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Current Opinion on Therapeutic Patents Volume 2, 1992 - Issue 5
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Cardiovascular Agents (Including Blood Products)

Overview: Inhibition of Nitric Oxide Biosynthesis

Jeffrey P Whitten Marion Merrell Dow Research Institute, 2110 E Galbraith Road, Cincinnati, OH 45140, USA
&
Ian A McDonald Marion Merrell Dow Research Institute, 2110 E Galbraith Road, Cincinnati, OH 45140, USA
Pages 713-726 | Published online: 02 Mar 2011

References to Primary Literature

  • Palmer RMJ, Ferrige AG, Moncada S Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor. Nature 1987 327 524–526 The first published identification of EDRF as nitric oxide.
  • Ignarro LJ Biosynthesis and metabolism of endothelium-derived nitric oxide. Annu. Rev. Pharmacol. Toxicol. 1990 30 535–560 A review which discusses the early discovery of nitric oxide as a vasodilator and its possible formation of S-nitrosothiols as the active species.
  • Furchgott RF, Zawadzki JV The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine. Nature 1980 288 373–376 The first report which postulates that the intercellular messenger, EDRF, is a potent vasodilator.
  • Furchgott RF Studies on relaxation of rabbit aorta by sodium nitrite: The basis for the proposal that the acid-activatable factor from bovine retractor penis is inorganic nitrite and the endothelium-derived relaxing factor is nitric oxide. Mechanisms of Vasodilation Vanhoutte PM Raven New York 1988, 401–414.
  • Iganrro LJ, Lippton H, Edwards JC, Baricos WH, Hyman AL, Kadowitz PC, Gruetter CA 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. 1981 218 739–749.
  • Ignarro LJ, Edwards JC, Gruetter DY, Barry BK, Gruetter CA Possible involvement of S-nitrosothiols in the activation of guanylate cyclase by nitroso compounds. FEBS Lett. 1980 110 275–278.
  • Ignarro LJ, Barry BK, Gruetter DY, Edwards JC, Ohlstein EO, Gruetter CA, Baricos WH Guanylate cyclase activation by nitroprusside and nitrosoguanidine is related to the formation of S-nitrosothiol intermediates. Biochem. Biophys. Res. Commun. 1980 94 93–100.
  • Ignarro LJ, Gruetter CA Requirement of thiols for activation of coronary arterial guanylate cyclase by glyceryl trinitrate and sodium nitrite. Biochim. Biophys. Acta. 1980 631 221–231.
  • Gruetter CA, Barry BK, McNamara DB, Gruetter DY, Kadowitz PJ, IgnaroO LJ Relaxation of bovine coronary artery and activation of coronary arterial guanylate cyclase by nitric oxide, nitroprusside and a carcinogenic nitrosoamine. J. Cyclic Nucleotide Res. 1979 5 211–224.
  • Ignarro LJ, Byrns RE, Wood KS Biochemical and pharmacological properties of endothelium-derived relaxing factor and its similarity to nitric oxide radical. Mechanisms of Vasodilatation Vanhoutte PM Raven New York 1988, 427–435.
  • Ignarro LJ, Buga GM, Wood KS, Byrns RE, Chaudhuri G Endothelium-derived relaxing factor produced and released from artery and vein is nitric oxide. Proc. Natl. Acad. Sci. USA 1987 84 9265–9269.
  • Mellion BT, Ignarro LJ, Ohlstein EH, Pontecorvo EG, Hyman AL, Kadowitz PJ Evidence for the inhibitory role of guanosine 3′,5′-monophosphate in ADP-induced human platelet aggregation in the presence of nitric oxide and related vasodilators. Blood 1981 57 946–955.
  • Garthwaite J, Garthwaite G Cellular origins of cyclic GMP responses to excitatory amino acid receptor agonists in rat cerebellum in vitro. J. Neurochem. 1987 48 29–39.
  • Garthwaite J, Charles SL, Chess-Williams R Endothelium-derived relaxing factor release on activation of NMDA receptors suggests role as intercellular messenger in the brain. Nature 1988 336 385–388 Nitric oxide is identified as an important intercellular messenger in the brain.
  • Knowles RG, Palacios M, Palmer RMJ, Moncada S Formation of nitric oxide from L-arginine in the central nervous system: A transduction mechanism for stimulation of the soluble guanylate cyclase. Proc. Natl. Acad. Sci. USA 1989 86 5159–5162 The identification of nitric oxide formation from arginine in the brain.
  • Bredt DS, Snyerr SH Nitric oxide mediates glutamate-linked enhancement of cGMP levels in the cerebellum. Proc. Natl. Acad. Sci. USA 1989 86 9030–9033 This paper shows that nitric oxide mediates the effect of glutamate stimulated cGMP formation.
  • Stuehr DJ, Marletta MA Mammalian nitrate biosynthesis: Mouse macrophages produce nitrite and nitrate in response to Escherichia coli lipopolysaccharide. Proc. Natl. Acad. Sci. USA 1985 82 7738–7742 The authors show that stimulated macrophage cells are responsible for increased nitrite and nitrate formation.
  • Iyengar R, Stuehr DJ, Marletta MA Macrophage synthesis of nitrite, nitrate, and N-nitrosamines: Precursors and role of the respiratory burst. Proc. Natl. Acad. Sci. USA 1987 84 6369–6373.
  • Marletta MA, Yoon PS, Iyengar R, Leaf CD, Wishnok JS Macrophage oxidation of L-arginine to nitrite and nitrate: Nitric oxide is an intermediate. Biochem. 1988 27 8706–8711 This paper shows that arginine is oxidized to nitric oxide in the macrophage and that NG-methylarginine inhibits this transformation.
  • Hibbs JB, Vavrin Z, Taintor RR L-Arginine is required for expression of the activated macrophage effector mechanism causing selective metabolic inhibition in target cells. J. Immun. 1987 138 550–565 This paper also shows that arginine is the source of nitric oxide and explores the effect of alkyl substituted arginines on nitric oxide production.
  • Moncada S, Palmer RMJ, Higgs EA Nitric Oxide: Physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 1991 43 109–142 An extensive review covering the biology of nitric oxide.
  • Guoyao WU, Brosnan JT Macrophages can convert citrulline into arginine. Biochem. J. 1992 281 45–48.
  • Garthwaite J Glutamate, nitric oxide and cell-cell signalling in the nervous system. Trends Neurosci. 1991 14 60–67.
  • Murphy ME, Sies H Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase. Proc. Natl. Acad. Sci. USA 1991 88 10860–10864.
  • Gustafsson LE, Leone AM, Persson MG, Wiklund NP, Moncada S Endogenous nitric oxide is present in the exhaled air of rabbits, guinea pigs and humans. Biochem. Biophys. Res. Commun. 1991 181 852–857.
  • Tayeh MA, Marletta MA Macrophage oxidation of L-arginine to nitric oxide, nitrite, and nitrate. Tetrahydrobiopterin is required as a cofactor. J. Biol. Chem. 1989 264 19654–19658.
  • Kwon NS, Nathan CF, Stuehr DJ Reduced biopterin as a cofactor in the generation of nitrogen oxides by murine macrophages. J. Biol. Chem. 1989 264 20496–20501.
  • Kwon NS, Nathan CF, Gilker C, Griffith OW, Matthews DE, Steuhr DJ L-Citrulline production from L-arginine by macrophage nitric oxide synthase. J. Biol. Chem. 1990 265 13442–13445.
  • Giovanelli J, Campos KL, Kaufman S Tetrahydrobiopterin, a cofactor for rat cerebellar nitric oxide synthase, does not function as a reactant in the oxygenation of arginine. Proc. Natl. Acad. Sci. USA 1991 88 7091–7095.
  • Melsch A, Busse R Nitric oxide synthase in native and cultured endothelial cells: Calcium/calmodulin and tetrahydrobiopterin are cofactors. J. Cardiovasc. Pharmacol. 1991 17 S52–S56.
  • Bredt DS, Snyder SH Isolation of nitric oxide synthetase, a calmodulin- requiring enzyme. Proc. Natl. Acad. Sci. USA 1990 87 682.
  • Yui Y, Hattori R, Kosuga K, Eizawa H, Hiki K, Kawai C Purification of nitric oxide synthase from rat macrophages. J. Biol. Chem. 1991 266 12544–12547.
  • Hevel JM, White KA, Marletta MA Purification of the inducible murine macrophage nitric oxide synthase. Identification as a flavoprotein. J. Biol. Chem. 1991 266 22789–22791.
  • Gross SS, Jaffe EA, Levi R, Kilbourn RG Cytokine-activated endothelial cells express an isotype of nitric oxide synthase which is tetrahydrobiopterin-dependent, calmodulin-independent and inhibited by arginine analogs with a rank-order of potency characteristic of activated macrophages. Biochem. Biophys. Res. Commun. 1991 178 823–829.
  • Forstermann U, Schmidt HHHW, Pollock JS, Sheng H, Mitchell JA, Warner TD, Nakane M, Murad F Isoforms of nitric oxide synthase. Biochem. Pharmacol. 1991 42 1849–1857 This paper characterizes and classifies the isoforms of nitric oxide synthase.
  • Pollock JS, Forstermann U, Mitchell JA, Warner TD, Schmidt HHHW, Nakane M, Murad F Purification and characterization of particulate endothelium- derived relaxing factor synthase from cultured and native bovine aortic endothelial cells. Proc. Natl. Acad. Sci. USA 1991 88 10480–10484.
  • Bredt DS, Hwang PM, Glatt CE, Lowenstein C, Reed RR, Snyder SH Cloned and expressed nitric oxide synthase structurally resembles cytochrome P-450 reductase. Nature 1991 351 714–718 The published sequence of the constitutive nitric oxide synthase.
  • Wallace T, Vallace P Nitric oxide takes centre-stage with newly defined roles. Trends Pharmacol. Sci. 1992 13 1–6.
  • Leone AM, Palmer RM, Knowles RG, Francis PL, Ashton DS, Moncada S Constitutive and inducible nitric oxide synthases incorporate molecular oxygen into both nitric oxide and citrulline. J. Biol. Chem. 1991 266 23790–23795.
  • Wallace GC, Fukuto JM Synthesis and bioactivity of Nω-hydroxyarginine: A possible intermediate in the biosynthesis of nitric oxide from arginine. J. Med. Chem. 1991 34 1746–1748.
  • Feldman P Synthesis of the putative L-ariginine metabolite L-NG-hydroxyarginine. Tetrahedron Lett. 1991 32 875–878.
  • Stuehr DJ, Kwon NS, Nathan CF, Griffith OW, Feldman PL, Wiseman J Nω-Hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine. J. Biol. Chem. 1991 266 6259–6263.
  • Demaster EG, Raij L, Archer SL, Weir EK Hydroxylamine is a vasorelaxant and a possible intermediate in the oxidative conversion of L-arginine to nitric oxide. Biochem. Biophys. Res. Commun. 1989 163 527–533.
  • Pou S, Pou WS, Rosen GM, El-Fakahany EE N-Hydroxylamine is not an intermediate in the conversion of L-arginine to an activator of soluble guanylate cyclase in neuroblastoma N1E-115 cells. Biochem. J. 1991 273 547–552.
  • Moncada S, Palmer RMJ, Higgs A Biosynthesis of nitric oxide from L- arginine. Biochem. Pharmacol. 1989 38 1709–1715.
  • Petros A, Bennett D, Vallance P Effect of nitric oxide synthase inhibitors on hypotension in patients with septic shock. Lancet 1991 338 1557–1558 This paper demonstrates the important clinical benefits of nitric oxide synthase inhibitors for septic shock in the clinic.
  • Olken MO, Rusche KM, Richard MK, Marletta MA Inactivation of macrophage nitric oxide synthase by NG-methyl-L-arginine. Biochem. Biophys. Res. Commun. 1991 177 828–833 The authors show that NG-memylarginine is a time dependent irreversible inhibitor of NO synthase.
  • Nakajima T, Matsuoka Y, Kakimoto Y Isolation and identification of NG-monomethyl, NG,NG-dimethyl- and NG,N1G-dimethylarginine from the hydrolysate of proteins of bovine brain. Biochim. Biophys. Acta. 1970 230 212–222.
  • Kasai T, Sano M, Sakamura S Amino acid composition of broad bean (Vicia faba L.). Part II. NG-Methylated arginines in broad bean seed. Agric. Biol. Chem. 1976 40 2449–2553.
  • Kakimoto Y, Akazawab S Isolation and identification of NG,NG- and NG,N′G- dimethylarginine, N′-methyllysine NϵNϵ-dimethyllysine, and NϵNϵNϵ- trimethyllysine, and glucosylgalactosyl- and galactosyl-o-hydroxyllysine from human urine. J. Biol. Chem. 1970 245 5751–5758.
  • Olken NM, Marletta MA Irreversible inhibition of macrophage NO synthase by NG-substituted L-arginines. 2nd. Int. Meeting on Biology of Nitric Oxide London 1991.
  • Gold ME, Wood KS, Buga GM, Byrnes RE, Ignarro LJ L-Arginine causes whereas L-argininosuccinic acid inhibits endothelium-dependent vascular smooth muscle relaxation. Biochem. Biophys. Res. Commun. 1989 161 536–543.
  • Ishii K, Chang B, Kerwin JF, Huang ZJ, Murad F Nω-Nitro-L-arginine: A potent inhibitor of endothelium-derived relaxing factor formation. Eur. J. Pharmacol. 1990 176 219–223.
  • Lambert LE, Whitten JP, Baron BM, Cheng HC, Doherty NS, McDonald IA Nitric oxide synthesis in the CNS, endothelium and macrophages differs in its sensitivity to inhibition by arginine analogues. Life Sci. 1991 48 69–74.
  • Gross SS, Stuehr DJ, Aisaka SK, Jaffe EA, Levi R, Griffith OW Macrophage and endothelial cell nitric oxide synthesis: Cell-type selective inhibition by NG-aminoarginine, NG-nitroarginine and NG-methylarginine. Biochem. Biophys. Res. Commun. 1990 170 96–103.
  • Dwyer MA, Bredt DS, Snyder SH Nitric oxide synthase: Irreversible inhibition by LNG-nitroarginine in brain in vitro and in vivo.. Biochem. Biophys. Res. Commun. 1991 176 1136–1141.
  • Turan A, Patthy A, Bajusz S Removal of the nitro group from nitroarginine and nitroarginine peptides. Acta Chim. Acad. Sci. Hung., Tomus 1975 85 327–332.
  • Fukuto JM, Wood KS, Byrns RE, Ignarro LJ NG-Amino-L-arginine: A new potent antagonist of L-arginine-mediated endothelium-dependent relaxation. Biochem. Biophys. Res. Commun. 1990 168 458–465.
  • McCall TB, Feelisch M, Palmer RMJ, Moncada S Identification of N-iminoethyl-L-ornithine as an irreversible inhibitor of nitric oxide synthase in phagocytic cells. Br. J. Pharmacol. 1990 102 234–238.
  • Bogle RG, Pearson JD, Mann GE Identification of selective inhibitors of arginine transport and nitric oxide synthase in vascular endothelial cells. 2nd Int Meeting on Biology of Nitric Oxide London 1991 Abstract Book Poster No. 68.
  • Lambert LE, French JF, Whitten JP, Baron BM, McDonald IA Characterization of the cell selectivity of two novel inhibitors of nitric oxide synthesis. Eur. J. Pharmacol. In press.

References to Patent Literature

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