Correlation between nitric oxide formation during degradation of organic nitrates and activation of guanylate cyclase

European Journal of Pharmacology - Tập 139 - Trang 19-30 - 1987
Martin Feelisch1, Eike A. Noack1
1Department of Pharmacology, University of Düsseldorf, Düsseldorf, F.R.G.

Tài liệu tham khảo

Asahi, 1971, Chemical and kinetic study on stabilities of 3-morpholinosydnonimine and its N-ethoxy-carbonyl derivative, Chem. Pharm. Bull., 19, 1079, 10.1248/cpb.19.1079 Axelsson, 1984, Nitroglycerin tolerance in vitro: effect of cGMP turnover in vascular smooth muscle, Acta Pharmacol. Toxicol., 55, 203, 10.1111/j.1600-0773.1984.tb02038.x Baker, 1952, Hydrolytic decomposition of esters of nitric acid. Part I: General experimental techniques. Alkaline hydrolysis and neutral solvolysis of methyl, ethyl, i-propyl, and t-butyl nitrates in aqueous alcohol, J. Chem. Soc., 1193 Bashir, 1982, Pharmacokinetic studies of various preparations of glyceryl trinitrate, Br. J. Clin. Pharmacol., 14, 779, 10.1111/j.1365-2125.1982.tb02036.x Bennett, 1986, Requirement for reduced, unliganded hemoprotein for the hemoglobin- and myoglobin-mediated biotransformation of glyceryl trinitrate, J. Pharmacol. Exp. Ther., 237, 629 Bennett, 1984, Biotransformation of glyceryl trinitrate to glyceryl dinitrate by human hemoglobin, Can. J. Physiol. Pharmacol., 62, 1194, 10.1139/y84-199 Böhme, 1978, Effects of sodium nitroprusside and other smooth muscle relaxants on cyclic GMP-formation in smooth muscle and platelets, Adv. Cycl. Nucl. Res., 9, 131 Böhme, 1985, Biochemischer Wirkungsmechanismus von Molsidomin, Med. Klin. Sondernummer, 1, 12 Böhme, 1982, Wirksamer Metabolit von Molsidomin und Stimulation der cGMP-Bildung durch Sydnonimine Craven, 1983, Requirement of heme in the activation of purified guanylate cyclase by nitric oxide, Biochim. Biophys. Acta, 745, 310, 10.1016/0167-4838(83)90063-8 Doyle, 1981, Oxidation of nitrogen oxides by bound dioxygen in hemoproteins, J. Inorg. Biochem., 14, 351, 10.1016/S0162-0134(00)80291-3 Gerzer, 1981, Soluble guanylate cyclase purified from bovine lung contains heme and copper, FEBS Lett., 132, 71, 10.1016/0014-5793(81)80429-2 Gruetter, 1980, Methylene blue inhibits coronary arterial relaxation and guanylate cyclase activation by nitroglycerin, sodium nitroprusside and amyl nitrite, Can. J. Physiol. Pharmacol., 59, 150, 10.1139/y81-025 Haussmann, 1985, Nitric oxide and nitrite formation during the degradation of N-nitrosamines, Naunyn-Schmiedeb. Arch. Pharmacol., 329, R 21 Haussmann, H.J. and J. Werringloer, On the mechanism and the control of the denitrosation of N-nitrosodimethylamine, in: Proceedings 9th International Meeting on ‘N-Nitroso compounds: Relevance to Human Cancer’ (IARC Sci. Publ., Lyon) (in press). Ignarro, 1980, Requiirement of thiols for the activation of coronary arterial guanylate cyclase by glyceryl trinitrate and sodium nitrite, Biochim. Biophys. Acta, 631, 221, 10.1016/0304-4165(80)90297-4 Ignarro, 1981, Evidence that regulation of hepatic guanylate cyclase activity involves interactions between catalytic site SH-groups and both substrate and activator, Arch. Biochem. Biophys., 208, 75, 10.1016/0003-9861(81)90125-9 Ignarro, 1981, Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: evidence for the involvementof S-nitrosothiols as active intermediates, J. Pharmacol. Exp. Ther., 218, 739 Katsuki, 1977, Stimulation of guanylate cyclase by sodium nitroprusside, nitroglycerin and nitric oxide in various tissue preparations and comparison to the effects of sodium azide and hydroxylamine, J. Cycl. Nucl. Res., 3, 23 Kertesz, 1974, Electron spin resonance studies of free radicals in soution. III: pH dependence of thiyl free radical of cysteine, J. Pharm. Sci., 63, 880, 10.1002/jps.2600630616 Kimura, 1975, Activation of guanylate cyclase from rat liver and other tissues by sodium azide, J. Biol. Chem., 250, 8016, 10.1016/S0021-9258(19)40809-0 Kobayashi, 1980, The effects of nitroglycerin on cyclic nucleotides in the coronary artery in vivo, Life Sci., 27, 1679, 10.1016/0024-3205(80)90643-8 Kosaka, 1979, Stoichiometry of the reaction of oxyhemoglobin with nitrite, Biochim. Biophys. Acta, 581, 184, 10.1016/0005-2795(79)90235-6 Kukovetz, 1986, Mode of action of nitrates in regard to vasodilation and tolerance, Z. Kardiol., 75, 8 Kuropteva, 1985, Change in paramagnetic blood and liver complexes in animals under the influence of nitroglycerin (Russian), Dokl. Akad. Nauk. SSSR, 281, 189 Leuenberger, 1980, Determination of nitrate and bromide in foodstuffs by high-performance liquid chromatography, J. Chromatogr., 202, 461, 10.1016/S0021-9673(00)91832-6 Park, 1985, Formation of N-nitrosamines from sodium nitroprusside and secondary amines, N. Engl. J. Med., 313, 1547, 10.1056/NEJM198512123132418 Parks, 1981, Nitrogen-13-labeled nitrite and nitrate: distribution and metabolism after intratracheal administration, Science, 212, 58, 10.1126/science.7209517 Rapoport, 1983, Endothelium-dependent and nitrosovasodilator-induced relaxation of vascularmooth muscle: role of cyclic GMP, J. Cycl. Nucl. Prot. Phos. Res., 9, 281 Schmidt, 1985, Stimulation of coronary guanylate cyclase by nicorandil (SG-75) as a mechanism of its vasodilating action, J. Cycl. Nucl. Prot. Phos. Res., 10, 43 Schröder, 1985, Untersuchungen zur Strukturabhängigkeit der pharmakologischen Wirkung organisher Nitrate auf subzellulärer Ebene Schröder, 1986, New results in thiol-dependent activation of guauylate cyclase by organic nitrates, Z. Kardiol., 75, 20 Schröder, 1985, Evidence for a correlation between nitric oxide formation by cleavage of organic nitrates and activation of guanylate cyclase, J. Mol. Cell. Cardiol., 17, 931, 10.1016/S0022-2828(85)80106-1 Van Assendelft, 1970 Vanin, 1984, Nitric oxide appearance in animal tissues in vivo (Russian), Stud. Biophys., 102, 135 Yeates, 1985, The reaction between organic nitrates and sulfhydryl compounds — A possible model system for the activation of organic nitrates, Mol. Pharmacol., 28, 555