Reduction of organic nitrites to nitric oxide catalyzed by xanthine oxidase: Possible role in metabolism of nitrovasodilators

Biochemical and Biophysical Research Communications

Volumn 270, Issue 3, 2000, Pages 880-885

  Doel, Justin J ^a   Godber, Ben L J ^a   Goult, Tracey A ^a   Eisenthal, Robert ^a   Harrison, Roger ^a  

^a University of Bath   (United Kingdom)

Author keywords

Amyl nitrite; Butyl nitrite; Nitric oxide; Xanthine oxidase

Indexed keywords

AMYL NITRITE; NITRIC OXIDE; NITRITE; URATE; VASODILATOR AGENT; XANTHINE; XANTHINE OXIDASE;

ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; DRUG TOLERANCE; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; REDUCTION; STEADY STATE;

EID: 0034696803     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1006/bbrc.2000.2534     Document Type: Article

References (48)

1. Murrell W. Nitroglycerin as a remedy for angina pectoris. Lancet. i:1879;80-81.
2. Ahlner J., Andersson R. G. G., Torfgard K., Axelsson K. L. Organic nitrate esters: Clinical use and mechanisms of actions. Pharmacol. Rev. 43:1991;351-423.
3. Parker J. D., Parker J. O. Nitrate therapy for stable angina pectoris. New Engl. J. Med. 338:1998;520-531.
4. Brunton T. L. On the use of nitrite of amyl in angina pectoris. Lancet. ii:1867;97-98.
5. Lembo N. J., Dell-Italia L. J., Crawford M. H. Bedside diagnosis of systolic murmurs. New Engl. J. Med. 318:1988;1572-1578.
6. Holland M. A., Kozlowski L. M. Clinical features and management of cyanide poisoning. Clin. Pharmacol. 5:1986;737-741.
7. Sigell L. T., Kapp F. T., Nelson E. D., Falck R. S. Popping and snorting volatile nitrites: A current fad for getting high. Am. J. Psychiatry. 135:1978;1216-1218.
8. Goedert J. J. Recreational drugs: Relationship to AIDS. Ann. N.Y. Acad. Sci. 437:1984;192-199.
9. Haverkos H. W., Dougherty J. Health hazards of nitrite inhalants. Am. J. Med. 84:1988;479-482.
10. Bauer J. A., Fung H-L. Non-nitrate nitric oxide donors. J. Myocard. Isch. 7:1995;17-22.
11. Fung H. L., Chung S. J., Bauer J. A., Chong S., Kowaluk E. A. Biochemical mechanism of organic nitrate action. Am. J. Cardiol. 70:1992;4B-10B.
12. Harrison D. G., Bates J. N. The nitrovasodilators: new ideas about old drugs. Circulation. 87:1993;1461-1467.
13. Lau D. T., Benet L. Z. Differential formation of dinitrate metabolites from glyceryl trinitrate in subcellular fractions of rabbit liver. Biochem. Pharmacol. 38:1989;543-546.
14. Hill K. E., Hunt R. W., Jones R., Hoover R. C., Burk R. F. Metabolism of nitroglycerin by smooth muscle cells. Involvement of glutathione and glutathione-S-transferase. Biochem. Pharmacol. 43:1992;561-566.
15. 2 formation. Biochem. J. 292:1993;545-550.
16. Salvemini D., Pistelli A., Vane J. Conversion of glyceryl trinitrite to nitric oxide in tolerant and non-tolerant smooth muscle and endothelial cells. Br. J. Pharmacol. 108:1993;162-169.
17. Servent D., Delaforge M., Ducrocq C., Mansuy D., Lenfant M. Nitric oxide formation during microsomal hepatic denitration of glyceryl trinitrate: involvement of cytochrome P450. Biochem. Biophys. Res. Commun. 163:1989;1210-1216.
18. McDonald B. J., Bennett B. M. Cytochrome P-450 mediates biotransformation of organic nitrates. Can J. Physiol. Pharmacol. 68:1990;1552-1557.
19. Schroder H. Cytochrome P-450 mediates bioactivation of organic nitrates. J. Pharmacol. Exp. Ther. 262:1992;298-302.
20. Yuan R., Sumi M., Benet L. Z. Investigation of aortic CYP3A bioactivation of nitroglycerin in vivo. J. Pharmacol. Exp. Ther. 281:1997;1499-1505.
21. Chung S-J., Fung H-L. Identification of the subcellular site for nitroglycerin metabolism to nitric oxide in bovine coronary smooth muscle. J. Pharmacol. Exp. Ther. 253:1990;614-619.
22. Chung S-J., Fung H-L. Glutathione-S-transferase activity was not identical to nitric oxide-generating activity from nitroglycerin in microsomes of bovine smooth muscle cells. Pharm. Res. 7:1990;S-262.
23. Kowaluk E. A., Fung H-L. Vascular nitric oxide-generating activities for organic nitrates and nitrites are distinct. J. Pharmacol. Exp. Ther. 259:1991;519-525.
24. Bauer J. A., Nolan T., Fung H-L. Vascular and hemodynamic differences between organic nitrates and nitrites. J. Pharmacol. Exp. Ther. 280:1997;326-331.
25. Meyer D. J., Kramer H., Ketterer B. Human glutathione transferase catalysis of the formation of S-nitrosoglutathione from organic nitrites plus glutathione. FEBS Lett. 351:1994;427-428.
26. Ji Y., Akerboom T. P. M., Sies H. Microsomal formation of S-nitrosoglutathione from organic nitrites: possible role of membrane-bound glutathione transferase. Biochem. J. 313:1996;377-380.
27. Akerboom T. P. M., Ji Y., Wagner G., Sies H. Subunit specificity and organ distribution of glutathione transferase-catalysed S-nitrosoglutathione formation from alkyl nitrites in the rat. Biochem. Pharmacol. 53:1996;117-120.
28. Millar T. M., Stevens C. R., Benjamin N., Eisenthal R., Harrison R., Blake D. R. Xanthine oxidoreductase catalyses the reduction of nitrates and nitrite to nitric oxide under hypoxic conditions. FEBS Lett. 427:1998;225-228.
29. Bray R. C. Molybdenum iron-sulfur flavin hydroxylases and related enzymes. Boyer P. D. The Enzymes. 1975;299-419 Academic Press, New York.
30. Hille R. The mononuclear molybdenum enzymes. Chem. Rev. 96:1996;2757-2816.
31. McCord J. M. Oxygen-derived free radicals in post-ischemic tissue injury. New Engl. J. Med. 312:1975;159-163.
32. Bulkley G. B. Physiology of reactive oxidant-mediated signal transduction: An overview. Biochem. Soc. Trans. 25:1997;804-812.
33. Jarasch E-D., Grund C., Bruder G., Heid H. W., Keenan T. W., Franke W. W. Localization of xanthine oxidase in mammary gland epithelium and capillary endothelium. Cell. 25:1981;67-82.
34. Rouquette M., Page S., Bryant R., Benboubetra M., Stevens C. R., Blake D. R., Whish W. D., Harrison R., Tosh D. Xanthine oxidoreductase is asymmetrically localised on the outer surface of human endothelial and epithelial cells in culture. FEBS Lett. 426:1998;397-401.
35. Godber B. L. J., Doel J. J., Sapkota G. P., Blake D. R., Stevens C. R., Eisenthal R., Harrison R. Reduction of nitrite to nitric oxide catalysed by xanthine oxidoreductase. J. Biol. Chem., 2000.
36. Massey V., Komai H., Palmer G., Elion G. On the mechanism of inactivation of xanthine oxidase by allopurinol and other pyraxolo[3,4-d]-pyrimidines. J. Biol. Chem. 245:1970;2837-2844.
37. Avis P. G., Bergel F., Bray R. C. Cellular constituents. The chemistry of xanthine oxidase. Part III. Estimations of the co-factors and the catalytic activities of enzyme fractions from cow's milk. J. Chem. Soc., 1956;1219-1226.
38. Wahl R. C., Rajagopalan K. V. Evidence for the inorganic nature of the cyanolyzable sulfur of molybdenum hydroxylases. J. Biol. Chem. 257:1982;1354-1359.
39. Ichimori K., Fukahori M., Nakazawa H., Okamoto K., Nishino T. Inhibition of xanthine oxidase and xanthine dehydrogenase by nitric oxide. J. Biol. Chem. 274:1999;7763-7768.
40. Feelisch M., Brands F., Kelm M. Human endothelial cells bioactivate organic nitrates to nitric oxide: Implications for the reinforcement of endothelial defence mechanisms. Eur. J. Clin. Invest. 25:1995;737-745.
41. Kooij A., Schiller H. J., Schijns M., Van Noorden C. J. F., Frederiks W. M. Conversion of xanthine dehydrogenase into xanthine oxidase in rat liver and plasma at the onset of reperfusion after ischemia. Hepatology. 19:1994;1488-1491.
42. Radi R., Rubbo H., Bush K., Freeman B. A. Xanthine oxidase binding to glycosaminoglycans: kinetics and superoxide dismutase interactions of immobilized xanthine oxidase-heparin complexes. Arch. Biochem. Biophys. 339:1997;125-135.
43. Munzel T., Harrison D. G. Evidence for a role of oxygen-derived free radicals and protein kinase C in nitrate tolerance. J. Mol. Med. 75:1997;891-900.
44. Abrams J., Elkayam U., Thadani U., Fung H-L. Tolerance: Historical overview. Am. J. Cardiol. 81:1998;3A-14A.
45. Hinz B., Schroeder H. Nitrate tolerance is specific for nitric acid esters and its recovery requires an intact protein synthesis. Biochem. Biophys. Res. Commun. 252:1998;232-235.
46. 1 cells. Pharmaceut. Res. 16:1999;633-636.
47. Kojda G., Patzner M., Hacker A., Noack E. Nitric oxide inhibits vascular bioactivation of glyceryl trinitrate: A novel mechanism to explain preferential venodilation of organic nitrates. Mol. Pharmacol. 53:1998;547-554.
48. Hasegawa K., Taniguchi T., Takakura K., Goto Y., Muramatsu I. Possible involvement of nitroglycerin converting step in nitroglycerin tolerance. Life Sci. 64:1999;2199-2206.