Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase

Journal of Medicinal Chemistry

Volumn 42, Issue 10, 1999, Pages 1842-1848

  Ichimori, Kohji ^a,c   Stuehr, Dennis J ^a   Atkinson, Robert N ^b   King, S Bruce ^b  

^a LERNER RESEARCH INSTITUTE   (United States)

^b WAKE FOREST UNIVERSITY   (United States)

^c TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE DERIVATIVE; CITRULLINE; HEME; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; OMEGA N AMINO LEVO THIOCITRULLINE TRIFLUOROACETATE; OMEGA N AMINO METHYL LEVO ISOTHIOCITRULLINE TRIFLUOROACETATE; OMEGA N HYDROXYMETHYL LEVO THIOCITRULLINE TRIFLUOROACETATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SPECIFICITY;

ARGININE; CITRULLINE; ENZYME INHIBITORS; HEME; ISOENZYMES; NADPH OXIDASE; NEURONS; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE II; NITRIC OXIDE SYNTHASE TYPE III; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033587103     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980232x     Document Type: Article

References (23)

1. Kerwin, J. F., Jr.; Lancaster, J. R., Jr.; Feldman, P. F. Nitric Oxide: A New Paradigm for Second Messengers. J. Med. Chem. 1995, 38, 4343-4362.
2. ω-Hydroxy-L-Arginine is an Intermediate in the Biosynthesis of Nitric Oxide from L-Arginine. J. Biol. Chem. 1991, 266, 6259-6263.
3. Griffith, O. W.; Stuehr, D. J. Nitric Oxide Synthases: Properties and Catalytic Mechanism. Annu. Rev. Physiol. 1995, 57, 707-736.
4. Crane, B. R.; Arvai, A. S.; Gachhui, R.; Wu, C.; Ghosh, D. K.; Getzoff, E. D.; Stuehr, D. J.; Tainer, J. A. The Structure of Nitric Oxide Synthase Oxygenase Domain and Inhibitor Complexes. Science 1997, 278, 425-431.
5. Crane, B. R.; Arvai, A. S.; Ghosh, D. K.; Wu, C.; Getzoff, E. D.; Stuehr, D. J.; Tainer, J. A. Structure of Nitric Oxide Synthase Oxygenase Dimer with Pterin and Substrate. Science 1998, 279, 2121-2126.
6. G-Methyl-L-Arginine Functions as an Alternative Substrate and Mechanism Based Inhibitor of Nitric Oxide Synthase. Biochemistry 1993, 32, 9677-9685.
7. G-Methylarginine Requires NADPH-dependent Hydroxylation. J. Med. Chem. 1993, 36, 491-496.
8. G-Nitroarginine. Biochemistry 1993, 32, 8512-8517.
9. ω-Nitro-L-Arginine Must be Hydrolyzed to Become Active NO Synthase Inhibitors. Br. J. Pharmacol. 1993, 109, 12.
10. G-Amino-L-Arginine: A New Potent Antagonist of L-Arginine Mediated Endothelium Dependent Relaxation. Biochem. Biophys. Res. Commun. 1990, 168, 458-465.
11. 6-(1-iminoethyl)lysine: A Selective Inhibitor of Inducible Nitric Oxide Synthase. J. Med. Chem. 1994, 37, 3886-3888.
12. (a) 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.
13. (b) 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 by S-Methyl-L-Thiocitrulline and S-Ethyl-Thiocitrulline. J. Biol. Chem. 1994, 269, 26677-26683.
14. G-Hydroxyarginine. Tetrahedron Lett, 1991, 32, 875-878.
15. ω-Hydroxyindospicine and p-Hydroxyamidinophenylalanine. J. Chem. Soc., Perkin Trans. 1 1996, 645-648.
16. (a) Stolze, K.; Nohl, H. EPR Studies on the Oxidation of Hydroxyurea to Paramagnetic Compounds by Oxyhemoglobin. Biochem. Pharmacol. 1990, 40, 799-802.
17. (b) Pacelli, R.; Taira, J.; Cook, J. A.; Wink, D. A.; Krishna, M. C. Hydroxyurea Reacts with Heme Proteins to Generate Nitric Oxide. Lancet 1996, 347, 900.
18. Abu-Soud, H. M.; Feldman, P. L.; Clark, P.; Stuehr, D. J. Electron Transfer in NO Synthases: Characterization of L-Arginine Analogues that Block Heme Iron Reduction. J. Biol. Chem. 1994, 269, 32318-32326.
19. Wolff, D. J.; Gauld, D. S.; Neulander, M. J.; Southan, G. Inactivation of Nitric Oxide Synthase by Substituted Aminoguanidines and Aminoisothioureas. J. Pharmacol. Exp. Ther. 1997, 283, 265-273.
20. Sennequier, N.; Stuehr, D. J. Analysis of Substrate Induced Electronic, Catalytic, and Structural Changes in Inducible NO Synthase. Biochemistry 1996, 35, 5883-5892.
21. McMillan, K.; Masters, B. S. S. Optical Difference Spectrophotometry as a Probe of Rat Brain Nitric Oxide Synthase Heme-Substrate Interaction. Biochemistry 1993, 32, 9875-9880.
22. 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.
23. Wu, C.; Zhang, J.; Abu-Soud, H.; Ghosh, D. K.; Stuehr, D. J. High-Level Expression of Mouse Inducible Nitric Oxide Synthase in Escherichia Coli Requires Coexpression with Calmodulin. Biochem. Biophys. Res. Commun. 1996, 222, 439-444.