Nitric Oxide: A New Paradigm for Second Messengers

Journal of Medicinal Chemistry

Volumn 38, Issue 22, 1995, Pages 4343-4362

  Kerwin, James F ^a   Lancaster, Jack R ^b   Feldman, Paul L ^c  

^a ABBOTT LABORATORIES   (United States)

^b LOUISIANA STATE UNIV MEDICAL CENTER   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVINE ADENINE NUCLEOTIDE; FLAVINE MONONUCLEOTIDE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; PROTOPORPHYRIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TETRAHYDROBIOPTERIN;

BLOOD PRESSURE REGULATION; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG HALF LIFE; DRUG SYNTHESIS; ELECTRON TRANSPORT; ENZYME ACTIVATION; ENZYME INHIBITION; REVIEW; SIGNAL TRANSDUCTION; STOICHIOMETRY;

ANIMAL; HUMAN; METALS; MOLECULAR STRUCTURE; NITRIC OXIDE; NITRIC-OXIDE SYNTHASE; SECOND MESSENGER SYSTEMS; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0028815563     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00022a001     Document Type: Article

References (193)

1. Stamler, J. S.; Singel, D. J.; Loscalzo, J. Biochemistry of nitric oxide and its redox-activated forms. Science 1992, 258, 1898-1902.
2. Ignarro, L. J. Biosynthesis and metabolism of endothelium- derived nitric oxide. Annu. Rev. Pharmacol. Toxicol. 1990, 30, 535-560.
3. Shaw, A. W.; Vosper, A. J. Solubility of Nitric Oxide in Aqueous and Nonaqueous Solvents. J. Chem. Soc., Faraday Trans. 1977, 8, 1239-1244.
4. Malinski, T.; Taha, Z.; Grunfeld, S.; Patton, S.; Kapturczak, M.; Tomboulian, P. Diffusion of nitric oxide in the aorta wall monitored in situ by porphyrinic microsensors. Biochem. Bio- phys. Res. Commun. 1993, 193, 1076-1082.
5. Wise, D. L.; Houghton, G. Diffusion Coefficients of Neon, Krypton, Xenon, Carbon Monoxide and Nitric Oxide in Water at 10-60 °C. Chem. Eng. Sci. 1968, 23, 1211-1216.
6. Lancaster, J. R., Jr. Simulation of the Diffusion and Reaction of Endogenously Produced Nitric Oxide. Proc. Natl. Acad. Sci. U. SA. 1994, 91, 8137-8141.
7. Wood, J.; Garthwaite, J. Models of Diffusional Spread of Nitric Oxide: Implications for Neural Nitric Oxide Signalling and its Pharmacological Properties. Neuropharmacology 1994, 33, 1235-1244.
8. Wink, D. A.; Darbyshire, J. F.; Nims, R. W.; Saavedra, J. E.; Ford, P. C. Reactions of the bioregulatory agent nitric-oxide in oxygenated aqueous-media-determination of the kinetics for oxidation and nitrosation by intermediates generated in the NO/ O2 reaction. Chem. Res. Toxicol. 1993, 6, 23-27.
9. Ridd, J. H. Nitrosation, diazotisation, and deamination. Q. Rev. 1961, 15, 418-441.
10. Miwa, M.; Stuehr, D. J.; Marietta, M. A.; Wishnok, J. S.; Tannenbaum, S. R. Nitrosation of amines by stimulated macrophages. Carcinogenesis 1987, 8, 955-958.
11. Ohshima, H.; Bartsch, H. Chronic infections and inflammatory processes as cancer risk factors: possible role of nitric oxide in carcinogenesis. Mutat. Res. 1994, 305, 253-264.
12. Williams, D. L. H. S-Nitrosation and the Reactions of S-Nitroso Compounds. Chem. Soc. Rev. 1985, 14, 171-196.
13. Gatti, R. M.; Radi, R.; Augusto, O. Peroxynitrite-mediated oxidation of albumin to the protein-thiyl free radical. FEBS Lett. 1994, 348, 287-290.
14. King, P. A.; Jamison, E.; Strahs, D.; Anderson, V. E.; Brenowitz, M. ‘Footprinting’ proteins on DNA with peroxonitrous acid. Nucleic Acids Res. 1993, 21, 2473-2478.
15. Radi, R.; Beckman, J. S.; Bush, K. M.; Freeman, B. A. Peroxy- nitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 1991, 288, 481-487.
16. Ischiropoulos, H.; Zhu, L.; Chen, J.; Tsai, M.; Martin, J. C.; Smith, C. D.; Beckman, J. S. Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase. Arch. Biochem. Biophys. 1992, 298, 431-437.
17. Beckman, J. S.; Ischiropoulos, H.; Zhu, L.; van der Woerd, M.; Smith, C.; Chen, J.; Harrison, J.; Martin, J. C.; Tsai, M. Kinetics of superoxide dismutase- and iron-catalyzed nitration of phe- nolics by peroxynitrite. Arch. Biochem. Biophys. 1992, 298, 438-445.
18. Pryor, W. A.; Squadrito, G. L. The chemistry of peroxynitrite-A product from the reaction of nitric-oxide with superoxide. Am. J. Physiol. 1995, 268, L699-L722.
19. Zhu, L.; Gunn, C.; Beckman, J. S. Bactericidal activity of peroxynitrite. Arch. Biochem. Biophys. 1992, 298, 452-457.
20. Crow, J. P.; Spruell, C.; Chen, J.; Gunn, C.; Ischiropoulos, H.; Tsai, M.; Smith, C. D.; Radi, R.; Koppenol, W. H.; Beckman, J. S. On the pH-dependent yield of hydroxyl radical products from peroxynitrite. Free Radic. Biol. Med. 1994, 16, 331-338.
21. Rubbo, H.; Radi, R.; Trujillo, M.; Telleri, R.; Kalyanaraman, B.; Barnes, S.; Kirk, M.; Freeman, B. A. Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives. J. Biol. Chem. 1994, 269, 26066-26075.
22. McCleverty, J. A. Reactions of Nitric Oxide Coordinated to Transition Metals. Chem. Rev. 1979, 79, 53-76.
23. Henry, Y.; Lepoivre, M.; Drapier, J. C.; Ducrocq, C.; Boucher, J. L.; Guissani, A. EPR characterization of molecular targets for NO in mammalian cells and organelles. FABEB J. 1993, 7, 1224-1134.
24. Griscavage, J. M.; Fukuto, J. M.; Komori, Y.; Ignarro, L. J. Nitric oxide inhibits neuronal nitric oxide synthase by interacting with the heme prosthetic group. J. Biol. Chem. 1994, 269, 21644-21649.
25. Doyle, M. P.; Hoekstra, J. W. Oxidation of nitrogen oxides by bound dioxygen in hemoproteins. J. Inorg. Biochem. 1981, 14, 351-358.
26. Gibson, Q. H.; Roughton, F. J. W. The Kinetics and Equilibria of the Reactions of Nitric Oxide with Sheep Hemoglobin. J. Physiol. 1957, 136, 507-526.
27. Ignarro, L. J.; Fukuto, J. M.; Griscavage, J. M.; Rogers, N. E.; Byms, R. E. Oxidation of nitric-oxide in aqueous-solution to nitrite but not nitrate-comparison with enzymatically formed nitric-oxide from L-arginine. Proc. Natl. Acad. Sci. U. SA. 1993, 90, 8103-8107.
28. Iyengar, R.; Stuehr, D. J.; Marietta, M. A. Macrophage synthesis of nitrite, nitrate, and N-nitrosamines: Precursors and role of the respiratory burst. Proc. Natl. Acad. Sci. U. SA. 1987, 84, 6369-6373.
29. Kerwin, J. F., Jr.; Heller, M. The arginine-nitric oxide pathway: a target for new drugs. Med. Res. Rev. 1994, 14, 23-74.
30. Stuehr, D. J.; Griffith, O. W. Mammalian nitric oxide synthases. Adv. Enzymol. Relat. Areas Mol. Biol. 1992, 65, 287-346.
31. Palmer, R. M. J.; Ferrige, A. G.; Moncada, S. Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor. Nature 1987, 327, 524-526.
32. Green, L. C.; DeLuzuriga, K. R.; Wagner, D. A.; Rand, W.; Istefen, N.; Young, V. R.; Tannenbaum, S. R. Nitrate biosynthesis in man. Proc. Natl. Acad. Sci. U. SA. 1981, 78, 7764-7768.
33. Stuehr, D. J.; Marietta, M. A. Mammalian nitrate biosynthesis: Mouse macrophages produce nitrite and nitrate in response to Escherichia coli lipopolysaccharide. Proc. Natl. Acad. Sci. U. SA. 1985, 82, 7738-7742.
34. Hibbs, J. B.; Taintor, R. R.; Vavrin, Z. Macrophage Cytotoxicity: Role for L-Arginine Deiminase and imino nitrogen oxidation to nitrite. Science 1987, 235, 473-476.
35. Marietta, M. A.; Yoon, P. S.; Iyengar, R.; Leaf, C. D.; Wishnok, J. S. Macrophage oxidation of L-arginine to nitrite and nitrate: nitric oxide is an intermediate. Biochemistry 1988, 27, 8706-8711.
36. Garthwaite, J.; Charles, S. L.; Chess-Williams, R. Endothelium- derived relaxing factor release on activation of NMD A receptors suggests role as intercellular messenger in the brain. Nature 1988, 336, 385-388.
37. Nathan, C.; Xie, Q. W. Regulation of biosynthesis of nitric oxide. J. Biol. Chem. 1994, 269, 13725-13728.
38. Forstermann, U. Biochemistry and molecular biology of nitric oxide synthases. Arzneimittelforschung 1994, 44, 402-407.
39. Nakane, M.; Schmidt, H. H. H. W.; Pollock, J. S.; Forstermann, U.; Murad, F. Cloned human brain nitric-oxide synthase is highly expressed in skeletal-muscle. FEBS Lett. 1993, 316, 175-180.
40. Hokari, A.; Zeniya, M.; Esumi, H. Cloning and functional expression of human inducible nitric oxide synthase (NOS) cDNA from a glioblastoma cell line A-172. J. Biochem. 1994, 116, 575-581.
41. Garvey, E. P.; Tuttle, J. V.; Covington, K.; Merrill, B. M.; Wood, E. R.; Baylis, S. A.; Charles, I. G. Purification and characterization of the constitutive nitric oxide synthase from human placenta. Arch. Biochem. Biophys. 1994, 311, 235-241.
42. Nakane, M.; Pollock, J. S.; Klinghofer, V.; Basha, F.; Marsden, P. A.; Hokari, A.; Ogura, T.; Esumi, H.; Carter, G. W. Functional expression of three isoforms of human nitric oxide synthase in baculovirus-infected insect cells. Biochem. Biophys. Res. Com- mun. 1995, 206, 511-517.
43. Xie, Q. W.; Cho, H.; Kashiwabara, Y.; Baum, M.; Weidner, J. R.; Elliston, K.; Mumford, R.; Nathan, C. Carboxyl terminus of inducible nitric oxide synthase. Contribution to NADPH binding and enzymatic activity. J. Biol. Chem. 1994, 269, 28500-28505.
44. Busconi, L.; Michel, T. Endothelial nitric oxide synthase. N- terminal myristolyation determines subcellular localization. J. Biol. Chem. 1993, 268, 8410-8413.
45. Michel, T.; Li, G. K.; Busconi, L. Phosphorylation and subcellular translocation of endothelial nitric oxide synthase. Proc. Natl. Acad. Sci. U. SA. 1993, 90, 6252-6256.
46. Bredt, D. S.; Synder, S. H. Nitric Oxide: A physiologic messenger molecule. Annu. Rev. Biochem. 1994, 63, 175-179.
47. Andersson, K. E.; Persson, K. Nitric oxide synthase and nitric oxide-mediated effects in lower urinary tract smooth muscles. World J. Urol. 1994, 12, 274-280.
48. Cho, H. J.; Xie, Q. W.; Calaycay, J.; Mumford, R. A.; Swiderek, K. M.; Lee, T. D.; Nathan, C. Calmodulin is a subunit of nitric oxide synthase from macrophages. J. Exp. Med. 1992, 176, 599-604.
49. Marietta, M. A. Nitric oxide synthase function and mechanism. Adv. Exp. Med. Biol. 1993, 338, 281-284.
50. Feldman, P. L.; Griffith, O. W.; Stuehr, D. J. The surprising Life of Nitric Oxide. Chem. Eng. News 1993, 71, 26-38.
51. Masters, B. S. S. Nitric-oxide synthases-why so complex. Annu. Rev. Nutrition 1994, 14, 131-145.
52. Kwon, N. S.; Nathan, C. F.; Gilker, C.; Griffith, O. W.; Matthews, D. E.; Stuehr, D. J. L-citrulline production from L-arginine by macrophage nitric oxide synthase. The ureido oxygen derives from dioxygen. J. Biol. Chem. 1990, 265, 13442-13445.
53. Feldman, P. L. Synthesis of the putative L-arginine metabolite L-N°-hydroxyarginine. Tetrahedron Lett. 1991, 32, 875-878.
54. ω-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine. J. Biol. Chem. 1991, 266, 6259-6263.
55. Leone, A. M.; Palmer, R. M. J.; Knowles, R. G.; Francis, P. L.; Ashton, D. S.; Moncada, S. Constitutive and inducible nitric oxide synthases incorporate molecular oxygen into both nitric oxide and citrulline. J. Biol. Chem. 1991, 266, 23790-23795.
56. Stuehr, D. J.; Baek, K. J. Unpublished results.
57. Marietta, M. A. Nitric oxide synthase structure and mechanism. J. Biol. Chem. 1993, 268, 12231-12234.
58. Bredt, D. S.; Hwang, P. M.; Glatt, C. E.; Lowenstein, C.; Reed, R. R.; Snyder, S. H. Cloned and expressed nitric oxide synthase structurally resembles cytochrome P-450 reductase. Nature 1991, 351, 714-718.
59. Vermilion, S. L.; Ballou, D. P.; Massey, V.; Coon, M. J. Separate roles for FMN and FAD catalysis by liver microsomal NADPH- cytochrome P-450 reductase. J. Biol. Chem. 1981, 256, 266-277.
60. Griffith, O. W.; Stuehr, D. J. Nitric Oxides Synthases-Properties and Catalytic Mechanism. Annu. Rev. Physiol. 1995, 57, 707-736.
61. Stuehr, D. J.; Ikeda-Saito, M. Spectral characterization of brain and macrophage nitric oxide synthases. Cytochrome P-450-like hemeproteins that contain a flavin semiquinone radical. J. Biol. Chem. 1992, 267, 20547-20550.
62. Feldman, P. L.; Griffith, O. W.; Hong, H.; Stuehr, D. J. Irreversible inactivation of macrophage and brain nitric oxide synthase by L-N°-methylarginine requires NADPH-dependent hydroxy- lation. J. Med. Chem. 1993, 36, 491-496.
63. Clement, B.; Immel, M.; Pfunder, H.; Schmitt, S.; Zimmerman, M. New Aspects of the microsomal N-hydroxylation of benza- midines in N-oxidations of drugs: biochemistry, pharmacology, toxicology, Chapman and Hall: London, 1991; pp 185-205.
64. Korth, H. G.; Sustmann, R.; Thater, C.; Butler, A. R.; Ingold, K. U. On the mechanism of the nitric-oxide synthase-catalyzed conversion of N“-hydroxy-L-arginine to citrulline and nitric- oxide. J. Biol. Chem. 1994, 269, 17776-17779.
65. ω-hydroxy-L-arginine by nitric oxide synthase. J. Med. Chem. 1993, 36, 2666-2670.
66. Abu-Soud, H. M.; Stuehr, D. J. Nitric oxide synthases reveal a role for calmodulin in controlling electron transfer. Proc. Natl. Acad. Sci. U. SA. 1993, 90, 10769-10772.
67. Baek, K. J.; Thiel, B. A.; Lucas, S.; Stuehr, D. J. Macrophage nitric-oxide synthase subunits-purification, characterization, and role of prosthetic groups and substrate in regulating their association into a dimeric enzyme. J. Biol. Chem. 1993, 268, 21120-21129.
68. Ghosh, D. K.; Stuehr, D. J. Macrophage NO synthases: Characterization of isolated oxygenase and reductase domains reveals a head-to-head subunit interaction. Biochemistry 1995, 34, 8017.
69. Sheta, E. A.; McMillan, K.; Masters, B. S. S. Evidence for a bidomain structure of constitutive cerebellar nitric oxide synthase. J. Biol. Chem. 1994, 269, 15147-15153.
70. Klatt, P.; Schmid, M.; Leopold, E.; Schmidt, K.; Werner, E. R.; Mayer, B. The pteridine binding site of brain nitric oxide synthase. Tetrahydrobiopterin binding kinetics, specificity, and allosteric interaction with the substrate domain. J. Biol. Chem. 1994, 269, 13861-13866.
71. Marietta, M. A. Approaches toward selective-inhibition of nitric- oxide synthase. J. Med. Chem. 1994, 37, 1899-1907.
72. Fukuto, J. M.; Wood, K. S.; Byms, R. E.; Ignarro, L. J. N°-amino-L-arginine: a new potent antagonist of L-arginine- mediated endothelium-dependent relaxation. Biochem. Biophys. Res. Commun. 1990, 168, 458-465.
73. Southan, G. J.; Gross, S. S.; Vane, J. R. Amides and esters of N (cu)-nitro-L-arginine (eg L-NAME) must be hydrolyzed to become active NO synthase inhibitors. Br. J. Pharmacol. 1993, 109, 12.
74. G- nitroarginine. Biochemistry 1993, 32, 8512-8517.
75. G-hydroxy-L- arginine by nitric oxide synthase: evidence for the involvement of the heme in catalysis. Biochem. Biophys. Res. Commun. 1993, 193, 963-970.
76. G-methyl-L-argin- ine: Evidence for heme. Biochemistry 1994, 33, 14784-14791.
77. McCall, T. B.; Feelisch, M.; Palmer, R. M.; Moncada, S. Identification of N-iminoethyl-L-ornithine as an irreversible inhibitor of nitric oxide synthase in phagocytic cells. Br. J. Pharmacol. 1991, 102, 234-238.
78. Narayanan, K.; Griffith, O. W. Synthesis of L-thiocitrulline, L-homothiocitrulline, and S-methyl-L-thiocitrulline: a new class of potent nitric oxide synthase inhibitors. J. Med. Chem. 1994, 37, 885-887.
79. Abu-Saud, H. M.; Feldman, P. L.; Clark, P.; Stuehr, D. J. Electron transfer in NO synthases: Characterization of L- arginine analogs that block heme iron reduction. J. Biol. Chem. 1994, 269, 32318-32326.
80. Frey, C.; Narayanan, K.; McMillan, K.; Spack, L.; Gross, S. S.; Masters, B. S. S.; Griffith, O. M. L-thiocitrulline-A stereospecific, heme-binding inhibitor of nitric-oxide synthases. J. Biol. Chem. 1994, 269, 26083-26091.
81. Furfine, E. S.; Harmon, M. F.; Paith, J. E.; Knowles, R. G.; Salter, M.; Kiff, R. J.; Duffy, C.; Hazelwood, R.; Oplinger, J. A.; Garvey, E. P. Potent and selective-inhibition of human nitric-oxide synthases-selective-inhibition of neuronal nitric-oxide synthase by S-methyl-L-thiocitrulline and S-ethyl-L-thiocitrulline. J. Biol. Chem. 1994, 269, 26677-26683.
82. Moore, W. M.; Webber, R. K.; Jerome, G. M.; Tjoeng, F. S.; Misko, T. P.; Currie, M. G. L-N-6-(l-iminoethyl) lysine - a selective inhibitor of inducible nitric-oxide synthase. J. Med. Chem. 1994, 37, 3886-3888.
83. Vallance, P.; Leone, A.; Calver, A.; Collier, J.; Moncada, S. Endogenous dimethylarginine as an inhibitor of nitric-oxide synthesis. J. Cardiovasc. Pharmacol. 1992, 20.
84. Vallance, P.; Leone, A.; Calver, A.; Collier, J.; Moncada, S. Accumulation of an endogenous inhibitor of nitric oxide synthesis in chronic renal failure. Lancet 1992, 339, 572-575.
85. G- methylarginine derivatives in myelin basic-protein from developing and mutant mouse-brain. Biochem. J. 1992, 287, 929-935.
86. McAllister, R. J.; Fickling, S. A.; St. J. Whitley, G.; Vallance, P. Metabolism of methylarginines by human vasculature: implications for the regulation of nitric oxide synthesis. Br. J. Pharmacol. 1994, 112, 43-48.
87. Hasan, K.; Heesen, B. J.; Corbett, J. A.; McDaniel, M. L.; Chang, K.; Allison, W.; Wolffenbuttel, B. H.; Williamson, J. R.; Tilton, R. G. Inhibition of nitric oxide formation by guanidines. Eur. J. Pharmacol. 1993, 249, 101-106.
88. Corbett, J. A.; Tilton, R. G.; Chang, K.; Hasan, K. S.; Ido, Y.; Wang, J. L.; Sweetland, M. A.; Lancaster, J., Jr.; Williamson, J. R.; McDaniel, M. L. Aminoguanidine, a novel inhibitor of nitric oxide formation, prevents diabetic vascular dysfunction. Diabetes 1992, 41, 552-556.
89. Garvey, E. P.; Oplinger, J. A.; Tanoury, G. J.; Sherman, P. A.; Fowler, M.; Marshall, S.; Harmon, M. F.; Paith, J. E.; Furfine, E. S. Potent and selective-inhibition of human nitric-oxide synthases-inhibition by non-amino acid isothioureas. J. Biol. Chem. 1994, 269, 26669-26676.
90. McMillian, K.; Masters, B. S. S. Optical difference spectroscopy as a probe of rat brain nitric oxide synthase heme-substrate interaction. Biochemistry 1993, 32, 9875-9880.
91. Feldman, P. L.; Chi, S.; Sennequier, N.; Stuehr, D. J. Unpublished results.
92. Baydoun, A. R.; Mann, G. E. Selective targeting of nitric oxide synthase inhibitors to system y+ in activated macrophages. Biochem. Biophys. Res. Commun. 1994, 200, 726-731.
93. Petros, A. J. Down-regulation of endogenous nitric oxide production after prolonged administration. Lancet 1994, 344, 191.
94. Rosenkranz-Weiss, P.; Sessa, W. C.; Milstien, S.; Kaufman, S.; Watson, C. A.; Pober, J. S. Regulation of nitric oxide synthesis by proinflammatory cytokines in human umbilical vein endothelial cells. Elevations in tetrahydrobiopterin levels enhance endothelial nitric oxide synthase specific activity. J. Clin. Invest. 1994, 93, 2236-2243.
95. Wolff, D. J.; Gribin, B. J. The inhibition of the constitutive and inducible nitric oxide synthase isoforms by indazole agents. Arch. Biochem. Biophys. 1994, 311, 300-306.
96. Mayer, B.; Klatt, P.; Werner, E. R.; Schmidt, K. Molecular mechanisms of inhibition of porcine brain nitric oxide synthase by the antinociceptive drug 7-nitro-indazole. Neuropharmacology 1994, 33, 1253-1259.
97. Moore, P. K.; Wallace, P.; Gaffen, Z.; Hart, S. L.; Babbedge, R. C. Characterization of the novel nitric oxide synthase inhibitor 7-nitroindazole and related indazoles: antinociceptive and cardiovascular effects. Br. J. Pharmacol. 1993, 110, 219-224.
98. Medhurst, A. D.; Greenlees, C.; Parsons, A. A.; Smith, S. J.; Nitric oxide synthase inhibitors 7- and 6-nitroindazole relax smooth muscle in vitro. Eur. J. Pharmacol. 1994, 256, R5-R6.
99. Schmidt, K.; Werner, E. R.; Mayer, B.; Wachter, H.; Kukovetz, W. R. Tetrahydrobiopterin-dependent formation of endothelium- derived relaxing factor (nitric oxide) in aortic endothelial cells. Biochem. J. 1992, 281, 297-300.
100. Gross, S. S.; Levi, R. Tetrahydrobiopterin synthesis - an absolute requirement for cytokine-induced nitric-oxide generation by vascular smooth-muscle. J. Biol. Chem. 1992, 267, 25722-25729.
101. Smith, G. K.; Duch, D. S.; Edelstein, M. P.; Bigham, E. C. New inhibitors of sepiapterin reductase. J. Biol. Chem. 1992, 267, 5599-5607.
102. Sessa, W. C. The nitric oxide synthase family of proteins. J. Vase. Res. 1994, 31, 131-143.
103. Dawson, T. M.; Steiner, J. P.; Dawson, V. L.; Dinerman, J. L.; Uhl, G. R.; Snyder, S. H. Immunosuppressant FK506 enhances phosphorylation of nitric-oxide synthase and protects against glutamate neurotoxicity. Proc. Natl. Acad. Sci. U. SA. 1993, 90, 9808-9812.
104. Korth, H. G.; Sustmann, R.; Lommes, P.; Paul, T.; Ernst, A.; de Groot, H.; Hughes, L.; Ingold, K. U. Nitric oxide cheletropic traps (NOCTs) with improved thermal stability and water solubility. J. Am. Chem. Soc. 1994, 116, 2767-2777.
105. Kilbourn, R. G.; Joly, G.; Cashon, B.; DeAngelo, J.; Bonaventura, J. Cell-free hemoglobin reverses the endotoxin-mediated hypo- responsivity of rat aortic rings to alpha-adrenergic agents. Biochem. Biophys. Res. Commun. 1994, 199, 155-162.
106. Althaus, J. S.; Oien, T. T.; Fici, G. J.; Scherch, H. M.; Sethy, V. H.; VonVolgtlander, P. F. Structure activity relationships of peroxynitrite scavengers an approach to nitric oxide neurotoxicity. Res. Commun. Chem. Pathol. Pharmacol. 1994, S3, 243-254.
107. Ignarro, L. J.; Ballot, B.; Wood, K. S. Regulation of soluble guanylate cyclase activity by porphyrins and metalloporphyrins. J. Biol. Chem. 1984, 259, 6201-6207.
108. Traylor, T. G.; Magde, D.; Marsters, J.; Jongeward, K.; Wu, G. Z.; Walda, K. Geminate processes in the reaction of nitric-oxide with l-methylimidazole-iron (ii) porphyrin complexes - steric, solvent polarity, and viscosity effects. J. Am. Chem. Soc. 1993, 115, 4808-4813.
109. McDonald, L. J.; Moss, J. Nitric oxide and NAD-dependent protein modification. Mol. Cell. Biochem. 1994, 138, 201-206.
110. Zhang, J.; Dawson, V. L.; Dawson, T. M.; Snyder, S. H. Nitric- oxide activation of poly (ADP-ribose) synthetase in neurotoxicity. Science 1994, 687-689.
111. Hess, D. T.; Patterson, S. I.; Smith, D. S.; Pate Skene, J. H. Neuronal growth cone collapse and inhibition of protein fatty acylation by nitric oxide. Nature 1993, 366, 562-565.
112. Miller, M. J. S.; Sadowska-Krowicka, H.; Zhang, X. J.; Clark, D. A. Nitrotyrosine a marker for peroxynitrite, colocalizes with nitric-oxide synthase in chronic gut inflammation. FASEB J. 1994, A363.
113. Lepoivre, M.; Flaman, J. M.; Bobe, P.; Lemaire, G.; Henry, Y. Quenching of the tyrosyl free-radical of ribonucleotide reductase by nitric-oxide - relationship to cytostasis induced in tumor-cells by cytotoxic macrophages. J. Biol. Chem. 1994, 21891-21897.
114. Hibbs, J. B. Synthesis of nitric-oxide from L-arginine - a recently discovered pathway induced by cytokines with antitumor and antimicrobial activity. Res. Immunol. 1991, 142, 565-569.
115. Lepoivre, M.; Fieschi, F.; Coves, J.; Thelander, L.; Fontecave, M. Inactivation of Ribonucleotide reductase by nitric oxide. Biochem. Biophys. Res. Commun. 1991, 179, 442-448.
116. Granger, D. L.; Lehninger, A. L. Sites of inhibition of mitochondrial electron transport in macrophage-injured neoplastic cells. J. Cell. Biol. 1982, 95, 527-535.
117. Hibbs, J. B.; Taintor, R. R.: Vavrin, Z. Iron depletion: possible cause of tumor cell cytotoxicity induced by activated macrophages. Biochem. Biophys. Res. Commun. 1984, 123, 716-723.
118. Drapier, J. C.; Pellat, C.; Henry, Y. Generation of EPR-detectable nitrosyl-iron complexes in tumor target cells cocultured with activated macrophages. J. Biol. Chem. 1991, 266, 10162-10167.
119. Lancaster, J. R.; Hibbs, J. B. EPR demonstration of iron-nitrosyl complex formation by cytotoxic activated macrophages. Proc. Natl. Acad. Sci. U. SA. 1990, 87, 1223-1227.
120. Radi, R.; Rodriguez, M.; Castro, L.; Telleri, R. Inhibition of mitochondrial electron transport by peroxynitrite. Arch. Biochem. Biophys. 1994, 308, 89-95.
121. Rubanyi, G. M. Endothelium-derived relaxing and contracting factors. J. Cell. Biochem. 1991, 46, 27-36.
122. Yao, S. K.; Ober, J. C.; Krishnaswami, A.; Ferguson, J. J.; Anderson, H. V.; Golino, P.; Buja, L. M.; Willerson, J. T. Endogenous nitric-oxide protects against platelet-aggregation and cyclic flow variations in stenosed and endothelium-injured arteries. Circulation 1992, 86, 1302-1309.
123. Calver, A.; Collier, J.; Vallance, P. Nitric oxide and cardiovascular control. Exp. Physiol. 1993, 78, 303-326.
124. Calver, A.; Collier, J.; Vallance, P. Inhibition and stimulation of nitric oxide synthesis in the human forearm arterial bed of patients with insulin-dependent diabetes. J. Clin. Invest. 1992, 90, 2548-2554.
125. Shibuki, K. Nitric oxide, an intracellular messenger in cerebellar synaptic plasticity. Biomed. Res. 1994, 15, 65-67.
126. Dawson, D. A. Nitric Oxide and focal cerebral-ischemia - multiplicity of actions and diverse outcome. Cerebrovasc. Brain Metab. Rev. 1994, 6, 299-324.
127. Lee, H. C. A signalling pathway involving cyclic ADP-ribose, cGMP, and nitric oxide. News Physiol. Sci. 1994, 9, 134-137.
128. 2+-independent synaptic vesicle release. Neuron 1994, 12, 1235-1244.
129. Schuman, E. M.; Madison, D. V. A requirement for the intercellular messenger nitric oxide in long-term potentiation. Science 1991, 254, 1503-1506.
130. Dinerman, J. L.; Dawson, T. M.; Schell, M. J.; Snowman, A.; Snyder, S. H. Endothelial nitric oxide synthase localized to hippocampal pyramidal cells: implications for synaptic plasticity. Proc. Natl. Acad. Sci. U. SA. 1994, 91, 4214-4218.
131. Hawkins, R. D.; Zhou, M.; Arancio, O. Nitric oxide and carbon monoxide as possible retrograde messengers in hippocampal long term potentiation. J. Neurobiol. 1994, 25, 652-655.
132. O’Dell, T. J.; Huang, P. L.; Dawson, T. M.; Dinerman, J. L.; Snyder, S. H.; Kandel, E. R.; Fishman, M. C. Endothelial NOS and the blockade of LTP by NOS inhibitors in mice lacking neuronal NOS. Science 1994, 265, 542-546.
133. Rand, M. J. Nitrergic transmission: nitric oxide as a mediator of non-adrenergic, non-cholinergic neuro-effector transmission. Clin. Exp. Pharmacol. Physiol. 1992, 19, 147-169.
134. Toda, N. Mediation by nitric-oxide of neurally-induced human cerebral-artery relaxation. Experientia 1993, 49, 51-53.
135. Tottrup, A.; Svane, D.; Forman, A. Nitric oxide mediating NANC inhibition in opposum lower esophageal sphincter. Am. J. Physiol. 1991, 260, G385-G389.
136. Pique, J. M.; Esplugues, J. V.; Whittle, B. J. Endogenous nitric- oxide as a mediator of gastric-mucosal vasodilation during acid- secretion. Gastroenterology 1992, 102, 168-174.
137. Miller, M. J. S.; Munshi, U. K.; Sadowska-Krowicka, H.; Kakkis, J. L.; Zhang, X.-J.; Elboy-Childress, S.; Clark, D. A. Inhibition of calcium-dependent nitric oxide synthase causes ileitis and leukocytosis in guinea pigs. Dig. Dis. Sci. 1994, 39, 1185-1192.
138. Huang, P. L.; Dawson, T. M.; Bredt, D. S.; Snyder, S. H.; Fishman, M. C. Targeted disruption of the neuronal nitric oxide synthase gene. CeU 1993, 75, 1273-1286.
139. Rajfer, J.; Aronson, W. J.; Bush, P. A.; Dorey, F. J.; Ignarro, L. J. Nitric oxide as a mediator of relaxation of the corpus cavemosum in response to nonadrenergic, noncholinergic neurotransmission. N. Engl. J. Med. 1992, 326, 90-94.
140. Hellstrom, W. J.; Monga, M.; Wang, R.; Domer, F. R.; Kadowitz, P. J.; Roberts, J. A. Penile erection in the primate: induction with nitric-oxide donors. J. Urol. 1994, 151, 1723-1727.
141. Melis, M. R.; Argiolas, A. Nitric-oxide synthase inhibitors prevent apomorphine-induced and oxytocin-induced penile erection and yawning in male-rats. Brain Res. Bull. 1993, 32, 71-74.
142. Trigo-Rocha, F.; Hsu, G. L.; Donatucci, C. F.; Martinez-Pineiro, L.; Lue, T. F.; Tanagho, E. A. Intracellular mechanism of penile erection in monkeys. Neuromol. Urodyn. 1994, 13, 71-80.
143. Kobzik, L.; Reid, M. B.; Bredt, D. S.; Stamler, J. S. Nitric oxide in skeletal muscle. Nature 1994, 372, 546-548.
144. Nishikawa, T.; Kirsch, J. R.; Koehler, R. C.; Miyabe, M.; Traystman, R. J. Nitric oxide synthase inhibition reduces caudate injury following transient focal ischemia in cats. Stroke 1994, 25, 877-885.
145. Zhang, F.; Iadecola, C. Reduction of focal cerebral ischemic damage by delayed treatment with nitric oxide donors. J. Cereb. Blood Flow Metab. 1994, 14, 574-580.
146. Dalkara, T.; Yoshida, T.; Irikura, K.; Moskowitz, M. A. Dual role of nitric oxide in focal cerebral ischemia. Neuropharmacology 1994, 33, 1447-1452.
147. Zhang, Z. G.; Chopp, M.; Gautam, S.; Zaloga, C.; Zhang, R. L.; Schmidt, H. H. H. W.; Pollock, J. W.; Forstermann, U. Upregulation of neuronal nitric oxide synthase and mRNA, and selective sparing of nitric oxide synthase-containing neurons after focal ischemia in rat. Brain Res. 1994, 654, 85-95.
148. Huang, Z.; Huang, P.; Panahian, N.; Dalkara, T.; Fishman, M.; Moskowitz, M. A. Mice deficient in neuronal nitric oxide synthase gene expression exhibit decreased focal infarct volume and neurological deficits after middle cerebral artery occlusion. Science 1994, 265, 1883-1885.
149. Iadecola, C.; Xu, X.; Zhang, F.; El-Fakahany, E. E.; Ross, M. E. Marked induction of calcium-independent nitric oxide synthase activity after focal cerebral ischemia. J. Cereb. Blood Flow Metab. 1995, 15, 52-59.
150. Wu, W.; Liuzzi, F. J.; Schinco, F. P.; Depto, A. S.; Li, Y.; Mong, J. A.; Dawson, T. M.; Snyder, S. H. Neuronal nitric oxide synthase is induced in spinal neurons by traumatic injury. Neuroscience 1994, 61, 719-726.
151. Lipton, S. A.; Stamler, J. S. Actions of redox-related congeners of nitric oxide at the NMDA receptor. Neuropharmacology 1994, 33, 1229-1233.
152. Reif, D. W.; Simmons, R. D. Nitric oxide mediates iron release from ferritin. Arch. Biochem. Biophys. 1990, 283, 537-541.
153. Jaffrey, S. R.; Cohen, N. A.; Rouault, T. A.; Klausner, R. D.; Snyder, S. H. The iron-responsive element binding protein: A target for synaptic actions of nitric oxide. Proc. Natl. Acad. Sci. U. SA. 1994, 91, 12994-12998.
154. Meda, L.; Cassatella, M. A.; Szendrei, G. I.; Otvos, L. J.; Baron, P. V.; Villalba, M.; Ferrari, D.; Rossi, F. Activation of microglia cells by /3-amyloid protein and interferon-y. Nature 1995, 374, 647-650.
155. Bo, L.; Dawson, T. M.; Wesselingh, S.; Mork, S.; Choi, S.; Kong, P. A.; Hanley, D.; Trapp, B. D. Induction of nitric oxide synthase in demyelinating regions of multiple sclerosis brains. Ann. Neurol. 1994, 36, 778-786.
156. Thomsen, L. L.; Iversen, H. K.; Lassen, L. H.; Olesen, J. The role of nitric oxide in migraine pain. CNS Drugs 1994, 2, 417-422.
157. Olesen, J.; Thomsen, L. L.; Iversen, H. Nitric oxide is a key molecule in migraine and other vascular headaches. Trends Pharmacol. Sci. 1994, 15, 149-153.
158. Flavahan, N. A. Atherosclerosis or lipoprotein-induced endothelial dysfunction. Potential mechanisms underlying reduction in EDRF/nitric oxide activity. Circulation 1992, 85, 1927-1938.
159. Anggard, E. Nitric oxide: mediator, murderer, and medicine. Lancet 1994, 343, 1199-1206.
160. Vallance, P.; Moncada, S. Nitric-oxide - from mediator to medicines. J. R. Coll. Phys. London 1994, 209-219.
161. Cayatte, A. J.; Palacino, J. J.; Horten, K.; Cohen, R. A. Chronic inhibition of nitric oxide production accelerates neointima formation and impairs endothelial function in hypercholester- olemic rabbits. Arterioscl. Thromb. 1994, 14, 753-759.
162. Schini, V. B.; Busse, R.; Vanhoutte, P. M.; Vasodilators: Atrial natriuretic peptide, eicosanoids and nitric oxide. Exp. Nephrol. 1994, 2, 139-144.
163. Williams, M.; Summers, J. Septic shock the continuing challenge of an effective therapy. Expert. Opin. Invest. Drugs 1994, 3, 1051-1056.
164. Minor, R. L. J.; Myers, P. R.; Guerra, R. J.; Bates, J. N.; Harrison, D. G. Diet-induced atherosclerosis increases the release of nitrogen oxides from rabbit aorta. J. Clin. Invest. 1990, 86, 2109-2116.
165. Mehta, J. L.; Lawson, D. L.; Nicolini, F. A.; Cain, D. A.; Mehta, P.; Schreier, H. Evidence for generation of a large amount of nitric oxide-like vascular smooth muscle relaxant by cholesterol- rich neutrophils. Biochem. Biophys. Res. Commun. 1990, 173, 438-442.
166. 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. U. SA. 1990, 87, 1620-1624.
167. G- methyl-L-arginine, an inhibitor of nitric-oxide formation, reverses IL-2-mediated hypotension in dogs. J. Appl. Physiol. 1994, 1130-1137.
168. Petros, A.; Lamb, G.; Leone, A.; Moncada, S.; Bennett, D.; Vallance, P. Effects of a nitric oxide synthase inhibitor in humans with septic shock. Cardiovasc. Res. 1994, 28, 34-39.
169. Myers, P. R.; Parker, J. L.; Tanner, M. A.; Adams, H. R. Effects of cytokines tumor necrosis factor a and interleukin If on endotoxin-mediated inhibition of EDRF bioactivity and nitric oxide production in vascular endothelium. Shock 1994, 1, 7378.
170. Christopher, T. A.; Ma, X.; Lefer, A. M. Beneficial actions of S-nitroso-N-acetylpenicillamine, a nitric oxide donor, in murine traumatic shock. Shock 1994, 1, 19-24.
171. Winlaw, D. S.; Smythe, G. A.; Keogh, A. M.; Schyvens, C. G.; Spratt, P. M.; McDonald, P. S. Increased nitric oxide production in heart failure. Lancet 1994, 344, 373-374.
172. Langrehr, J. M.; Hoffman, R. A.; Lancaster, J. R.; Simmons, R. L. Nitric oxide - a new endogenous immunomodulator. Transplantation 1993, 55, 1205-1212.
173. Mueller, A. R.; Platz, K.-P.; Langrehr, J. M.; Hoffman, R. A.; Nussler, A. K.; Nalesnik, M.; Billiar, T. R.; Schraut, W. H. The effects of administration of nitric oxide inhibitors during small bowel preservation and reperfusion. Transplantation 1994, 58, 1309-1316.
174. Salvemini, D.; Misko, T. P.; Masferrer, J. L.; Seibert, K.; Currie, M. G.; Needleman, P. Nitric Oxide activates cyclooxygenase enzymes. Proc. Natl. Acad. Sci. U. SA. 1993, 90, 7240-7244.
175. Lefer, A. M.; Lefer, D. J. Therapeutic role of nitric oxide donors in the treatment of cardiovascular disease. Drugs Future 1994, 19, 665-672.
176. Vanderford, P. A.; Wong, J.; Chang, R.; Keefer, L. K.; Soifer, S. J.; Fineman, J. R. Diethylamine nitric-oxide (NO) adduct, an NO donor, produces potent pulmonary and systemic vasodilation in intact newborn lambs. J. Cardiovasc. Pharmacol. 1994, 113-119.
177. Civelli, M.; Caruso, P.; Giossi, M.; Bergamaschi, M.; Razzetti, R.; Bongrani, S.; Gasco, A. CHF 2206, a new potent vasodilating and antiaggregating drug as potential nitric oxide donor. Eur. J. Pharmacol. 1994, 255, 17-24.
178. Ohtsuka, M.; Honbo, T.; Esumi, K. FK 409: A new vasodilator with nitric oxide-donating ability. Cardiovasc. Drugs Rev. 1994, 12, 2-15.
179. Roy, B.; d’Hardemare, A. M.; Fontecave, M. New thionitrites: Synthesis, stability, and nitric oxide generation. J. Org. Chem. 1994, 59, 7019-7026.
180. Salas, E.; Moro, M. A.; Askew, S.; Hodson, H. F.; Butler, A. R.; Radomski, M. W. Comparative pharmacology of analogues of S-nitroso-N-acetyl-D, L-penicillamine on human platelets. Br. J. Pharmacol. 1994, 112, 1071-1076.
181. Di Stilo, A.; Fruttero, R.; Boschi, D.; Gasco, A. M.; Sorba, G.; Gasco, A.; Orsetti, M. Use of nitric oxide releasing furoxan system in the design of hybrids: Substitution of furoxan moieties for the furan ring in prazosin. Med. Chem. Res. 1993, 3, 554-566.
182. Wessel, D. L.; Adatia, I.; Thompson, J. E.; Hickey, P. R. Delivery and monitoring of inhaled nitric oxide in patients with pulmonary hypertension. Crit. Care Med. 1994, 22, 930-938.
183. Lonnqvist, P. A.; Winberg, P.; Lundell, B.; Sellden, H.; Olsson, G. L. Inhaled nitric oxide in neonates and children with pulmonary hypertension. Acta Paediatrica 1994, 83, 1132-1136.
184. Petros, A. J.; Cox, P.; Bohn, D. A simple method for monitoring the concentration of inhaled nitric oxide. Anaesthesia 1994, 49, 317-319.
185. Heaton, J. P. W.; Morales, A.; Adams, M. A.; Johnston, B.; El-Rashidy, R. Recovery of erectile function by the oral administration of apomorphine. Urology 1995, 45 (2), 200-206.
186. Corbett, J. A.; McDaniel, M. L. Does Nitric Oxide Mediate Autoimmune Destruction of beta-Cells? Possible Therapeutic Interventions in IDDM. Diabetes 1992, 41, 897-903.
187. Corbett, J. A.; Sweetland, M. A.; Wang, J. L.; Lancaster, J., Jr.; McDaniel, M. L. Nitric oxide mediates cytokine-induced inhibition of insulin secretion by human islets of Langerhans. Proc. Natl. Acad. Sci. U. SA. 1993, 90, 1731-1735.
188. Burkart, V.; Imai, Y.; Kallmann, B.; Kolb, H. Cyclosporine-A protects pancreatic-islet cells from nitric oxide-dependent macrophage cytotoxicity. FEBS Lett. 1992, 313, 56-58.
189. Laskin, J. D.; Heck, D. E.; Laskin, D. L. Multifunctional role of nitric oxide in inflammation. Trends Endocrinol. Metab. 1994, 5, 377-382.
190. Kuo, H. P.; Liu, S. F.; Barnes, P. J. The effect of endogenous nitric-oxide on neurogenic plasma exudation in guinea-pig airways. Eur. J. Pharmacol. 1992, 221, 385-388.
191. Miller, M. J.; Sadowska-Krowicka, H.; Chotinaruemol, S.; Kakkis, J. L.; Clark, D. A. Amelioration of chronic ileitis by nitric oxide synthase inhibition. J. Pharmacol. Exp. Ther. 1993, 264, 11-16.
192. McCartney-Francis, N.; Allen, J. B.; Mizel, D. E.; Albina, J. E.; Xie, Q.; Nathan, C.; Wahl, S. M. Suppression of arthritis by an inhibitor of nitric oxide synthase. J. Exp. Med. 1993, 178, 74954.
193. Ialenti, A.; Moncada, S.; Di Rosa, M. Modulation of adjuvant arthritis by endogenous nitric-oxide. Br. J. Pharmacol. 1993, 110, 701-706.