Benzo [k]fluoranthene enhancement and suppression of 17beta-estradiol catabolism in MCF-7 breast cancer cells

Journal of Toxicology and Environmental Health - Part A

Volumn 58, Issue 7, 1999, Pages 413-426

  Arcaro, Kathleen F ^a   Yang, Yi ^b   Gierthy, John F ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b WADSWORTH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; BENZO[K]FLUORANTHENE; ESTRADIOL; FLUORANTHENE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; BREAST CANCER; CANCER CELL; CATABOLISM; COMPETITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; HUMAN; HUMAN CELL; INCUBATION TIME; PRIORITY JOURNAL; RADIOMETRY;

EID: 0033544865     PISSN: 15287394     EISSN: 10872620     Source Type: Journal    
DOI: 10.1080/009841099157142     Document Type: Article

References (49)

1. Agency for Toxic Substances and Disease Registry, 1995. Toxicological Profile for Polycyclic Aromatic Hydrocarbons (PAHs). Atlanta, GA: ATSDR.
2. Arcaro, K. F., O' Keefe, P. W., Yang, Y., Clayton, W., and Gierthy, J. F. 1999a. Antiestrogenicity of environmental polycyclic aromatic hydrocarbons in human breast cancer cells. Toxicology 133:115-127.
3. Arcaro, K. F., Yi, L. D., Seegal, R. F., Vakharia, D. D., Yang, Y., Spink, D. C., Brosch, K., and Gierthy, J. F. 1999b. 2,2',6,6'-Tetrachlorobiphenyl is estrogenic in vitro and in vivo. J. Cell. Biochem. 72:94-102.
4. Baker, J. E., and Eisenreich, S. J. 1990. Concentrations and fluxes of polycyclic aromatic hydrocarbons and polychlorinated biphenyls across the air-water interface of Lake Superior. Environ. Sci. Technol. 23:342-352.
5. Benner, B. A. J., Gordon, G. E., and Wise, S. A. 1989. Mobile sources of atmospheric polycyclic aromatic hydrocarbons: A roadway tunnel study. Environ. Sci. Technol. 23:1269-1278.
6. Bieniek, G. 1998. Aromatic and polycyclic hydrocarbons i n air and their urinary metabolites in coke plant workers. Am. J. Ind. Med. 34:445-454.
7. Bigelow, S. W., and Nebert, D. W. 1982. The Ah regulatory gene product. Survey of nineteen polycyclic aromatic compounds' and fifteen benzo[a]pyrene metabolites' capacity to bind to the cytosolic receptor. Toxicol. Lett. 10:109-118.
8. Boese, B. L., Lamberson, J. O., Swartz, R. C., Ozretich, R., and Cole, F. 1997. Photoinduced toxicity of PAHs and alkylated PAHs to a marine infaunal amphiod (Rhepoxynius abronius). Arch. Environ. Contam. Toxicol. 34:235-240.
9. Chaloupka, K., Krishnan, V., and Safe, S. 1992. Polynuclear aromatic hydrocarbon carcinogens as antiestrogens in MCF-7 human breast cancer cells: Role of the Ah receptor. Carcinogenesis 13: 2233-2239.
10. Chaloupka, K., Harper, N., Krishnan, V., Santostefano, M., Rodriguez, L. V., and Safe, S. 1993. Synergistic activity of polynuclear aromatic hydrocarbon mixtures as aryl hydrocarbon (Ah) receptor agonists. Chem. Biol. Interact. 89:141-158.
11. Chaloupka, K., Steinberg, M., Santostefano, M., Rodriguez, L. V., Goldstein, L., and Safe, S. 1995. Induction of Cyp1a-1 and Cyp1a-2 gene expression by a reconstituted mixture of polynuclear aromatic hydrocarbons i n B6C3F1 mice. Chem. Biol. Interact. 96:207-221.
12. Clemons, J. H., Allan, L. M., Marvin, C. H., Wu, Z., Mc Carry, B. E. B. D. W., and Zacharewski, T. R. 1998. Evidence of estrogen- and TCDD-like activities in crude and fractionated extracts of PM10 air particulate material using in vitro gene expression assays. Environ. Sci. Technol. 32: 1853-1860.
13. Conney, A. H., Chang, R. L., Jerina, D. M., and Wei, S. J. 1994. Studies on the metabolism of benzo a]pyrene and dose-dependent differences in the mutagenic profile of its ultimate carcinogenic metabolite. Drug Metab. Rev. 26:125-163.
14. Crosby, N. T., Hunt, D. C., Philp, L. A., and Patel, I. 1981. Determination of polynuclear aromatic hydrocarbons i n food, water and smoke using high-performance liquid chromatography. Analyst 106:135-145.
15. Denison, M. S., and Wilkinson, C. F. 1985. Identification of the Ah receptor in selected mammalian species and induction of aryl hydrocarbon hydroxylase. Eur. J. Biochem. 147:429-435.
16. Fielden, M. R., Chen, I., Chittim, B., Safe, S. H., and Zacharewski, T. R. 1997. Examination of the estrogenicity of 2,4,6,2',6'-pentachlorobiphenyl (PCB 104), its hydroxylated metabolite 2,4,6,2',6'-pentachloro-4-biphenylol (HO-PCB 104), and a further chlorinated derivative, 2,4,6,2',4',6'-hexachlorobiphenyl (PCB 155). Environ. Health Perspect. 105:1238-1248.
17. Garner, C. E., Jefferson, W. N., Burka, L. T., Matthews, H. B., and Newbold, R. R. 1999. In vitro estrogenicity of the catechol metabolites of selected polychlorinated biphenyls. Toxicol. Appl. Pharmacol. 154:188-197.
18. Gierthy, J. F., Lincoln, D. W., Kampcik, S. J., Dickerman, H. W., Bradlow, H. L., Niwa, T., and Swaneck, G. E. 1988. Enhancement of 2- and 1 6-alpha-estradiol hydroxylation in MCF-7 human breast cancer cells by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biochem. Biophys. Res. Commun. 157:515-520.
19. Guenthner, T. M., Fysh, J. M., and Nebert, D. W. 1979. 2,3,7,8-Tetrachlorodibenzo-p-dioxin: Covalent binding of reactive metabolic intermediates principally to protein in vitro. Pharmacology 19:12-22.
20. Hahn, M. E., Lamb, T. M., Schultz, M. E., Smolowitz, R. M., and Stegeman, J. J. 1993. Cytochrome P501A1 induction and inhibition by 3,3',4,4'-tetrachlorobiphenyl in an Ah receptor-containing fish hepatoma cell line (PLHC-1). Aquat. Toxicol. 26:185-208.
21. Hecht, S. S., el-Bayoumy, K., Rivenson, A., and Amin, S. 1994. Potent mammary carcinogenicity in female CD rats of a fjord region diol-epoxide of benzo[c]phenanthrene compared to a bay region diol-epoxide of benzo[a]pyrene. Cancer Res. 54:21-24.
22. Hileman, B. 1996. Environmental hormone disrupters focus of major research initiatives. Chem. Eng. News 13 May:28-35.
23. Krishnan, V., Porter, W., Santostefano, M., Wang, X. H., and Safe, S. H. 1995. Molecular mechanism of inhibition of estrogen-induced cathepsin D gene expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in MCF-7 cells. Mol. Cell. Biol. 15:6710-6719.
24. Levin, W., Wood, A., Chang, R., Ryan, D., Thomas, P., Yagi, H., Thakker, D., Vyas, K., Boyd, C., Chu, S. Y., Conney, A., and Jerina, D. 1982. Oxidative metabolism of polycyclic aromatic hydrocarbons to ultimate carcinogens. DrugMetab. Rev. 13:555-580.
25. Mastrangelo, G., Fadda, E., and Marzia, V. 1996. Polycyclic aromatic hydrocarbons and cancer in man. Environ. Health Perspect. 104:1166-1170.
26. Meek, M. D. 1998. Ah receptor and estrogen receptor-dependent modulation of gene expression by extracts of diesel exhaust particles. Environ. Res. 79:114-121.
27. Menzie, C. A., Potocki, B. B., and Santodonato, J. 1992. Exposure to carcinogenic PAHs in the environment. Environ. Sci. Technol. 26:1278-1284.
28. Naes, K., and Oug, E. 1998. The distribution and environmental relationships of polycyclic aromatic hydrocarbons (PAHs) in sediments from Norwegian smelter-affected fjords. Chemosphere 36:561-576.
29. Nesaretnam, K., and Darbre, P. 1997. 3,5,3',5'-Tetrachlorobiphenyl is a weak oestrogen agonist in vitro and in vivo. J. Ster. Biochem. Mol. Biol. 62:409-418.
30. Newman, W. C., and Moon, R. C. 1969. Anti-uterotrophic response of immature mice to 3-methyl-cholanthrene. Nature 221:89.
31. O'Keefe, P. W., Miller, J., Smith, R., Connor, S., Clayton, W., and Storm, R. 1997. Separation of extracts from biological tissues into polycyclic aromatic hydrocarbon, polychlorinated biphenyl, and polychlorinated dibenzo-p-dioxin polychlorinated dibenzofuran fractions prior to analysis. J. Chromatogr. 771:169-179.
32. Olea, N., Pazos, P., and Exposito, J. 1998. Inadvertent exposure to xenoestrogens. Eur. J. Cancer Prevent. 7(suppl. 1):17-23.
33. Pang, S., Cao, J. Q., Katz, B. H., Hayes, C. L., Sutter, T. R., and Spink, D. C. 1999. Inductive and inhibitory effects of non-ortho-substituted polychlorinated biphenyls on estrogen metabolism and human cytochromes P450 1 A1 and 1 B1. Biochem. Pharmacol. 58:29-38.
34. Phillips, D. H., and Grover, P. L. 1994. Polycyclic hydrocarbon activation: Bay regions and beyond. Drug Metab. Rev. 26:443-467.
35. Piskorska-Pliszczynska, J., Keys, B., Safe, S., and Newman, M. S. 1986. The cytosolic receptor binding affinities and AhH induction potencies of 29 polynuclear aromatic hydrocarbons. Toxicol. Lett. 34:67-74.
36. Ramamoorthy, K., Gupta, M. S., Sun, G. L., McDougal, A., and Safe, S. H. 1999. 3,3',4,4'-Tetrachlorobiphenyl exhibits antiestrogenic and antitumorigenic activity in the rodent uterus and mammary cells and in human breast cancer cells. Carcinogenesis 20:115-123.
37. Safe, S. H. 1995. Environmental and dietary estrogens and human health: Is there a problem? Environ. Health Perspect. 103:346-351.
38. Safe, S. H. 1997. Xenoestrogens and breast cancer. N. Engl. J. Med. 337:1303-1304.
39. Schneider, S. L., Alks, V., Morreal, C. E., Sinha, D. K., and Dao, T. L. 1976. Estrogenic properties of 3,9-dihydroxybenz[a]anthracene, a potential metabolite of benz[a]anthracene. J. Natl. Cancer Inst. 57:1351-1354.
40. Shaw, G. R., and Connell, D. W. 1994. Prediction and monitoring of the carcinogenicity of polycyclic aromatic compounds (PACs). Rev. Environ. Contam. Toxicol. 135:1-62.
41. Shou, M., Krausz, K. W., Gonzalez, F. J., and Gelboin, IH. V. 1996. Metabolic activation of the potent carcinogen dibenz[a, h]anthracene by cDNA-expressed human cytochromes P450. Arch. Biochem. Biophys. 328:201-207.
42. Spink, D. C., Lincoln, D. W. I., Dickerman, H. W., and Gierthy, J. F. 1990. 2,3,7,8-Tetrachlorodi-benzo-p-dioxin causes an extensive alteration of 17P-estradiol metabolism in MCF-7 breast tumor cells. Proc. Natl. Acad. Sci. USA 87:6917-6921.
43. Spink, D. C., Hayes, C. L., Young, N. R., Christou, M., Sutter, T. R., Jefcoate, C. R., and Gierthy, J. F. 1994. The effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on estrogen metabolism in MCF-7 breast cancer cells: Evidence for induction of a novel 17 beta-estradiol 4-hydroxylase. J. Ster. Biochem. Mol. Biol. 51:251-258.
44. Till, M., Riebniger, D., Schmitz, H.-J., and Schrenk, D. 1999. Potency of various polycyclic aromatic hydrocarbons as inducers of CYP1A1 in rat hepatocyte cultures. Chem. Biol. Interact. 117:135-190.
45. Tran, D. Q., Ide, C. F., McLachlan, J. A., and Arnold, S. F. 1996. The anti-estrogenic activity of selected polynuclear aromatic hydrocarbons in yeast expressing human estrogen receptor. Biochem. Biophys. Res. Comm. 229:102-108.
46. Willett, K. L., Gardinali, P. R., Sericano, J. L., Wade, T. L., and Safe, S. H. 1997. Characterization of the H4IIE rat hepatoma cell bioassay for evaluation of environmental samples containing polynuclear aromatic hydrocarbons (PAHs). Arch. Environ. Contam. Toxicol. 32:442-448.
47. Willett, K. L., Randerath, K., Zhou, G.-D., and Safe, S. H. 1998. Inhibition of CYP1A1-dependent activity by the polynuclear aromatic hydrocarbon (PAH) fluoranthene. Biochem. Pharmacol. 55:831-839.
48. Yang, N. C., Castro, A. J., Lewis, M., and Wong, T. W. 1961. Polynuclear aromatic hydrocarbons, steroids and carcinogenesis. Science 134:386-387.
49. Zhao, W., and Ramos, K. S. 1998. Cytotoxic response of cultured rat hepatocytes to selected aromatic hydrocarbons. Toxicol. In Vitro 12:175-182.