Inactivation of nitric oxide synthases and cellular nitric oxide formation by N6-iminoethyl-L-lysine and N5-iminoethyl-L-ornithine

European Journal of Pharmacology

Volumn 350, Issue 2-3, 1998, Pages 325-334

  Wolff, Donald J ^a   Lubeskie, Andrew ^a   Gauld, Douglas S ^a   Neulander, Matthew J ^a  

^a UNIVERSITY OF MEDICINE AND DENTISTRY OF NEW JERSEY   (United States)

Author keywords

Kinetics; Mechanism based inactivation; N5 Iminoethyl L ornithine; N6 Iminoethyl L lysine; Nitric oxide (NO) synthesis

Indexed keywords

ARGININE; CITRULLINE; CYCLOHEXIMIDE; LYSINE DERIVATIVE; N5 IMINOETHYLORNITHINE; N6 (IMINOETHYL)LYSINE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; ORNITHINE DERIVATIVE; SUICIDE SUBSTRATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INACTIVATION; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; CYTOKINES; ENZYME INHIBITORS; GUANIDINES; ISOENZYMES; KINETICS; LYSINE; METHEMOGLOBIN; MICE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; ORNITHINE; OXYHEMOGLOBINS;

EID: 0032486150     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-2999(98)00267-2     Document Type: Article

References (36)

1. Bandyapadhyah U., Bhattachryya D.K., Banerjee R.K. Mechanism-based inactivation of gastric peroxidase by mercaptomethylimidazole. Biochem. J. 296:1993;79-84.
2. + in activated macrophages. Biochem. Biophys. Res. Commun. 200:1994;726-731.
3. Bohme G.A., Bon C., Lemaire M., Reibaud M., Piot O., Stutzmann J.-M., Doble A., Blanchard J.-C. Altered synaptic plasticity and memory formation in nitric oxide synthase inhibitor-treated rats. Proc. Natl. Acad. Sci. USA. 90:1993;9191-9194.
4. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
5. Bredt D.S., Snyder S.H. Isolation of nitric oxide synthase, a calmodulin-requiring enzyme. Proc. Natl. Acad. Sci. USA. 87:1990;682-685.
6. Bredt D.S., Snyder S.H. Nitric oxide: a physiologic messenger molecule. Annu. Rev. Biochem. 63:1994;175-184.
7. Connor J.R., Manning P.T., Settle S.L., Moore W.M., Jerome G.M., Webber R.K., Tjoeng F.S., Currie M.G. Suppression of adjuvant-induced arthritis by selective inhibition of inducible nitric oxide synthase. Eur. J. Pharmacol. 273:1995;15-24.
8. Fitzpatrick P.F., Villafranca J.J. The mechanism of inactivation of dopamine-β-hydroxylase by hydrazines. J. Biol. Chem. 261:1986;4510-4518.
9. Griffith O.W., Stuehr D.J. Nitric oxide synthases: aspects concerning structure and catalysis. Annu. Rev. Physiol. 57:1995;707-736.
10. + basic amino acid transporter. Biochemistry. 32:1993;5781-5785.
11. Kitz R., Wilson I.B. Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase. J. Biol. Chem. 237:1962;3245-3249.
12. MacMicking J.D., Xie Q.-W., Nathan C. Nitric oxide and macrophage function. Annu. Rev. Immunol. 15:1997;323-350.
13. McCall T.B., Feelish M., Palmer R.M.J., Moncada S. Identification of N-iminoethyl-L-ornithine as an irreversible inhibitor of nitric oxide synthase in phagocytic cells. Br. J. Pharmacol. 102:1991;234-238.
14. Meyer J., Richter N., Hecker M. High-performance liquid chromatographic determination of nitric oxide synthase-related arginine derivatives in vitro and in vivo. Anal. Biochem. 247:1997;11-16.
15. Moncada S., Higgs E.A. Molecular mechanisms and therapeutic strategies related to nitric oxide. FASEB J. 9:1995;1319-1330.
16. Moore W.M., Webber R.K., Fok K.M., Jerome G.M., Conner J.R., Manning P.T., Wyatt P.S., Misko T.P., Tjoeng F.S., Currie M.G. 2-Iminopeperidine and other 2-iminoheterocycles as potent inhibitors of human nitric oxide synthase isoforms. J. Med. Chem. 39:1996;669-672.
17. Nathan C. Nitric oxide as a secretory product of mammalian cells. FASEB J. 6:1992;3051-3064.
18. Noack E., Kubitzak D., Kodja I. Spectrophotometric determination of nitric oxide using hemoglobin. Neuroprotocols. 1:1992;133-139.
19. Rando R.R. Mechanism-based enzyme inactivators. Pharmacol. Rev. 36:1984;111-138.
20. Rees D.D., Palmer R.M.J., Moncada S. Role of endothelium-derived nitric oxide in the regulation of blood pressure. Proc. Natl. Acad. Sci. USA. 86:1989;3375-3378.
21. Rees D.D., Palmer R.M.J., Schulz R., Hodson H.F., Moncada S. Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo. Br. J. Pharmacol. 101:1990;746-752.
22. Samdani A.F., Dawson T.M., Dawson V.L. Nitric oxide synthase in models of focal ischemia. Stroke. 8:1997;1283-1288.
23. Schmidt K., Klatt P., Mayer B. Uptake of nitric oxide synthase inhibitors by macrophage RAW 264.7 cells. Biochem. J. 301:1994;313-316.
24. Sennequier N., Stuehr D.J. Analysis of substrate-induced electronic, catalytic and structural changes in inducible nitric oxide synthase. Biochemistry. 35:1996;5883-5892.
25. Silverman, R.B., 1988. Mechanism-based Enzyme Inactivation: Chemistry and Enzymology, Vol. I. CRC Press Boca Raton, FL, pp. 1-27.
26. G-monomethyl-arginine in vitro and in vivo. Eur. J. Pharmacol. 294:1995;703-712.
27. Stuehr D.J. Structure-function aspects in the nitric oxide synthases. Annu. Rev. Pharmacol. Toxicol. 37:1997;339-359.
28. Szabo C. Alterations of nitric oxide production in various forms of circulatory shock. New Horiz. 3:1995;2-32.
29. Thiemermann C., Czabo C., Mitchell J.A., Vane J.R. Vascular hyporeactivity to vasoconstrictor agents and hemodynamic decompensation in hemorrhagic shock is mediated by nitric oxide. Proc. Natl. Acad. Sci. USA. 90:1993;267-271.
30. G-monomethyl-L-arginine. J. Exp. Med. 179:1994;651-660.
31. White M.F. The transport of cationic amino acids across the plasma membrane of mammalian cells. Biochim. Biophys. Acta. 822:1985;355-374.
32. 3 pituitary cells. Biochem. J. 284:1992;201-206.
33. Wolff D.J., Gribin B.J. γ-Interferon inducible murine macrophage nitric oxide synthase: Studies on the mechanism of inhibition by imidazole agents. Arch. Biochem. Biophys. 311:1994;293-299.
34. Wolff D.J., Lubeskie A. Aminoguanidine is an isoform-selective, mechanism-based inactivator of nitric oxide synthase. Arch. Biochem. Biophys. 316:1995;290-301.
35. Wolff D.J., Lubeskie A., Umansky S. The inhibition of the constitutive bovine endothelial nitric oxide synthase by imidazole and indazole agents. Arch. Biochem. Biophys. 312:1994;360-366.
36. Wolff D.J., Lubeskie A., Li C. Inactivation and recovery of nitric oxide synthetic capability in cytokine-induced RAW 264.7 cells treated with 'irreversible' NO synthase inhibitors. Arch. Biochem. Biophys. 333:1997;73-82.