Metabolism of 14C-labelled 5-nitro-1,2,4-triazol-3-one by rat liver microsomes: Evidence for the participation of cytochrome P-450

European Journal of Biochemistry

Volumn 248, Issue 2, 1997, Pages 401-406

  Le Campion, Laurence ^a   Delaforge, Marcel ^b   Noel, J Pierre ^c   Ouazzani, Jamal ^a  

^a CNRS   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

^c DIF   (France)

Author keywords

Cytochrome P 450; Denitrification; Dexamethasone; Nitroreductase; Nitrotriazolone

Indexed keywords

CYTOCHROME P450; DEXAMETHASONE; DRUG METABOLITE; EXPLOSIVE; NITROREDUCTASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; 3 METHYLCHOLANTHRENE; 5 NITRO 1,2,4 TRIAZOL 3 ONE; 5-NITRO-1,2,4-TRIAZOL-3-ONE; CARBON; CLOFIBRATE; FUNGAL PROTEIN; GLUCOCORTICOID; NITRO DERIVATIVE; PHENOBARBITAL; TRIAZOLE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DENITRIFICATION; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; ISOTOPE LABELING; LIVER METABOLISM; LIVER MICROSOME; MALE; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; RAT; ANIMAL; DRUG EFFECT; METABOLISM; OXIDATION REDUCTION REACTION; SPRAGUE DAWLEY RAT; SYNTHESIS;

ANIMALIA; MURINAE;

ANIMALS; CARBON RADIOISOTOPES; CLOFIBRATE; CYTOCHROME P-450 ENZYME SYSTEM; DEXAMETHASONE; FUNGAL PROTEINS; GLUCOCORTICOIDS; MALE; METHYLCHOLANTHRENE; MICROSOMES, LIVER; NITRO COMPOUNDS; OXIDATION-REDUCTION; PHENOBARBITAL; RATS; RATS, SPRAGUE-DAWLEY; TRIAZOLES;

EID: 0030613556     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00401.x     Document Type: Article

References (35)

1. Chipen, G. I., Bokalder, R. P. & Grinshtein, V. Y. (1966) 1,2,4-Triazol-3-one and its nitro and amino derivatives, Khim. Geterotsikl. Soedin. 2, 110.
2. Becuwe, A. & Delclos, A. (1987) Hydroxynitrotriazole and its use as an insensitive explosive, Int. Jahrestag.-Fraunhofer-Inst. Treib-Explosivst. Technol. Energ. Mater.
3. Becuwe, A. & Delclos, A. (1993) Low-sensitivity explosive compounds for low vulnerability warheads. Propellants, Explosives, Pyrotechnics 18, 1-10.
4. Sublette, K. L., Ganapathy, E. V. & Schwartz, S. (1992) Degradation of munition wastes by Phanerochaete chrysosporium, Appl. Biochem. Biotechnol. 34-35, 709-723.
5. Nikolic, S., Medic-Saric, M., Rendic, S. & Trinajstic, N. (1994) Toxic effects and a structure-property study of organic explosives, propellants, and related compounds, Drug Metab. Rev. 26, 717-738.
6. Von Oettigen, W. F., Donahue, D. D., Yagoda, H., Monaco, A. R. & Harris, M. R. (1949) Toxicity and potential dangers of cyclotrimethylene trinitramine (RDX), J. Ind. Hyg. Toxicol. 31, 21-31.
7. Lee, K. Y., Chapman, L. B. & Coburn, M. D. (1987) 3-Nitro-1,2,4-triazol-5-one, a less sensitive explosive, J. Energ. Mat. 2, 27.
8. Won, W. D., DiSalo, L. H. & Ng, J. (1976) Toxicity and mutagenicity of 2,4,6-trinitrotoluene and its microbial metabolites, Appl. Environ. Microbiol. 31, 576-580.
9. Schneider, N. R., Sharon, L. B. & Andersen, M. E. (1977) Toxicology of cyclotrimethylenetrinitramine: distribution and metabolism in rat and the miniature swine, Toxicol. Appl. Pharmacol. 39, 531-541.
10. McCoy, E. C., Rosenkranz, H. S. & Mermelstein, R. (1981) Evidence for the existence of a family of bacterial nitroreductases capable of activating nitrated polycyclics to mutagens, Environ. Mutagen. 3, 421-427.
11. Walton, M. I. & Workman, P. (1987) Nitroimidazole bioreductive metabolism - Quantification and characterisation of mouse tissue benznidazole nitroreductases in vivo and in vitro, Biochem. Pharmacol. 36, 887-896.
12. Koch, R. L., Chrystal, E. J. T., Beaulieu, B. B. & Goldman, P. Jr (1979), Acetamide - a metabolite of metronidazole formed by the intestinal flora, Biochem. Pharmacol. 28, 3611-3615.
13. Kohl, C., Morgan, P. & Gescher, A. (1995) Metabolism of the genotoxicant 2-nitropropane to nitric oxide species, Chem. Biol. Interact. 97, 175-184.
14. Feller, D. R., Morita, M. & Gillette, J. R. (1971) Enzymatic reduction of niridazole by rat liver microsomes, Biochem. Pharmacol. 20, 203-215.
15. Saito, K., Kamataki, T. & Kato, R. (1984) Participation of cytochrome P-450 in reductive metabolism of 1-nitropyrene by rat liver microsomes, Cancer Res. 44, 3169-3173.
16. Hewick, D. S. (1982) Reductive metabolism of nitrogen-containing functional groups, in Metabolic basis of detoxication (Jakoby, W. B., Bend, J. R. & Caldwell, J., eds) pp. 151, Academic Press, New York.
17. Tatsumi, K., Kitamura, S. & Narai, N. (1986) Reductive metabolism of aromatic nitro compounds including carcinogens by rabbit liver preparations, Cancer Res. 46, 1089-1093.
18. Wolpert, M. K., Althaus, J. R. & Johns, D. G. (1973) Nitroreductase activity of mammalian liver aldehyde oxidase, J. Pharmacol. Exp. Therapeut. 185, 202-213.
19. Kröger, C. F., Miethchen, R., Frank, H., Siemer, M. & Pilz, S. (1969) Die Nitrierung und Bromierung von 1,2,4-Triazolonen, Chem. Ber. 102, 755-766.
20. 14C-formate, J. Labelled Compds. Radio. Pharm. 23, 677.
21. 14C-3) (ST1118), J. Labelled Compds 22, 95.
22. Kremers, P., Beaune, Ph., Cresteil, T., De Graeve, J., Columelli, S., Leroux, J. P. & Gielen, J. (1981) Cytochrome P-450 monooxygenases activity in human and rat liver microsomes, Eur. J. Biochem. 118, 599-606.
23. 5. Eur. J. Biochem. 207, 109-116.
24. Le Campion, L., Adeline, M. T. & Ouazzani, J. (1997) Separation of NTO-related 1,2,4-triazole-3-one derivatives by high performance liquid chromatography and capillary electrophoresis, Propellants, Explosives, Pyrotechnics, in the press.
25. Buzukov, A. A., Il'asova, V. B., Tabak, M. Meirelles, N. C. & Degterev, I. A. (1996) An ESR and spectrophotometric study of the denitration of nitroheterocyclic drugs by liver homogenates and their metabolic consumption by liver microsomes from cytochrome P-450-induced mice, Chem. Biol. Interact. 100, 113-124.
26. Raha, C., Hart-Anstey, M., Cheung, M.-S. & Bresnick, E. (1986) 6-Nitrobenzo[a]pyrene can be denitrated during mammalian metabolism, J. Toxicol. Environ. Health 19, 55-64.
27. Dalke, C. & Andrae, U. (1992) Propane 2-nitronate is more rapidly denitrified and is more genotoxic than 2-nitropropane in cultured rat hepatoma cells, Toxicol. Lett. 61, 149-157.
28. Dayal, R., Goodwin, B., Linhart, I., Mynett, K. & Gescher, A. (1991) Oxidative denitrification of 2-nitropropane and propane-2-nitronate by mouse liver microsomes: lack of correlation with hepatocytotoxic potential, Chem.-Biol. Interact. 79, 103-114.
29. Degterev, I. A., Tatarskaya. N. K. & Zaikov, G. E. (1989) Spectral investigation of the mechanism of biological transformation of quinifuryl, Pharm. Chem. J. 23, 664-667.
30. Delaforge, M., Sevent, D., Wirsta, P., Ducrocq, C., Mansuy, D. & Lenfant, M. (1993) Particular ability of cytochrome P-450 CYP3A to reduce glyceryl trinitrate in rat liver microsomes: subsequent formation of nitric oxide, Chem.-Biol. Interact. 86, 103-117.
31. Degterev, I. A., Buzukov, A. A., Sharf, V. G., Popov, K. N., Serebriyaniy, A. M. & Zaikov, G. E. (1986) Comparative study of the ledacrine metabolism in vitro in microsomes of Erlich's ascites carcinoma cells and mouse liver cells, Pharm. Chem. J. 20, 412-416.
32. Myers, L. A., Witmer, C. M. & Gallo, M. A. (1988) Characterization and identification of an indirect cytochrome P-450-initiated denitrosation of 2,6-dichloro-4-nitroaniline in rat hepatic microsomes, Toxicol. Appl. Pharmacol. 95, 139-152.
33. Ohshima, H. & Bartsch, H. (1994) Chronic infections and inflammatory processes as cancer risk factors: possible role of nitric oxide in carcinogenesis, Mut. Res. 305, 253-264.
34. Orna, M. V. & Mason, R. P. (1988) Correlation of kinetic parameters of nitroreductase enzymes with redox properties of nitroaromatic compounds, J. Biol. Chem. 264, 12 379-12 384.
35. Aufrere, M. B., Hoemer, B.-A. & Vore, M. (1978) Reductive metabolism of nitrofurantoin in the rat, Am. Soc. Pharmacol. Exp. Therapeut. 6, 403-411.