Diastereospecific kinetics of nicotine N-oxidation in rat liver microsomes

References

• BECKETT, A. H., GORROD, J. W. and JENNER, P., 1971, The analysis of nicotine-1 '-N-oxide in urine, in the presence of nicotine and cotinine, and its application to the study of in vivo nicotine metabolism in man. Journal of Pharmacy and Pharmacology, 23, 55S–61S.
   Google Scholar
• BECKETT, A. H., JENNER, P. and GORROD, J. W., 1973, Characterization of diastereoisomers of nicotine-V-N-oxide, a metabolite of nicotine, and other possible oxidation products by nuclear magnetic resonance spectroscopy. Xenobiotica, 3, 557–562.
   PubMed Web of Science ®Google Scholar
• BOOTH, J. and BOYLAND, E., 1970, The metabolism of nicotine into two optically-active stereoisomers of nicotine-1'-oxide by animal tissues in vitro and by cigarette smokers. Biochemical Pharmacology, 19, 733–742.
   PubMed Web of Science ®Google Scholar
• CASHMAN, J. R., PARK, S. B., YANG, Z.-C., WRIGHTON S. A., JACOB, P. III and BENOWITZ, N. L., 1992, Metabolism of nicotine by human liver microsomes: stereoselective formation of trans-nicotine N'-oxide. Chemical Research in Toxicology, 5, 639–646.
   Google Scholar
• CASHMAN, J. R., PARK, S. B., BERKMAN, C. E. and CASHMAN, L. E., 1995, Role of hepatic flavin-containing monooxygenase 3 in drug and chemical metabolism in adult humans. Chemico-Biological Interactions, 96, 33–46.
   PubMed Web of Science ®Google Scholar
• DAJANI, R. M., GORROD, J. W. and BECKETT, A. H., 1972, Hepatic and extrahepatic reduction of nicotine V-N-oxide in rats. Biochemical Journal, 130, 88p.
   Google Scholar
• DAMANI, L. A., PooL, W. F., CROOKS, P. A., KADERLIK, R. K. and ZIEGLER, D. M., 1988, Stereo-selectivity in the N'-oxidation of nicotine isomers by flavin-containing monooxygenase. Molecular Pharmacology, 33, 702–705.
   PubMed Web of Science ®Google Scholar
• GOLD, M. S. and ZIEGLER, D. M., 1973, Dimethylaniline N-oxidase and aminopyrine N-demethylase activities of human liver tissue. Xenobiotica, 3, 179–189.
   PubMed Web of Science ®Google Scholar
• GORROD, J. W. and JENNER, P., 1975, The metabolism of tobacco alkaloids. Essays in Toxicology, 6, 35–78.
   Google Scholar
• GORROD, J. W., JENNER, P., KEYSELL, G. and BECKETT, A. H., 1971, Selective inhibition of alternative oxidative pathways of nicotine metabolism. Chemko-Biological Interactions, 3, 269–270.
   PubMed Web of Science ®Google Scholar
• HIS, R. N., CASHMAN, J. R., PHILPOT, R. M., WILLIAMS, D. E. and ZIEGLER, D. M., 1994, The mammalian flavin-containing monooxygenases : molecular characterization and regulation of expression. Toxicology and Applied Pharmacology, 125, 1–6.
   PubMedGoogle Scholar
• FROH, K., KITAMURA, T., YOKOI, T., Frox, S. and KAMATAKI, T., 1993, Rat liver flavin-containing monooxygenase (FMO): cDNA cloning and expression in yeast. Biochimica et Biophisica Acta, 1173, 165–171.
   PubMedGoogle Scholar
• JENNER, P., GORROD, J. W. and BECKETT, A. H., 1973a, Factors affecting the in vitro metabolism of R-(+)- and S-( — )-nicotine by guinea pig liver preparations. Xenobiotica, 3, 563–572.
   PubMed Web of Science ®Google Scholar
• JENNER, P., GORROD, J. W. and BECKETT, A. H., 1973b, Species variation in the metabolism of R-( + )-and S-( — )-nicotine by a-C- and N-oxidation in vitro. Xenobiotica, 3, 573–580.
   PubMed Web of Science ®Google Scholar
• JENNER, P., GORROD, J. W. and BECKETT, A. H., 1973c, The absorption of nicotine-V-N-oxide and its reduction in the gastro-intestinal tract in man. Xenobiotica, 3, 341–349.
   PubMed Web of Science ®Google Scholar
• KAMATAKI, T. and KITAGAWA, H., 1974, Effects of lyophilization and storage of rat liver microsomes on activity of aniline hydroxylase, contents of cytochrome b., and cytochrome P-450 and aniline-induced P-450 difference spectrum. Japanese Journal of Pharmacology, 24, 195–203.
   PubMedGoogle Scholar
• KYEREMATEN, G. A., MORGAN, M., WARNER, G., MARTIN, L. F. and VESELL, E. S., 1990, Metabolism of nicotine by hepatocytes. Biochemical Pharmacology, 40, 1747–1756.
   PubMedGoogle Scholar
• LOWRY, O. H., ROSENBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   PubMed Web of Science ®Google Scholar
• NAKAYAMA, H., 1988, Nicotine metabolism in mammals. Drug Metabolism and Drug Interactions, 6, 95–122.
   PubMedGoogle Scholar
• PARK, S. B., JACOB, P. III, BENOWITZ, N. L. and CASHMAN, J. R., 1993, Stereoselective metabolism of (S)-(— )-nicotine in humans: formation of trans-(S)-(— )-nicotine N-1'-oxide. Chemical Research in Toxicology, 6, 880–888.
   PubMed Web of Science ®Google Scholar
• PAPADOPOULOS, N. M., 1964, Nicotine-1'-oxide: a metabolite of nicotine in animal tissues. Archives of Biochemistry and Biophysics, 106, 182–185.
   PubMedGoogle Scholar
• PAPADOPOULOS, N. M. and KINTZIOS, J. A., 1963, Formation of metabolites from nicotine by a rabbit liver preparation. Journal of Pharmacology and Experimental Therapeutics, 140, 269–277.
   PubMed Web of Science ®Google Scholar
• PEARSON, K., 1895, Skew variation in homogeneous material. In Philosophical Transactions of the Royal Society of London, edited by E. S. Pearson (London: Cambridge University Press), A 186, pp. 343–414.
   Google Scholar
• SEPKOVIC, D. W., HALEY, N. J., AXELRAD, C. M., SHIGEMATSU, A. and LA VOlE, E. J., 1986, Short-term studies on the in vivo metabolism of N-oxides of nicotine in rats. Journal of Toxicology and Environmental Health, 18, 205–214.
   PubMed Web of Science ®Google Scholar
• TAYLOR, E. C. and BOYER, N. E., 1959, Pyridine-1-oxides. IV. Nicotine-1-oxide, nicotine-1'-oxide, and nicotine-1,1'-dioxide. Journal of Organic Chemistry, 24, 275–277.
   Google Scholar
• THOMPSON, J. A., NORRIS, K. J. and PETERSEN, D. R., 1985, Isolation and analysis of N-oxide metabolites of tertiary amines: quantitation of nicotine-1'-N-oxide formation in mice. journal of Chromatography, 341, 349–359.
   PubMedGoogle Scholar