Microbial models of mammalian metabolism: Involvement of cytochrome P450 in the N-demethylation of N-methylcarbazole by Cunningham ella echin ula ta

References

• Augusto O., Boilan H. S., Ortiz De Montellano P. R. The catalytic mechanism of cytochrome P-450. Journal of Biological Chemistry 1982; 257: 11288–11295
   PubMed Web of Science ®Google Scholar
• Auret B. J., Boyd D. R., Robinson P. M., Watson C. G., Dale J. W., Jerina D. M. The NIH shift during the hydroxylation of aromatic substances by fungi. Journal of the Chemical Society 1971; 24: 1585–1587, Chemical Communications
   Google Scholar
• Cerniglia C. E., Althaus J. R., Evans F. E., Freeman J. P., Mitchum R. K., Yang S. K. Sereochemistry and evidence for an arene oxide-NIH shift pathway in the fungal metabolism of naphthalene. Chemico-Biological Interactions 1983; 44: 119–132
   PubMed Web of Science ®Google Scholar
• Davis D. J., Glade J. C., Clark A. M., Smith R. V. N-demethylation by lergotrile by Streptomyces platensis. Applied and Environmental Microbiology 1979; 38: 891–893
   PubMed Web of Science ®Google Scholar
• Ferris J. P., Fasco M. J., Stylianopolou F. L., Jerina D. M., Daly J. W., Jeffrey A. M. Monooxygenase activity in Cunninghamella bainieri: evidence for a fungal system similar to liver microsomes. Archives of Biochemistry and Biophysics 1973; 156: 97–103
   PubMed Web of Science ®Google Scholar
• Ferris J. P., Macdonald L. H., Patrie M. A., Martin M. A. Aryl hydrocarbon hydroxylase activity in the fungus Cunninghamella bainieri: evidence for the presence of cytochrome P-450. Archives of Biochemistry and Biophysics 1976; 175: 443–452
   PubMed Web of Science ®Google Scholar
• Gibson M., Scoper C. J., Parfitt R. T., Sewell G. J. Studies on the mechanism of microbial N-demethylation of codeine by cell-free extracts of Cunninghamella bainieri. Enzyme and Microbial Technology 1984; 6: 471–475
   Google Scholar
• Griffin B. W., Ting P. L. Mechanism of N-demethylation of aminopyrine by hydrogen peroxide catalyzed by horseradish peroxidase, metmyoglobin, and protohemin. Biochemistry 1978; 17: 2206–2211
   PubMed Web of Science ®Google Scholar
• Guengerich F. P. Oxidative cleavage of carboxylic esters by cytochrome P-450. Journal of Biological Chemistry 1987; 262: 8459–8462
   PubMed Web of Science ®Google Scholar
• Hanzlik R. P., Tullman R. H. Suicidal inactivation of cytochrome P-450 by cyclopropy lamines: evidence for cation-radical intermediates. Journal of the American Chemical Society 1982; 104: 2048–2050
   Web of Science ®Google Scholar
• Hollenberg P. F. Mechanisms of cytochrome P450 and peroxidase-catalyzed xenobiotic metabolism. FASEB Journal 1992; 6: 686–694
   PubMed Web of Science ®Google Scholar
• Hufford C. D., Capiton G. A., Clark A. M., Baker J. K. Metabolism of imipramine by microorganisms. Journal of Pharmaceutical Science 1981; 70: 151–157
   PubMed Web of Science ®Google Scholar
• Kedderis G. L., Dwyer L. A., Richert D. E., Hollenberg P. F. Source of the oxygen atom in the product of cytochrome P-450-catalyzed N-demethylation reactions. Molecular Pharmacology 1983; 23: 758–760
   PubMed Web of Science ®Google Scholar
• Kedderis G. L., Rickert D. E., Pandey R. N., Hollenberg P. F. 18O studies of the peroxidase-catalyzed oxidation of N-methycarbazole. Journal of Biological Chemistry 1986; 261: 15910–15914
   PubMed Web of Science ®Google Scholar
• Koop D. R., Hollenberg P. F. Liver microsomal metabolism of N-methycarbozole: a probe for induction, inhibition, and species differences. Molecular Pharmacology 1980a; 17: 118–127
   PubMed Web of Science ®Google Scholar
• Koop D. R., Hollenberg P. F. Kinetics of the hydroperoxide-dependent dealkylation reaction catalyzed by rabbit liver microsomal cytochrome P-450. Journal of Biological Chemistry 1980b; 255: 9685–9692
   PubMed Web of Science ®Google Scholar
• Matsubara T., Rouchi A. Hepatic aminopyrine N-demethylase system: effect of cyanide on microsomal N-demethylase activity. Japanese Journal of Pharmacology 1977; 27: 701–708
   PubMedGoogle Scholar
• Miwa G. T., Walsh J. S., Kedderis G. L., Hollenberg P. F. The use of intramolecular isotope effects to distinguish between deprotonation and hydrogen atom abstraction mechanisms in cytochrome P-450- and peroxidase-catalyzed N-demethylation reactions. Journal of Biological Chemistry 1983; 258: 14445–14449
   PubMed Web of Science ®Google Scholar
• Nash T. The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochemical Journal 1953; 55: 416–421
   PubMed Web of Science ®Google Scholar
• Novak R. F., Koop D. R., Hollenberg P. F. Liver microsomal metabolism of N methycarbazole: structural identification of the four major metabolites of N-methylcarbazole using 1H fourier transform NMR spectroscopy. Molecular Pharmacology 1980; 17: 128–136
   PubMed Web of Science ®Google Scholar
• Orrenius S. On the mechanism of drug hydroxylation in rat liver microsomes. Journal of Cell Biology 1965; 26: 713–723
   PubMed Web of Science ®Google Scholar
• Rizzo J., Davies P. J. Microbial models of mammalian metabolism: conversion of warfarin to 4′-hydroxywarfarin using Cunninghamella bainieri. Journal of Pharmaceutical Sciences 1989; 78: 183–188
   PubMedGoogle Scholar
• Rose J., Castagnoli N. The metabolism of tertiary amines. Medicinal Research Review 1983; 3: 73–88
   PubMed Web of Science ®Google Scholar
• Selader H. G., Jerina D. M., Daly J. W. Metabolism of acetanilide with hepatic microsomes and reconstituted cytochrome monoxygenase system. Archives of Biochemistry and Biophysics 1974; 164: 241–246
   PubMedGoogle Scholar
• Shea J. P., Valentine G. L., Nelson S. D. Source of oxygen in cytochrome P-450 catalyzed carbinolamine formation. Biochemistry and Biophysics Research Communication 1982; 109: 231–235
   PubMedGoogle Scholar
• Shoun H., Sudo Y., Seto Y., Beppu T. Purification and properties of a cytochrome P-450 of a fungus Fusarium oxysporum. Journal of Biochemistry 1983; 94: 1219–1229
   PubMed Web of Science ®Google Scholar
• Smith R. V., Davis P. J. Induction of xenobiotic monooxygenases. Advances in Biochemical Engineering 1978; 4: 61–100
   Google Scholar
• Smith R. V., Davis P. J., Clark A. M., Prasatik S. K. Mechanism of biphenyl hydroxylation by Cunninghamella elegans. Biochemical Journal 1981; 196: 369–371
   PubMed Web of Science ®Google Scholar
• Yang W., Davis P. J. Microbial models of mammalian metabolism: biotransformation of N-methylcarbazole using the fungus Cunninghamella echinulata. Drug Metabolism Disposition 1992; 20: 38–46
   PubMed Web of Science ®Google Scholar
• Yang W., Jiang T., Acosta D., Davis P. J. Production of a toxic, novel mammalian metabolite of N-methylcarbazole predicted by a fungal cell model of mammalian metabolism. Toxicology Letters 1992; 60: 307–314
   PubMed Web of Science ®Google Scholar
• Yang W., Jiang T., Davis P. J., Acosta D. In vitro metabolism and toxicology assessment of N-methylcarbazole in primary cultured rat hepatocytes. Toxicology 1991; 68: 217–226
   PubMed Web of Science ®Google Scholar