메뉴 건너뛰기




Volumn 25, Issue 4, 1997, Pages 481-488

Rat liver cytochrome P450 metabolism of N-acetylbenzidine and N,N'- diacetylbenzidine

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,4 DICHLORO 6 PHENYLPHENOXY)ETHYLAMINE; AJMALINE; ALPHA NAPHTHOFLAVONE; BENZIDINE DERIVATIVE; BETA NAPHTHOFLAVONE; CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; DISULFIRAM; ELLIPTICINE; FURAFYLLINE; PROADIFEN; SULFINPYRAZONE; THIAMAZOLE; TROLEANDOMYCIN; YOHIMBINE;

EID: 0030912472     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (26)

References (45)
  • 1
    • 0021868587 scopus 로고
    • Hepatic N-oxidation, acetyl-transfer and DNA-binding of the acetylated metabolites of the carcinogen, benzidine
    • C.B. Frederick, C. C. Weis, T. J. Flammang, C. N. Martin, and F. F. Kadlubar: Hepatic N-oxidation, acetyl-transfer and DNA-binding of the acetylated metabolites of the carcinogen, benzidine. Carcinogenesis 6, 959-965 (1985).
    • (1985) Carcinogenesis , vol.6 , pp. 959-965
    • Frederick, C.B.1    Weis, C.C.2    Flammang, T.J.3    Martin, C.N.4    Kadlubar, F.F.5
  • 4
    • 0028979269 scopus 로고
    • N-Acetylbenzidine and N,N′-diacetylbenzidine formation by rat and human liver slices exposed to benzidine
    • V. M. Lakshmi, D. A. Bell, M. A. Watson, T. V. Zenser, and B. B. Davis: N-Acetylbenzidine and N,N′-diacetylbenzidine formation by rat and human liver slices exposed to benzidine. Carcinogenesis 16, 1565-1571 (1995).
    • (1995) Carcinogenesis , vol.16 , pp. 1565-1571
    • Lakshmi, V.M.1    Bell, D.A.2    Watson, M.A.3    Zenser, T.V.4    Davis, B.B.5
  • 6
    • 0016806372 scopus 로고
    • Benzidine revisited: A review of the literature and problems associated with the use of benzidine and its congeners
    • T. J. Haley: Benzidine revisited: a review of the literature and problems associated with the use of benzidine and its congeners. Clin. Toxicol. 8, 13-42 (1975).
    • (1975) Clin. Toxicol. , vol.8 , pp. 13-42
    • Haley, T.J.1
  • 7
    • 0018657507 scopus 로고
    • The primary aromatic amines: Their biological properties and structure-activity relationships
    • J. L. Radomski: The primary aromatic amines: their biological properties and structure-activity relationships. Annu. Rev. Pharmacol. Toxicol. 19, 129-157 (1979).
    • (1979) Annu. Rev. Pharmacol. Toxicol. , vol.19 , pp. 129-157
    • Radomski, J.L.1
  • 8
    • 0019953879 scopus 로고
    • Covalent binding of benzidine and N-acetylbenzidine to DNA at the C-8 atom of deoxyguanosine in vivo and in vitro
    • C. N. Martin, F. A. Beland, R. W. Roth, and F. F. Kadlubar: Covalent binding of benzidine and N-acetylbenzidine to DNA at the C-8 atom of deoxyguanosine in vivo and in vitro. Cancer Res. 42, 2678-2686 (1982).
    • (1982) Cancer Res. , vol.42 , pp. 2678-2686
    • Martin, C.N.1    Beland, F.A.2    Roth, R.W.3    Kadlubar, F.F.4
  • 9
    • 0021352586 scopus 로고
    • Binding of N-acetylbenzidine and N,N′-diacetylbenzidine to hepatic DNA of rat and hamster in vivo and in vitro
    • J. C. Kennelly, F. A. Beland, F. F. Kadlubar, and C. N. Martin: Binding of N-acetylbenzidine and N,N′-diacetylbenzidine to hepatic DNA of rat and hamster in vivo and in vitro. Carcinogenesis 5, 407-412 (1984).
    • (1984) Carcinogenesis , vol.5 , pp. 407-412
    • Kennelly, J.C.1    Beland, F.A.2    Kadlubar, F.F.3    Martin, C.N.4
  • 11
    • 0018762584 scopus 로고
    • Metabolism of benzidine to N-hydroxy-N,N′-diacetylbenzidine and subsequent nucleic acid binding and mutagenicity
    • K. C. Morton, C. M. King, and K. P. Baetcke: Metabolism of benzidine to N-hydroxy-N,N′-diacetylbenzidine and subsequent nucleic acid binding and mutagenicity. Cancer Res. 39, 3107-3113 (1979).
    • (1979) Cancer Res. , vol.39 , pp. 3107-3113
    • Morton, K.C.1    King, C.M.2    Baetcke, K.P.3
  • 12
    • 0018906385 scopus 로고
    • Metabolic activation of N-hydroxy-N,N′-diacetylbenzidine by hepatic sulfotransferase
    • K. C. Morton, F. A. Beland, F. E. Evans, N. F. Fullerton, and F. F. Kadlubar: Metabolic activation of N-hydroxy-N,N′-diacetylbenzidine by hepatic sulfotransferase. Cancer Res. 40, 751-757 (1980).
    • (1980) Cancer Res. , vol.40 , pp. 751-757
    • Morton, K.C.1    Beland, F.A.2    Evans, F.E.3    Fullerton, N.F.4    Kadlubar, F.F.5
  • 14
    • 0023821353 scopus 로고
    • 1 hydroxylation by the pregnenolone-16α-carbonitrile-inducible form of rat liver microsomal cytochrome P-450
    • Lond.
    • 1 hydroxylation by the pregnenolone-16α-carbonitrile-inducible form of rat liver microsomal cytochrome P-450. Carcinogenesis (Lond.) 9, 2103-2108 (1988).
    • (1988) Carcinogenesis , vol.9 , pp. 2103-2108
    • Halvorson, M.R.1    Safe, S.H.2    Parkinson, A.3    Philips, T.D.4
  • 15
    • 0028345654 scopus 로고
    • Consequences of 3-methylcholanthrene-type induction for the metabolism of 4-aminobiphenyl in isolated rat hepatocytes
    • A. Orzechowski, D. Schrenk, H. A. J. Schut, and K. W. Bock: Consequences of 3-methylcholanthrene-type induction for the metabolism of 4-aminobiphenyl in isolated rat hepatocytes. Carcinogenesis 15, 489-494 (1994).
    • (1994) Carcinogenesis , vol.15 , pp. 489-494
    • Orzechowski, A.1    Schrenk, D.2    Schut, H.A.J.3    Bock, K.W.4
  • 17
    • 0019459161 scopus 로고
    • A rapid and simple synthesis of reactive metabolites of carcinogenic aromatic amines in high yield
    • J. G. Westra: A rapid and simple synthesis of reactive metabolites of carcinogenic aromatic amines in high yield. Carcinogenesis 2, 355-357 (1981).
    • (1981) Carcinogenesis , vol.2 , pp. 355-357
    • Westra, J.G.1
  • 19
    • 0018215674 scopus 로고
    • Differential distribution of the mixed-function oxidase activities in rabbit kidney
    • T. V. Zenser, M. B. Mattammal, and B. B. Davis: Differential distribution of the mixed-function oxidase activities in rabbit kidney. J. Pharmacol. Exp. Ther. 207, 719-725 (1978).
    • (1978) J. Pharmacol. Exp. Ther. , vol.207 , pp. 719-725
    • Zenser, T.V.1    Mattammal, M.B.2    Davis, B.B.3
  • 20
    • 0020028678 scopus 로고
    • Estimation of isozymes of microsomal cytochrome P-450 in rats, rabbits, and humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis
    • F. P. Guengerich, P. Wang, and N. K. Davidson: Estimation of isozymes of microsomal cytochrome P-450 in rats, rabbits, and humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Biochemistry 21, 1698-1706 (1982).
    • (1982) Biochemistry , vol.21 , pp. 1698-1706
    • Guengerich, F.P.1    Wang, P.2    Davidson, N.K.3
  • 21
    • 0004923927 scopus 로고
    • Use of human peripheral blood lymphocytes to measure DNA binding capacity of chemical carcinogens
    • R. C. Gupta, K. Earley, and S. Sharma: Use of human peripheral blood lymphocytes to measure DNA binding capacity of chemical carcinogens. Proc. Natl. Acad. Sci. U.S.A. 85, 3513-3517 (1988).
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.85 , pp. 3513-3517
    • Gupta, R.C.1    Earley, K.2    Sharma, S.3
  • 22
    • 0020334611 scopus 로고
    • 32P-Postlabeling analysis of non-radioactive aromatic carcinogen-DNA adducts
    • Lond.
    • 32P-Postlabeling analysis of non-radioactive aromatic carcinogen-DNA adducts. Carcinogenesis (Lond.) 3, 1081-1092 (1982).
    • (1982) Carcinogenesis , vol.3 , pp. 1081-1092
    • Gupta, R.C.1    Reddy, M.V.2    Randerath, K.3
  • 23
    • 0022149817 scopus 로고
    • 32P-postlabeling analysis of aromatic carcinogen-DNA adducts
    • 32P-postlabeling analysis of aromatic carcinogen-DNA adducts. Cancer Res. 45, 5656-5662 (1985).
    • (1985) Cancer Res. , vol.45 , pp. 5656-5662
    • Gupta, R.C.1
  • 26
    • 0002212075 scopus 로고
    • Rat and human liver cytochromes P450
    • (P. R. Ortiz de Montellano, ed.), Plenum Press, New York
    • M. A. Correia: Rat and human liver cytochromes P450. In "Cytochrome P450: Structure, Mechanism, and Biochemistry" (P. R. Ortiz de Montellano, ed.), pp. 607-630. Plenum Press, New York, 1995.
    • (1995) Cytochrome P450: Structure, Mechanism, and Biochemistry , pp. 607-630
    • Correia, M.A.1
  • 28
    • 0019990422 scopus 로고
    • Cytochrome P-450- And flavin-containing monooxygenase-catalyzed formation of the carcinogen N-hydroxy-2-aminofluorene and its covalent binding to nuclear DNA
    • C. B. Frederick, J. B. Mays, D. M. Ziegler, F. P. Guengerich, and F. F. Kadlubar: Cytochrome P-450-and flavin-containing monooxygenase-catalyzed formation of the carcinogen N-hydroxy-2-aminofluorene and its covalent binding to nuclear DNA. Cancer Res. 42, 2671-2677 (1982).
    • (1982) Cancer Res. , vol.42 , pp. 2671-2677
    • Frederick, C.B.1    Mays, J.B.2    Ziegler, D.M.3    Guengerich, F.P.4    Kadlubar, F.F.5
  • 29
    • 0024343858 scopus 로고
    • PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines
    • PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc. Natl. Acad. Sci. U.S.A. 86, 7696-7700 (1989).
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 7696-7700
    • Butler, M.A.1    Iwasaki, M.2    Guengerich, F.P.3    Kadlubar, F.F.4
  • 30
    • 0026001335 scopus 로고
    • Cytochrome P4501A2 constitutively expressed from transduced DNA mediates metabolic activation and DNA-adduct formation of aromatic amine carcinogens in NIH 3T3 cells
    • N. Battula, H. A. J. Schut, and S. S. Thorgeirsson: Cytochrome P4501A2 constitutively expressed from transduced DNA mediates metabolic activation and DNA-adduct formation of aromatic amine carcinogens in NIH 3T3 cells. Mol. Carcinogen. 4, 407-414 (1991).
    • (1991) Mol. Carcinogen. , vol.4 , pp. 407-414
    • Battula, N.1    Schut, H.A.J.2    Thorgeirsson, S.S.3
  • 31
    • 0026040316 scopus 로고
    • Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon
    • R. J. Turesky, N. P. Lang, M. A. Butler, C. H. Teitel, and F. F. Kadlubar: Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis 12, 1839-1845 (1991).
    • (1991) Carcinogenesis , vol.12 , pp. 1839-1845
    • Turesky, R.J.1    Lang, N.P.2    Butler, M.A.3    Teitel, C.H.4    Kadlubar, F.F.5
  • 32
    • 0027380074 scopus 로고
    • Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline
    • K. L. Kunze and W. F. Trager: Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol. 6, 649-656 (1993).
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 649-656
    • Kunze, K.L.1    Trager, W.F.2
  • 33
    • 0022006601 scopus 로고
    • Metabolic oxidation of carcinogenic arylamines by rat, dog, and human hepatic microsomes and by purified flavin-containing and cytochrome P-450 monooxygenases
    • G. J. Hammons, F. P. Guengerich, C. C. Weis, F. A. Beland, and F. F. Kadlubar: Metabolic oxidation of carcinogenic arylamines by rat, dog, and human hepatic microsomes and by purified flavin-containing and cytochrome P-450 monooxygenases. Cancer Res. 45, 3578-3585 (1985).
    • (1985) Cancer Res. , vol.45 , pp. 3578-3585
    • Hammons, G.J.1    Guengerich, F.P.2    Weis, C.C.3    Beland, F.A.4    Kadlubar, F.F.5
  • 34
    • 0017365046 scopus 로고
    • Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis
    • F. F. Kadlubar, J. A. Miller, and E. C. Miller: Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res. 37, 805-814 (1977).
    • (1977) Cancer Res. , vol.37 , pp. 805-814
    • Kadlubar, F.F.1    Miller, J.A.2    Miller, E.C.3
  • 35
    • 0029562366 scopus 로고
    • Glucuronidation of N-hydroxy metabolites of N-acetylbenzidine
    • S. R. Babu, V. M. Lakshmi, F. F. Hsu, T. V. Zenser, and B. B. Davis: Glucuronidation of N-hydroxy metabolites of N-acetylbenzidine. Carcinogenesis 16, 3069-3074 (1995).
    • (1995) Carcinogenesis , vol.16 , pp. 3069-3074
    • Babu, S.R.1    Lakshmi, V.M.2    Hsu, F.F.3    Zenser, T.V.4    Davis, B.B.5
  • 36
    • 0029936205 scopus 로고    scopus 로고
    • Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites: PH stability and synthesis by human and dog liver
    • S. R. Babu, V. M. Lakshmi, G. P. W. Huang, T. V. Zenser, and B. B. Davis: Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites: pH stability and synthesis by human and dog liver. Biochem. Pharmacol. 51, 1679-1687 (1996).
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 1679-1687
    • Babu, S.R.1    Lakshmi, V.M.2    Huang, G.P.W.3    Zenser, T.V.4    Davis, B.B.5
  • 37
    • 0024568395 scopus 로고
    • Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases
    • M. A. Butler, F. P. Guengerich, and F. F. Kadlubar: Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases. Cancer Res. 49, 25-31 (1989).
    • (1989) Cancer Res. , vol.49 , pp. 25-31
    • Butler, M.A.1    Guengerich, F.P.2    Kadlubar, F.F.3
  • 38
    • 0029935767 scopus 로고    scopus 로고
    • Metabolism of 2-amino-α-carboline: A food-borne heterocyclic amine mutagen and carcinogen by human and rodent liver microsomes and by human cytochrome P4501A2
    • H. Raza, R. S. King, B. Squires, F. P. Guengerich, D. W. Miller, J. P. Freeman, N. P. Lang, and F. F. Kadlubar: Metabolism of 2-amino-α-carboline: a food-borne heterocyclic amine mutagen and carcinogen by human and rodent liver microsomes and by human cytochrome P4501A2. Drug Metab. Dispos. 24, 395-400 (1996).
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 395-400
    • Raza, H.1    King, R.S.2    Squires, B.3    Guengerich, F.P.4    Miller, D.W.5    Freeman, J.P.6    Lang, N.P.7    Kadlubar, F.F.8
  • 39
    • 0022253914 scopus 로고
    • DNA adducts formed by ring-oxidation of the carcinogen 2-naphthylamine with prostaglandin H synthase in vitro and in the dog urothelium in vivo
    • Y. Yamazoe, D. W. Miller, C. C. Weis, K. L. Dooley, T. V. Zenser, F. A. Beland, and F. F. Kadlubar: DNA adducts formed by ring-oxidation of the carcinogen 2-naphthylamine with prostaglandin H synthase in vitro and in the dog urothelium in vivo. Carcinogenesis 6, 1379-1387 (1985).
    • (1985) Carcinogenesis , vol.6 , pp. 1379-1387
    • Yamazoe, Y.1    Miller, D.W.2    Weis, C.C.3    Dooley, K.L.4    Zenser, T.V.5    Beland, F.A.6    Kadlubar, F.F.7
  • 40
    • 0023812845 scopus 로고
    • Acetylator genotype and arylamine-induced carcinogenesis
    • D. W. Hein: Acetylator genotype and arylamine-induced carcinogenesis. Biochim. Biophys. Acta 948, 37-66 (1988).
    • (1988) Biochim. Biophys. Acta , vol.948 , pp. 37-66
    • Hein, D.W.1
  • 41
    • 0000037422 scopus 로고
    • Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons
    • (C. S. Cooper and P. L. Grover, eds.). Springer-Verlag, Berlin
    • F. A. Beland and F. F. Kadlubar: Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In "Handbook of Experimental Pharmacology" (C. S. Cooper and P. L. Grover, eds.). Springer-Verlag, Berlin, 1994.
    • (1994) Handbook of Experimental Pharmacology
    • Beland, F.A.1    Kadlubar, F.F.2
  • 42
    • 0020628133 scopus 로고
    • Induction of two immunochemically related rat liver cytochrome P-450 isozymes, cytochromes P-450c and P-450d, by structurally diverse xenobiotics
    • P. E. Thomas, L. M. Reik, D. E. Ryan, and W. Levin: Induction of two immunochemically related rat liver cytochrome P-450 isozymes, cytochromes P-450c and P-450d, by structurally diverse xenobiotics. J. Biol. Chem. 258, 4590-4598 (1983).
    • (1983) J. Biol. Chem. , vol.258 , pp. 4590-4598
    • Thomas, P.E.1    Reik, L.M.2    Ryan, D.E.3    Levin, W.4
  • 43
    • 0025073192 scopus 로고
    • The inducibility and catalytic activity of cytochromes P450c (P450IA1) and P450d (P450IA2) in rat tissues
    • D. Sesardic, K. J. Cole, R. J. Edwards, D. S. Davies, P. E. Thomas, W. Levin, and A. R. Boobis: The inducibility and catalytic activity of cytochromes P450c (P450IA1) and P450d (P450IA2) in rat tissues. Biochem. Pharmacol. 39, 499-506 (1990).
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 499-506
    • Sesardic, D.1    Cole, K.J.2    Edwards, R.J.3    Davies, D.S.4    Thomas, P.E.5    Levin, W.6    Boobis, A.R.7
  • 44
    • 0030067683 scopus 로고    scopus 로고
    • Differential effects of nonhydroxylated flavonoids as inducers of cytochrome P450 1A and 2B isozymes in rat liver
    • M. Canivenc-Lavier, M. Bentejac, M. Miller, J. Leclerc, M. L. Siess, and M. Suschetet: Differential effects of nonhydroxylated flavonoids as inducers of cytochrome P450 1A and 2B isozymes in rat liver. Toxicol. Appl. Pharmacol. 136, 348-353 (1996).
    • (1996) Toxicol. Appl. Pharmacol. , vol.136 , pp. 348-353
    • Canivenc-Lavier, M.1    Bentejac, M.2    Miller, M.3    Leclerc, J.4    Siess, M.L.5    Suschetet, M.6
  • 45
    • 0020434524 scopus 로고
    • Purification and characterization of liver microsomal cytochromes P-450: Electrophorectic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or β-naphthoflavone
    • F. P. Guengerich, G. A. Dannan, S. T. Wright, M. V. Martin, and L. S. Kaminsky: Purification and characterization of liver microsomal cytochromes P-450: electrophorectic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or β-naphthoflavone. Biochemistry 21, 6019-6030 (1982).
    • (1982) Biochemistry , vol.21 , pp. 6019-6030
    • Guengerich, F.P.1    Dannan, G.A.2    Wright, S.T.3    Martin, M.V.4    Kaminsky, L.S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.