Biological chemistry and clinical potential of S-nitrosothiols
Tài liệu tham khảo
Oae, 1983, Organic thionitrites and related substances, Organic Preparations and Procedures International, 15, 165, 10.1080/00304948309355444
Field, L.; Dilts, R. V.; Ravichandran, R.; Lanhert, P. G.; Carnahan, P. G. J. Chem. Soc. Chem. Commun. 249–250;1978.
Hart, 1985, Some observations concerning the S-nitroso and S-phenylsulphonyl derivatives of L-cysteine and glutathione, Tetrahedron Lett., 26, 2013, 10.1016/S0040-4039(00)98368-0
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.
Kharitonov, 1995, Kinetics of nitrosation of thiols by nitric oxide in the presence of oxygen, J. Biol. Chem., 270, 28158, 10.1074/jbc.270.47.28158
Wink, 1994, 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, 519, 10.1021/tx00040a007
Williams, 1996, S-nitrosothiols and role of metal ions in decomposition to nitric oxide, Methods Enzymol., 268, 299, 10.1016/S0076-6879(96)68032-X
Singh, 1996, Mechanism of nitric oxide release from S-nitrosothiols, J. Biol. Chem., 271, 18596, 10.1074/jbc.271.31.18596
Sexton, 1994, Visible light photochemical release of nitric oxide from S-nitrosoglutathione, Photochem. Photobiol., 59, 463, 10.1111/j.1751-1097.1994.tb05065.x
Vanin, 1997, Iron catalyzes both decomposition and synthesis of S-nitrosothiols, Nitric Oxide, 1, 191, 10.1006/niox.1997.0122
Askew, S. C.; Barnett, D. J.; McAninly, J.; Williams, D. L. H. Catalysis by Cu2+ of nitric oxide release from S-nitrosothiols (RSNO). J. Chem. Soc. Perkin Trans. 2 741–745; 1995.
Singh, 1999, Mechanism of superoxide dismutase/H2O2-mediated nitric oxide release from S-nitrosoglutathione—role of glutamate, Arch. Biochem. Biophys., 372, 8, 10.1006/abbi.1999.1447
Kashiba-Iwatsuki, 1996, Role of ascorbic acid in the metabolism of S-nitroso-glutathione, FEBS Lett., 389, 149, 10.1016/0014-5793(96)00560-1
Scorza, 1997, 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, 633, 10.1016/S0891-5849(96)00378-4
Butler, 1997, Chemistry, analysis, and biological roles of S-nitrosothiols, Anal. Biochem., 249, 1, 10.1006/abio.1997.2129
Dicks, A. P.; Swift, H. R.; Williams, D. L.; Butler, A. R.; Al-Sa’doni, H. H.; Cox, B. G. Identification of Cu+ as the effective reagent in nitric oxide formation from S-nitrosothiols (RSNO). J. Chem. Soc. Perkin Trans. 2 481–487; 1996.
Al-Sa’doni, 1997, Neocuproine, a selective Cu(I) chelator, and the relaxation of rat vascular smooth muscle by S-nitrosothiols, Br. J. Pharmacol., 121, 1047, 10.1038/sj.bjp.0701218
Aleryani, 1998, Superoxide-mediated decomposition of biological S-nitrosothiols, J. Biol. Chem., 273, 6041, 10.1074/jbc.273.11.6041
Hogg, 1997, S-Nitrosoglutathione as a substrate for gamma-glutamyl transpeptidase, Biochem. J., 323, 477, 10.1042/bj3230477
Jourd’heuil, 1998, The reaction of S-nitrosoglutathione with superoxide, Biochem. Biophys. Res. Commun., 244, 525, 10.1006/bbrc.1998.8227
Beckman, 1990, Apparent hydroxyl radical production by peroxynitrite, Proc. Natl. Acad. Sci. USA, 87, 1620, 10.1073/pnas.87.4.1620
Hogg, 1999, The kinetics of S-Transnitrosation—a reversible second-order reaction, Anal. Biochem., 272, 257, 10.1006/abio.1999.4199
Patel, 1999, Biochemical characterization of human S-nitrosohemoglobin, J. Biol. Chem., 274, 15487, 10.1074/jbc.274.22.15487
Meyer, 1994, Kinetics and equilibria of S-nitrosothiol-thiol exchange between glutathione, cysteine, penicillamines and serum albumin, FEBS Lett., 345, 177, 10.1016/0014-5793(94)00429-3
Stamler, 1995, S-nitrosothiols and the bioregulatory actions of nitrogen oxides through reactions with thiol groups, Curr. Topics Microbiol. Immunol., 196, 19
Mannick, 1999, Fas-induced caspase denitrosylation, Science, 284, 651, 10.1126/science.284.5414.651
Ruiz, 1998, Nitric oxide inactivates rat hepatic methionine adenosyltransferase in vivo by s-nitrosylation, Hepatology, 28, 1051, 10.1002/hep.510280420
Dimmeler, 1998, Nitric oxide inhibits APO-1/Fas-mediated cell death, Cell Growth Differ., 9, 415
Park, 1988, Reaction of S-nitrosoglutathione with sulfhydryl groups in protein, Biochem. Biophys. Res. Commun., 152, 916, 10.1016/S0006-291X(88)80127-X
Arnelle, 1995, NO+, NO, and NO− donation by S-nitrosothiols, Arch. Biochem. Biophys., 318, 279, 10.1006/abbi.1995.1231
Hogg, 1996, The role of glutathione in the transport and catabolism of nitric oxide, FEBS Lett., 382, 223, 10.1016/0014-5793(96)00086-5
Wong, 1998, Reaction between S-nitrosothiols and thiols, Biochemistry, 37, 5362, 10.1021/bi973153g
Ji, 1999, S-Nitrosylation and S-glutathiolation of protein sulfhydryls by S-nitrosoglutathione, Arch. Biochem. Biophys., 362, 67, 10.1006/abbi.1998.1013
Mohr, 1999, Nitric oxide-induced S-glutathionylation and inactivation of glyceraldehyde-3-phosphate dehydrogenase, J. Biol. Chem., 274, 9427, 10.1074/jbc.274.14.9427
Konorev, E. A.; Kalyanaraman, B.; Hogg, N. Modification of creatine kinase by S-nitrosothiols: S-Nitrosation vs. S-Thiolation. (In Preparation)
Padgett, 1998, Cellular responses to nitric oxide—role of protein S-thiolation/dethiolation, Arch. Biochem. Biophys., 358, 232, 10.1006/abbi.1998.0859
Fukuto, 1993, Conversion of nitroxyl (HNO) to nitric oxide (NO) in biological systems, Biochem. Biophys. Res. Commun., 196, 707, 10.1006/bbrc.1993.2307
Turk, 1992, Oxidation of dithiothreitol during turnover of nitric oxide reductase, Biochem. Biophys. Res. Commun., 183, 983, 10.1016/S0006-291X(05)80287-6
Haj-Yehia, 1996, In vivo depletion of free thiols does not account for nitroglycerin-induced tolerance, J. Pharmacol. Exp. Ther., 278, 1296
Askew, 1995, Chemical mechanisms underlying the vasodilator and platelet anti-aggregating properties of S-nitroso-N-acetyl-DL-penicillamine and S-nitrosoglutathione, Bioorg. Med. Chem., 3, 1, 10.1016/0968-0896(94)00139-T
Jourd’heuil, 1999, Effect of superoxide dismutase on the stability of S-nitrosothiols, Arch. Biochem. Biophys., 361, 323, 10.1006/abbi.1998.1010
Ignarro, 1980, Possible involvement of S-nitrosothiols in the activation of guanylate cyclase by nitroso compounds, FEBS Lett., 110, 275, 10.1016/0014-5793(80)80091-3
Ignarro, 1981, Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide, J. Pharmacol. Exp. Ther., 218, 739
Edwards, 1984, Relaxation of intrapulmonary artery and vein by nitrogen oxide-containing vasodilators and cyclic GMP, J. Pharmacol. Exp. Ther., 228, 33
Schrammel, 1998, Activation of soluble guanylyl cyclase by the nitrovasodilator 3-morpholinosydnonimine involves formation of S-nitrosoglutathione, Mol. Pharmacol., 54, 207, 10.1124/mol.54.1.207
Kowaluk, 1990, Spontaneous liberation of nitric oxide cannot account for in vitro vascular relaxation by S-nitrosothiols, J. Pharmacol. Exp. Ther., 255, 1256
Mathews, 1993, Biological activity of S-nitrosothiols, J. Pharmacol. Exp. Ther., 267, 1529
De Man, 1995, Comparison of the pharmacological profile of S-nitrosothiols, nitric oxide and the nitrergic neurotransmitter in the canine ileocolonic junction, Br. J. Pharmacol., 114, 1179, 10.1111/j.1476-5381.1995.tb13331.x
De Man, 1996, Effect of Cu2+ on relaxations to the nitrergic neurotransmitter, NO and S-nitrosothiols in the rat gastric fundus, Br. J. Pharmacol., 119, 990, 10.1111/j.1476-5381.1996.tb15769.x
De Man, 1998, S-nitrosothiols and the nitrergic neurotransmitter in the rat gastric fundus, Br. J. Pharmacol., 123, 1039, 10.1038/sj.bjp.0701692
Lipton, 1993, A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds, Nature, 364, 626, 10.1038/364626a0
Davisson, 1997, Stereoselective actions of S-nitrosocysteine in central nervous system of conscious rats, Am. J. Physiol., 272, H2361
Brendeford, 1998, Nitric oxide (NO) disrupts specific DNA binding of the transcription factor c-Myb in vitro, FEBS Lett., 425, 52, 10.1016/S0014-5793(98)00196-3
Hu, 1997, Direct inhibition of expressed cardiac L-type Ca2+ channels by S-nitrosothiol nitric oxide donors, Circ. Res., 81, 742, 10.1161/01.RES.81.5.742
Campbell, 1996, Redox modulation of L-type calcium channels in ferret ventricular myocytes. Dual mechanism regulation by nitric oxide and S-nitrosothiols, J. Gen. Physiol., 108, 277, 10.1085/jgp.108.4.277
Catani, 1998, Inhibition of clotting factor xiii activity by nitric oxide, Biochem. Biophys. Res. Commun., 249, 275, 10.1006/bbrc.1998.9130
Clark, 1988, Inhibition of glutathione S-transferases from rat liver by S-nitroso-L-glutathione, Biochem. Pharmacol., 37, 3199, 10.1016/0006-2952(88)90321-8
Li, 1997, Nitric oxide reversibly inhibits seven members of the caspase family via S-nitrosylation, Biochem. Biophys. Res. Commun., 240, 419, 10.1006/bbrc.1997.7672
Hausladen, 1996, Nitrosative stress, Cell, 86, 719, 10.1016/S0092-8674(00)80147-6
Rauhala, 1996, S-nitrosothiols and nitric oxide, but not sodium nitroprusside, protect nigrostriatal dopamine neurons against iron-induced oxidative stress in vivo, Synapse, 23, 58, 10.1002/(SICI)1098-2396(199605)23:1<58::AID-SYN7>3.0.CO;2-G
Hogg, 1993, Inhibition of low-density lipoprotein oxidation by nitric oxide. Potential role in atherogenesis, FEBS Lett., 334, 170, 10.1016/0014-5793(93)81706-6
Rubbo, 1994, Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives, J. Biol. Chem., 269, 26066, 10.1016/S0021-9258(18)47160-8
Chamulitrat, 1998, Nitric oxide inhibited peroxyl and alkoxyl radical formation with concomitant protection against oxidant injury in intestinal epithelial cells, Arch. Biochem. Biophys., 355, 206, 10.1006/abbi.1998.0731
Gutierrez, 1996, Nitric oxide regulation of superoxide-dependent lung injury, Free Radic. Biol. Med., 21, 43, 10.1016/0891-5849(95)02226-0
Struck, 1995, Nitric oxide donor compounds inhibit the toxicity of oxidized low-density lipoprotein to endothelial cells, FEBS Lett., 361, 291, 10.1016/0014-5793(95)00178-C
Bouton, 1996, Modulation of iron regulatory protein functions. Further insights into the role of nitrogen- and oxygen-derived reactive species, J. Biol. Chem., 271, 2300, 10.1074/jbc.271.4.2300
Kaye, 1997, S-nitrosothiols inhibit neuronal norepinephrine transport, Am. J. Physiol., 272, H875
Stamler, 1992, Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin, Proc. Natl. Acad. Sci. USA, 89, 7674, 10.1073/pnas.89.16.7674
Marley, 2000, A chemiluminescence based assay for S-nitrosoalbumin and other plasma S-nitrosothiols, Free Radic. Res., 32, 1, 10.1080/10715760000300011
DelaTorre, 1999, Endotoxin-mediated S-nitrosylation of p50 alters NF-κ B-dependent gene transcription in ANA-1 murine macrophages, J. Immunol., 162, 4101, 10.4049/jimmunol.162.7.4101
Kluge, 1997, S-nitrosoglutathione in rat cerebellum, J. Neurochem., 69, 2599, 10.1046/j.1471-4159.1997.69062599.x
Park, 1997, Fluorometric detection of biological S-nitrosothiols, Anal. Biochem., 249, 61, 10.1006/abio.1997.2159
Pfeiffer, 1998, Electrochemical determination of s-nitrosothiols with a clark-type nitric oxide electrode, Anal. Biochem., 258, 68, 10.1006/abio.1998.2562
Jia, 1996, S-nitrosohaemoglobin, Nature, 380, 221, 10.1038/380221a0
Ferranti, 1997, Characterisation of S-nitrosohaemoglobin by mass spectrometry, FEBS Lett., 400, 19, 10.1016/S0014-5793(96)01258-6
Stamler, 1997, Blood flow regulation by S-nitrosohemoglobin in the physiological oxygen gradient, Science, 276, 2034, 10.1126/science.276.5321.2034
Mellion, 1983, Inhibition of human platelet aggregation by S-nitrosothiols. Heme-dependent activation of soluble guanylate cyclase and stimulation of cyclic GMP accumulation, Mol. Pharmacol., 23, 653
Gordge, 1995, Copper chelation-induced reduction of the biological activity of S-nitrosothiols, Br. J. Pharmacol., 114, 1083, 10.1111/j.1476-5381.1995.tb13317.x
Hirayama, 1999, S-nitrosothiols are stored by platelets and released during platelet-neutrophil interactions, Nitric Oxide, 3, 95, 10.1006/niox.1999.0208
Howard, 1998, S-nitrosoglutathione/glutathione disulphide/Cu2+-dependent stimulation of l-arginine transport in human platelets, Thromb. Res., 91, 113, 10.1016/S0049-3848(98)00060-7
Molloy, 1998, S-nitrosoglutathione reduces the rate of embolization in humans, Circulation, 98, 1372, 10.1161/01.CIR.98.14.1372
Salas, 1998, S-nitrosoglutathione inhibits platelet activation and deposition in coronary artery saphenous vein grafts in vitro and in vivo, Heart, 80, 146, 10.1136/hrt.80.2.146
de Belder, 1995, Treatment of HELLP syndrome with nitric oxide donor, Lancet, 345, 124, 10.1016/S0140-6736(95)90088-8
Kowaluk, 1987, Tolerance to relaxation in rat aorta, Eur. J. Pharmacol., 144, 379, 10.1016/0014-2999(87)90392-X
Bauer, 1991, Differential hemodynamic effects and tolerance properties of nitroglycerin and an S-nitrosothiol in experimental heart failure, J. Pharmacol. Exp. Ther., 256, 249
Henry, 1989, S-nitrosothiols as vasodilators, Br. J. Pharmacol., 98, 757, 10.1111/j.1476-5381.1989.tb14603.x
Jansen, 1992, The relaxant properties in guinea pig airways of S-nitrosothiols, J. Pharmacol. Exp. Ther., 261, 154
Bannenberg, 1995, Characterization of bronchodilator effects and fate of S-nitrosothiols in the isolated perfused and ventilated guinea pig lung, J. Pharmacol. Exp. Ther., 272, 1238
Perkins, 1998, cGMP-independent mechanism of airway smooth muscle relaxation induced by s-nitrosoglutathione, Am. J. Physiol. Cell Physiol., 44, C468, 10.1152/ajpcell.1998.275.2.C468
Gaston, 1993, Endogenous nitrogen oxides and bronchodilator S-nitrosothiols in human airways, Proc. Natl. Acad. Sci. USA, 90, 10957, 10.1073/pnas.90.23.10957
Gordge, 1998, Evidence for a cyclic gmp-independent mechanism in the anti-platelet action of s-nitrosoglutathione, Br. J. Pharmacol., 124, 141, 10.1038/sj.bjp.0701821
Barbier, 1994, Influence of S-nitrosothiols and nitrate tolerance in the rat gastric fundus, Br. J. Pharmacol., 111, 1280, 10.1111/j.1476-5381.1994.tb14884.x
Konorev, 1996, The mechanism of cardioprotection by S-nitrosoglutathione monoethyl ester in rat isolated heart during cardioplegic ischaemic arrest, Br. J. Pharmacol., 119, 511, 10.1111/j.1476-5381.1996.tb15701.x
Konorev, 1995, 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, 200
Hoshida, 1996, A nitric oxide donor reverses myocardial injury in rabbits with acute hypercholesterolemia, J. Pharmacol. Exp. Ther., 278, 741
Brunner, 1997, Interaction of nitric oxide and endothelin-1 in ischemia/reperfusion injury of rat heart, J. Mol. Cell. Cardiol., 29, 2363, 10.1006/jmcc.1997.0470
Ali, 1998, Cardioprotection by activation of NO/cGMP pathway after cardioplegic arrest and 8-hour storage, Ann. Thorac. Surg., 65, 1303, 10.1016/S0003-4975(98)00182-9
Liew, 1990, Macrophage killing of Leishmania parasite in vivo is mediated by nitric oxide from l-arginine, J. Immunol., 144, 4794, 10.4049/jimmunol.144.12.4794
Guillemard, 1996, Activity of nitric oxide-generating compounds against encephalomyocarditis virus, Antimicrob. Agents Chemother., 40, 1057, 10.1128/AAC.40.4.1057
De Groote, 1996, Homocysteine antagonism of nitric oxide-related cytostasis in Salmonella typhimurium, Science, 272, 414, 10.1126/science.272.5260.414
Singh, 1995, Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production, FEBS Lett., 360, 47, 10.1016/0014-5793(95)00065-H
Ewing, 1999, Nitrosylated bovine serum albumin derivatives as pharmacologically active nitric oxide congeners, J. Pharmacol. Exp. Ther., 283, 947
Bauer, 1991, Chemical stabilization of a vasoactive S-nitrosothiol with cyclodextrins without loss of pharmacologic activity, Pharm. Res., 8, 1329, 10.1023/A:1015824417569
Hou, 1999, Targeting nitric oxide to cancer cells, Bioorg. Med. Chem. Lett., 9, 2255, 10.1016/S0960-894X(99)00363-7
