Non-enzymatic reduction of aliphatic tertiary amine N-oxides mediated by the haem moiety of cytochrome P450

References

• BICKEL, M. H., 1969, The pharmacology and biochemistry of N-oxides. Pharmacological Review, 21, 325–355.
   PubMed Web of Science ®Google Scholar
• CLEMENT, B. and JUNG, F., 1994, N-Hydroxylation of the antiprotozoal drug pentamidine catalysed by rabbit liver cytochrome P-450 2C3 or human liver microsomes, microsomal retroreduction, and further oxidative transformation of the formed amidoximes. Drug Metabolism and Disposition, 22, 486–497.
   PubMed Web of Science ®Google Scholar
• CLEMENT, B., LOMB, R. and MOLLER, W., 1997, Isolation and characterization of the protein components of the liver microsomal 02-insensitive NADH-benzamidoxime reductase. Journal of Biological Chemistry, 272, 19615–19620.
   PubMed Web of Science ®Google Scholar
• CLEMENT, B., SCHULTZE-MOSGAU, M. H., RICHTER, P. H. and BESCH, A., 1994, Cytochrome P450-dependent N-hydroxylation of an aminoguanidine (amidinohydrazone) and microsomal retro-reduction of the N-hydroxylated product. Xenobiotica, 24, 671–688.
   Google Scholar
• CLEMENT, B., SCHULTZE-MOSGAU, M. H. and WOHLERS, H., 1993, Cytochrome P450 dependent N-hydroxylation of a guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of the N-hydroxy-guanidine metabolite to the urea derivative. Biochemical Phar-macology, 46, 2249–2267.
   Google Scholar
• CRICHTON, R. R., ROMAN, F. and WAUTERS, M., 1975, Reductive mobilization of ferritin iron by reduced nicotinamide-adenine dinucleotide fiavin mononucleotide. Biochemical Society Transactions, 3, 946–948.
   Google Scholar
• DIETRIC H., 1967, 5-Dialkylaminoalky1-5H-dibenz[b,f]azepine N-oxides. Chemical Abstract, 66, 10857n.
   Google Scholar
• GILLESPIE, S. G. and DUFFEL, M. W., 1989, Peroxidase as a model for reduction of tertiary amine oxides catalysed by rat hepatic supernatant and microsomal fractions. Biochemical Pharmacology, 38, 573–579.
   PubMedGoogle Scholar
• GUENGERICH, F. P., DANNAN, G. A., WRIGHT, S. T., MARTIN, M. V. and KAMINSKY, L. S., 1982, Purification and characterization of liver microsomal cytochrome P-450. Biochemistry, 21, 6019–6030.
   PubMed Web of Science ®Google Scholar
• ImAI, Y. and SATO, R., 1967, Conversion of cytochrome P-450 to P-420 by neutral salts and some other reagents. European Journal of Biochemistry, 1, 419–426.
   PubMedGoogle Scholar
• IwAsmu, K., Nocucm, H., KATO, R., ImAI, Y. and SATO, R., 1977, Reduction of tertiary amine N-oxide by purified cytochrome P-450. Biochemical and Biophysical Research Communication, 77, 1143–1149.
   PubMedGoogle Scholar
• KAMM, J. J. and GILLETTE, J. R., 1963, Mechanism of stimulation of mammalian nitro reductase by fiavins. Life Sciences, 4, 254–260.
   Google Scholar
• KATO, R., IwAsmu, K. and Nocucm, H., 1976, Stimulatory effect of FMN and methyl viologen on cytochrome P-450 dependent reduction of tertiary amine N-oxide. Biochemical and Biophysical Research Communication, 72, 267–274.
   PubMedGoogle Scholar
• KIT AMURA, S., SUGIHARA, K. and TATSUMI, K., 1999, A unique tertiary amine N-oxide reduction system composed of quinone reductase and haem in rat liver preparations. Drug Metabolism and Disposition, 27, 92–97.
   PubMedGoogle Scholar
• KITAMURA, S. and TATSUMI, K., 1984a, Involvement of liver aldehyde oxidase in the reduction of nicotinamide N-oxide. Biochemical and Biophysical Research Communication, 120, 602–606.
   PubMed Web of Science ®Google Scholar
• KITAMURA, S. and TATSUMI, K., 1984b, Reduction of tertiary amine N-oxides by liver preparations: function of aldehyde oxidase as a major N-oxide reductase. Biochemical and Biophysical Research Communication, 121,749–754.
   PubMed Web of Science ®Google Scholar
• LOWRY, 0. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   Google Scholar
• MATSUBARA, T., KOIKE, M., TOCHINO, A. and SUGENO, K., 1976, Quantitative determination of cytochrome P-450 in rat liver homogenate. Analytical Biochemistry, 2,264–289.
   Google Scholar
• MURRAY, K. N. and CHAYKIN, S., 1966, The reduction of nicotinamide N-oxide by xanthine oxidase. Journal of Biological Chemistry, 241, 3468–3473.
   PubMed Web of Science ®Google Scholar
• PATTERSON, L. H. and GORROD, J. W., 1978, The metabolism of some 4-substituted N-ethyl-N-methylaniline N-oxides. In J. W. Gorrod (ed.), Biological Oxidation of Nitrogen (Amsterdam: Elsevier), pp. 471–478.
   Google Scholar
• Powis, G. and DEGRAW, C., 1980, N-Oxide reduction by haemoglobin, cytochrome c and ferrous ions. Research Communications Chemical Pathology and Pharmacology, 30, 143–150.
   PubMedGoogle Scholar
• Powis, G., SVINGEN, B. A. and DEGRAW, C., 1982, Iron-EDTA stimulated reduction of indicine N-oxide by hepatic microsomal fraction, isolated hepatocytes, and the intact rat. Biochemical Pharmacology, 31,293–299.
   PubMed Web of Science ®Google Scholar
• Powis, G. and WINCENTSEN, L., 1980, Pyridine nucleotide cofactor requirements of indicine N-oxide reduction by hepatic microsomal cytochrome P-450. Biochemical Pharmacology, 29, 347–351.
   PubMed Web of Science ®Google Scholar
• SINGER, T. P. and KEARNEY, F. B., 1950, The non-enzymatic reduction of cytochrome c by pyridine nucleotides and its catalysis by various flavins. Journal of Biological Chemistry, 183, 409–429.
   Google Scholar
• ST6HRER, G. and BROWN, G. B., 1969, Purine N-oxides XXVIII. The reduction of purine N-oxides by xanthine oxidase. Journal of Biological Chemistry, 244, 2498–2502.
   Google Scholar
• SUGIHARA, K., KITAMURA, S. and TATSUMI, K., 1996, S-(-)-Nicotine-1'-N-oxide reductase activity of rat liver aldehyde oxidase. Biochemistry and Molecular Biology International, 40, 535–541.
   PubMedGoogle Scholar
• SUGIURA, M., IWASAKI, K. and KATO, R., 1976, Reduction of tertiary amine N-oxides by liver microsomal cytochrome P-450. Molecular Pharmacology, 12, 322–334.
   PubMed Web of Science ®Google Scholar
• SUGIURA, M., WASAKI, K., Nocucm, H. and KATO, R., 1974, Evidence for the involvement of cytochrome P-450 in tiaramide N-oxide reduction. Life Sciences, 15, 1433–1442.
   PubMed Web of Science ®Google Scholar
• TAKEKAWA, K., SUGIHARA, K., KITAMURA, S. and TATSUMI, K., 1997, Non-enzymatic reduction of brucine N-oxide by the haem group of cytochrome P450. Biochemistry and Molecular Biology International, 42, 977–981.
   PubMedGoogle Scholar
• TERAYAMA, H., 1963, Aminoazo dye amine-N-oxide as a possible intermediate metabolite preceding N-demethylation and ortho-hydroxylation, as well as azo dye-protein binding. Gann, 55, 195–204.
   Google Scholar
• VAISEY, E. B., 1956, The non-enzymic reduction of trimethylamine oxide to trimethylamine, dimethyl-amine, and formaldehyde. Canadian Journal of Biochemical Physiology, 34, 1085–1090.
   PubMedGoogle Scholar
• Yu, C.-A. and GUNSALUS, I. C., 1974, Cytochrome P-450cam III. Removal and replacement of ferriprotoporphyrin IX. Journal of Biological Chemistry, 249, 107–110.
   Google Scholar
• YUBISUI, T., MATSUKAWA, S. and YONEYAMA, Y., 1980, Stopped flow studies on the non-enzymatic reduction of methemoglobin by reduced flavin mononucleotide. Journal of Biological Chemistry, 255, 11694–11697.
   PubMedGoogle Scholar
• ZIEGLER, D. M., 1980, Microsomal flavin-containing monooxygenase. In W. B. Jakoby (ed.), Enzymatic Basis of Detoxicat ion, vol. 1 (New York: Academic Press), pp. 201–227.
   Google Scholar