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Center for Biotechnology and Department of Medical Nutrition (G.G.J.M.K., J.-Å.G.), Karolinska Institute and KaroBio AB (B.C.) Huddinge, Sweden; Hubrecht Laboratory, Netherlands Institute for Developmental Biology (B.v.d.B., P.T.v.d.S., J.G.L.) Utrecht, The Netherlands; Chemical Industry Institute of Toxicology (J.C.C.), Research Triangle Park, North Carolina; Department of Veterinary Physiology and Pharmacology (S.H.S.), Texas A&M University, College Station, Texas 77843-4466
Address all correspondence and requests for reprints to: Dr. George Kuiper, Center for Biotechnology, NOVUM, S-14186 Huddinge, Sweden. E-mail: george.kuiper{at}csb.ki.se
The rat, mouse and human estrogen receptor (ER) exists as two subtypes,
ER
and ERß, which differ in the C-terminal ligand-binding domain
and in the N-terminal transactivation domain. In this study, we
investigated the estrogenic activity of environmental chemicals and
phytoestrogens in competition binding assays with ER or ERß
protein, and in a transient gene expression assay using cells in which
an acute estrogenic response is created by cotransfecting cultures with
recombinant human ER or ERß complementary DNA (cDNA) in the
presence of an estrogen-dependent reporter plasmid.
Saturation ligand-binding analysis of human ER and ERß protein
revealed a single binding component for
[3H]-17ß-estradiol (E2) with high affinity
[dissociation constant (Kd) = 0.05 - 0.1 nM].
All environmental estrogenic chemicals [polychlorinated
hydroxybiphenyls, dichlorodiphenyltrichloroethane (DDT) and
derivatives, alkylphenols, bisphenol A, methoxychlor and chlordecone]
compete with E2 for binding to both ER subtypes with a
similar preference and degree. In most instances the relative binding
affinities (RBA) are at least 1000-fold lower than that of
E2. Some phytoestrogens such as coumestrol, genistein,
apigenin, naringenin, and kaempferol compete stronger with
E2 for binding to ERß than to ER. Estrogenic
chemicals, as for instance nonylphenol, bisphenol A, o, p'-DDT and
2',4',6'-trichloro-4-biphenylol stimulate the transcriptional activity
of ER and ERß at concentrations of 100-1000 nM.
Phytoestrogens, including genistein, coumestrol and zearalenone
stimulate the transcriptional activity of both ER subtypes at
concentrations of 1–10 nM. The ranking of the estrogenic
potency of phytoestrogens for both ER subtypes in the transactivation
assay is different; that is, E2 >> zearalenone =
coumestrol > genistein > daidzein > apigenin =
phloretin > biochanin A = kaempferol = naringenin
> formononetin = ipriflavone = quercetin = chrysin for
ER and E2 >> genistein = coumestrol >
zearalenone > daidzein > biochanin A = apigenin =
kaempferol = naringenin > phloretin = quercetin =
ipriflavone = formononetin = chrysin for ERß.
Antiestrogenic activity of the phytoestrogens could not be detected,
except for zearalenone which is a full agonist for ER and a mixed
agonist-antagonist for ERß. In summary, while the estrogenic potency
of industrial-derived estrogenic chemicals is very limited, the
estrogenic potency of phytoestrogens is significant, especially for
ERß, and they may trigger many of the biological responses that are
evoked by the physiological estrogens.
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 H. Marini, L. Minutoli, F. Polito, A. Bitto, D. Altavilla, M. Atteritano, A. Gaudio, S. Mazzaferro, A. Frisina, N. Frisina, et al. Effects of the Phytoestrogen Genistein on Bone Metabolism in Osteopenic Postmenopausal Women: A Randomized Trial Ann Intern Med, June 19, 2007; 146(12): 839 - 847. [Abstract] [Full Text] [PDF]
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A. M Dorward, K. L Shultz, and W. G Beamer LH analog and dietary isoflavones support ovarian granulosa cell tumor development in a spontaneous mouse model Endocr. Relat. Cancer, June 1, 2007; 14(2): 369 - 379. [Abstract] [Full Text] [PDF]
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M. Penza, C. Montani, A. Romani, P. Vignolini, P. Ciana, A. Maggi, B. Pampaloni, L. Caimi, and D. Di Lorenzo Genistein Accumulates in Body Depots and Is Mobilized during Fasting, Reaching Estrogenic Levels in Serum that Counter the Hormonal Actions of Estradiol and Organochlorines Toxicol. Sci., June 1, 2007; 97(2): 299 - 307. [Abstract] [Full Text] [PDF]
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J. L. Kipp, S. M. Kilen, S. Bristol-Gould, T. K. Woodruff, and K. E. Mayo Neonatal Exposure to Estrogens Suppresses Activin Expression and Signaling in the Mouse Ovary Endocrinology, May 1, 2007; 148(5): 1968 - 1976. [Abstract] [Full Text] [PDF]
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T. Tiido, A. Rignell-Hydbom, B.A.G. Jonsson, L. Rylander, A. Giwercman, and Y.L. Giwercman Modifying effect of the AR gene trinucleotide repeats and SNPs in the AHR and AHRR genes on the association between persistent organohalogen pollutant exposure and human sperm Y : X ratio Mol. Hum. Reprod., April 1, 2007; 13(4): 223 - 229. [Abstract] [Full Text] [PDF]
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 S. K. Gruvberger-Saal, P.-O. Bendahl, L. H. Saal, M. Laakso, C. Hegardt, P. Eden, C. Peterson, P. Malmstrom, J. Isola, A. Borg, et al. Estrogen Receptor {beta} Expression Is Associated with Tamoxifen Response in ER{alpha}-Negative Breast Carcinoma Clin. Cancer Res., April 1, 2007; 13(7): 1987 - 1994. [Abstract] [Full Text] [PDF]
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 E. T. Chang, V. S. Lee, A. J. Canchola, C. A. Clarke, D. M. Purdie, P. Reynolds, H. Anton-Culver, L. Bernstein, D. Deapen, D. Peel, et al. Diet and Risk of Ovarian Cancer in the California Teachers Study Cohort Am. J. Epidemiol., April 1, 2007; 165(7): 802 - 813. [Abstract] [Full Text] [PDF]
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 M. S. Touillaud, A. C. M. Thiebaut, A. Fournier, M. Niravong, M.-C. Boutron-Ruault, and F. Clavel-Chapelon Dietary Lignan Intake and Postmenopausal Breast Cancer Risk by Estrogen and Progesterone Receptor Status J Natl Cancer Inst, March 21, 2007; 99(6): 475 - 486. [Abstract] [Full Text] [PDF]
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Y.-C. Chen, M. L Nagpal, D. M Stocco, and T. Lin Effects of genistein, resveratrol, and quercetin on steroidogenesis and proliferation of MA-10 mouse Leydig tumor cells J. Endocrinol., March 1, 2007; 192(3): 527 - 537. [Abstract] [Full Text] [PDF]
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A. L. Quinn, J. M. Regan, J. M. Tobin, B. J. Marinik, J. M. McMahon, D. A. McNett, C. M. Sushynski, S. D. Crofoot, P. A. Jean, and K. P. Plotzke In Vitro and In Vivo Evaluation of the Estrogenic, Androgenic, and Progestagenic Potential of Two Cyclic Siloxanes Toxicol. Sci., March 1, 2007; 96(1): 145 - 153. [Abstract] [Full Text] [PDF]
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M. Verheus, C. H. van Gils, L. Keinan-Boker, P. B. Grace, S. A. Bingham, and P. H.M. Peeters Plasma Phytoestrogens and Subsequent Breast Cancer Risk J. Clin. Oncol., February 20, 2007; 25(6): 648 - 655. [Abstract] [Full Text] [PDF]
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A. Cvoro, S. Paruthiyil, J. O. Jones, C. Tzagarakis-Foster, N. J. Clegg, D. Tatomer, R. T. Medina, M. Tagliaferri, F. Schaufele, T. S. Scanlan, et al. Selective Activation of Estrogen Receptor-{beta} Transcriptional Pathways by an Herbal Extract Endocrinology, February 1, 2007; 148(2): 538 - 547. [Abstract] [Full Text] [PDF]
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B. K. Chacko, R. T. Chandler, T. L. D'Alessandro, A. Mundhekar, N. K. H. Khoo, N. Botting, S. Barnes, and R. P. Patel Anti-Inflammatory Effects of Isoflavones are Dependent on Flow and Human Endothelial Cell PPAR{gamma} J. Nutr., February 1, 2007; 137(2): 351 - 356. [Abstract] [Full Text] [PDF]
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 H. A. Harris Estrogen Receptor-{beta}: Recent Lessons from in Vivo Studies Mol. Endocrinol., January 1, 2007; 21(1): 1 - 13. [Abstract] [Full Text] [PDF]
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 I. M. Medina-Diaz, G. Arteaga-Illan, M. B. de Leon, B. Cisneros, A. Sierra-Santoyo, L. Vega, F. J. Gonzalez, and G. Elizondo Pregnane X Receptor-Dependent Induction of the CYP3A4 Gene by o,p'-1,1,1,-Trichloro-2,2-Bis (p-Chlorophenyl)ethane Drug Metab. Dispos., January 1, 2007; 35(1): 95 - 102. [Abstract] [Full Text] [PDF]
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S. Assinder, R. Davis, M. Fenwick, and A. Glover Adult-only exposure of male rats to a diet of high phytoestrogen content increases apoptosis of meiotic and post-meiotic germ cells Reproduction, January 1, 2007; 133(1): 11 - 19. [Abstract] [Full Text] [PDF]
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L. N. Vandenberg, M. V. Maffini, P. R. Wadia, C. Sonnenschein, B. S. Rubin, and A. M. Soto Exposure to Environmentally Relevant Doses of the Xenoestrogen Bisphenol-A Alters Development of the Fetal Mouse Mammary Gland Endocrinology, January 1, 2007; 148(1): 116 - 127. [Abstract] [Full Text] [PDF]
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G. Bises, E. Bajna, T. Manhardt, W. Gerdenitsch, E. Kallay, and H. S. Cross Gender-Specific Modulation of Markers for Premalignancy by Nutritional Soy and Calcium in the Mouse Colon J. Nutr., January 1, 2007; 137(1): 211S - 215S. [Abstract] [Full Text] [PDF]
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S. Rice and S. A Whitehead Phytoestrogens and breast cancer -promoters or protectors? Endocr. Relat. Cancer, December 1, 2006; 13(4): 995 - 1015. [Abstract] [Full Text] [PDF]
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 K. Dahlman-Wright, V. Cavailles, S. A. Fuqua, V. C. Jordan, J. A. Katzenellenbogen, K. S. Korach, A. Maggi, M. Muramatsu, M. G. Parker, and J.-A. Gustafsson International Union of Pharmacology. LXIV. Estrogen Receptors Pharmacol. Rev., December 1, 2006; 58(4): 773 - 781. [Full Text] [PDF]
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M. Penza, C. Montani, A. Romani, P. Vignolini, B. Pampaloni, A. Tanini, M. L. Brandi, P. Alonso-Magdalena, A. Nadal, L. Ottobrini, et al. Genistein Affects Adipose Tissue Deposition in a Dose-Dependent and Gender-Specific Manner Endocrinology, December 1, 2006; 147(12): 5740 - 5751. [Abstract] [Full Text] [PDF]
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K. J. McInnes, A. Corbould, E. R. Simpson, and M. E. Jones Regulation of Adenosine 5',Monophosphate-Activated Protein Kinase and Lipogenesis by Androgens Contributes to Visceral Obesity in an Estrogen-Deficient State Endocrinology, December 1, 2006; 147(12): 5907 - 5913. [Abstract] [Full Text] [PDF]
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S. C. Laws, S Yavanhxay, R. L. Cooper, and J. C. Eldridge Nature of the Binding Interaction for 50 Structurally Diverse Chemicals with Rat Estrogen Receptors Toxicol. Sci., November 1, 2006; 94(1): 46 - 56. [Abstract] [Full Text] [PDF]
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 K. W. Wilhelms, C. G. Scanes, and L. L. Anderson Lack of estrogenic or antiestrogenic actions of soy isoflavones in an avian model: the Japanese quail. Poult. Sci., November 1, 2006; 85(11): 1885 - 1889. [Abstract] [Full Text] [PDF]
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M. Raschke, I. R. Rowland, P. J. Magee, and B. L. Pool-Zobel Genistein protects prostate cells against hydrogen peroxide-induced DNA damage and induces expression of genes involved in the defence against oxidative stress Carcinogenesis, November 1, 2006; 27(11): 2322 - 2330. [Abstract] [Full Text] [PDF]
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A. R. Thomsen, K. Almstrup, J. E. Nielsen, I. K. Sorensen, O. W. Petersen, H. Leffers, and V. M. Breinholt Estrogenic Effect of Soy Isoflavones on Mammary Gland Morphogenesis and Gene Expression Profile Toxicol. Sci., October 1, 2006; 93(2): 357 - 368. [Abstract] [Full Text] [PDF]
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C. Borras, J. Gambini, M. C. Gomez-Cabrera, J. Sastre, F. V. Pallardo, G. E. Mann, and J. Vina Genistein, a soy isoflavone, up-regulates expression of antioxidant genes: involvement of estrogen receptors, ERK1/2, and NF{kappa}B FASEB J, October 1, 2006; 20(12): 2136 - 2138. [Abstract] [Full Text] [PDF]
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 C. Bolego, E. Vegeto, C. Pinna, A. Maggi, and A. Cignarella Selective Agonists of Estrogen Receptor Isoforms: New Perspectives for Cardiovascular Disease Arterioscler Thromb Vasc Biol, October 1, 2006; 26(10): 2192 - 2199. [Abstract] [Full Text] [PDF]
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