Specific binding of hydroxylated polychlorinated biphenyl metabolites and other substances to bovine calf uterine estrogen receptor: Structure-binding relationships

Science of the Total Environment

Volumn 233, Issue 1-3, 1999, Pages 141-161

  Kramer, Vincent J ^a   Giesy, John P ^a  

^a Inst Environ Toxicol Michigan S   (United States)

Author keywords

Endocrine disruption; Estrogen receptor; Polychlorinated biphenyls; QSAR

Indexed keywords

1,1,1 TRICHLORO 2 (2 CHLOROPHENYL) 2 (4 CHLOROPHENYL)ETHANE; ESTROGEN RECEPTOR; MITOTANE; POLYCHLORINATED BIPHENYL;

ANIMAL CELL; ANIMAL TISSUE; BINDING AFFINITY; CATTLE; CONFERENCE PAPER; ENDOCRINE FUNCTION; ESTROGEN ACTIVITY; MODEL; NONHUMAN; POLLUTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR BINDING;

ANIMALS; BINDING, COMPETITIVE; CATTLE; ENVIRONMENTAL MONITORING; ENVIRONMENTAL POLLUTANTS; FEMALE; MODELS, MOLECULAR; POLYCHLORINATED BIPHENYLS; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; UTERUS;

BOVINAE;

EID: 0032786636     PISSN: 00489697     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0048-9697(99)00221-1     Document Type: Conference Paper

References (93)

1. Adlercreutz H. Phytoestrogens: epidemiology and a possible role in cancer protection. Environ Health Perspect. 103(suppl. 7):1995;102-112.
2. Akaike H. A new look at the statistical model identification. IEEE Transactions on Automatic Control. 1974;AC-19(6):716-723.
3. Anstead G.M., Carlson K.E., Katzenellenbogen J.A. The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids. 62:1997;268-303.
4. Archuleta M.M., Schieven G.L., Ledbetter J.A., Deanin G.G., Burchiel S.W. 7,12-Dimethylbenz[a]anthracene activates protein-tyrosine kinases Fyn and Lck in the HPB-ALL human T-cell line and increases tyrosine phosphorylation of phospholipase C-g1, Formation of inositol 1,4,5-trisphosphate, and mobilization of intracellular calcium. Proc Natl Acad Sci USA. 90:1993;6105-6109.
5. Arnold S.F., Obourn J.D., Jaffe H., Notides A.C. Serine 167 is the major estradiol-induced phosphorylation site on the human estrogen receptor. Mol Endocrinol. 8(9):1994;1208-1214.
6. Arnold S.F., Vorojeikina T., Notides A.C. Phosphorylation of Tyrosine 537 on the human estrogen receptor is required for binding to an estrogen response element. J Biol Chem. 270(50):1995;30205-30212.
7. Aronica S.M., Katzenellenbogen B.S. Stimulation of estrogen receptor-mediated transcription and alteration in the phosphorylation state of the rat uterine estrogen receptor by estrogen, cyclic adenosine monophosphate, and insulin-like growth factor. Mol Endocrinol. 7(6):1993;743-752.
8. Barrett J. Phytoestrogens: friends or foes'? Environ Health Perspect. 104:1996;478-482.
9. Becker KL. Principles and practice of endocrinology and metabolism. Philadelphia, PA: Lippincott, 1990:78-80, 970.
10. Bergman A., Athanasiadou M., Bergek S., Haraguchi K., Jensen S., Klasson-Wehler E. PCB and PCB methyl sulphones in mink treated with PCB and various PCB fractions. Ambio. 21:1992;570-576.
11. Bergman A., Klasson-Wehler E., Kuroki H. Selective retention of hydroxylated PCB metabolites in blood. Environ Health Perspect. 102:1994;464-469.
12. Blankenship A., Matsumura F. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) causes an ah receptor-dependent and ARNT-independent increase in membrane levels and activity of p60Src. Environ Toxicol Pharmacol. 3:1997;211-220.
13. Bondy K.L., Zacharewski T.R. ICI 164,384: A control for investigating estrogen responsive genes. Nucleic Acids Res. 21:1993;5277-5278.
14. Bradbury S.P., Mekenyan O.G., Ankley G.T. Quantitative structure-activity relationships for polychlorinated hydroxybiphenyl estrogen receptor binding affinity: an assessment of conformer flexibility. Environ Toxicol Chem. 15:1997;1945-1954.
15. Brooks S.C., Wappler N.L., Corombos J.D., Doherty L.M., Horwitz J.P. Estrogen structure-receptor function relationships. Moudgil V.K. Recent advances in steroid hormone action. 1987;343-366 W. De Gruyer, New York.
16. Brouwer A., Klasson-Wehler E., Boddam M., Morse D.C., Traag W.A. Competitive inhibition of thyroxin binding to transthyretin by monohydroxy metabolites of 3,4,3',4'-tetrachlorobiphenyl. Chemosphere. 20:1990;1257-1262.
17. Bruce R.D., Versteeg D.J. A statistical procedure for modelling continuous toxicity data. Environ Toxicol Chem. 11:1992;1485-1494.
18. Brzozowski A.M., Pike A.C.W., Dauter Z. et al. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature. 389:1997;753-758.
19. Bulger W.H., Muccitelli R.M., Kupfer D. Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites. Role of hepatic mono-oxygenase in methoxychlor activation. Biochem Pharmacol. 27:1978;2417-2423.
20. Chae K., Gibson M.K., Korach K.S. Estrogen receptor stereochemistry: ligand binding orientation and influence on biological activity. Mol Pharmacol. 40:1991;806-811.
21. Cho H., Katzenellenbogen B.S. Synergistic activation of estrogen receptor-mediated transcription by estradiol and protein kinase activators. Mol Endocrinol. 7:1993;441-452.
22. Colborn T., Vom Saal F.S., Soto A.M. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect. 101:1993;378-384.
23. Colborn T. Environmental estrogens: health implications for humans and wildlife. Environ Health Perspect. 103(suppl. 7):1995;135-136.
24. Connor K., Ramamoorthy K., Moore M. et al. Hydroxylated polychlorinated biphenyls (PCBs) as estrogens and antiestrogens: structure-activity relationships. Toxicol Appl Pharmacol. 145:1997;111-123.
25. Cooper R.L., Kavlock R.H. Endocrine disruptors and reproductive development: a weight of evidence overview. J Endocrinol. 152:1997;159-166.
26. 14C] -biphenyl in pregnant mice: enrichment of phenol and methyl sulphone metabolites in late gestational fetuses. Xenobiotica. 16:1986;295-306.
27. DeWailly E., Nantel A., Weber J., Meyer F. High levels of PCBs in breast milk of Inuit women from arctic Quebec. Bull Environ Contam Toxicol. 43:1989;641-646.
28. Dibb S. Swimming in a sea of estrogens, chemical hormone disrupters. The Ecologist. 25:1995;27-31.
29. Enan E., Matsumura F. Activation of phosphoinositide/protein kinase C pathway in rat brain tissue by pyrethroids. Biochem Pharmacol. 45:1993;703-710.
30. Evans R.M. The steroid and thyroid hormone receptor superfamily. Science. 240:1988;889-895.
31. Fawell S.E., White R., Hoare S., Sydenham M., Page M., Parker M.G. Inhibition of estrogen receptor DNA binding by the 'pure' anti-estrogen ICI 164,384 appears to be mediated by impaired receptor dimerization. Proc Natl Acad Sci USA. 87:1990;6883-6887.
32. Feldman D., Krishnan A. Estrogens in unexpected places: Possible implications for researchers and consumers. Environ Health Perspect. 103(suppl. 7):1995;129-133.
33. Fielden M.R., Chen I., Chittin B., Safe S.H., Zacharewski T.R. Examination of the estrogenicity of 2,4,6,2',6'-pentachlorobiphenyl (PCB104), 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. 105:1997;1238-1249.
34. Gorski J., Furlow J.D., Murdoch F.E. Perturbations in the model of estrogen receptor regulation of gene expression. Biol Reprod. 48:1993;8-14.
35. Guillette L.J., Crain D.A., Rooney A.A., Pickford D.B. Organization versus activation: the role of endocrine disrupting contaminants (EDCs) during embryonic development in wildlife. Environ Health Perspect. 103(suppl. 7):1995;157-164.
36. Hendry L.B., Chu C.K., Copland J.A., Mahesh V.B. Antiestrogenic piperidinediones designed prospectively using computer graphics and energy calculations of DNA-ligand comlexes. J Steroid Biochem Molec Biol. 48:1994;495-505.
37. Hendry L.B., Chu C.K., Rosser M.L., Copland J.A., Wood J.A., Mahesh V.B. Design of novel antiestrogens. J Steroid Biochem Molec Biol. 49:1994;269-280.
38. Hoare S.A., Jobling S., Parker M.G., Sumpter J.P., White R. Environmental persistent alkylphenolic compounds are estrogenic. Endocrinology. 135:1994;175-182.
39. Ignar-Trowbridge D.M., Nelson K.G., Bidwell M.C. Coupling of dual signaling pathways: epidermal growth factor action involves the estrogen receptor. Proc Natl Acad Sci USA. 89:1992;4658-4662.
40. Ignar-Trowbridge D.M., Pimentel M., Parker M.G., McLachlan J.A., Korach K.S. Peptide growth factor cross-talk with the estrogen receptor requires the A/B domain and occurs independently of protein kinase C or estradiol. Endocrinology. 137:1996;1735-1744.
41. Jansson B., Andersson R., Asplund L., Litzen K., Nylund K., Sellstrom U., Uvemo U.B., Wahlberg C., Wideqvist U., Odsjó T., Oisson M. Chlorinated and brominated persistent organic compounds in biological samples from the environment. Environ Toxicol Chem. 12:1993;1163-1174.
42. Jarman W.M., Simon M., Norstrom R.J. et al. Global distribution of tris(4chlorophenyl)methanol in high trophic level birds and mammals. Environ Sci Technol. 26:1992;1770-1774.
43. Jobling S., Sumpter J.P. Detergent compounds in sewage effluents are weakly oestrogenic to fish: an in vitro study using rainbow trout (Onchorhyncus mykiss) hepatocytes. Aquat Toxicol. 27:1993;361-372.
44. Johnson L., Casillas E., Sol S., Collier T., Stein J., Varanasi U. Contaminant effects on reproductive success in selected benthic fish. Mar Env Res. 35:1993;165-170.
45. Jordan V.C., Kock R., Lieberman M.E. Structure-activity relationships of nonsteroidal estrogens and anti-estrogens. Jordan V.C. Estrogen/anti-estrogen action and breast cancer therapy. 1986;19-41 University of Wisconsin Press, Madison.
46. Karlsson S., Hirsimaki Y., Mantyla E. et al. A two year dietary carcinogenicity study of the antiestrogen toremifene in Sprague-Dawley rats. Drug Chem Toxicol. 19:1996;245-266.
47. Katzenellenbogen B.S., Montano M.M., LeGoff P. et al. Antiestrogens: mechanisms and actions in target cells. J Steroid Biochem Molec Biol. 53:1995;387-393.
48. Katzenellenbogen B.S. Estrogen receptors: bioactivities and interactions with cell signaling pathways. Biol Reprod. 54:1996;287-293.
49. Koga N., Beppu M., Yoshimura H. Metabolism in vivo of 3,4,5,3',4'-pentachlorobiphenyl and toxicological assessment of the metabolite in rats. J Pharmacobio-Dyn. 13:1990;497-506.
50. Koistinen J., Nevalainen T., Tarhanen J. Identification and level estimation of aromatic coeluates of polychlorinated dibenzo-p-dioxins and dibenzofurans in pulp mill products and wastes. Environ Sci Technol. 26:1992;2499-2507.
51. Korach K.S., Levy L.A., Sarver P.J. Estrogen receptor stereochemistry: receptor binding and hormonal responses. J Steroid Biochem. 27:1987;281-290.
52. Korach K.S., Sarver P., Chae K., McLachlan J.A., McKinney J.D. Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: conformationally restricted structural probes. Molec Pharmacol. 33:1988;120-126.
53. Kramer V.J., Helferich W.G., Bergman Å., Klasson-Wehler E., Giesy J.P. Hydroxylated polychlorinated biphenyl metabolites are anti-estrogenic in a stably transfected human breast adenocarcinoma (MCF7) cell line. Toxicol Appl Pharmacol. 144:1997;363-376.
54. Krishnan V., Safe S. Polychlorinated biphenyls (PCBs) dibenzo-p-dioxins (PCDDS) and dibenzofurans (PCDFS) as antiestrogens in MCF-7 human breast cancer cell: quantitative structure-activity relationships. Toxicol Appl Pharm. 120:1993;55-61.
55. Kuiper G.G., Brinkman A.O. Steroid hormone receptor phosphorylation: is there a physiological role? Mol Cell Endocrinol. 100:1994;103-107.
56. Kuiper G.G., Carlsson B., Grandien K. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors a and b. Endocrinology. 138:1997;863-870.
57. Kumar V., Chambon P. The estrogen receptor binds tightly to its responsive element as a ligand induced homodimer. Cell. 55:1988;145-156.
58. Landel C.C., Kushner P.J., Greene G.L. Estrogen receptor accessory proteins: effects on receptor-DNA interactions. Environ Health Perspect. 103(suppl 7):1995;23-28.
59. Le Goff P., Montano M.M., Schodin D.J., Katzenellenbogen B.S. Phosphorylation of the human estrogen receptor. J Biol Chem. 269:1994;4458-4466.
60. Madhukar B.V., Brewster D.W., Matsumura F. Effects of in vivo administration of 2,3,7,8-TCDD on receptor binding of epidermal growth factor in the hepatic plasma membrane of rat, guinea pig, mouse, and hamster. Proc Natl Acad Sci. 81:1984;7407-7411.
61. Makela S., Santti R., Salo L., McLachlan J.A. Phytoestrogens are partial estrogen agonists in the adult male mouse. Environ Health Perspect. 103(suppl 7):1995;123-127.
62. Mangelsdorf D.J., Thummel C., Beato M. The nuclear receptor superfamily: the second decade. Cell. 83:1995;835-839.
63. McLachlan J.A., Arnold S.F. Environmental estrogens. Am Sci. 84:1996;452-461.
64. McLachlan J.A., Korach K.S., Newbold R.R., Degen G.H. Diethylstilbestrol and other estrogens in the environment. Fund Appl Toxicol. 4:1984;686-691.
65. Meek D.W., Street A.J. Nuclear protein phosphorylation and growth control. Biochem J. 287:1992;1-15.
66. Mellanen P., Petanen T., Lehtimaki J. et al. Wood-derived estrogens: studies in vitro with breast cancer cell lines and in vivo in trout. Toxicol Appl Pharmacol. 136:1996;381-388.
67. Miksicek R.J. Commonly occurring plant flavonoids have estrogenic activity. Molec Pharmacol. 44:1993;37-43.
68. Moore M., Mustain M., Daniel K. et al. Antiestrogenic activity of hydroxylated polychlorinated biphenyl congeners identified in human serum. Toxicol Appl Pharmacol. 142:1997;160-168.
69. Morse D.C., Klasson-Wehler E., van der Pas M., de Bie A.T.H.J., van Bladeren P.J., Brouwer A. Metabolism and biochemical effects of 3,3',4,4'-tetrachlorobiphenyl in pregnant and fetal rats. Chem-Biol Interact. 95:1995;41-56.
70. Murdoch F.E., Meier D.A., Furlow J.D., Grunwald K.A.A., Gorski J. Estrogen receptor binding to a DNA response element in vitro is not dependent upon estradiol. Biochem. 29:1990;8377-8385.
71. Nathan L., Chaudhuri G. Estrogens and atherosclerosis. Annu Rev Pharmacol Toxicol. 37:1997;477-515.
72. Paasivirta J., Heinola K., Humpi T. et al. Polychlorinated phenols, guaicols, and catechols in the environment. Chemosphere. 14:1985;469-491.
73. Paech K., Webb P., Kuiper G.G.J.M. et al. Differential ligand activation of estrogen receptors ERα and ERβ at AP1 sites. Science. 277:1997;1508-1510.
74. Romkes M., Piskorska-Pliszczynska J., Safe S. Effects of 2,3,7,8-Tetrachlorodibenzo-p-dioxin on hepatic and uterine estrogen receptor levels in rats. Toxicol Appl Pharmacol. 87:1987;306-314.
75. Ruenitz P.C., Moore S.A., Kraft K.S., Bourne C.S. Estrogenic tamoxifen derivatives: categorization of intrinsic estrogenicity in MCF-7 cells. J Steroid Biochem Molec Biol. 63:1997;203-209.
76. Safe S., Astroff B., Harris M. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) and related compounds as antiestrogens: Characterization and mechanism of action. Pharmacol Toxicol. 69:1991;400-409.
77. ® Statistics and graphics guide, Version 3.1 SAS Institute, Cary NC, 1995:197-212.
78. Schlenk D., Stresser D.M., McCants J.C., Nimrod A.C., Benson W.H. Influence of ß-naphthoflavone and methoxychlor pretreatment on the biotransformation and estrogenic activity of methoxychlor in channel catfish (Ictalurus punctatus). Toxicol Appl Pharmacol. 145:1997;349-356.
79. Smith D.F., Toft D.O. Steroid receptors and their associated proteins. Mol Endocrinol. 7:1993;4-11.
80. Solmssen U.V. Synthetic estrogens and the relation between their structure and their activity. Chem Rev. 37:1945;481-598.
81. Soto A.M., Lin T.M., Justicia H., Silvia R.M., Sonnennschein C. An 'in culture' bioassay to assess the estrogenicity of xenobiotics (E-screen). Colburn T., Clement C. Chemically induced alterations in sexual and functional development: the wildlife/human connection. 1992;295-309 Princeton Scientific Publishing, Princeton.
82. Spink D.C., Lincoln D.W., Johnson J.A., Dickerman H.W., Gierthy J.F. Stimulation of 17ß-estradiol metabolism in MCF-7 breast cancer cells by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Chemosphere. 25:1992;87-90.
83. Standeven A.M., Blazer D.G., Goldsworthy T.L. Investigation of antiestrogenic properties of unleaded gasoline in female mice. Toxicol Appl Pharmacol. 127:1994;233-240.
84. Sundstrom G., Hutzinger O., Safe S. The metabolism of chlorobiphenyls - a review. Chemosphere. 5:1976;267-298.
85. Van der Kuur J.A., Wiese T., Brooks S.C. Influence of estrogen structure on nuclear binding and progesterone receptor induction by the receptor complex. Biochemistry. 32:1993;7002-7008.
86. Waller C.L., Minor D.L., McKinney J.D. Using three dimensional quantitative structure-activity relationships to examine estrogen receptor binding affinities of polychlorinated hydroxybiphenyls. Environ Health Perspect. 103:1995;702-707.
87. Waller C.L., Oprea T.I., Chae K. et al. Ligand-based identification of environmental estrogens. Chem Res Toxicol. 9:1996;1240-1248.
88. Waller C.L., Booker W.J., Gray L.E., Kelce W.R. Three-dimensional quantitative structure- activity relationships for androgen receptor ligands. Toxicol Appl Pharmacol. 137:1996;219-227.
89. Welch R.M., Levin W., Conney A.H. Estrogenic action of DDT and its analogs. Toxicol Appl Pharmacol. 14:1969;358-367.
90. Wolff M.S., Toniolo P.G., Lee E.W., Rivera M., Dubin N. Blood levels of organochlorine residues and risk of breast cancer. J Natl Cancer Inst. 85:1993;648-652.
91. Yager J.D., Liehr J.G. Molecular mechanisms of estrogen carcinogenesis. Annu Rev Pharmacol Toxicol. 36:1996;203-232.
92. Zacharewski T., Harris M., Safe S. Evidence for the mechanism of action of 2,3,7,8-tetrachlorodibenzo-p-dioxin mediated decrease of nuclear estrogen receptor levels in wild-type and mutant mouse Hepa lclc7 cells. Biochem Pharmacol. 41:1991;1931-1939.
93. Zacharewski T. In vitro bioassays for assessing estrogenic substances. Environ Sci Technol. 31:1997;613-623.