Antiestrogenic activity of hydroxylated polychlorinated biphenyl congeners identified in human serum

Toxicology and Applied Pharmacology

Volumn 142, Issue 1, 1997, Pages 160-168

  Moore, M ^a   Mustain, M ^a   Daniel, K ^a   Chen, I ^a   Safe, S ^a   Zacharewski, T ^b   Gillesby, B ^b   Joyeux, A ^c   Balaguer, P ^c  

^a TEXAS A AND M UNIVERSITY   (United States)

^b UNIVERSITY OF WESTERN ONTARIO   (Canada)

^c INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIESTROGEN; ESTROGEN RECEPTOR; POLYCHLORINATED BIPHENYL;

ARTICLE; BREAST CANCER; CANCER CELL; CELL PROLIFERATION; ESTROGEN ACTIVITY; FEMALE; HUMAN; HYDROXYLATION; NONHUMAN; RAT; RECEPTOR BINDING; UTERUS;

EID: 0031027995     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1996.8022     Document Type: Article

References (69)

1. Ballschmiter, K., Rappe, C., and Buser, H. R. (1989). Chemical properties, analytical and environmental levels of PCBs, PCTs, PCNs and PCBs. In Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products (R. D. Kimbrough and A. A. Jensen, Eds.), pp. 47-69. Elsevier-North Holland, Amsterdam.
2. Bergeron, J. M., Crews, D., and McLachlin, J. A. (1994). PCBs as environmental estrogens: Turtle sex determination as a biomarker of environmental contamination. Environ. Health Perspect. 102, 786-791.
3. Bergman, Å., Klasson-Wehler, E., and Kuroki, H. (1994). Selective retention of hydroxylated PCB metabolites in blood. Environ. Health Perspect. 102, 464-469.
4. Bitman, J., Cecil, H. C., Harris, S. J., and Fries, G. F. (1968). Estrogenic activity of o,p′-DDT in the mammalian uterus and avian oviduct. Science 162, 371-372.
5. Bitman, J., and Cecil, H. C. (1970). Estrogenic activity of DDT analogs and polychlorinated biphenyls. J. Agric. Food Chem. 18, 1108-1112.
6. Brasier, A. R., Tate, J. E., and Habener, J. F. (1989). Optimized use of the firefly luciferase assay as a reporter gene in mammalian cell lines. Biotechniques 7, 1116-1122.
7. Brouwer, A., Blaner, W. S., Kukler, A., and Van den Berg, K. J. (1988). Study on the mechanism of interference of 3,4,3′,4′-tetrachlorobiphenyl with the plasma retinol-binding proteins in rodents. Chem.-Biol. Interact. 68, 203-217.
8. Brouwer, A., Klasson-Wehler, E., Bokdam, M., Morse, D. C., and Traag, W. A. (1990). Competitive inhibition of thyroxin binding to transthyretin by mono-hydroxy metabolites of 3,4,3′,4′-tetrachlorobiphenyl. Chemosphere 20, 1257-1262.
9. Brouwer, A., and Van den Berg, K. J. (1986). Binding of a metabolite of 3,4,3′,4′-tetrachlorobiphenyl to transthyretin reduces serum vitamin A transport by inhibiting the formation of the protein complex carrying both retinol and thyroxin. Toxicol. Appl. Pharmacol. 85, 301-312.
10. Brown, A. P., and Ganey, P. E. (1995). Neutrophil degranulation and superoxide production induced by polychlorinated biphenyls are calcium dependent. Toxicol. Appl. Pharmacol. 131, 198-205.
11. Buchmann, A., Kunz, W., Wolf, C. R., Oesch, F., and Robertson, L. W. (1986). Polychlorinated biphenyls, classified as either phenobarbital-or 3-methylcholanthrene-type inducers of cytochrome P-450, are both heptic tumor promoters in diethylnitrosamine-initiated rats. Cancer Lett. 32, 243-253.
12. Buchmann, A., Ziegler, S., Wolf, A., Robertson, L. W., Durham, S. K., and Schwarz, M. (1991). Effects of polychlorinated biphenyls in rat liver: Correlation between primary subcellular effects and promoting activity. Toxicol. Appl. Pharmacol. 111, 454-468.
13. Colborn, T., Vom Saal, F. S., and Soto, A. M. (1993). Development effects of endocrine-disrupting chemicals in wildlife and humans. Environ. Health Perspect. 101, 378-384.
14. Connor, K., Safe, S., Jefcoate, C. R., and Larsen, M. (1996). Structure-dependent induction of CYP2B by polychlorinated biphenyl congeners in female Sprague-Dawley rats. Biochem. Pharmacol., 50, 1913-1920.
15. Davis, D. L., Bradlow, H. L., Wolff, M., Woodruff, T., Hoel, D. G., and Anton-Culver, H. (1993). Medical hypothesis: Xenoestrogens as preventable causes of breast cancer. Environ. Health Perspect. 101, 372-377.
16. Denomme, M. A., Bandiera, S., Lambert, I., Copp, L., Safe, L., and Safe, S. (1983). Polychlorinated biphenyls as phenobarbitone-type inducers of microsomal enzymes - Structure activity relationships for a series of 2,4-dichloro-substituted congeners. Biochem. Pharmacol. 32, 2955-2963.
17. Dickerson, R., Howie-Keller, L., and Safe, S. (1995). Alkyl polychlorinated dibenzofurans and related compounds as antiestrogens in the female rat uterus: Structure-activity studies. Toxicol. Appl. Pharmacol. 135, 287-298.
18. Ebner, K. V., and Braselton, W. E. (1987). Structural and chemical requirements of hydroxylated polychlorinated biphenyls (PCBOH) for inhibition of energy-dependent swelling of rat liver mitochondria. Chem.-Biol. Interact. 63, 139-155.
19. Ecobichon, D. J., and MacKenzie, D. O. (1974). The uterotropic activity of commercial and isomerically-pure chlorobiphenyls in the rat. Res. Commun. Chem. Pathol. Pharmacol. 9, 85-95.
20. Gagne, D., Balaguer, P., Demirpence, E., Trousse, F., Nicolas, J. C., and Pons, M. (1994). Stable transfectant cells to study steroid receptor biological activity. J. Biolum. Chem. 9, 201-209.
21. Gellert, R. J. (1978). Uterotrophic activity of polychlorinated biphenyls (PCB) and induction of precocious reproductive aging in neonatally treated female rats. Environ. Res. 16, 123-130.
22. Gorman, C. M., Moffat, L. F., and Howard, B. H. (1982). Recombinant genomes which express chloramphenicol acetyltransferase in mammalian cells. Mol. Cell. Biol. 2, 1044-1051.
23. Hunter, D. J., and Kelsey, K. T. (1993). Pesticide residues and breast cancer: The harvest of a silent spring. J. Natl. Cancer Inst. 85, 598-599.
24. Hutzinger, O., Safe, S., and Zitko, V. (1974). Preparation, gas chromatography behavior, and spectroscopic properties of hydroxylated chlorobiphenyls. J. Assoc. Off. Anal. Chem. 57, 1061-1067.
25. Jansson, B., Jensen, S., Olsson, M., Renberg, L., Sundström, G., and Vaz, R. (1975). Identification by GC-MS of phenolic metabolites of PCB and p,p′-DDE isolated from Baltic guillemot and seal. Ambio 4, 93-97.
26. Jausons-Loffreda, N., Gelmini, N., Pazzagli, N., Joyeux, A., Balaguer, P., Pons, M., and Nicolas, J. C. (1994). Chimeric receptor genes as a tool for measuring biological activities of steroid hormones. J. Biolum. Chem. 49, 31-38.
27. Kannan, N., Tanabe, S., Ono, M., and Tatsukawa, R. (1989). Critical evaluation of polychlorinated biphenyl toxicity in terrestrial and marine mammals: Increasing impact of non-ortho and mono-ortho coplanar polychlorinated biphenyls from land to oce. Arch. Environ. Contam. Toxicol. 18, 850-857.
28. Klasson Wehler, E., Kuroki, H., Athanasiadou, M., and Bergman, Å. (1992). Selective retention of hydroxylated PCBs in blood. Organohalogen Compounds, Dioxin '92 10, 121-122. [Abstract]
29. Klein-Hitpass, L., Schorpp, M., Wagner, U., and Ryffel, G. U. (1986). An estrogen-responsive element derived from the 5′-flanking region of the xenopus vitellogenin A2 gene functions in transfected human cells. Cell 46, 1053-1061.
30. Kodavanti, P. R. S., Shin, D., Tilson, H. A., and Harry, G. J. (1993). Comparative effects of two polychlorinated biphenyl congeners on calcium homeostasis in rat cerebellar granule cells. Toxicol. Appl. Pharmacol. 123, 97-106.
31. 3H]phorbol ester binding in rat cerebellar granule cells by polychlorinated biphenyl mixtures and congeners: Structure-activity relationships. Toxicol. Appl. Pharmacol. 130, 140-148.
32. Koga, N., Beppu, M., and Yoshimura, H. (1990). Metabolism in vivo of 3,4,5,3′,4′-pentachlorobiphenyl and toxicological assessment of the metabolite in rats. J. Pharmacobio-Dyn. 13, 497-506.
33. Korach, K. S., Sarver, P., Chae, K., McLachlin, J. A., and McKinney, J. D. (1988). Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: Conformationally restricted structural probes. Mol. Pharmacol. 33, 120-126.
34. Krishnan, A. V., Starhis, P., Permuth, S. F., Tokes, L., and Feldman, D. (1993). Bisphenol-A: An estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132, 2279-2286.
35. Laib, R. M., Rose, N., and Bunn, H. (1991). Hepatocarcinogenicity of PCB congeners. Toxicol. Environ. Chem. 34, 19-22.
36. Lans, M. C., Klasson-Wehler, E., Willemsen, M., Meussen, E., Safe, S., and Brouwer, A. (1993). Structure-dependent competitive interaction of hydroxy-polychlorobiphenyls, -dibenzo-p-dioxins and -dibenzofurans with human transthyretin. Chem.-Biol. Interact. 88, 7-21.
37. Li, M., Zhao, Y. D., and Hansen, L. G. (1994). Multiple dose toxicokinetic influence on the estrogenicity of 2,2′,4,4′,5,5′-hexachlorobiphenyl. Bull. Environ. Contam. Toxicol. 53, 583-590.
38. Li, M., and Hansen, L. G. (1995). Uterotropic and enzyme induction effects of 2,2′,5-trichlorobiphenyl. Bull. Environ. Contam. Toxicol. 54, 494-500.
39. Maier, W. E., Kodavanti, P. R., Harry, G. J., and Tilson, H. A. (1994). Sensitivity of adenosine triphosphatases in different brain regions to polychlorinated biphenyl congeners. J. Appl. Toxicol. 14, 225-229.
40. McDonnell, D. P., Clemm, D. L., Hermann, T., Goldman, M. E., and Pike, J. W. (1995). Analysis of estrogen receptor function in vitro reveals three distinct classes of antiestrogens. Mol. Endocrinol. 9, 659-669.
41. McFarland, V. A., and Clarke, J. U. (1989). Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: Considerations for a congener-specific analysis. Environ. Health Perspect. 81, 225-239.
42. Narasimhan, T. R., Kim, H. L., and Safe, S. (1991). Effects of hydroxylated polychlorinated biphenyls on mouse liver mitochondrial oxidative phosphorylation. J. Biochem. Toxicol. 6, 229-236.
43. Nishihara, Y. (1988). Comparative toxicity of 4-chlorobiphenyl and its metabolite 4-chloro-4′-biphenylol in isolated rat liver mitochondria. Biochem. Pharmacol. 37, 2915-2926.
44. Nishihara, Y., and Utsumi, K. (1987). 4-Chloro-4′-biphenylol as an uncoupler and an inhibitor of mitochondrial oxidative phosphorylation. Biochem. Pharmacol. 36, 3453-3457.
45. Parkinson, A., Robertson, L., Safe, L., and Safe, S. (1981a). Polychlorinated biphenyls as inducers of hepatic microsomal enzymes: Effects of diortho substitution. Chem.-Biol. Interact. 31, 1-12.
46. Parkinson, A., Robertson, L., Safe, L., and Safe, S. (1981b). Polychlorinated biphenyls as inducers of hepatic microsomal enzymes: Structure-activity rules. Chem.-Biol. Interact. 30, 271-285.
47. Parkinson, A., Safe, S., Robertson, L., Thomas, P. E., Ryan, D. E., and Levin, W. (1983). Immunochemical quantitation of cytochrome P-450 isozymes and epoxide hydrolase in liver microsomes from polychlorinated and polybrominated biphenyls: A study of structure activity relationships. J. Biol. Chem. 258, 5967-5976.
48. Parkinson, A., Thomas, P. E., Ryan, D. E., Levin, W., Fujita, T., and Safe, S. (1988). Induction of rat liver microsomal cytochrome P-450 isozymes and epoxide hydrolase by a series of 4′-substituted-2,3,4,5-tetrachlorodibiphenyls. Toxicology 53, 289-300.
49. Pons, M., Gagne, D., Nicolas, J. C., and Methali, M. (1990). A new cellular model of response to estrogens: A bioluminescent test to characterize (anti)estrogen molecules. BioTechniques 9, 450-459.
50. Safe, S. (1984). Polychlorinated biphenyls (PCBs) and polybrominated biphenyls (PBBs): Biochemistry, toxicology and mechanism of action. CRC Crit. Rev. Toxicol. 12, 319-395.
51. Safe, S. (1989). Polyhalogenated aromatics: uptake, disposition and metabolism. In Halogenated Biphenyls, Naphthalene, Dibenzodioxins and Related Compounds (R. D. Kimbrough and A. A. Jensen, Eds.), pp. 51-69. Elsevier-North Holland, Amsterdam.
52. Safe, S. (1990). Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs) and related compounds: Environmental and mechanistic considerations which support the development of toxic equivalency factors (TEFs). CRC Crit. Rev. Toxicol. 21, 51-88.
53. Safe, S. (1994). Polychlorinated biphenyls (PCBs): Environmental impact, biochemical and toxic responses, and implications for risk assessment. CRC Crit. Rev. Toxicol. 24, 87-149.
54. Safe, S. (1995). Environmental and dietary estrogens and human health -Is there a problem? Environ. Health Perspect. 103, 346-351.
55. Safe, S., Washburn, K., Zacharewski, T., and Phillips, T. D. (1995). Synthesis and characterization of hydroxylated polychlorinated biphenyls (PCBs) identified in human serum. Chemosphere 31, 3017-3023.
56. Sargent, L., Dragan, Y. P., Erickson, C., Laufer, C. J., and Pilot, H. C. (1991). Study of the separate and combined effects of the non-planar 2,5,2′,5′-and the planar 3,4,3′,4′-tetrachlorobiphenyl in liver and lymphocytes in vivo. Carcinogenesis 12, 793-800.
57. Schulz, D. E., Petrick, G., and Duinker, J. C. (1989). Complete characterization of polychlorinated biphenyl congeners in commercial Aroclor and Clophen mixtures by multidimensional gas chromatography-electron capture detection. Environ. Sci. Technol. 23, 852-859.
58. Seegal, R. F., Bush, B., and Shain, W. (1990). Lightly chlorinated ortho-substituted PCB congener decrease dopamine in nonhuman primate brain and in tissue culture. Toxicol. Appl. Pharmacol. 106, 136-144.
59. Seegal, R. F., Bush, B., and Brosch, K. O. (1991). Comparison of effects of Aroclors 1016 and 1260 on non-human primate catecholamine function. Toxicology 66, 145-163.
60. Sharpe, R. M., and Skakkebaek, N. F. (1993). Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract. Lancet 341, 1392-1395.
61. Sipes, I. G., and Schnellmann, R. G. (1987). Biotransformation of PCBs: Metabolic pathways and mechanisms. In Polychlorinated Biphenyls (PCBs): Mammalian and Environmental Toxicology (S. Safe and O. Hutzinger, Eds.), pp. 97-110. Springer-Verlag, Heidelberg.
62. Soontornchat, S., Li, M., Cooke, P. S., and Hansen, L. G. (1994). Toxicokinetic and toxicodynamic influences on endocrine disruption by polychlorinated biphenyls. Environ. Health Perspect. 102, 568-571.
63. Soto, A. M., Justicia, H., Wray, J. W., and Sonnenschein, C. (1991). p-Nonylphenol: An estrogenic xenobiotic released from "modified" polystyrene. Environ. Health Perspect. 92, 167-173.
64. Soto, A. M., Chung, K. L., and Sonnenschein, C. (1994). The pesticides endosulfan, toxaphene, and dieldrin have estrogenic effects on human estrogen-sensitive cells. Environ. Health Perspect. 102, 380-383.
65. Stadnicki, S. S., and Allen, J. R. (1979). Toxicity of 2,2′,5,5′-tetrachlorobiphenyl and its metabolites, 2,2′,5,5′-tetrachlorobiphenyl-3,4-oxide and 2,2′,5,5′-tetrachlorobiphenyl-4-o1 to cultured cells in vitro. Bull. Environ. Contam. Toxicol. 23, 788-796.
66. Tithof, P. K., Contreras, M. L., and Ganey, P. E. (1996). Aroclor 1242 stimulates the production of inositol phosphates in polymorphonuclear neutrophils. Toxicol. Appl. Pharmacol. 131, 136-143.
67. White, R., Jobling, S., Hoare, S. A., Sumpter, J. P., and Parker, M. G. (1993). Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135, 175-182.
68. Yoshimura, H., Yonemoto, Y., Yamada, H., Koga, N., Oguri, K., and Saeki, S. (1987). Metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl and toxico-logical assessment of the metabolites in rats. Xenobiotica 17, 897-910.
69. Zacharewski, T., Bondy, K., McDonell, P., and Wu, Z. F. (1994). Antiestrogenic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on 17β-estradiol-induced pS2 expression. Cancer Res. 54, 2707-2713.