Pseudoenzymatic reduction of N-hydroxy-2-acetylaminofluorene to 2-acetylaminofluorene mediated by cytochrome P450

Carcinogenesis

Volumn 20, Issue 2, 1999, Pages 347-350

  Kitamura, Shigeyuki ^a   Takekawa, Koji ^a   Sugihara, Kazumi ^a   Tatsumi, Kiyoshi ^a   Ohta, Shigeru ^a  

^a HIROSHIMA UNIV SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; FLAVINE ADENINE NUCLEOTIDE; FLUORENYLACETOHYDROXAMIC ACID; HEMATIN; HEME; N (2 FLUORENYL)ACETAMIDE; QUERCETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; LIVER MICROSOME; MALE; NONHUMAN; PHOTOCHEMISTRY; PRIORITY JOURNAL; RAT; REDUCTION;

EID: 0032959821     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/20.2.347     Document Type: Article

References (25)

1. Miller, J.A. (1970) Carcinogenesis by chemicals: an overview - G.H.A. Clowes memorial lecture. Cancer Res., 30, 559-576.
2. Miller, J.A., Cramer, J.W. and Miller, E.C. (1960) The N-and ring-hydroxylation of 2-acetylaminofluorene during carcinogenesis in the rat. Cancer Res., 20, 950-962.
3. Cramer, J.W., Miller, J.A. and Miller, E.C. (1960) N-hydroxylation: a new metabolic reaction observed in the rat with the carcinogen 2-acetylaminofluorene. J. Biol. Chem., 235, 885-888.
4. Irving, C.C. (1962) N-hydroxylation of 2-acetylaminofluorene in the rabbit. Cancer Res., 22, 867-873.
5. Razzouk, C., Batardy-Gregoire, M. and Roberfroid, M. (1982) Metabolism of N-hydroxy-2-acetylaminofluorene and N-hydroxy-2-aminofluorene by guinea pig liver microsomes. Cancer Res., 42, 4712-4718.
6. Weisburger, J.H., Grantham, P.H., Horton, R.E. and Weisburger, E.K. (1970) Metabolism of the carcinogen N-hydroxy-N-2-fluorenylacetamide in germ-free rats. Biochem. Pharmacol., 19, 151-162.
7. Grantham, P.H., Horton, R.E., Weisburger, E.K. and Weisburger, J.H. (1970) Metabolism of the carcinogen N-hydroxy-N-2-fluorenylacetamide in germ-free and conventional rats. Biochem. Pharmacol., 19, 163-171.
8. Williams, J.R., Grantham, P.H., Marsh, H.H., Weisburger, J.H. and Weisburger, E.K. (1970) Participation of liver fractions and of intestinal bacteria in the metabolism of N-hydroxy-N-2-fluorenylacetamide in the rat. Biochem. Pharmacol., 19, 173-188.
9. 14C in vitro. J. Biol. Chem., 239, 1589-1596.
10. Lotlikar, P.D., Miller, E.C., Miller, J.A. and Margreth, A. (1965) The enzymatic reduction of the N-hydroxy derivatives of 2-acetylaminofluorene and related carcinogens by tissue preparations. Cancer Res., 25, 1743-1752.
11. Grantham, P.H., Weisburger, E.K. and Weisburger, J.H. (1965) Dehydroxylation and deacelylation of N-hydroxy-N-2-fluorenylacetamide by rat liver and brain homogenates. Biochim. Biophys. Acta, 107, 414-424.
12. Gutmann, H.R. and Erickson, R.R. (1969) The conversion of the carcinogen N-hydroxy-2-fluorenylacetamide to o-amidophenols by rat liver in vitro. J. Biol. Chem., 244, 1729-1740.
13. Lenk, W. and Scharmer, U. (1980) Reaction of microsomal and cytosolic enzymes with N-arylacetohydroxamic acids. Xenobiotica, 10, 573-591.
14. Yamazoe, Y., Ishii, K., Yamaguchi, N., Kamataki, T. and Kato, R. (1980) Reduction of N-hydroxy-2-acetylaminofluorene by liver microsomes. Biochem. Pharmacol., 29, 2183-2188.
15. Irving, C.C. (1966) Enzymatic deacetylation of N-hydroxy-2-acetylaminofluorene by liver microsomes. Cancer Res., 26, 1390-1396.
16. Weisburger, J.H. and Weisburger, E.K. (1973) Biochemical formation and pharmacological, toxicological, and pathological properties of hydroxylamines and hydroxamic acids. Pharmacol. Rev., 25, 1-66.
17. Kitamura, S. and Tatsumi, K. (1985) Purification of N-hydroxy-2-acetylaminofluorene reductase from rabbit liver cytosol. Biochem. Biophys. Res. Commun., 133, 67-74.
18. Kitamura, S., Sugihara, K. and Tatsumi, K. (1994) Reductase activity of aldehyde oxidase toward the carcinogen N-hydroxy-2-acetylaminofluorene and the related hydroxamic acids. Biochem. Mol. Biol. Int., 34, 1197-1203.
19. Yubisui, T., Matsukawa, S. and Yoneyama, Y. (1980) Stopped flow studies on the nonenzymatic reduction of methemoglobin by reduced flavin mononucleotide. J. Biol. Chem., 255, 11694-11697.
20. Guengerich, F.P., Dannan, G.A., Wright, S.T., Martin, M.V. and Kaminsky, L.S. (1982) Purification and characterization of liver microsomal cytochromes P-450: electrophoretic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or β-naphthoflavone. Biochemistry, 21, 6019-6030.
21. Imai, Y. and Sato, R. (1967) Conversion of P-450 to P-420 by neutral salts and some other reagents. Eur. J. Biochem., 1, 419-426.
22. Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R.J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193, 265-275.
23. Kato, R., Iwasaki, K. and Noguchi, H. (1976) Stimulatory effect of FMN and methyl viologen on cytochrome P-450 dependent reduction of tertiary amine N-oxide. Biochem. Biophys. Res. Commun., 72, 267-274.
24. Singer, T.P. and Kearney, F.B. (1950) The non-enzymatic reduction of cytochrome c by pyridine nucleotides and its catalysis by various flavins. J. Biol. Chem., 183, 409-429.
25. Sugihara, K. and Tatsumi, K. (1986) Participation of liver aldehyde oxidase in reductive metabolism of hydroxamic acids to amides. Arch. Biochem. Biophys., 247, 289-293.