Synthesis and evaluation of peptidomimetics as selective inhibitors and active site probes of nitric oxide synthases

Journal of Medicinal Chemistry

Volumn 43, Issue 15, 2000, Pages 2938-2945

  Huang, Hui ^a   Martásek, Pavel ^b   Roman, Linda J ^b   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID DERIVATIVE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; PEPTIDE DERIVATIVE;

ARTICLE; DRUG BINDING; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION;

BINDING SITES; DIPEPTIDES; ENZYME INHIBITORS; MOLECULAR MIMICRY; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE I; PEPTOIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0342647320     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000127z     Document Type: Article

References (35)

1. Kerwin, J. F., Jr.; Lancaster, J. R., Jr.; Feldman, P. L. Nitric Oxide: A New Paradigm for Second Messengers. J. Med. Chem. 1995, 38, 4342-4362.
2. Kerwin, J. F., Jr.; Heller, M. The Arginine-Nitric Oxide Pathway: A target for New Drugs. Med. Res. Rev. 1994, 14, 23-74.
3. Stuehr, D. J.; Griffith, O. W.; Mammalian Nitric Oxide Synthases. Adv. Enzymol. Relat. Areas Mol. Biol. 1992, 65, 287-346.
4. Schmidt, H. H. H. W.; Murad, F. Purification and Characterization of Human NO Synthase. Biochem. Biophys. Res. Commun. 1991, 181, 1372-1377.
5. Schmidt, H. H. H. W.; Walter, U. NO at Work. Cell 1994, 78, 919-925.
6. Förstermann, U.; Pollock, J. S.; Schmidt, H. H. H. W.; Heller, M.; Murad, F. Calmodulin-Dependent Endothelium-Derived Relaxing Factor/Nitric Oxide Synthase Activity Is Present in the Particulate and Cytosolic Fractions of Bovine Aortic Endothelial Cells. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1788-1792.
7. MacMicking, J.; Xie, Q. W.; Nathan, C. Nitric Oxide and Macrophage Function. Annu. Rev. Immunol. 1997, 15, 323-350.
8. Knowles, R. G.; Moncada, S. Nitric Oxide Synthases in Mammals. Biochem. J. 1994, 198, 249-258.
9. Griffith, O. W.; Stuehr, D. J. Nitric Oxide Synthases: Properties and Catalytic Mechanism. Annu. Rev. Physiol. 1995, 57, 707-736.
10. Marletta, M. A. Approaches Toward Selective Inhibition of Nitric Oxide Synthase. J. Med. Chem. 1994, 37, 1899-1907.
11. Moncada, S.; Higgs, E. A. Molecular Mechanism and Therapeutic Strategies related to Nitric Oxide. FASEB J. 1995, 9, 1319-1330.
12. G-Methyl-L-Arginine Functions as an Alternative Substrate and Mechanism-based Inhibitor of Nitric Oxide Synthase. Biochemistry 1993, 32, 9677-9685.
13. G-Nitroarginine. Biochemistry 1993, 32, 8512-8517.
14. o-(Iminoethyl)-L-Ornithine as an Irreversible Inhibitor of Nitric Oxide Synthase in Phagocytic Cells. Br. J. Pharmacol. 1991, 102, 234-238.
15. Narayanan, K.; Spack, L.; McMillan, K.; Kilbourn, R. G.; Hayward, M. A.; Masters, B. S. S.; Griffith, O. W. S-Alkyl-L-thiocitrullines. J. Biol. Chem. 1995, 270, 11103-11110.
16. Collins, J. L.; Shearer, B. G.; Oplinger, J. A.; Lee, S.; Garvey, E. P.; Salter, M.; Duffy, C.; Burnette, T. C.; Furfine, E. S. N-Phenylamidines as Selective Inhibitors of Human Neuronal Nitric Oxide Synthase: Structure - activity Studies and Demonstration of in vivo Activity. J. Med. Chem. 1998, 41, 2858-2871.
17. Wolff, D. J.; Lubeskie, A. Aminoguanidine is an Isoform-selective, Mechanism-based Inactivator of Nitric Oxide Synthase. Arch. Biochem. Biophys. 1995, 316, 290-301.
18. Jang, D.; Szabo, C.; Murell, G. A. C. S-Substituted Isothioureas are Potent Inhibitors of Nitric Oxide Biosynthesis in Cartilage. Eur. J. Pharmacol. 1996, 312, 341-347.
19. Griffith, O. W.; Gross, S. S. Inhibitors of Nitric Oxide Synthases. In Methods in Nitric Oxide Research; Feelisch, M., Stamler, J. S., Eds.; John Wiley and Sons: New York, 1996; pp 187-208.
20. Fröhlich, L. G.; Kotsonis, P.; Traub, H.; Taghavi-Moghadam, S.; Al-Masoudi, N.; Hofmann, H.; Strobel, H.; Matter, H.; Pfleiderer, W.; Schmidt, H. H. H. W. Inhibition of Neuronal Nitric Oxide Synthase by 4-Amino Pteridine Derivatives: Structure - Activity Relationship of Antagonists of (6R)-5,6,7,8-Tetrahydrobiopterin Cofactor. J. Med. Chem. 1999, 42, 4108-4121.
21. ω-Nitroarginine-Containing Dipeptide Amides. Potent and Highly Selective Inhibitors of Neuronal Nitric Oxide Synthase. J. Med. Chem. 1999, 42, 3147.
22. Miller, S. M.; Simon, R. J.; Ng, S.; Zuckerman, R. N.; Kerr, J. M.; Moos, W. H. Comparison of the proteolytic susceptibilities of homologous L-amino acid, D-amino acid, and N-substituted glycine peptide and peptoid oligomers. Drug Dev. Res. 1995, 35, 20-32.
23. Yang, L.; Chiu, K. Solid-Phase Synthesis of Fmoc N-Methyl Amino Acids: Application of the Fukuyama Amine Synthesis. Tetrahedron Lett. 1997, 38, 7307-7310.
24. ω-Nitroarginine and D-2,4-Diaminobutyric Acid as Inhibitors of Neuronal Nitric Oxide Synthase. Bioorg. Med. Chem., submitted.
25. 60c-src SH2 Domain. J. Med. Chem. 1998, 41, 1894-1908.
26. ω-Aminoethylated Derivatives. Liebigs Ann. Chem. 1993, 941-945.
27. Anderson, G. W.; Callahan, F. M. tert-Butyl Esters of Amino Acids and Peptides and Their Use in Peptide Synthesis. J. Am. Chem. Soc. 1960, 82, 3359.
28. t Protected Amino Acids Incorporating Aminodiacettic Acid Moiety. Tetrahedron letters 1993, 34, 4493-4496.
29. ω-Nitroarginine- and Phenylalanine-Containing Dipeptides and Dipeptide Esters. J. Med. Chem. 1997, 40, 2813-2817.
30. Hevel, J. M.; White, K. A.; Marletta, M. A. Purification of the Inducible Murine Macrophage Nitric Oxide Synthase. J. Biol. Chem. 1991, 266, 22789-22791.
31. Roman, L. J.; Sheta, E. A.; Martasek, P.; Gross, S. S.; Liu, Q.; Masters, B. S. S. High-Level Expression of Functional Rat Neuronal Nitric Oxide Synthase in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8428-8432.
32. Gerber, N. C.; Montellano, P. R. Neuronal Nitric Oxide Synthase: Expression in Escherichia coli, Irreversible Inhibition by Phenyldiazene, and Active Site Topology. J. Biol. Chem. 1995, 270, 17791-17796.
33. Martasek, P.; Liu, Q.; Roman, L. J.; Gross, S. S.; Sessa, W. C.; Masters, B. S. S. Characterization of Bovine Endothelial Nitric Oxide Synthase Expressed in Escherichia coli. Biochem. Biophys. Res. Commun. 1996, 219, 359-365.
34. Hevel, J. M.; Marletta, M. A. Nitric Oxide Synthase Assays. Methods Enzymol. 1994, 133, 250-258.
35. Segel, I. H. Enzyme Kinetics; John Wiley and Sons: New York, 1975; p 105.