Nitric oxide (NO)-releasing pathway of FK409 in the presence of sulfhydryl-bearing compounds

Pharmaceutical Research

Volumn 13, Issue 8, 1996, Pages 1238-1242

  Fukuyama, Shinichi ^a   Azuma, Toshio ^a   Hirasawa, Yoshimi ^a   Morokoshi, Noritugu ^a   Akama, Toshihiro ^a   Koda, Shigetaka ^a   Kita, Yasuhiro ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

FK409; Glutathione; L cysteine; Nitric oxide

Indexed keywords

4 ETHYL 2 HYDROXYIMINO 5 NITRO 3 HEXENAMIDE; CYSTEINE; GLUTATHIONE; NITRIC OXIDE; THIOL GROUP;

ARTICLE; DRUG DEGRADATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PRIORITY JOURNAL;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; NITRIC OXIDE; NITRO COMPOUNDS; PLATELET AGGREGATION INHIBITORS; SULFHYDRYL COMPOUNDS; VASODILATOR AGENTS;

EID: 0029764149     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1016076623060     Document Type: Article

References (15)

1. M. Hino, M. Iwami, M. Okamoto, K. Yoshida, H. Haruta, M. Okuhara, J. Hosoda, M. Kohsaka, H. Aoki, and H. Imanaka. FK409, a novel vasodilator isolated from the acid-treated fermentation broth of Streptomyces griseosporeus. I. Taxonomy, fermentation, isolation and physico-chemical and biological characteristics. J. Antibiotics, 42:1578-1583 (1989).
2. Y. Kita, T. Sugimoto, Y. Hirasawa, K. Yoshida and K. Maeda. Close correlation of the cardioprotective effect of FK409, a spontaneous NO releaser, with an increase in plasma cyclic GMP level. Br. J. Pharmacol., 113:5-6 (1994).
3. K. D. Schultz, K. Schultz and G. Schultz. Sodium nitroprusside and other smooth muscle-relaxants increase cyclic GMP levels in rat ductus deferons. Nature, 265:750-751 (1977).
4. Y. Kita, Y. Hirasawa, K. Maeda, M. Nishio and K. Yoshida. Spontaneous nitric oxide release accounts for the potent pharmacological actions of FK409. Eur. J. Pharmacol. 257:123-130 (1994).
5. S. Fukuyama, Y. Hirasawa, D. Cox, S. Koda and Y. Kita. Acceleration of nitric oxide (NO) release from FK409, a spontaneous NO releaser, in the presence of sulfhydryl-bearing compounds. Pharm. Res. 12:1948-1952 (1995).
6. M. Feelisch and E. Noack. Correlation between nitric oxide formation during degradation of organic nitrates and activation of guanylate cyclase. Eur. J. Pharmacol. 139:19-30 (1987).
7. M. Feelisch. The biochemical pathways of nitric oxide formation from nitrovasodilators: appropriate choice of exogenous NO donors and aspects of preparation and handling of aqueous NO solution. J. Cardiovasc. Pharmacol. 17 (Suppl.3):S25-S33 (1991).
8. S. Fukuyama, Y. Kita, Y. Hirasawa, T. Azuma, A. Sato, Y. Morokoshi, S. Koda, T. Yasuda, S. Oka and H. Sakurai. A new nitric oxide (NO) releaser: spontaneous NO release from FK409. Free Rad. Res., 23:443-452 (1995).
9. G. L. Ellman. A colorimetric method for determining low concentrations of mercaptans. Arch. Biochem. Biophys. 74:443-450 (1958).
10. Y. Kita, S. Fukuyama and Y. Hirasawa. Close correlation between NO formation from and biological activities of NO releasers in rats. Jpn. J. Pharmacol. 69:69-74 (1995).
11. J. S. Stamler, D. I. Simon, J. A. Osborne, M. E. Mullins, O. Jaraki, T. Michel, D. J. Singel and J. Loscalzo. S-nitrosylation of proteins by nitric oxide: synthesis and characterization of novel biologically active compounds. Proc. Natl. Acad. Sci. USA. 89:444-448 (1991).
12. L. J. Ignarro, H. Lippton, J. C. Edwards, W. H. Baricos, A. L. Hyman, P. J. Kadowitz and C. A. Gruetter. Mechanism of vascular smooth muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric oxide: evidence for the involvement of S-nitrosothiols as active intermediates. J. Pharmacol. Exp. Ther. 218:739-749 (1981).
13. W. A. Pryor, D. F. Church, C. K. Govindan and G. Crank. Oxidation of thiols by nitric oxide and nitrogen dioxide: synthetic utility and toxicological implications. J. Org. Chem., 47:156-159 (1982).
14. J. F. Keaney, D. I. Simon, J. S. Stamler, O. Jaraki, J. Scharfstein, J. A. Vita and J. Loscalzo. NO forms an adduct with serum albumin that has endothelium-derived relaxing factor-like properties. J. Clin. Invest. 91:1582-1589 (1993).
15. P. R. Myers, R. L. Minor Jr., R. Guerra Jr., J. N. Bates and D. G. Harrison. Vasorelaxant properties of the endothelium-derived relaxing factor more closely resemble S-nitrosocysteine than nitric oxide. Nature 345:161-163 (1990).