Metabolic activation of the potent carcinogen dibenzo[a,l]pyrene by human recombinant cytochromes P450, lung and liver microsomes

Carcinogenesis

Volumn 17, Issue 11, 1996, Pages 2429-2433

  Shou, Magang ^a   Krausz, Kristopher W ^a   Gonzalez, Frank J ^a   Gelboin, Harry V ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE DERIVATIVE; CARCINOGEN; CYTOCHROME P450; RECOMBINANT PROTEIN;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; HUMAN; LIVER MICROSOME METABOLISM; LUNG; METABOLIC ACTIVATION; MICROSOME; PRIORITY JOURNAL;

EID: 0029850968     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.11.2429     Document Type: Article

References (35)

1. Snook, M.E., Severson, R.F., Arrendale, R.F., Higman, H.C. and Chortyk, O.T. (1977) The identification of high molecular weight polynuclear aromatic hydrocarbons in a biologically active fraction of cigarette smoke condensate. Beitr. Tabakforsch, 9, 79-101.
2. Mumford, J.L., Harris, D.B., Williams, K., Chuang, J.C. and Cooke, M. (1987) Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion. Environ. Sci. Technol., 21, 308-311.
3. Kozin, I.S., Gooijer, C. and Velthorst, N.H. (1995) Direct determination of dibenzo[a,l]pyrene in crude extracts of environmental samples by laser-excited shpol'skii spectroscopy. Anal. Chem., 67, 1623-1626.
4. Cavalieri, E.L., Higginbotham, S., Rama Krishna, N.V.S., Devanesan, P.D., Todorovic, R., Rogan, E.G. and Salmasi, S. (1991) Comparative dose-tumorigenicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland. Carcinogenesis, 12, 1939-1944.
5. Cavalieri, E.L., Rogan, E.G., Higginbotham, S., Cremonesi, P. and Salmasi, S. (1989) Tumor initiating activity in mouse skin and carcinogenicity in rat mammary gland of dibenzo[a]pyrenes: The very potent activity of dibenzo[a,l]pyrene. J. Cancer Res. Clin. Oncol., 115, 67-72.
6. Higginbotham, S., RamaKrishna, V.V.S., Johansson,S.L., Rogan, E.G. and Cavalieri, E.L. (1989) Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benz [a]pyrene at low doses in mouse skin. Cacinogenesis, 14, 875-878.
7. Amin, S., Desaim, D., Dai, W., Harvey, R.G. and Hecht, S.S. (1995) Tumorigenicity in newborn mice of fjord region and other sterically hindered diol-epoxides of benzo[g]chrysene, dibenzo[a,l]pyrene (dibenzo[def,p]chrysene), 4H-cyclopenta[def]chrysene and fluoranthene. Carcinogenesis, 16, 2813-2817.
8. Devanesan, P.D., Cremonesi, P., Nunnally, J.E., Rogan, E.G. and Cavalieri, E.L. (1990) Metabolism and mutagenicity of dibenzo[a,e]pyrene and the very potent environmental carcinogen dibenzo[a,l]pyrene. Chem. Res. Toxicol., 3, 580-586.
9. Ralston, S.L., Seidel, A., Luch, A., Platt, K.L. and Baird, W.M. (1995) Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti(11R, 12R,13S,14R)-and(+)-syn(11S, 12R, 13S, 14R)-11,12-diol-13,14-epoxides which bind extensively to deoxyadenosine residues of DNA in the human mammary carcinoma cell line MCF-7. Carcinogenesis, 16, 2899-2907.
10. Ralston, S.L., Lau, H.H.S., Seidel, A., Luch, A., Platt, K.L. and Baird, W.M. (1994) The potent carcinogen dibenzo[a,l]pyrene is metabolically activated to fjord-region 11,12-diol 13,14-epoxides in human mammary carcinoma MCF-7 cell cultures. Cancer Res., 54, 887-890.
11. Buters, J.T.M., Shou, M. Hardwick, J.P., Korzekwa, K.R. and Gonzalez, F.J. (1995) cDNA-directed expression of human cytochrome P450 CYP1A1 using baculovirus: purification, dependency on NADPH-P450 oxidoreductase, and reconstitution of catalytic properties without purification. Drug Metab. Disp., 23, 696-701.
12. Gonzalez, F.J., Aoyama, T. and Gelboin, H.V. (1991) Expression of mammalian cytochrome P450 using vaccinia virus. Methods Enzymol., 206, 85-92.
13. Chakrabarti, S., Brechling, K. and Moss, B. (1985) Vaccinia virus expression vector: coexpression of β-galactosidase provides visual screening of recombinant virus plagues. Mol. Cell Biol., 5, 3403-3409.
14. Shou, M., Korzekwa, K.R., Crespi, C.L., Gonzalez, F.J. and Gelboin, H.V. (1994) The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism of benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol. Mol. Carcinog., 10, 159-168.
15. Wang, P.P., Beaune, P., Kaminsky, L.S., Dannan, G.A., Kadlubar, F.F., Larrey, D. and Guengerich, F.P. (1983) Purification and characterization of six cytochrome P450 isozymes from human liver microsomes. Biochemistry, 22, 5375-5383.
16. Li, K.-M., Todorovic, R., Rogan, E.G., Cavalieri, E.L., Ariese, F., Suh, M., Jankowiak, R. and Small, G.J. (1994) Identification and quantitation of dibenzo[a,l]pyrene-DNA adducts formed by rat liver microsomes in vitro: Preponderance of depurinating adducts. Biochemistry, 34, 8043-8049.
17. RamaKrishna, N.V.S., Padmavathi, N.S., Cavalieri, E.L., Rogan, E.G., Cerny, R.L. and Gross, M.L. (1993) Synthesis and structure determination of the adducts formed by electrochemical oxidation of the potent carcinogen dibenzo[a,l]pyrene in the presence of nucleosides. Chem. Res. Toxicol., 6, 554-560.
18. Hecht, S.S., Amin, S., Melikian, A.A., LaVoie, E.J. and Hoffmann, D. (1985) Effects of methyl and fluorine substitution on the metabolic activation and tumorigenicily of polycyclic aromatic hydrocarbons. In Harvey, R.G. (ed.) Polycyclic Aromatic Hydrocarbon and Carcinogenesis. American Chemical Society, Washington, D.C., pp. 86-105.
19. Levin, W., Wood, A.W., Chang, R.L., Ittah, Y., Croisy-Delcey, M., Yagi, H., Jerina, D.M. and Conney, A.H. (1980) Exceptionally high tumor-initiating activity of benzo[c]phenanthrene bay-region diol-epoxides on mouse skin. Cancer Res., 40, 3910-3914.
20. Hecht, S.S., Radok, L., Amin, S., Huie, K., Melikian, A.A., Hoffmann, D., Pataki, J. and Harvey, R.G. (1985) Tumorigenicity of 5-methylchrysene dihydrodiols and dihydrodiol-epoxides in newborn mice and on mouse skin. Cancer Res., 45, 1449-1452.
21. Gill, H.S., Kole, P.L., Wiley, J.C. Li, K.M., Higginbotham, S., Rogan, E.G. and Cavalieri, E.L. (1994) Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn and anti-fjord-region diol-epoxides. Carcinogenesis, 15, 2455-2460.
22. Rice, J.E., Jordan, K., Little, P. and Hussain, N. (1988) Comparative tumor-initiating activity of methylene-bridged and bay-region methylated derivatives of benz[a]anthracene and chrysene. Carcinogenesis, 9, 2275-2278.
23. Szeliga, J., Lee, H., Harvey, R.G., Page, J.E., Ross, H.L., Routledge, M.N., Hilton, B.D. and Dipple, A. (1994) Reaction with DNA and mutagenic specificity of syn-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide. Chem. Res. Toxicol., 7, 420-427.
24. Szeliga, J., Page, J.E., Hilton, B.D., Kiselyov, A.S., Harvey, R.G., Dunayevskiy, Y.M., Vouros, P. and Dipple, A. (1995) Characterization of DNA adducts formed by anti-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide. Chem. Res. Toxicol., 8, 1014-1019.
25. Dipple, A., Pigott, M.A., Agarwal, S.K., Yagi, H., Sayer, J.M. and Jerina, D.M. (1987) Optically active benzo[c]phenanthrene diol epoxides bind extensively to adenine in DNA. Nature, 327, 535-536.
26. Dipple, A. (1994) Reactions of polycyclic aromatic hydrocarbons with DNA. In Hemminki, K., Dipple, A., Shuker, D.E.G., Kadlubar, F.F., Segerbäck, D. and Bartsch, H. (eds) DNA adducts: Identification and Biological Significance. Lyon, pp. 107-129.
27. Shou, M., Krausz, K.W., Gonzalez, F.J. and Gelboin, H.V. (1996) Metabolic activation of the potent carcinogen dibenzo[a,h]anthracene by cDNA-expressed human cytochrmes P450. Arch. Biochem. Biophys., 328, 201-207.
28. Kawajiri, K., Watanabe, J., Eguchi, H. and Hayashi, S. (1995) Genetic polymorphism of drug-metabolizing enzymes and lung cancer susceptibility. Pharmacogenetics, 5, S70-S73.
29. Omiecinski, C.J., Redlich, C.A. and Costa, P. (1990) Induction and developmental expression of cytochrome P450IAI messenger RNA in rat and human tissues: detection by the polymerase chain reaction. Cancer Res., 50, 4315-4321.
30. McLemore, T.L., Adelberg, S., Liu, M.C. et al. (1990) Expression of CYP1A1 gene in patients with lung cancer: evidence for cigarette smoke-induced gene expression in normal lung tissue and for altered gene regulation in primary pulmonary carcinomas. J. Natl Cancer Inst., 82, 1333-1339.
31. Murray, G.I., and Durke, M.D. (1995) Immunohistochemistry of drug-metabolizing enzymes. Biochem. Pharmacol., 50, 895-903.
32. Murray, G.I., Barnes, T.S., Sewell, H.F., Ewen, S.W.B., Melvin, W.T., Shaw, P.M., Fowler, J. and Burke, M.D. (1987) Cytochrome P450 localization in normal human adult and fetal liver by immunocytochemistry using a monoclonal antibody against human cytochrome P450. Histochem. J., 19, 537-545.
33. Czerwinski, M., McLemore, T.L., Gelboin, H.V. and Gonzalez, F.J. (1994) Quantitation of CYP2B7, CYP4B1, and CYPOR messenger RNAs in normal lung and lung tumors. Cancer Res., 54, 1085-1091.
34. Kivisto, K.T., Fritz, P., Linder, A., Friedel, G., Beaune, P. and Kroemer, H.K. (1995) Immunohistochemical localization of cytochrome P450 3A in human pulmonary carcinomas and normal bronchial tissue. Histochemistry, 103, 25-29.
35. Wheeler, C.W., Wrighton, S.A. and Guenthner, T.M. (1992) Detection of human lung cytochromes P450 that are immunochemically related to cytochrome P450IIE1 and cytochrome P450IIIA. Biochem Pharmacol., 44, 183-186.