor. Lancet. 345:1995;124-125.
84. Kowaluk E.A., Poliszczuk R., Fung H.L. Tolerance to relaxation in rat aorta comparison of an S-nitrosothiol with nitroglycerin . Eur. J. Pharmacol. 144:1987;379-383.
85. Bauer J.A., Fung H.L. Differential hemodynamic effects and tolerance properties of nitroglycerin and an S-nitrosothiol in experimental heart failure. J. Pharmacol. Exp. Ther. 256:1991;249-254.
86. Henry P.J., Drummer O.H., Horowitz J.D. S-nitrosothiols as vasodilators implications regarding tolerance to nitric oxide-containing vasodilators . Br. J. Pharmacol. 98:1989;757-766.
87. Jansen A., Drazen J., Osborne J.A., Brown R., Loscalzo J., Stamler J.S. The relaxant properties in guinea pig airways of S-nitrosothiols. J. Pharmacol. Exp. Ther. 261:1992;154-160.
88. Bannenberg G., Xue J., Engman L., Cotgreave I., Moldeus P., Ryrfeldt A. Characterization of bronchodilator effects and fate of S-nitrosothiols in the isolated perfused and ventilated guinea pig lung. J. Pharmacol. Exp. Ther. 272:1995;1238-1245.
89. Perkins W.J., Pabelick C., Warner D.O., Jones K.A. cGMP-independent mechanism of airway smooth muscle relaxation induced by s-nitrosoglutathione. Am. J. Physiol. Cell Physiol. 44:1998;C468-C474.
90. Gaston B., Reilly J., Drazen J.M., Fackler J., Ramdev P., Arnelle D., Mullins M.E., Sugarbaker D.J., Chee C., Singel D.J. Endogenous nitrogen oxides and bronchodilator S-nitrosothiols in human airways. Proc. Natl. Acad. Sci. USA. 90:1993;10957-10961.
91. Gordge M.P., Hothersall J.S., Noronhadutra A.A. Evidence for a cyclic gmp-independent mechanism in the anti-platelet action of s-nitrosoglutathione. Br. J. Pharmacol. 124:1998;141-148.
92. Barbier A.J., Lefebvre R.A. Influence of S-nitrosothiols and nitrate tolerance in the rat gastric fundus. Br. J. Pharmacol. 111:1994;1280-1286.
93. Konorev E.A., Joseph J., Tarpey M.M., Kalyanaraman B. The mechanism of cardioprotection by S-nitrosoglutathione monoethyl ester in rat isolated heart during cardioplegic ischaemic arrest. Br. J. Pharmacol. 119:1996;511-518.
94. Konorev E.A., Tarpey M.M., Joseph J., Baker J.E., Kalyanaraman B. S-nitrosoglutathione improves functional recovery in the isolated rat heart after cardioplegic ischemic arrest-evidence for a cardioprotective effect of nitric oxide. J. Pharmacol. Exp. Ther. 274:1995;200-206.
95. Hoshida S., Yamashita N., Igarashi J., Nishida M., Hori M., Kuzuya T., Tada M. A nitric oxide donor reverses myocardial injury in rabbits with acute hypercholesterolemia. J. Pharmacol. Exp. Ther. 278:1996;741-746.
96. Brunner F. Interaction of nitric oxide and endothelin-1 in ischemia/reperfusion injury of rat heart. J. Mol. Cell. Cardiol. 29:1997;2363-2374.
97. Ali I.S., Gandhi M., Finegan B.A., Koshal A., Clanachan A.S. Cardioprotection by activation of NO/cGMP pathway after cardioplegic arrest and 8-hour storage. Ann. Thorac. Surg. 65:1998;1303-1309.
98. Liew F.Y., Millott S., Parkinson C., Palmer R.M., Moncada S. Macrophage killing of Leishmania parasite in vivo is mediated by nitric oxide from L-arginine. J. Immunol. 144:1990;4794-4797.
99. Guillemard E., Geniteau-Legendre M., Kergot R., Lemaire G., Petit J.F., Labarre C., Quero A.M. Activity of nitric oxide-generating compounds against encephalomyocarditis virus. Antimicrob. Agents Chemother. 40:1996;1057-1059.
100. De Groote M.A., Testerman T., Xu Y., Stauffer G., Fang F.C. Homocysteine antagonism of nitric oxide-related cytostasis in Salmonella typhimurium. Science. 272:1996;414-417.
101. Singh R.J., Hogg N., Joseph J., Kalyanaraman B. Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production. FEBS Lett. 360:1995;47-51.
102. Ewing J.F., Young D.V., Janero D.R., Garvey D.S., Grinnell T.A. Nitrosylated bovine serum albumin derivatives as pharmacologically active nitric oxide congeners. J. Pharmacol. Exp. Ther. 283:1999;947-954.
103. Bauer J.A., Fung H.L. Chemical stabilization of a vasoactive S-nitrosothiol with cyclodextrins without loss of pharmacologic activity. Pharm. Res. 8:1991;1329-1334.
104. Hou Y.C., Wang J.Q., Andreana P.R., Cantauria G., Tarasia S., Sharp L., Braunschweiger P.G., Wang P.G. Targeting nitric oxide to cancer cells cytotoxicity studies of glyco-S-nitrosothiols . Bioorg. Med. Chem. Lett. 9:1999;2255-2258.