Inactivation of nitric oxide synthase by substituted aminoguanidines and aminoisothioureas

Journal of Pharmacology and Experimental Therapeutics

Volumn 283, Issue 1, 1997, Pages 265-273

  Wolff, Donald J ^a   Gauld, Douglas S ^a   Neulander, Matthew J ^a   Southan, Garry ^b  

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

^b SAIC FREDERICK INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYLAMINOGUANIDINE; AMINOGUANIDINE; CYCLOHEXIMIDE; NITRIC OXIDE SYNTHASE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; ENZYME INACTIVATION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME REGULATION; ENZYME SPECIFICITY; PRIORITY JOURNAL; PROTEIN SYNTHESIS INHIBITION; REGULATORY MECHANISM;

ANIMALS; CATTLE; CYTOKINES; GUANIDINES; KINETICS; MICE; NADPH OXIDASE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA;

EID: 0030808463     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. BANDYAPADHYAH, U., BHATTACHRYYA, D. K., AND BANERJEE, R. K.: Mechanism-based inactivation of gastric peroxidase by mercaptomethylimidazole. Bioehem. J. 296: 79-84, 1993.
2. 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: 248-254, 1976.
3. BREDT, D. S., HUANG, P. M., GLATT, C. E., LOWENSTEIN, C., REED, R. R. AND SYNDER, S. H.: Cloned and expressed nitric oxide synthase resembles cytochrome P-450 reductase. Nature 351: 714-718, 1991.
4. BREDT, D. S. AND SYNDER, S. H.: Isolation of nitric oxide synthase, a calmodulin-requiring enzyme. Proc. Natl. Acad. Sci. USA 87: 682-685, 1990.
5. BREDT, D. S. AND SYNDER, S. H.: Nitric oxide: A physiologic nessenger molecule. Annu. Rev. Biochem. 63: 175-184, 1994.
6. 50) of an enzymatic reaction. Biochem. Pharmacol. 22: 3099-3108, 1973.
7. CRAIG, D. A.: The Cheng-Prusoff relationship: Something lost in the translation. Trends Pharmacol. Sci. 14: 89-92, 1993.
8. FITZPATRICK, P. F. AND VILLAFRANCA, J. J.: The mechanism of inactivation of dopamine-β-hydroxylase by hydrazines. J. Biol. Chem. 261: 4510-4518, 1986.
9. GARVEY, E. P., OPLINGER, J. A., TANCURY, G. J., SHERMAN, P. A., FOWLER, M., MARSHALL, S., HARMAN, M., PAITH, J. E. AND FURFINE, E. S.: Potent and selective inhibition of human nitric oxide synthases: Inhibition by non-amino acid isothioureas. J. Biol. Chem. 269: 26669-26676, 1994.
10. GARVEY, E. P., OPUNGER, J. A., FURFINE, E. S., KIFF, P. J., LASZLO, F., WHITTLE, B. J. R. AND KNOWLES, R. G.: 1400W is a slow, tight binding and highly selective inhibitor of inducible nitric oxide synthase in vitro and in vivo. J. Biol. Chem. 272: 4959-4963, 1997.
11. GRIFFTTH, O. W. AND STUEHR, D. J.: Nitric oxide synthases: Aspects concerning structure and catalysis. Annu. Rev. Physiol. 57: 707-736, 1995.
12. G-Methyl-L-arginine inhibits tumor necrosis factor-induced hypotension: Implications for the involvement of nitric oxide. Proc. Natl. Acad. Sci. USA 87: 3629-3632, 1990.
13. KITZ, R. AND WILSON, I. B.: Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase. J. Biol. Chem. 237: 3245-3249, 1962.
14. KLATT, P., SCHMIDT, K., URAY, G. AND MAYER, B.: Multiple catalytic functions of brain nitric oxide synthase. J. Biol. Chem. 268: 14781-14787, 1993.
15. MAKITA, Z., VLASSARA, H., RAYFIELD, E., CARTWRIGHT, K., FRIEDMAN, E., RODBY, R., CARAMI, A. AND BUCALA, R.: Hemoglobin AGE: A circulation marker of advanced glycosylation. Science 258: 651-653, 1992.
16. MARLETTA, M. A.: Nitric oxide synthase: Aspects concerning structure and catalysis. Cell 78: 927-930, 1994.
17. MAYER, B., JOHN, M., HEINZEL, B., WERNER, E. R., WACHTER, H., SCHULZ, G. AND BOHME, E.: Brain nitric oxide synthase is a biopterin and flavin-containing multi-functional oxido-reductase. FEES Lett. 288: 187-191, 1991.
18. MONCADA, S. AND HIGGS, E. A.: Molecular mechanisms and therapeutic strategies related to nitric oxide. FASEB J. 9: 1319-1330, 1995.
19. NAKANE, M., KLINGHOFER, V., KUK, J. E., DONNELLY, J. L., BUDZIK, G. P., POLLACK, J. S., BASHA, F. AND CARTER, G. W.: Novel potent and selective inhibitors of inducible nitric oxide synthase. J. Pharmacol. Exp. Ther. 47: 831-834, 1995.
20. NATHAN, C.: Nitric oxide as a secretory product of mammalian cells. FASEB J. 6: 3051-3064, 1992.
21. NOACK, E., KUBITZAK, D. AND KODJA, I.: Spectrophotometric determination of nitric oxide using hemoglobin. Neuroprotocols 1: 133-139, 1992.
22. RANDO, R. R.: Mechanism-based enzyme inactivators. Pharmacol. Rev. 36: 111-138, 1984.
23. REID, E. E.: Organic Chemistry of Bivalent Sulfur, Vol. V, Chemical Publishing, New York, 1963.
24. RUETTEN, H., SOUTHAN, G. J., ABATE, A. AND THIEMERMANN, C.: Attenuation of endotoxin induced multiple organ dysfunction by 1-amino-2-hydroxyguanidine, a potent inhibitor of inducible nitric oxide synthase. Br. J. Pharmacol. 118: 261-270, 1996.
25. SESSA, W. C., HARRISON, J. K., BARBER, C., ZENG, D., DURIEUX, M. E., D'ANGELO, D. D., LYNCH, K. K. AND PEACH, M. J.: Molecular cloning and expression of a cDNA encoding endothelial nitric oxide synthase. J. Biol. Chem. 267: 15274-15276, 1992.
26. SILVERMAN, R. B.: Mechanism-based Enzyme Inactivation: Chemistry and Enzymology, Vol. I, pp. 1-27, CRC Press, Boca Raton, FL, 1988.
27. SIMMONS, W. W., CLOSS, E. I., CUNNINGHAM, J. M., SMITH, T. W. AND KELLY, R. A.: Cytokines and insulin induce cationic amino acid transporter (CAT) expression in cardiac myocytes. J. Biol. Chem. 271: 11694-11702, 1992.
28. SOUTHAN, G. J., SZABO, C., O'CONNOR, M. P., SALZMAN, A. L. AND THIEMERMANN, C.: Amidines are potent inhibitors of constitutive and inducible nitric oxide synthases: Preferential inhibition of the inducible isoform. Eur. J. Pharmacol. 291: 311-318, 1995a.
29. SOUTHAN, G. J., SZABO, C. AND THIEMERMANN, C.: Isothioureas: Potent inhibitors of nitric oxide synthases with variable isoform selectivity. Br. J. Pharmacol. 114: 510-516, 1995b.
30. STUEHR, D. J., CHO, H. C., KWON, N. S., WEISE, M. F. AND NATHAN, C. F.: Purification and characterization of the cytokine-induced macrophage nitric oxide synthase: An FAD- and FMN-containing flavoprotein. Proc. Natl. Acad. Sci. USA 88: 7773-7777, 1991.
31. SZABO, C., SOUTHAN, G. J. AND THIEMERMANN, C.: Beneficial effects and improved survival in rodent models of septic shock treated with S-methylisothiourea sulfate, a potent and selective inhibitor of inducible nitric oxide synthase. Proc. Natl. Acad. Sci. USA 91: 12472-12476, 1994.
32. G-nitro-L-arginine in focal stroke in the 7-day old rat. Eur. J. Pharmacol. 218: 197-198, 1992.
33. 3 pituitary cells. Biochem. J. 284: 201-206, 1992.
34. WOLFF, D. J. AND GRIBIN, B. J.: γ-Interferon inducible murine macrophage nitric oxide synthase: Studies on the mechanism of inhibition by imidazole agents. Arch. Biochem. Biophys. 311: 293-299, 1994.
35. WOLFF, D. J., LUBESKIE, A. AND UMANSKY, S.: The inhibition of the constitutive bovine endothelial nitric oxide synthase by imidazole and indazole agents. Arch. Biochem. Biophys. 312: 360-366, 1994.
36. WOLFF, D. J. AND LUBESKIE, A.: Aminoguanidine is an isoform-selective, mechanism-based inactivator of nitric oxide synthase. Arch. Biochem. Biophys. 316: 290-301, 1995.
37. G-amino-L-arginine. Arch. Biochem. Biophys. 325: 227-234, 1996.
38. WOLFF, D. J., LUBESKIE, A. AND 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: 73-82, 1997.
39. Yu, L., GENGARO, P. E., NEIDERBERGER, N., BURKE, T. J. AND SCHRIER, D. E.: Nitric oxide: A mediator in rat tubular hypoxia/reoxygenation injury. Proc. Natl. Acad. Sci. USA 91: 1691-1695, 1994.