Importance of CYP1A1 and CYP1B1 in bioactivation of benzo[a]pyrene in human lung cell lines

Toxicology Letters

Volumn 192, Issue 2, 2010, Pages 221-228

  Uppstad, Heidi ^a   Øvrebø, Steinar ^a   Haugen, Aage ^a   Mollerup, Steen ^a  

^a NATIONAL INSTITUTE OF OCCUPATIONAL HEALTH   (Norway)

Author keywords

Benzo a pyrene; CYP1A1; CYP1B1; Human; Lung; Metabolism

Indexed keywords

7,8 DIHYDRO 7,8 DIHYDROXYBENZO[A]PYRENE; BENZO[A]PYRENE; BENZO[A]PYRENE TETROL I 1; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; MESSENGER RNA; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; BRONCHUS MUCOSA; CANCER CELL CULTURE; CONTROLLED STUDY; ENZYME ACTIVITY; FLUORESCENCE ANALYSIS; GENE EXPRESSION REGULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LUNG CARCINOGENESIS; METABOLIC ACTIVATION; PRIORITY JOURNAL; RNA INTERFERENCE; TOXICOKINETICS;

ARYL HYDROCARBON HYDROXYLASES; BENZO(A)PYRENE; CELL LINE; CYTOCHROME P-450 CYP1A1; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; LUNG; RNA, SMALL INTERFERING;

RODENTIA;

EID: 73749083124     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2009.10.025     Document Type: Article

References (36)

1. Aklillu E., Øvrebø S., Botnen I.V., Otter C., and Ingelman-Sundberg M. Characterization of common CYP1B1 variants with different capacity for benzo[a]pyrene-7,8-dihydrodiol epoxide formation from benzo[a]pyrene. Cancer Res. 12 (2005) 5105-5111
2. Berge G., Mollerup S., Øvrebø S., Hewer A., Phillips D.H., Eilertsen E., and Haugen A. Role of estrogen receptor in regulation of polycyclic aromatic hydrocarbon metabolic activation in lung. Lung Cancer 3 (2004) 289-297
3. Cooper C.S., Grover P.L., and Sims P. The metabolism and activation of benzo[a]pyrene. In: Bridges J.W., and Chasseaud L.F. (Eds). Progress in Drug Metabolism vol. 1 (1983), John Wiley and Sons, New York (NY) 295-396
4. Conney A.H. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G.H.A. Clowes Memorial Lecture. Cancer Res. 12 (1982) 4875-4917
5. Gautier J.C., Lecoeur S., Cosme J., Perret A., Urban P., Beaune P., and Pompon D. Contribution of human cytochrome P450 to benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol metabolism, as predicted from heterologous expression in yeast. Pharmacogenetics 6 (1996) 489-499
6. Hanlon P.R., Zheng W., Ko A.Y., and Jefcoate C.R. Identification of novel TCDD-regulated genes by microarray analysis. Toxicol. Appl. Pharmacol. 202 (2005) 215-228
7. Hecht S.S. Carcinogenesis due to tobacco; molecular mechanisms. Encycloped. Cancer 1 (1996) 220-232
8. Hecht S.S. Tobacco smoke carcinogens and lung cancer. J. Natl. Cancer Inst. 91 (1999) 1194-1210
9. Hoffman D. The changing cigarette, 1950-1995. J. Toxicol. Environ. Health 4 (1997) 307-364
10. Jiang H., Shen Y.M., Quinn A.M., and Penning T.M. Competing roles of cytochrome P450 1A1/1B1 and aldo-keto reductase 1A1 in the metabolic activation of (±)-7,8-dihydroxy-7,8-dihydro-benzo[a]pyrene in human bronchoalveolar cell extracts. Chem. Res. Toxicol. 2 (2005) 365-374
11. Kawajiri K., and Fujii-Kuriyama Y. Cytochrome P450 gene regulation and physiological functions mediated by the aryl hydrocarbon receptor. Arch. Biochem. Biophys. 464 (2007) 207-212
12. Kim J.H., Stansbury K.H., Walker N.J., Trush M.A., Strickland P.T., and Sutter T.R. Metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8-diol by human cytochrome P450 1B1. Carcinogenesis 19 (1998) 1847-1853
13. King L.C., Adams L., Allison J., Kohan M.J., Nelson G., Desai D., Amin S., and Ross J.A. A quantitative comparison of dibenzo[a,l]pyrene-DNA adduct formation by recombinant human cytochrome P450 microsomes. Mol. Carcinog. 2 (1999) 74-82
14. Kleiner H.E., Vulimiri S.V., Hatten W.B., Reed M.J., Nebert D.W., Jefcoate C.R., and DiGiovanni. Role of cytochrome P4501 family members in the metabolic activation of polycyclic aromatic hydrocarbons in mouse epidermis. J. Chem. Res. Toxicol. 12 (2004) 1667-1674
15. Kondraganti S.R., Fernandez-Salguero P., Gonzalez F.J., Ramos K.S., Jiang W., and Moorthy B. Polycyclic aromatic hydrocarbon-inducible DNA adducts: evidence by 32P-postlabeling and use of knockout mice for Ah receptor-independent mechanisms of metabolic activation in vivo. Int. J. Cancer 1 (2003) 5-11
16. Kouri R.E., McKinney C.E., Slomiany D.J., Snodgrass D.R., Wray N.P., and McLemore T.L. Positive correlation between high aryl hydrocarbon hydroxylase activity and primary lung cancer as analyzed in cryopreserved lymphocytes. Cancer Res. 12 (1982) 5030-5037
17. Lewis D.F., Dickins M., Eddershaw P.J., Tarbit M.H., and Goldfarb P.S. Cytochrome P450 substrate specificities, substrate structural templates and enzyme active site geometries. Drug Metabol. Drug Interact. 1 (1999) 1-49
18. Mollerup S., Ryberg D., Hewer A., Phillips D.H., and Haugen A. Sex differences in lung CYP1A1 expression and DNA adduct levels among lung cancer patients. Cancer Res. 14 (1999) 3317-3320
19. Mollerup S., Berge G., Bæra R., Skaug V., Hewer A., Phillips D.H., Stangeland L., and Haugen A. Sex differences in risk of lung cancer: expression of genes in the PAH bioactivation pathway in relation to smoking and bulky DNA adducts. Int. J. Cancer 4 (2006) 741-744
20. Mollerup S., Ovrebø S., and Haugen A. Lung carcinogenesis: resveratrol modulates the expression of genes involved in the metabolism of PAH in human bronchial epithelial cells. Int. J. Cancer 1 (2001) 18-25
21. Murray G.I., Melvin W.T., Greenlee W.F., and Burke M.D. Regulation, function, and tissue-specific expression of cytochrome P450 CYP1B1. Annu. Rev. Pharmacol. Toxicol. 41 (2001) 297-316
22. Oie H.K., Russell E.K., Carney D.N., and Gazdar A.F. Cell culture methods for the establishment of the NCI series of lung cancer cell lines. J. Cell. Biochem. Suppl. 24 (1996) 24-31
23. Pelkonen O., and Nebert D.W. Metabolism of polycyclic aromatic hydrocarbons: etiologic role in carcinogenesis. Pharmacol. Rev. 34 (1982) 189-222
24. Quinn A.M., and Penning T.M. Comparisons of (±)-benzo[a]pyrene-trans-7,8-dihydrodiol activation by human cytochrome P450 and aldo-keto reductase enzymes: effect of redox state and expression levels. Chem. Res. Toxicol. 5 (2008) 1086-1094
25. Ryberg D., Hewer A., Phillips D.H., and Haugen A. Different susceptibility to smoking-induced DNA damage among male and female lung cancer patients. Cancer Res. 22 (1994) 5801-5803
26. Sagredo C., Øvrebø S., Haugen A., Fujii-Kuriyama Y., Baera R., Botnen I.V., and Mollerup S. Quantitative analysis of benzo[a]pyrene biotransformation and adduct formation in Ahr knockout mice. Toxicol. Lett. 3 (2006) 173-182
27. Sagredo C., Mollerup S., Cole K.J., Phillips D.H., Uppstad H., and Øvrebø S. Biotransformation of benzo[a]pyrene in Ahr knockout mice is dependent on time and route of exposure. Chem. Res. Toxicol. (2009) Epub ahead of print. February 16
28. Safe S. Molecular biology of the Ah receptor and its role in carcinogenesis. Toxicol. Lett. 120 (2001) 1-7
29. Schwarz D., Kisselev P., Honeck H., Cascorbi I., Schunck W.H., and Roots I. Co-expression of human cytochrome P4501A1 (CYP1A1) variants and human NADPH-cytochrome P450 reductase in the baculovirus/insect cell system. Xenobiotica 6 (2001) 345-356
30. Shimada T., and Guengerich F.P. Inhibition of human cytochrome P450 1A1-, 1A2-, and 1B1-mediated activation of procarcinogens to genotoxic metabolites by polycyclic aromatic hydrocarbons. Chem. Res. Toxicol. 2 (2006) 288-294
31. Shimada T., Oda Y., Gillam E.M., Guengerich F.P., and Inoue K. Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella typhimurium NM2009. Drug. Metab. Dispos. 9 (2001) 1176-1182
32. Shou M., Korzekwa K.R., Crespi C.L., Gonzalez F.J., and Gelboin H.V. Metabolism of benzo[a]pyrene by seven cDNA expressed human cytochromes P450. Polycyclic Aromat. Compd. 7 (1994) 1-9
33. Uno S., Dalton T.P., Derkenne S., Curran C.P., Miller M.L., Shertzer H.G., and Nebert D.W. Oral exposure to benzo[a]pyrene in the mouse: detoxication by inducible cytochrome P450 is more important than metabolic activation. Mol. Pharmacol. 5 (2004) 1225-1237
34. Uno S., Dalton T.P., Dragin N., Curran C.P., Derkenne S., Miller M.L., Shertzer H.G., Gonzalez F.J., and Nebert D.W. Oral benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication. CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate. Mol. Pharmacol. 4 (2006) 1103-1114
35. Veglia F., Loft S., Matullo G., Peluso M., Munnia A., Perera F., Phillips D.H., Tang D., Autrup H., Raaschou-Nielsen O., Tjønneland A., Vineis P., and for the Genair-EPIC investigators. DNA adducts and cancer risk in prospective studies: a pooled analysis and a meta-analysis. Carcinogenesis 5 (2008) 932-936
36. Willey J.C., Broussoud A., Sleemi A., Bennett W.P., Cerutti P., and Harris C.C. Immortalization of normal human bronchial epithelial cells by human papillomaviruses 16 or 18. Cancer Res. 51 (1991) 5370-5377