Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β

Endocrinology

Volumn 139, Issue 10, 1998, Pages 4252-4263

  Kuiper, George G J M ^a,f   Lemmen, Josephine G ^c   Carlsson, Bo ^b   Corton, J Christopher ^d   Safe, Stephen H ^e   Van Der Saag, Paul T ^c   Van Der Burg, Bart ^c   Gustafsson, Jan Åke ^a  

^a Center for Biotechnology   (Sweden)

^b Karo Bio   (Sweden)

^c HUBRECHT INSTITUTE   (Netherlands)

^d CIIT CENTERS FOR HEALTH RESEARCH   (United States)

^e TEXAS A AND M UNIVERSITY   (United States)

^f Center for Biotechnology   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

4,4' ISOPROPYLIDENEDIPHENOL; ALKYLPHENOL; APIGENIN; CHLORDECONE; CHLORPHENOTANE; COUMESTROL; DAIDZEIN; ESTROGEN; ESTROGEN RECEPTOR; GENISTEIN; KAEMPFEROL; METHOXYCHLOR; NARINGENIN; NONYLPHENOL; PHYTOESTROGEN; POLYCHLORINATED BIPHENYL; RECEPTOR SUBTYPE; ZEARALENONE;

ARTICLE; BINDING AFFINITY; DISSOCIATION CONSTANT; GENE EXPRESSION; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL; PROTEIN PROTEIN INTERACTION; RECEPTOR BINDING; TRANSACTIVATION;

EID: 0031733298     PISSN: 00137227     EISSN: None     Source Type: Journal    
DOI: 10.1210/endo.139.10.6216     Document Type: Article

References (83)

1. Korach KS, Migliaccio S, Davis VL 1994 Estrogens. In: Munson PL (ed) Principles of Pharmacology-Basic Concepts and Clinical Applications. Chapman and Hall, New York, pp 809-825
2. Turner RT, Riggs BL, Spelsberg TC 1994 Skeletal effects of estrogens. Endocr Rev 15:275-300
3. Farhat MY, Lavigne MC, Ramwell PW 1996 The vascular protective effects of estrogen. FASEB J 10:615-624
4. Iafrati MD, Karas RH, Aronovitz M, Kim S, Sullivan TR, Lubahn DB, O'Donnell TF, Korach KS, Mendelsohn ME 1997 Estrogen inhibits the vascular injury response in estrogen receptor α deficient mice. Nature Med 3:545-548
5. Jensen EV 1995 Steroid hormones, receptors and antagonists. Ann NY Acad Sci 761:1-17
6. Beato M, Herrlich P, Schutz G 1995 Steroid hormone receptors: many actors in search of a plot. Cell 83:851-857
7. Tsai M-J, O'Malley BW 1995 Molecular mechanisms of action of steroid/ thyroid receptor superfamily members. Annu Rev Biochem 63:451-486
8. Kuiper GGJM, Enmark E, Pelto-Huikko M, Nilsson S, Gustafsson J-Å 1996 Cloning of a novel estrogen receptor expressed in rat prostate and ovary. Proc Natl Acad Sci USA 93:5925-5930
9. Chu S, Fuller PJ 1997 Identification of a splice variant of the rat estrogen receptor β gene. Mol Cell Endocrinol 132:195-199
10. Petersen DN, Tkalcevic GT, Koza-Taylor PH, Turi TG, Brown TA 1998 Identification of estrogen receptor β2, a functional variant of estrogen receptor β expressed in normal rat tissues. Endocrinology 139:1082-1092
11. Tremblay GB, Tremblay A, Copeland NG, Gilbert DJ, Jenkins NA, Labrie F, Giguere V 1997 Cloning, chromosomal localization, and functional analysis of the murine estrogen receptor β. Mol Endocrinol 11:353-365
12. Pettersson K, Grandien K, Kuiper GGJM, Gustafsson J-Å 1997 Mouse estrogen receptor β forms estrogen response element-binding heterodimers with estrogen receptor α. Mol Endocrinol 11:1486-1496
13. Ogawa S, Inoue S, Watanabe T, Hiroi H, Orimo A, Hosoi T, Ouchi Y, Muramatsu M 1998 The complete primary structure of human estrogen receptor β and its heterodimerization with ERα in vivo and in vitro. Biochem Biophys Res Commun 243:122-126
14. Enmark E, Pelto-Huikko M, Grandien K, Lagercrantz S, Lagercrantz J, Fried G, Nordenskjöld M, Gustafsson J-Å 1997 Human estrogen receptor β- gene structure, chromosomal localization and expression pattern. J Clin Endocrinol Metab 82:4258-4265
15. Kuiper GGJM, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson J-Å 1997 Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors α and β. Endocrinology 138:863-870
16. Shughrue PJ, Lane MV, Merchenthaler I 1997 Comparative distribution of estrogen receptor-α and -β mRNA in the rat central nervous system. J Comp Neurol 388:507-525
17. Österlund M, Kuiper GGJM, Gustafsson J-Å, Hurd YL 1998 Differential distribution and regulation of estrogen receptor-α and -β mRNA within the female rat brain. Mol Brain Res 54:175-180
18. Nimrod AC, Benson WH 1996 Environmental estrogenic effects of alkylphenol ethoxylates. Crit Revi Toxicol 26:335-363
19. Gimeno S, Gerritsen A, Bowmer T, Komen H 1996 Feminization of male carp. Nature 384:221-222
20. Sharpe RM, Skakkebaek NE 1993 Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet 341:1392-1395
21. LeBlanc GA, Bain LJ, Wilson VS 1997 Pesticides: multiple mechanisms of demasculinization. Mol Cell Endocrinol 126:1-5
22. Feldman D 1997 Editorial: estrogens from plastic: are we being exposed? Endocrinology 138:1777-1779
23. Greco TL, Duello TM, Gorski J 1993 Estrogen receptors, estradiol, and diethylstilbestrol in early development: the mouse as a model for the study of estrogen receptors and estrogen sensitivity in embryonic development of male and female reproductive tracts. Endocr Rev 14:59-71
24. Korach KS, Sarver P, Chae K, McLachlan JA, McKinney JD 1988 Estrogen receptor-binding activity of polychlorinated hydroxybiphenyls: conformationally restricted structural probes. Mol Pharmacol 33:120-126
25. Moore M, Mustain M, Daniel K, Chen I, Safe S, Zacharewski T, Gillesby B, Joyeux A, Balaguer P 1997 Antiestrogenic activity of hydroxylated polychlorinated biphenyl congeners identified in human serum. Toxicol Appl Pharmacol 142:160-168
26. Chen CW, Hurd C, Vorojeikina DP, Arnold SF, Notides AC 1997 Transcriptional activation of the human estrogen receptor by DDT isomers and metabolites in yeast and MCF-7 cells. Biochem Pharmacol 53:1161-1172
27. Hammond B, Katzenellenbogen BS, Krauthammer N, McConnell J 1979 Estrogenic activity of the insecticide chlordecone (Kepone) and interaction with uterine estrogen receptors. Proc Natl Acad Sci USA 76:6641-6645
28. Routledge EJ, Sumpter JP 1997 Structural features of alkylphenolic chemicals associated with estrogenic activity. J Biol Chem 272:3280-3288
29. Krishnan AV, Stathis P, Permuth SF, Tokes L, Feldman D 1993 Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132:2279-2286
30. White R, Jobling S, Hoare SA, Sumpter JP, Parker MG 1994 Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135:175-182
31. Prins GS, Marmer M, Woodham C, Chang W, Kuiper GGJM, Gustafsson J-Å, Birch L 1998 Estrogen receptor β mRNA ontogeny in the rat prostate and effects of neonatal estrogen exposure on the expression pattern. Endocrinology 139:874-883
32. Salo LK, Mäkelä SI, Stancel GM, Santti RSS 1997 Neonatal exposure to diethylstilbestrol permanently alters the basal and 17β-estradiol induced expression of c-fos proto-oncogene in mouse urethroprostatic complex. Mol Cell Endocrinol 126:133-141
33. vom Saal FS, Timms BG, Montano MM, Palanza P, Thayer KA, Nagel SC, Dhar MD, Ganjam VK, Parmigiani S, Welshons WV 1997 Prostate enlargement in mice due to fetal exposure to low doses of estradiol or diethylstilbestrol and opposite effects at high doses. Proc Natl Acad Sci USA 94:2056-2061
34. Saunders PTK, Fisher JS, Sharpe RM, Millar MR 1998 Expression of oestrogen receptor β occurs in multiple cell types, including some germ cells, in the rat testis. J Endocrinol 156:R13-R17
35. Majdic G, Sharpe RM, Saunders PTK 1997 Maternal oestrogen/xenoestrogen exposure alters expression of steroidogenic factor-1 (SF-1/Ad4BP) in the fetal testis. Mol Cell Endocrinol 127:91-98
36. Brandenberger AW, Meng Kian Tee, Lee JY, Chao V, Jaffe RB 1997 Tissue distribution of estrogen receptors ERα and ERβ mRNA in the midgestational human fetus. J Clin Endocrinol Metab 82:3509-3512
37. Mäkelä S, Davis VL, Tally WC, Korkman J, Salo L, Vihko R, Santti R, Korach KS 1994 Dietary estrogens act through estrogen receptor-mediated processes and show no antiestrogenicity in cultured breast cancer cells. Environ Health Perspect 102:572-581
38. Miksicek RJ 1993 Commonly occurring plant flavonoids have estrogenic activity. Mol Pharmacol 44:37-43
39. Markiewicz L, Garey J, Adlercreutz H, Gurpide E 1993 In vitro bioassays of non-steroidal phytoestrogens. J Steroid Biochem Mol Biol 45:399-405
40. Messina MJ, Persky V, Setchell KDR, Barnes S 1994 Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutr Cancer 21:113-131
41. Mäkelä SI, Pylkkänen LH, Santii RSS, Adlercreutz H 1995 Dietary soy-bean may be antiestrogenic in male mice. J Nutr 125:437-445
42. Kurzer MS, Xu X 1997 Dietary phytoestrogens. Annu Rev Nutr 17:353-381
43. Safe S, Washburn K, Zacharewski T, Phillips T 1995 Synthesis and characterisation of hydroxylated polychlorinated biphenyls identified in human serum. Chemosphere 31:3017-3023
44. Connor K, Ramamoorthy K, Moore M, Mustain M, Chen I, Safe S, Zacharewski T, Gillesby B, Joyeux A, Balaguer P 1997 Hydroxylated polychlorinated biphenyls as estrogens and antiestrogens: structure-activity relationships. Toxicol Appl Pharmacol 145:111-123
45. Barkhem T, Carlsson B, Simons J, Moller B, Berkenstam A, Gustafsson J-Å, Nilsson S 1991 High level expression of functional full length human thyroid hormone receptor β1 in insect cells using a recombinant baculovirus. J Steroid Biochem Mol Biol 38:667-675
46. Häggblad J, Carlsson B, Kivelä P, Siittari H 1995 Scintillating micro-titration plates as platform for determination of estradiol binding constants for hER-HBD. BioTechniques 18:146-151
47. Schults JR, Ruppel PI, Johnson MA Pharmaceutical lead discovery, and optimization. In: Peace KE (ed) Biopharmaceutical Statistics for Drug Development. Marcel Dekker, New York, pp 21-82
48. Salomonsson M, Carlsson B, Häggblad J 1994 Equilibrium hormone binding to human estrogen receptors in highly diluted cell extracts is non-cooperative and has a Kd of approximately 10 pM. J Steroid Biochem Mol Biol 50:313-318
49. Wells JW 1992 Analysis and interpretation of binding at equilibrium. In: Hulme EC (ed) Receptor Ligand Interactions. IRL Press, Oxford-UK, pp 289-397
50. Hulme EC, Birdsall NJM 1992 Strategy and tactics in receptor-binding studies. In: Hulme EC (ed) Receptor Ligand Interactions. IRL Press, Oxford-UK, pp 163-176
51. Chu G, Sharp PA 1981 SV40 DNA transfection of cells in suspension: analysis of the efficiency of transcription and translation of T-antigen. Gene 13:197-202
52. Pfahl M, Tzukerman M, Zhang X-K, Hermann JM, Wills KN, Graupner G 1990 Nuclear retinoic acid receptors: cloning, analysis and function. Methods Enzymol 189:256-270
53. Obourn JD, Koszewski NJ, Notides AC 1993 Hormone- and DNA-binding mechanisms of the recombinant human estrogen receptor. Biochemistry 32:6229-6236
54. Luckow VA, Summers MD 1988 Trends in the development of baculovirus expression vectors. BioTechnology 6:47-55
55. Yang NN, Venugopalan M, Hardikar S, Glasebrook A 1996 Identification of an estrogen response element activated by metabolites of 17β-estradiol and raloxifene. Science 273:1222-1225 (correction appeared Science 275:1279)
56. Kelce WR, Stone CR, Laws SC, Gray LE, Kemppainen JA, Wilson EM 1995 Persistent DDT metabolite p, p′-DDT is a potent androgen receptor antagonist. Nature 375:581-585
57. Bicknell RJ, Herbison AE, Sumpter JP 1995 Oestrogenic activity of an environmentally persistent alkylphenol in the reproductive tract but not the brain of rodents. J Steroid Biochem Mol Biol 54:7-9
58. Steinmetz R, Brown NG, Allen DL, Bigsby RM, Ben-Jonathan N 1997 The environmental estrogen Bisphenol A stimulates prolactin release in vitro and in vivo. Endocrinology 138:1780-1786
59. Arányi P 1980 Kinetics of the hormone-receptor interaction - competition experiments with slowly equilibrating ligands. Biochim Biophys Acta 628:220-227
60. Lapcik O, Hampl R, Al-Maharik N, Salakka A, Wähälä K, Adlercreutz H 1997 A novel radioimmunoassay for daidzein. Steroids 62:315-320
61. Peterson TG, Coward L, Kirk M, Falany CN, Barnes S 1996 The role of metabolism in mammary epithelial cell growth inhibition by the isoflavones genistein and biochanin A. Carcinogenesis 17:1861-1869
62. Anstead GM, Carlson KE, Katzenellenbogen JA 1997 The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids 62:268-303
63. Brzozowski AM, Pike ACW, Dauter Z, Hubbard RE, Bonn T, Engström O, Öhman L, Greene GL, Gustafsson J-Å, Carlquist M 1997 Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389:753-758
64. Mueller GC, Kim UH 1978 Displacement of estradiol from estrogen receptors by simple alkylphenols. Endocrinology 102:1429-1435
65. Tong W, Perkins R, Li Xing, Welsh WJ, Sheehan DM 1997 QSAR models for binding of estrogenic compounds to estrogen receptor α and β subtypes. Endocrinology 138:4022-4025
66. Arnold SF, Klotz DM, Collins BM, Vonier PM, Guilette LJ, McLachlan JA 1996 Synergistic activation of estrogen receptor with combinations of environmental chemicals. Science 272:1489-1492 (retraction 277:462-463)
67. Ramamoorthy K, Wang F, Chen C, Norris JD, McDonnell DP, Leonard LS, Gaido KW, Bocchinfuso WP, Korach KS, Safe S 1997 Estrogenic activity of a dieldrin/toxaphene mixture in the mouse uterus, MCF-7 human breast cancer cells, and yeast-based estrogen receptor assays: no apparent synergism. Endocrinology 138:1520-1527
68. Nichols M, Rientjens JMJ, Logie C, Stewart AF 1997 FLP-recombinase/ estrogen receptor fusion proteins require the receptor D domain for responsiveness to antagonists, but not agonists. Mol Endocrinol 11:950-961
69. Feil R, Brocard J, Mascrez B, LeMeur M, Metzger D, Chambon P 1996 Ligand-activated site-specific recombination in mice. Proc Natl Acad Sci USA 93:10887-10890
70. Cowley SM, Hoare S, Mosselman S, Parker MG 1997 Estrogen receptors α and β form heterodimers on DNA. J Biol Chem 272:19858-19862
71. Watanabe T, Inoue S, Ogawa S, Ishii Y, Hiroi H, Ikeda K, Orimo A, Muramatsu M 1997 Agonistic effect of tamoxifen is dependent on cell type, ERE-promoter context, and estrogen receptor subtype: functional difference between estrogen receptors α and β. Biochem Biophys Res Commun 236:140-145
72. Dotzlaw H, Leygue E, Watson PH, Murphy LC 1997 Expression of estrogen receptor-β in human breast tumors. J Clin Endocrinol Metab 82:2371-2374
73. Messina M, Barnes S, Setchell KD 1997 Phytoestrogens and breast cancer -commentary. Lancet 350:971-972
74. Ingram D, Sanders K, Kolybaba M, Lopez D 1997 Case-control study of phytoestrogens and breast cancer. Lancet 350:990-994
75. Lee HP, Gourley L, Duffy SW, Esteve J, Lee J, Day NE 1991 Dietary effects on breast cancer risk in Singapore. Lancet 337:1197-1200
76. Ruh MF, Zacharewski T, Connor K, Howell J, Chen I, Safe S 1995 Naringenin, a weakly estrogenic bioflavonoid that exhibits antiestrogenic activity. Biochem Pharmacol 50:1485-1493
77. Fotsis T, Pepper MS, Aktas E, Breit S, Rasku S, Adlercreutz H, Wähälä K, Montesano R, Schweigerer L 1997 Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Cancer Res 57:2916-2921
78. Wang TTY, Sathyamoorthy N, Phang JM 1996 Molecular effects of genistein on estrogen receptor mediated pathways. Carcinogenesis 17:271-275
79. Peterson G, Barnes S 1991 Genistein inhibition of the growth of human breast cancer cells: independence from estrogen receptors and the multi-drug resistance gene. Biochem Biophys Res Commun 179:661-667
80. Onoe Y, Miyaura C, Ohta H, Nozawa S, Suda T 1997 Expression of estrogen receptor β in rat bone. Endocrinology 138:4509-4512
81. Arts J, Kuiper GGJM, Janssen JMMF, Gustafsson J-Å, Löwik CWGM, Pols HAP, van Leeuwen JPTM 1997 Differential expression of estrogen receptors α and β mRNA during differentiation of human osteoblast SV-HFO cells. Endocrinology 138:5067-5070
82. Kim SK, Lindner V, Karas RH, Kuiper GGJM, Gustafsson J-Å, Mendelsohn ME 1998 Expression of estrogen receptor β mRNA in normal and injured blood vessels. Circ Res 83:224-229
83. Adlercreutz H, Mazur W 1997 Phyoestrogens and Western diseases. Ann Med 29:95-120