Characterization of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one as a heme-site inhibitor of nitric oxide-sensitive guanylyl cyclase

Molecular Pharmacology

Volumn 50, Issue 1, 1996, Pages 1-5

  Schrammel, Astrid ^a   Behrends, Sönke ^b   Schmidt, Kurt ^a   Koesling, Doris ^b   Mayer, Bernd ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1H 1,2,4 OXADIAZOLO[4,3 A]QUINOXALIN 1 ONE; 2,2 DIETHYL 1 NITROSO OXYHYDRAZINE; CYCLIC GMP; FERRIC ION; FERROUS ION; GUANYLATE CYCLASE; HEME; NITRIC OXIDE; NITROSO DERIVATIVE; QUINOXALINE DERIVATIVE; S NITROSOGLUTATHIONE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ANIMAL CELL; ARTICLE; BINDING SITE; CONTROLLED STUDY; DRUG BINDING; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME INHIBITION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SIGNAL TRANSDUCTION;

ANIMALS; BINDING SITES; CATTLE; ENZYME INHIBITORS; GUANYLATE CYCLASE; HEME; KINETICS; LUNG; NITRIC OXIDE; OXADIAZOLES; QUINOXALINES; SPECTROPHOTOMETRY;

EID: 0029938767     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Moncada, S., R. M. J. Palmer, and E. A. Higgs. Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 43:109-142 (1991).
2. Garthwaite, J. Neural nitric oxide signalling. Trends Neurosci. 18:51-52 (1995).
3. Waldman, S., and F. Murad. Cyclic GMP synthesis and function. Pharmacol. Rev. 39:163-195 (1987).
4. Ignarro, L. J. Heme-dependent activation of guanylate cyclase by nitric oxide: a novel signal transduction mechanism. Blood Vessels 28:67-73 (1991).
5. Koesling, D., E. BÖhme, and G. Schultz. Guanylyl cyclases, a growing family of signal transducing enzymes. FASEB J. 5:2785-2791 (1991).
6. Schulz, S., P. S. T. Yuen, and D. L. Garbers. The expanding family of guanylyl cyclases. Trends Pharmacol. Sci. 12:116-120 (1991).
7. Gerzer, R., E. Böhme, F. Hofmann, and G. Schultz. Soluble guanylate cyclase purified from bovine lung contains heme and copper. FEBS Lett. 132:71-74 (1981).
8. Ignarro, L. J., J. N. Degnan, W. H. Baricos, P. J. Kadowitz, and M. S. Wolin. Activation of purified guanylate cyclase by nitric oxide requires heme: comparison of heme-deficient, heme-reconstituted and heme-containing forms of soluble enzyme from bovine lung. Biochim. Biophys. Acta 718:49-59 (1982).
9. 1 subunit yields a nitric oxide-insensitive form of soluble guanylyl cyclase. Proc. Natl. Acad. Sci. USA 91:2592-2596 (1994).
10. Stone, J. R., and M. A. Marletta. Soluble guanylate cyclase from bovine lung: activation with nitric oxide and carbon monoxide and spectral characterization of the ferrous and ferric states. Biochemistry 33:5636-5640 (1994).
11. Stone, J. R., R. H. Sands, W. R. Dunham, and M. A. Marletta. Electron paramagnetic resonance spectral evidence for the formation of a pentacoordinate nitrosyl-heme complex on soluble guanylate cyclase. Biochem. Biophys. Res. Commun. 207:572-577 (1995).
12. Yu, A. E., S. Z. Hu, T. G. Spiro, and J. N. Burstyn. Resonance raman spectroscopy of soluble guanylyl cyclase reveals displacement of distal and proximal heme ligands by NO. J. Am. Chem. Soc. 116:4117-4118 (1994).
13. Burstyn, J. N., A. E. Yu, E. A. Dierks, B. K. Hawkins, and J. H. Dawson. Studies of the heme coordination and ligand binding properties of soluble guanylyl cyclase (sGC): characterization of Fe(II)sGC and Fe(II)sGC(CO) by electronic absorption and magnetic circular dichroism spectroscopies and failure of CO to activate the enzyme. Biochemistry 34:5896-5903 (1995).
14. Traylor, T. G., and V. S. Sharma. Why NO? Biochemistry 31:2847-2849 (1992).
15. Stone, J. R., and M. A. Marletta. Heme stoichiometry of heterodimeric soluble guanylate cyclase. Biochemistry 34:14668-14674 (1995).
16. Mayer, B., F. Brunner, and K. Schmidt. Inhibition of nitric oxide synthesis by methylene blue. Biochem. Pharmacol. 45:367-374 (1993).
17. Luo, D., S. Das, and S. R. Vincent. Effects of methylene blue and LY83583 on neuronal nitric oxide synthase and NADPH-diaphorase. Eur. J. Pharmacol. 290:247-251 (1995).
18. Garthwaite, J., E. Southam, C. L. Boulton, E. B. Nielsen, K. Schmidt, and B. Mayer. Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one. Mol. Pharmacol. 48:184-188 (1995).
19. Brunner, F., H. Stessel, and W. R. Kukovetz. Novel guanylyl cyclase inhibitor, ODQ reveals role of nitric oxide, but not of cyclic GMP in endothelin-1 secretion. FEBS Lett. 376:262-266 (1995).
20. Brunner, F., K. Schmidt, E. B. Nielsen, and B. Mayer. Novel guanylyl cyclase inhibitor potently inhibits cyclic GMP accumulation in endothelial cells and relaxation of bovine pulmonary artery. J. Pharmacol. Exp. Ther. 277:48-53 (1996).
21. Humbert, P., F. Niroomand, G. Fischer, B. Mayer, D. Koesling, K.-D. Hinsch, G. Schultz, and E. Böhme. Preparation of soluble guanylyl cyclase from bovine lung by immunoaffinity chromatography. Methods Enzymol. 195:384-391 (1991).
22. Schultz, G., and E. Böhme. Guanylate cyclase. GTP pyrophosphate-lyase (cyclizing), E.C. 4.6.1.2., in Methods of Enzymatic Analysis (H. U. Bergmeyer, J. Bergmeyer, and M. Graßl, eds.). Verlag Chemie, Weinheim, Germany, 379-389 (1984).