Imidazole-containing amino acids as selective inhibitors of nitric oxide synthases

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 9, 1999, Pages 1941-1951

  Lee, Younghee ^a   Martasek, Pavel ^b   Roman, Linda J ^b   Masters, Bettie Sue Siler ^b   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

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

Author keywords

Histidine analogues; Imidazole containing amino acids; Inhibitors; Nitric oxide synthase

Indexed keywords

AMINO ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; NITRIC OXIDE SYNTHASE INHIBITOR;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; BINDING SITE; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; ENZYME INHIBITORS; IMIDAZOLES; NITRIC OXIDE SYNTHASE; RECOMBINANT PROTEINS; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032860443     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00117-0     Document Type: Article

References (44)

1. Kerwin J.F. Jr., Lancaster J.R. Jr., Feldman P.L. J. Med. Chem. 38:1995;4342.
2. Kerwin J.F., Heller M. Med. Res. Rev. 14:1994;23.
3. Petros A., Bennett D., Vallance P. Lancet. 338:1991;1157.
4. McCartney-Francis N., Allen J.B., Mizel D.E., Albina J.E., Xie Q., Nathan C.F., Wahl S.M. J. Exp. Med. 178:1993;749.
5. MacIntyre I., Zaidi M., Towhidul Alam A.S.M., Datta H.K., Moonga B.S., Lidbury P.S., Hecker M., Vane J.R. Proc. Natl. Acad. Sci. USA. 88:1991;2936.
6. Ferrendelli J.A., Blank A.C., Gross R.A. Brain Res. 200:1980;93.
7. Das I., Khan N.S., Puri B.K., Sooranna S.R., de Belleroche J., Hirsch S.R. Biochem. Biophys. Res. Commun. 212:1995;375.
8. Dorheim M.A., Tracey W.R., Pollock J.S., Grammas P. Biochem. Biophys. Res. Commun. 205:1994;659.
9. Burnett A.L., Lowenstein C., Bredt D.S., Chang T.S.K., Snyder S.H. Science. 257:1992;401.
10. Hibbs, J. B., Jr.; Taintor, R. R.; Vavrin, Z.; Granger, D. L.; Drapier, J. C.; Amber, I. J.; Lancaster, J. R., Jr. In Nitric Oxide from L-Arginine: A Bioregulatory System; Moncada, D.; Higgs, E. A., Eds.; Elsevier: Armsterdam, 1990: pp 189-223.
11. Olken N.M., Marletta M.A. Biochemistry. 32:1993;9677.
12. Furfine E.S., Harmon M.F., Paith J.E., Garvey E.P. Biochemistry. 32:1993;8215.
13. Zhang H.Q., Fast W., Marletta M.A., Martasek P., Silverman R.B. J. Med. Chem. 40:1997;3869.
14. Babu B.R., Griffith O.W. J. Biol. Chem. 273:1998;8882.
15. 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. J. Biol.Chem. 269:1997;26669.
16. Shearer B.G., Lee S., Oplinger J.A., Frick L.W., Garvey E.P., Furfine E.S. J. Med. Chem. 40:1997;1901.
17. Moore W.M., Webber R.K., Jerome G.M., Tjoeng F.S., Misko T.P., Currie M.G. J. Med. Chem. 37:1994;3886.
18. Moore W.M., Webber R.K., Fok K.F., Jerome G.M., Kornmeier C.M., Tjoeng F., Currie M.G. Bioorg. Med. Chem. 4:1996;1559.
19. Moore W.M., Webber R.K., Fok K.F., Jerome G.M., Connor J.R., Manning P.T., Wyatt P.S., Misko T.P., Tjoeng F.S., Currie M.G. J. Med. Chem. 39:1996;699.
20. Webber R.K., Metz S., Moore W.M., Connor J.R., Currie M.G., Fok K.F., Hagen T.J., Hansen D.W. Jr., Jerome G.M., Manning P.T., Pitzele B.S., Toth M.V., Trivedi M., Zupec M.E., Tjoeng F.S. J. Med. Chem. 41:1998;96.
21. Garvey E.P., Oplinger J.A., Furfine E.S., Kiff R.J., Laszlo F., Whittle B.J.R., Knowles R.G. J. Biol.Chem. 272:1997;4959.
22. Wolff D.J., Lubeskie A. Arch. Biochem. Biophys. 316:1995;290.
23. Fast W., Huff M.E., Silverman R.B. Bioorg. Med. Chem. Lett. 7:1997;1449.
24. Wolff D.J., Gribin B. J. Arch. Biochem. Biophys. 311:1994;293.
25. Mayer B., Klatt P., Werner E.R., Schmidt K. FEBS Lett. 350:1994;199.
26. Wolff D.J., Gribin B. J. Arch. Biochem. Biophys. 311:1994;300.
27. Wolff D.J., Datto G.A., Samatovicz R.A., Tempsick R.A. J. Biol. Chem. 268:1993;9425.
28. Narayanan K., Griffith O.W. J. Med. Chem. 37:1994;885.
29. Frey C., Narayanan K., McMillan K., Spack L., Gross S.S., Masters B.S., Griffith O.W. J. Biol. Chem. 269:1994;26083.
30. Ulhaq S., Chinje E.C., Naylor M.A., Jaffar M., Stratford I.J., Threadgill M.D. Bioorg. Med. Chem. 6:1998;2139.
31. Schenkman, J. B.; Sligar, S. G.; Cinti, D. L. Pharmacol. Ther. 1981, 12, 43; Rogerson, T. D.; Wilkinson, T. F.; Hetarski, K. Biochem. Pharmacol. 1977, 26, 1039.
32. Schenkman, J. B.; Sligar, S. G.; Cinti, D. L. Pharmacol. Ther. 1981, 12, 43; Rogerson, T. D.; Wilkinson, T. F.; Hetarski, K. Biochem. Pharmacol. 1977, 26, 1039.
33. Swanson R.A., Dus K.M. J. Biol. Chem. 254:1979;7238.
34. Altman J., Wilchek M. Syn. Commun. 19:1989;2069.
35. Schollkopf U., Groth U., Deng C. Angew. Chem., Int. Ed. Engl. 20:1981;798.
36. Chadwick, D. J.; Ngochindo, R. I. J. Chem. Soc. Perkin Trans. 1 1984, 481.
37. Vollinga R.C., Menge W.M.P.B., Leurs R., Timmerman H. J. Med. Chem. 38:1995;266.
38. Hevel J.M., Marletta M.A. Methods Enzymol. 133:1994;250.
39. Durant G.J., Ganellin C.R., Parson M.E. J. Med. Chem. 18:1975;905.
40. Rusche, K. M.; Spiering, M. M.; Marletta, M. A., manuscript submitted.
41. Hevel J.M., White K.A., Marletta M.A. J. Biol. Chem. 266:1991;22789.
42. Martasek P., Liu Q., Liu J., Roman L.J., Gross S.S., Sessa W.C., Masters B.S.S. Biochem. Biophys. Res. Commun. 219:1996;359.
43. Roman L.J., Sheta E.A., Martasek P., Gross S.S., Liu Q., Masters B.S.S. Proc. Natl. Acad. Sci. USA. 92:1995;8428.
44. Dixon M. Biochem. J. 55:1953;170.