Mechanisms of action of particular endocrine-disrupting chemicals

Endocrine-Disrupting Chemicals in Food

Volumn , Issue , 2009, Pages 541-567

  Pakdel, F ^a   Kah, O ^a   Jegou B ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957674818     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1533/9781845695743.4.541     Document Type: Chapter

References (127)

1. Abdelrahim M., Ariazi E., Kim K., Khan S., Barhoumi R., Burghardt R., Liu S., Hill D., Finnell R., Wlodarczyk B., et al. 3-Methylcholanthrene and other aryl hydrocarbon receptor agonists directly activate estrogen receptor α. Cancer Res 2006, 66:2459-2467.
2. Andersen H.R., Andersson A.M., Arnold S.F., Autrup H., Barfoed M., Beresford N.A., Bjerregaard P., Christiansen L.B., Gissel B., Hummel R., et al. Comparison of short-term estrogenicity tests for identification of hormone-disrupting chemicals. Environ Health Perspect 1999, 107(1):89-108.
3. Anway M.D., Cupp A.S., Uzumcu M., Skinner M.K. Epigenetic transgenerational actions of endocrine disruptors and male fertility. Science 2005, 308:1466-1469.
4. Anway M.D., Memon M.A., Uzumcu M., Skinner M.K. Transgenerational effect of the endocrine disruptor vinclozolin on male spermatogenesis. J Androl 2006, 27:868-879.
5. Atsdr Toxicological profile of Di(2-ethylhexyl)phthalate. Agency for Toxic Substances and Disease Registry, Public Health Service 2002, US Department of Health and Human Services, Atlanta.
6. Balaguer P., Joyeux A., Denison M.S., Vincent R., Gillesby B.E., Zacharewski T. Assessing the estrogenic and dioxin-like activities of chemicals and complex mixtures using in vitro recombinant receptor-reporter gene assays. Can J Physiol Pharmacol 1996, 74:216-222.
7. Barlow N.J., Phillips S.L., Wallace D.G., Sar M., Gaido K.W., Foster P.M. Quantitative changes in gene expression in fetal rat testes following exposure to di(n-butyl) phthalate. Toxicol Sci 2003, 73:431-441.
8. Barouki R., Coumoul X., Fernandez-Salguero P.M. The aryl hydrocarbon receptor, more than a xenobiotic-interacting protein. FEBS Lett 2007, 581:3608-3615.
9. Borch J., Metzdorff S.B., Vinggaard A.M., Brokken L., Dalgaard M. Mechanisms underlying the anti-androgenic effects of diethylhexyl phthalate in fetal rat testis. Toxicology 2006, 223:144-155.
10. Brosens J.J., Parker M.G. Gene expression: oestrogen receptor hijacked. Nature 2003, 423:487-488.
11. Brzozowski A.M., Pike A.C., Dauter Z., Hubbard R.E., Bonn T., Engstrom O., Ohman L., Greene G.L., Gustafsson J.A., Carlquist M. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 1997, 389:753-758.
12. Carreau S., Bourguiba S., Lambard S., Galeraud-Denis I., Genissel C., Levallet J. Reproductive system: aromatase and estrogens. Mol Cell Endocrinol 2002, 193:137-143.
13. Carruthers C.M., Foster P.M. Critical window of male reproductive tract development in rats following gestational exposure to di-n-butyl phthalate. Birth Defects Res B Dev Reprod Toxicol 2005, 74:277-285.
14. Chang E.C., Frasor J., Komm B., Katzenellenbogen B.S. Impact of estrogen receptor β on gene networks regulated by estrogen receptor α in breast cancer cells. Endocrinology 2006, 147:4831-4842.
15. Chang H.S., Anway M.D., Rekow S.S., Skinner M.K. Transgenerational epigenetic imprinting of the male germline by endocrine disruptor exposure during gonadal sex determination. Endocrinology 2006, 147:5524-5541.
16. Chen I., Hsieh T., Thomas T., Safe S. Identification of estrogen-induced genes downregulated by AhR agonists in MCF-7 breast cancer cells using suppression subtractive hybridization. Gene 2001, 262:207-214.
17. Cheshenko K., Brion F., Le Page Y., Hinfray N., Pakdel F., Kah O., Segner H., Eggen R.I. Expression of zebra fish aromatase cyp19a and cyp19b genes in response to the ligands of estrogen receptor and aryl hydrocarbon receptor. Toxicol Sci 2007, 96:255-267.
18. Colborn T., Vom Saal F.S., Soto A.M. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect 1993, 101:378-384.
19. Escande A., Pillon A., Servant N., Cravedi J.P., Larrea F., Muhn P., Nicolas J.C., Cavailles V., Balaguer P. Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor α or β. Biochem Pharmacol 2006, 71:1459-1469.
20. Fent K. Ecotoxicological effects at contaminated sites. Toxicology 2004, 205:223-240.
21. Filardo E.J., Quinn J.A., Frackelton A.R., Bland K.I. Estrogen action via the G protein-coupled receptor, GPR30: stimulation of adenylyl cyclase and cAMP-mediated attenuation of the epidermal growth factor receptor-to-MAPK signaling axis. Mol Endocrinol 2002, 16:70-84.
22. Flouriot G., Pakdel F., Ducouret B., Valotaire Y. Influence of xenobiotics on rainbow trout liver estrogen receptor and vitellogenin gene expression. J Mol Endocrinol 1995, 15:143-151.
23. Frasor J., Danes J.M., Komm B., Chang K.C., Lyttle C.R., Katzenellenbogen B.S. Profiling of estrogen up- and down-regulated gene expression in human breast cancer cells: insights into gene networks and pathways underlying estrogenic control of proliferation and cell phenotype. Endocrinology 2003, 144:4562-4574.
24. Germain P., Staels B., Dacquet C., Spedding M., Laudet V. Overview of nomenclature of nuclear receptors. Pharmacol Rev 2006, 58:685-704.
25. Gray L.E., Ostby J., Cooper R.L., Kelce W.R. The estrogenic and antiandrogenic pesticide methoxychlor alters the reproductive tract and behavior without affecting pituitary size or LH and prolactin secretion in male rats. Toxicol Ind Health 1999, 15:37-47.
26. Gray L.E., Ostby J., Monosson E., Kelce W.R. Environmental antiandrogens: low doses of the fungicide vinclozolin alter sexual differentiation of the male rat. Toxicol Ind Health 1999, 15:48-64.
27. Gray L.E., Wolf C., Lambright C., Mann P., Price M., Cooper R.L., Ostby J. Administration of potentially antiandrogenic pesticides (procymidone, linuron, iprodione, chlozolinate, p,p'-DDE, and ketoconazole) and toxic substances (dibutyl- and diethylhexyl phthalate, PCB 169, and ethane dimethane sulphonate) during sexual differentiation produces diverse profiles of reproductive malformations in the male rat. Toxicol Ind Health 1999, 15:94-118.
28. Gray L.E., Ostby J., Furr J., Wolf C.J., Lambright C., Parks L., Veeramachaneni D.N., Wilson V., Price M., Hotchkiss A., et al. Effects of environmental antiandrogens on reproductive development in experimental animals. Hum Reprod Update 2001, 7:248-264.
29. Gray L.E., Wilson V.S., Stoker T., Lambright C., Furr J., Noriega N., Howdeshell K., Ankley G.T., Guillette L. Adverse effects of environmental antiandrogens and androgens on reproductive development in mammals. Int J Androl 2006, 29:96-104. discussion 105-108.
30. Gray T.J., Gangolli S.D. Aspects of the testicular toxicity of phthalate esters. Environ Health Perspect 1986, 65:229-235.
31. Grun F., Watanabe H., Zamanian Z., Maeda L., Arima K., Cubacha R., Gardiner D.M., Kanno J., Iguchi T., Blumberg B. Endocrine-disrupting organotin compounds are potent inducers of adipogenesis in vertebrates. Mol Endocrinol 2006, 20:2141-2155.
32. Guillette L.J., Gross T.S., Masson G.R., Matter J.M., Percival H.F., Woodward A.R. Developmental abnormalities of the gonad and abnormal sex hormone concentrations in juvenile alligators from contaminated and control lakes in Florida. Environ Health Perspect 1994, 102:680-688.
33. Gustafsson J.A. Therapeutic potential of selective estrogen receptor modulators. Curr Opin Chem Biol 1998, 2:508-511.
34. Habert R., Devif I., Gangnerau M.N., Lecerf L. Ontogenesis of the in vitro response of rat testis to gonadotropin-releasing hormone. Mol Cell Endocrinol 1991, 82:199-206.
35. Hess R.A., Bunick D., Lee K.H., Bahr J., Taylor J.A., Korach K.S., Lubahn D.B. A role for oestrogens in the male reproductive system. Nature 1997, 390:509-512.
36. Hewitt S.C., Deroo B.J., Korach K.S. Signal transduction. A new mediator for an old hormone?. Science 2005, 307:1572-1573.
37. Incardona J.P., Day H.L., Collier T.K., Scholz N.L. Developmental toxicity of 4-ring polycyclic aromatic hydrocarbons in zebrafish is differentially dependent on AH receptor isoforms and hepatic cytochrome P4501A metabolism. Toxicol Appl Pharmacol 2006, 217:308-321.
38. Jagadeesh S., Kyo S., Banerjee P.P. Genistein represses telomerase activity via both transcriptional and posttranslational mechanisms in human prostate cancer cells. Cancer Res 2006, 66:2107-2115.
39. Jegou B., Auger J., Multigner L., Pineau C., Thonneau P., Spira A., Jouannet P. The Male Gamete: From basic science to clinical applications. The saga of the sperm count decrease in humans wild and farm animals 1999, 445-454. Cach River Press, Vienna, IL, USA, 1999, Chap 41. C. Ganon (Ed.).
40. Higuchi T.T., Palmer J.S., Gray L.E., Veeramachaneni D.N. Effects of dibutyl phthalate in male rabbits following in utero, adolescent, or postpubertal exposure. Toxicol Sci 2003, 72:301-313.
41. Hotchkiss A.K., Ostby J.S., Vandenbergh J.G., Gray L.E. An environmental antiandrogen, vinclozolin, alters the organization of play behavior. Physiol Behav 2003, 79:151-156.
42. Jirtle R.L., Skinner M.K. Environmental epigenomics and disease susceptibility. Nat Rev Genet 2007, 8:253-262.
43. Johnson M.D., Kenney N., Stoica A., Hilakivi-Clarke L., Singh B., Chepko G., Clarke R., Sholler P.F., Lirio A.A., Foss C., et al. Cadmium mimics the in vivo effects of estrogen in the uterus and mammary gland. Nat Med 2003, 9:1081-1084.
44. Jordan V.C., Brodie A.M. Development and evolution of therapies targeted to the estrogen receptor for the treatment and prevention of breast cancer. Steroids 2007, 72:7-25.
45. Katzenellenbogen B.S., Choi I., Delage-Mourroux R., Ediger T.R., Martini P.G., Montano M., Sun J., Weis K., Katzenellenbogen J.A. Molecular mechanisms of estrogen action: selective ligands and receptor pharmacology. J Steroid Biochem Mol Biol 2000, 74:279-285.
46. Kavlock R., Cummings A. Mode of action: reduction of testosterone availability - molinate-induced inhibition of spermatogenesis. Crit Rev Toxicol 2005, 35:685-690.
47. Kazeto Y., Place A.R., Trant J.M. Effects of endocrine disrupting chemicals on the expression of CYP19 genes in zebrafish (Danio rerio) juveniles. Aquat Toxicol 2004, 69:25-34.
48. Kelce W.R., Lambright C.R., Gray L.E., Roberts K.P. Vinclozolin and p,p'-DDE alter androgen-dependent gene expression: in vivo confirmation of an androgen receptor-mediated mechanism. Toxicol Appl Pharmacol 1997, 142:192-200.
49. Khan S., Barhoumi R., Burghardt R., Liu S., Kim K., Safe S. Molecular mechanism of inhibitory aryl hydrocarbon receptor-estrogen receptor/Sp1 cross talk in breast cancer cells. Mol Endocrinol 2006, 20:2199-2214.
50. Kian Tee M., Rogatsky I., Tzagarakis-Foster C., Cvoro A., An J., Christy R.J., Yamamoto K.R., Leitman D.C. Estradiol and selective estrogen receptor modulators differentially regulate target genes with estrogen receptors alpha and beta. Mol Biol Cell 2004, 15:1262-1272.
51. Kim S.H., Tamrazi A., Carlson K.E., Katzenellenbogen J.A. A proteomic microarray approach for exploring ligand-initiated nuclear hormone receptor pharmacology, receptor selectivity, and heterodimer functionality. Mol Cell Proteomics 2005, 4:267-277.
52. Kishida M., Mclellan M., Miranda J.A., Callard G.V. Estrogen and xenoestrogens upregulate the brain aromatase isoform (P450aromB) and perturb markers of early development in zebrafish (Danio rerio). Comp Biochem Physiol B Biochem Mol Biol 2001, 129:261-268.
53. Klinge C.M. Estrogen receptor interaction with co-activators and co-repressors. Steroids 2000, 65:227-251.
54. Koch H.M., Preuss R., Angerer J. Di(2-ethylhexyl)phthalate (DEHP): human metabolism and internal exposure - an update and latest results. Int J Androl 2006, 29:155-165. discussion 181-155.
55. Kuiper G.G., Carlsson B., Grandien K., Enmark E., Haggblad J., Nilsson S., Gustafsson J.A. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors α and β. Endocrinology 1997, 138:863-870.
56. Kuiper G.G., Lemmen J.G., Carlsson B., Corton J.C., Safe S.H., Van Der Saag P.T., Van Der Burg B., Gustafsson J.A. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor β. Endocrinology 1998, 139:4252-4263.
57. Lambright C., Ostby J., Bobseine K., Wilson V., Hotchkiss A.K., Mann P.C., Gray L.E. Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats. Toxicol Sci 2000, 56:389-399.
58. Lassurguere J., Livera G., Habert R., Jegou B. Time- and dose-related effects of estradiol and diethylstilbestrol on the morphology and function of the fetal rat testis in culture. Toxicol Sci 2003, 73:160-169.
59. Le Guevel R., Pakdel F. Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods. Hum Reprod 2001, 16:1030-1036.
60. Le Guevel R.L., Petit F.G., Goff P.L., Metivier R., Valotaire Y., Pakdel F. Inhibition of rainbow trout (Oncorhynchus mykiss) estrogen receptor activity by cadmium. Biol Reprod 2000, 63:259-266.
61. Le Page Y., Scholze M., Kah O., Pakdel F. Assessment of xenoestrogens using three distinct estrogen receptors and the zebrafish brain aromatase gene in a highly responsive glial cell system. Environ Health Perspect 2006, 114:752-758.
62. Legler J., Van Den Brink C.E., Brouwer A., Murk A.J., Van Der Saag P.T., Vethaak A.D., Van Der Burg B. Development of a stably transfected estrogen receptor-mediated luciferase reporter gene assay in the human T47D breast cancer cell line. Toxicol Sci 1999, 48:55-66.
63. Levin E.R. Bidirectional signaling between the estrogen receptor and the epidermal growth factor receptor. Mol Endocrinol 2003, 17:309-317.
64. Levin E.R., Pietras R.J. Estrogen receptors outside the nucleus in breast cancer. Breast Cancer Res Treat 2007, 708:351-361.
65. Livera G., Rouiller-Fabre V., Habert R. Retinoid receptors involved in the effects of retinoic acid on rat testis development. Biol Reprod 2001, 64:1307-1314.
66. Maggiolini M., Vivacqua A., Fasanella G., Recchia A.G., Sisci D., Pezzi V., Montanaro D., Musti A.M., Picard D., Ando S. The G protein-coupled receptor GPR30 mediates c-fos up-regulation by 17β-estradiol and phytoestrogens in breast cancer cells. J Biol Chem 2004, 279:27008-27016.
67. Martin M.B., Reiter R., Pham T., Avellanet Y.R., Camara J., Lahm M., Pentecost E., Pratap K., Gilmore B.A., Divekar S., et al. Estrogen-like activity of metals in MCF-7 breast cancer cells. Endocrinology 2003, 144:2425-2436.
68. Matthews J., Wihlen B., Thomsen J., Gustafsson J.A. Aryl hydro-carbon re ependent recruitment of estrogen receptor α to 2,3,7,8-tetrachlorodibenzo-p-dioxin-responsive promoters. Mol Cell Biol 2005, 25:5317-5328.
69. Mcintyre B.S., Barlow N.J., Wallace D.G., Maness S.C., Gaido K.W., Foster P.M. Effects of in utero exposure to linuron on androgen-dependent reproductive development in the male Crl:CD(SD)BR rat. Toxicol Appl Pharmacol 2000, 167:87-99.
70. Mclachlan J.A. Environmental signaling: what embryos and evolution teach us about endocrine disrupting chemicals. Endocr Rev 2001, 22:319-341.
71. Mclachlan J.A., Burow M., Chiang T.C., Li S.F. Gene imprinting in developmental toxicology: a possible interface between physiology and pathology. Toxicol Lett 2001, 120:161-164.
72. Menuet A., Pellegrini E., Anglade I., Blaise O., Laudet V., Kah O., Pakdel F. Molecular characterization of three estrogen receptor forms in zebrafish: binding characteristics, transactivation properties, and tissue distributions. Biol Reprod 2002, 66:1881-1892.
73. Menuet A., Le Page Y., Torres O., Kern L., Kah O., Pakdel F. Analysis of the estrogen regulation of the zebrafish estrogen receptor (ER) reveals distinct effects of ERα, ERβ1 and ERβ2. J Mol Endocrinol 2004, 32:975-986.
74. Menuet A., Pellegrini E., Brion F., Gueguen M., Anglade I., Pakdel F., Kah O. Expression and the estrogen-dependent regulation of the zebrafish brain aromatase gene. J Comp Neurol 2005, 485:304-320.
75. Mitro N., Mak P.A., Vargas L., Godio C., Hampton E., Molteni V., Kreusch A., Saez E. The nuclear receptor LXR is a glucose sensor. Nature 2007, 445:219-223.
76. Molina-Molina J.M., Hillenweck A., Jouanin I., Zalko D., Cravedi J.P., Fernandez M.F., Pillon A., Nicolas J.C., Olea N., Balaguer P. Steroid receptor profiling of vinclozolin and its primary metabolites. Toxicol Appl Pharmacol 2006, 216:44-54.
77. Monosson E., Kelce W.R., Lambright C., Ostby J., Gray L.E. Peripubertal exposure to the antiandrogenic fungicide, vinclozolin, delays puberty, inhIbits the development of androgen-dependent tissues, and alters androgen receptor function in the male rat. Toxicol Ind Health 1999, 15:65-79.
78. Navas J.M., Chana A., Herradon B., Segner H. Induction of cytochrome P4501A (CYP1A) by clotrimazole, a non-planar aromatic compound. Computational studies on structural features of clotrimazole and related imidazole derivatives. Life Sci 2004, 76:699-714.
79. Nilsson S., Makela S., Treuter E., Tujague M., Thomsen J., Andersson G., Enmark E., Pettersson K., Warner M., Gustafsson J.A. Mechanisms of estrogen action. Physiol Rev 2001, 81:1535-1565.
80. Noriega N.C., Ostby J., Lambright C., Wilson V.S., Gray L.E. Late gestational exposure to the fungicide prochloraz delays the onset of parturition and causes reproductive malformations in male but not female rat offspring. Biol Reprod 2005, 72:1324-1335.
81. Ohtake F., Takeyama K., Matsumoto T., Kitagawa H., Yamamoto Y., Nohara K., Tohyama C., Krust A., Mimura J., Chambon P., et al. Modulation of oestrogen receptor signalling by association with the activated dioxin receptor. Nature 2003, 423:545-550.
82. Ostby J., Kelce W.R., Lambright C., Wolf C.J., Mann P., Gray L.E. The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro. Toxicol Ind Health 1999, 15:80-93.
83. Paech K., Webb P., Kuiper G.G., Nilsson S., Gustafsson J., Kushner P.J., Scanlan T.S. Differential ligand activation of estrogen receptors ERα and ERβ at AP1 sites. Science 1997, 277:1508-1510.
84. Pellegrini E., Menuet A., Lethimonier C., Adrio F., Mm G., Tasscon C., Anglade I., Pakdel F., Kah O. Relationships between aromatase and estrogen receptors in the brain of teleost fish. General Comparative Endocrinol 2005, 142:60-66.
85. Petit F., Le Goff P., Cravedi J.P., Valotaire Y., Pakdel F. Two complementary bioassays for screening the estrogenic potency of xenobiotics: recombinant yeast for trout estrogen receptor and trout hepatocyte cultures. J Mol Endocrinol 1997, 19:321-335.
86. Pike A.C., Brzozowski A.M., Hubbard R.E. A structural biologist's view of the oestrogen receptor. J Steroid Biochem Mol Biol 2000, 74:261-268.
87. Pocar P., Fischer B., Klonisch T., Hombach-Klonisch S. Molecular interactions of the aryl hydrocarbon receptor and its biological and toxicological relevance for reproduction. Reproduction 2005, 129:379-389.
88. Rajapakse N., Silva E., Kortenkamp A. Combining xenoestrogens at levels below individual no-observed-effect concentrations dramatically enhances steroid hormone action. Environ Health Perspect 2002, 110:917-921.
89. Revankar C.M., Cimino D.F., Sklar L.A., Arterburn J.B., Prossnitz E.R. A transmembrane intracellular estrogen receptor mediates rapid cell signaling. Science 2005, 307:1625-1630.
90. Robinson-Rechavi M., Escriva Garcia H., Laudet V. The nuclear receptor superfamily. J Cell Sci 2003, 116:585-586.
91. Routledge E.J., Sumpter J.P. Structural features of alkylphenolic chemicals associated with estrogenic activity. J Biol Chem 1997, 272:3280-3288.
92. Safe S. Molecular biology of the Ah receptor and its role in carcinogenesis. Toxicol Lett 2001, 120:1-7.
93. Safe S. Transcriptional activation of genes by 17-β-estradiol through estrogen receptor-Sp1 interactions. Vitam Horm 2001, 62:231-252.
94. Safe S. Cadmium's disguise dupes the estrogen receptor. Nat Med 2003, 9:1000-1001.
95. Safe S., Kim K. Nuclear receptor-mediated transactivation through interaction with Sp proteins. Prog Nucleic Acid Res Mol Biol 2004, 77:1-36.
96. Safe S., Wormke M. Inhibitory aryl hydrocarbon receptor-estrogen receptor alpha cross-talk and mechanisms of action. Chem Res Toxicol 2003, 16:807-816.
97. Sharpe R.M., Skakkebaek N.E. Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract?. Lancet 1993, 341:1392-1395.
98. Silva E., Rajapakse N., Kortenkamp A. Something from 'nothing' - eight weak estrogenic chemicals combined at concentrations below NOECs produce significant mixture effects. Environ Sci Technol 2002, 36:1751-1756.
99. Silva E., Lopez-Espinosa M.J., Molina-Molina J.M., Fernandez M., Olea N., Kortenkamp A. Lack of activity of cadmium in in vitro estrogenicity assays. Toxicol Appl Pharmacol 2006, 216:20-28.
100. Sohoni P., Sumpter J.P. Several environmental oestrogens are also anti-androgens. J Endocrinol 1998, 158:327-339.
101. Sonnenschein C., Soto A.M. An updated review of environmental estrogen and androgen mimics and antagonists. J Steroid Biochem Mol Biol 1998, 65:143-150.
102. Soto A.M., Sonnenschein C., Chung K.L., Fernandez M.F., Olea N., Serrano F.O. The E-SCREEN assay as a tool to identify estrogens: an update on estrogenic environmental pollutants. Environ Health Perspect 1995, 103(7):113-122.
103. Soto A.M., Michaelson C.L., Prechtl N.V., Weill B.C., Sonnenschein C., Olea-Serrano F., Olea N. Assays to measure estrogen and androgen agonists and antagonists. Adv Exp Med Biol 1998, 444:9-23. discussion 23-28.
104. Staub C., Rauch M., Ferriere F., Trepos M., Dorval-Coiffec I., Saunders P.T., Cobellis G., Flouriot G., Saligaut C., Jegou B. Expression of estrogen receptor ESR1 and its 46-kDa variant in the gubernaculum testis. Biol Reprod 2005, 73:703-712.
105. Stauffer S.R., Coletta C.J., Tedesco R., Nishiguchi G., Carlson K., Sun J., Katzenellenbogen B.S., Katzenellenbogen J.A. Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-α-selective agonists. J Med Chem 2000, 43:4934-4947.
106. Stoica A., Katzenellenbogen B.S., Martin M.B. Activation of estrogen receptor-alpha by the heavy metal cadmium. Mol Endocrinol 2000, 14:545-553.
107. Stoker T.E., Laws S.C., Crofton K.M., Hedge J.M., Ferrell J.M., Cooper R.L. Assessment of DE-71, a commercial polybrominated diphenyl ether (PBDE) mixture, in the EDSP male and female pubertal protocols. Toxicol Sci 2004, 78:144-155.
108. Stoker T.E., Cooper R.L., Lambright C.S., Wilson V.S., Furr J., Gray L.E. In vivo and in vitro anti-androgenic effects of DE-71, a commercial polybrominated diphenyl ether (PBDE) mixture. Toxicol Appl Pharmacol 2005, 207:78-88.
109. Stroheker T., Cabaton N., Nourdin G., Regnier J.F., Lhuguenot J.C., Chagnon M.C. Evaluation of anti-androgenic activity of di-(2-ethylhexyl) phthatate. Toxicology 2005, 208:115-121.
110. Sumpter J.P. Feminized responses in fish to environmental estrogens. Toxicol Lett 1995, 82-83:737-742.
111. Sumpter J.P., Jobling S. Male sexual development in 'a sea of oestrogen. Lancet 1993, 342:124-125.
112. Sumpter J.P., Jobling S. Vitellogenesis as a biomarker for estrogenic contamination of the aquatic environment. Environ Health Perspect 1995, 103(7):173-178.
113. Takiguchi M., Yoshihara S. New aspects of cadmium as endocrine disruptor. Environ Sci 2006, 13:107-116.
114. Thomas P., Dong J. Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. J Steroid Biochem Mol Biol 2006, 102:175-179.
115. Toppari J., Virtanen H., Skakkebaek N.E., Main K.M. Environmental effects on hormonal regulation of testicular descent. J Steroid Biochem Mol Biol 2006, 102:184-186.
116. Vinggaard A.M., Nellemann C., Dalgaard M., Jorgensen E.B., Andersen H.R. Antiandrogenic effects in vitro and in vivo of the fungicide prochloraz. Toxicol Sci 2002, 69:344-353.
117. Vivacqua A., Bonofiglio D., Albanito L., Madeo A., Rago V., Carpino A., Musti A.M., Picard D., Ando S., Maggiolini M. 17β-Estradiol, genistein, and 4-hydroxytamoxifen induce the proliferation of thyroid cancer cells through the g protein-coupled receptor GPR30. Mol Pharmacol 2006, 70:1414-1423.
118. Vivacqua A., Bonofiglio D., Recchia A.G., Musti A.M., Picard D., Ando S., Maggiolini M. The G protein-coupled receptor GPR30 mediates the proliferative effects induced by 17β-estradiol and hydroxytamoxifen in endometrial cancer cells. Mol Endocrinol 2006, 20:631-646.
119. Watson C.S., Alyea R.A., Jeng Y.J., Kochukov M.Y. Nongenomic actions of low concentration estrogens and xenoestrogens on multiple tissues. Mol Cell Endocrinol 2007, 274:1-7.
120. Whyte J.J., Jung R.E., Schmitt C.J., Tillitt D.E. Ethoxyresorufin-O-deethylase (EROD) activity in fish as a biomarker of chemical exposure. Crit Rev Toxicol 2000, 30:347-570.
121. Wilson V.S., Lambright C., Furr J., Ostby J., Wood C., Held G., Gray L.E. Phthalate ester-induced gubernacular lesions are associated with reduced insl3 gene expression in the fetal rat testis. Toxicol Lett 2004, 146:207-215.
122. Wilson V.S., Howdeshell K.L., Lambright C.S., Furr J., Earl Gray L. Differential expression of the phthalate syndrome in male Sprague-Dawley and Wistar rats after in utero DEHP exposure. Toxicol Lett 2007, 170:177-184.
123. Wormke M., Stoner M., Saville B., Walker K., Abdelrahim M., Burghardt R., Safe S. The aryl hydrocarbon receptor mediates degradation of estrogen receptor α through activation of proteasomes. Mol Cell Biol 2003, 23:1843-1855.
124. Wormuth M., Scheringer M., Vollenweider M., Hungerbuhler K. What are the sources of exposure to eight frequently used phthalic acid esters in Europeans?. Risk Anal 2006, 26:803-824.
125. Yamashita S. Expression of estrogen-regulated genes during development in the mouse uterus exposed to diethylstilbestrol neonatally. Curr Pharm Des 2006, 12:1505-1520.
126. Zhou C., Zhang S., Nanamori M., Zhang Y., Liu Q., Li N., Sun M., Tian J., Ye P.P., Cheng N., et al. Pharmacological characterization of a novel nonpeptide antagonist for formyl peptide receptor-like 1. Mol Pharmacol 2007, 72:976-983.
127. Zoeller R.T. Environmental chemicals as thyroid hormone analogues: new studies indicate that thyroid hormone receptors are targets of industrial chemicals?. Mol Cell Endocrinol 2005, 242:10-15.