Minimal amidine structure for inhibition of nitric oxide biosynthesis

Biochemical Pharmacology

Volumn 61, Issue 12, 2001, Pages 1581-1586

  Billack, Blase ^a   Heck, Diane E ^a   Porterfield, D Marshall ^b   Malchow, R Paul ^c   Smith, Peter J S ^d   Gardner, Carol R ^a   Laskin, Debra L ^a   Laskin, Jeffrey D ^e  

^a RUTGERS UNIVERSITY   (United States)

^b MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d MARINE BIOLOGICAL LABORATORY   (United States)

^e RUTGERS ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

Author keywords

Aminoguanidine; Formamidine; Nitric oxide; NOS2

Indexed keywords

1,4 DIHYDRO 2,6 DIMETHYL 5 NITRO 4 [2 (TRIFLUOROMETHYL)PHENYL] 3 PYRIDINECARBOXYLIC ACID METHYL ESTER; AMIDINE; ARGININE; FORMAMIDINE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CELL LINE; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG UPTAKE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; LIVER CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN STRUCTURE; RAT;

AMIDINES; ANIMALS; CELLS, CULTURED; GUANIDINES; HUMANS; MICE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE II; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035877186     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(01)00630-X     Document Type: Article

References (21)

1. Hobbs A.J., Higgs A., Moncada S. Inhibition of nitric oxide synthase as a potential therapeutic target. Annu Rev Pharmacol Toxicol. 39:1999;191-220.
2. Marletta M.A. Nitric oxide synthase structure and mechanism. J Biol Chem. 268:1993;12231-12234.
3. Marletta M.A. Approaches toward selective inhibition of nitric oxide synthase. J Med Chem. 37:1994;1899-1907.
4. 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 inhibiton of human nitric oxide synthases. J Biol Chem. 269:1994;26669-26676.
5. Southan G.J., Salzman A.L., Szabo C. Potent inhibition of the inducible isoform of nitric oxide synthase by aminoethylisoselenourea and related compounds. Life Sci. 58:1996;1139-1148.
6. Egolf R.A., Heindel N.D. Structure-activity relationships in NOS inhibitors. Laskin J.D., Laskin D.L. Cellular and molecular biology of nitric oxide. 1999;125-135 Marcel Dekker, New York.
7. Southan G.J., Szabo C., O'Connor M.P., Salzman A.L., Thiemermann C. Amidines are potent inhibitors of nitric oxide synthases preferential inhibition of the inducible isoform . Eur J Pharmacol. 291:1995;311-318.
8. 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. 2-Iminopiperidine and other 2-iminoazaheterocycles as potent inhibitors of human nitric oxide synthase isoforms. J Med Chem. 39:1996;669-672.
9. Southan G.J., Gauld D., Lubeskie A., Zingarelli B., Cuzzocrea S., Salzman A.L., Szabo C., Wolff D.J. Inhibition of nitric oxide synthase with pyrazole-1-carboxamidine and related compounds. Biochem Pharmacol. 54:1997;409-417.
10. Webber R.K., Metz S., Moore W.M., Connor J.R., Currie M.G., Fok K.F., Hagen T.J., Hansen D.W., Jerome G.M., Manning P.T., Pitzele B.S., Toth M.V., Trivedi M., Zupec M.E., Tjoeng F.S. Substituted 2-iminopiperidines as inhibitors of human nitric oxide synthase isoforms. J Med Chem. 41:1998;96-101.
11. Naka M., Nanbu T., Kobayashi K., Kamanaka Y., Komeno M., Yanase R., Fukutomi T., Fujimura S., Seo H.G., Fujiwara N., Ohuchida S., Suzuki K., Kondo K., Taniguchi N. A potent inhibitor of inducible nitric oxide synthase, ONO-1714, a cyclic amidine derivative. Biochem Biophys Res Commun. 270:2000;663-667.
12. Heck D.E., Laskin D.L., Gardner C.R., Laskin J.D. Epidermal growth factor suppresses nitric oxide and hydrogen peroxide in keratinocytes. Potential role of nitric oxide in the regulation of wound healing. J Biol Chem. 267:1992;21277-21280.
13. Gardner C.R., Heck D.E., Yang C.S., Thomas P.E., Zhang X.J., DeGeorge G.L., Laskin J.D., Laskin D.L. Role of nitric oxide in acetaminophen-induced hepatotoxicity in the rat. Hepatology. 27:1998;748-754.
14. Cooper G.R., Barr A., Wolff D.J. Neuronal nitric oxide synthase is refractory to mechanism-based inactivation in GH3 pituitary cells. Arch Biochem Biophys. 357:1998;195-206.
15. DeGeorge G.L., Heck D.E., Laskin J.D. Arginine metabolism in keratinocytes and macrophages during nitric oxide biosynthesis multiple modes of action of nitric oxide synthase inhibitors . Biochem Pharmacol. 54:1997;103-112.
16. Bredt D.S., Schmidt H.H.H.W. The citrulline assay. Feelisch M., Stamler J.S. Methods in nitric oxide research. 1996;249-255 John Wiley, New York.
17. White M.F. The transport of cationic amino acids across the plasma membrane of mammalian cells. Biochim Biophys Acta. 515:1985;355-374.
18. Wu G., Morris S.M. Arginine metabolism nitric oxide and beyond . Biochem J. 336:1998;1-17.
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. 283:1997;265-273.
20. 6-(1-iminoethyl)lysine. Biochemistry. 37:1998;4844-4852.
21. Pappano A.J/, Watanabe A.M. Cholinoceptor-activating and cholinesterase-inhibiting drugs. Katzung B.G. Basic and clinical pharmacology. 6th ed :1995;88-101 Appleton & Lange, Norwalk.