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Chemical Compound Review

BSPBio_001980     (13S,17S)-13-methyl- 6,7,8,9,11,12,14,15,16...

Synonyms: KBioGR_002489, KBioSS_001528, CCG-38366, SureCN10187407, NINDS_000238, ...
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Disease relevance of estradiol


Psychiatry related information on estradiol

  • These memory deficits were reversed in the group that received LAD plus E2 for 8 weeks coincident with an increase in plasma E2, whereas memory scores remained depressed in the group that received LAD plus placebo [6].
  • These results indicated that following the initial "priming" of central site(s) with low levels of circulating E2 during diestrus II, rapid elevations in ovarian estrogen secretion between 2300 hr of diestrus II and 0300 hr of proestrus facilitated the neural "trigger" of pituitary LH release during the critical period on proestrus [7].
  • To date, studies have demonstrated that estradiol (E2) appears to be a necessary component in the hormonal induction of maternal behavior in rats and other mammals [8].
  • These results, which are the first evidence of apoE mRNA localization to microglia in vivo and the control of apoE expression in brain cells by estrogens, are discussed in terms of the possible protective role of E2 in Alzheimer's disease and prior findings that emphasize the expression of apoE mRNA in astrocytes within the brain [9].
  • Using Japanese quail (Coturnix coturnix japonica) as an animal model, together with a newly devised procedure for quantifying aggressiveness, we recently showed that aggression is E2-dependent and that individual differences in behavioral intensity are correlated with aromatase in the hypothalamus/preoptic area (HPOA) [10].

High impact information on estradiol

  • Here we report that estradiol (E2) triggers a robust increase in the number of excitatory inputs to POMC neurons in the arcuate nucleus of wild-type rats and mice [11].
  • Besides altering the transcription of genes with estrogen-responsive elements, 17beta-estradiol (E2) also modifies androgen metabolism within distinct subunits of the pilosebaceous unit (i.e., hair follicle and sebaceous gland) [1].
  • Effects of strain, E2 dose, and the interaction of strain and E2 dose on testes weight and spermatogenesis were all highly significant (P < 0.0001) [12].
  • In contrast, mice of the widely used CD-1 line, which has been selected for large litter size, showed little or no inhibition of spermatid maturation even in response to 16 times as much E2 [12].
  • Spermatid maturation was eliminated by low doses of E2 in strains such as C57BL/6J and C17/Jls [12].

Chemical compound and disease context of estradiol


Biological context of estradiol


Anatomical context of estradiol


Associations of estradiol with other chemical compounds

  • Furthermore, the inhibition of tyrosine kinases or mitogen-activated protein (MAP) kinase kinase prevented the activation of eNOS by E2, and E2 caused rapid ER-dependent activation of MAP kinase [21].
  • DMBA treatment also upregulated the ratio of 16 alpha/C2 hydroxylation of E2 leading to increased formation of 16 alpha-OHE1 [19].
  • Four groups of 12 male hamsters were treated for 1 month with EE, 15 micrograms per kg per day, or placebo vehicle administered intraperitoneally and fed either a standard diet, 0.8 mg of cholesterol per g of food, or high cholesterol diet, 2.4 mg of cholesterol per g [24].
  • We have previously shown that a ligand-dependent interaction between the two AF-containing regions of ER was promoted by E2 and the antiestrogen trans-hydroxytamoxifen (TOT) [25].
  • The effect of ethinyl estradiol (EE2) and dexamethasone (Dex) upon plasma renin substrate (PRS) was studied in rats in relation to sexual maturation and pituitary function [26].

Gene context of estradiol

  • SHBG levels were 12% higher in parous women, but there was no difference in percentage of free E2 [27].
  • As homodimers the two have been recently shown to exhibit distinct transcriptional responses to estradiol (E2), antiestrogens, and coactivators, suggesting that the ER complexes are not functionally equivalent [28].
  • TCDD alone or in combination with E increases formation of ubiquitinated forms of ERalpha, and both coimmunoprecipitation and mammalian two-hybrid assays demonstrate that TCDD induces interaction of the AhR with ERalpha in the presence or absence of E [29].
  • Mutations of the ERalpha DNA binding domain did not block this rapid E2-dependent SRC-3 phosphorylation [30].
  • In contrast, E does not induce AhR-ERalpha interactions [29].

Analytical, diagnostic and therapeutic context of estradiol

  • Neither ovariectomy, AHPrBP, nor E2 treatment had a significant effect on the volume or rate of formation of cortical bone [31].
  • Motif-finding algorithms demonstrated that the estrogen response element (ERE) is the most common motif present in these promoters whereas conventional chromatin immunoprecipitation assays showed E2-modulated recruitment of coactivator AIB1 and RNA polymerase II at these loci [32].
  • In Fischer rats, after 63 days of E2, the pituitary weight, serum prolactin, and number of microspheres in the AP were 5-, 42-, and 18-fold greater than control values, respectively [33].
  • With cells transfected with reporter gene systems, the activation of estrogen response element-luciferase was studied, and using Western blot analysis, the expression of E2-responsive progesterone receptor (PR) and presnelin 2 protein was monitored [34].
  • Furthermore, the effect of resveratrol on formation of preneoplastic lesions (induced by 7,12-dimethylbenz(a)anthracene) and PR expression (with or without E2) was evaluated with mammary glands of BALB/c mice placed in organ culture [34].


  1. The hair follicle as an estrogen target and source. Ohnemus, U., Uenalan, M., Inzunza, J., Gustafsson, J.A., Paus, R. Endocr. Rev. (2006) [Pubmed]
  2. MUC1 oncoprotein stabilizes and activates estrogen receptor alpha. Wei, X., Xu, H., Kufe, D. Mol. Cell (2006) [Pubmed]
  3. Estrogen inhibits bone resorption by directly inducing apoptosis of the bone-resorbing osteoclasts. Kameda, T., Mano, H., Yuasa, T., Mori, Y., Miyazawa, K., Shiokawa, M., Nakamaru, Y., Hiroi, E., Hiura, K., Kameda, A., Yang, N.N., Hakeda, Y., Kumegawa, M. J. Exp. Med. (1997) [Pubmed]
  4. Prolactin and aging: X-irradiated and estrogen-induced rat mammary tumorigenesis. Ito, A., Naito, M., Watanabe, H., Yokoro, K. J. Natl. Cancer Inst. (1984) [Pubmed]
  5. Progesterone inhibits estrogen-induced cyclin D1 and cdk4 nuclear translocation, cyclin E- and cyclin A-cdk2 kinase activation, and cell proliferation in uterine epithelial cells in mice. Tong, W., Pollard, J.W. Mol. Cell. Biol. (1999) [Pubmed]
  6. "Add-back" estrogen reverses cognitive deficits induced by a gonadotropin-releasing hormone agonist in women with leiomyomata uteri. Sherwin, B.B., Tulandi, T. J. Clin. Endocrinol. Metab. (1996) [Pubmed]
  7. Observations on facilitation of the preovulatory rise of LH by estrogen. Kalra, S.P. Endocrinology (1975) [Pubmed]
  8. Hormonal regulation of maternal behavior in rats: stimulation following treatment with ectopic pituitary grafts plus progesterone. Bridges, R.S., Dunckel, P.T. Biol. Reprod. (1987) [Pubmed]
  9. Astrocytes and microglia respond to estrogen with increased apoE mRNA in vivo and in vitro. Stone, D.J., Rozovsky, I., Morgan, T.E., Anderson, C.P., Hajian, H., Finch, C.E. Exp. Neurol. (1997) [Pubmed]
  10. Estrogen receptors in quail brain: a functional relationship to aromatase and aggressiveness. Schlinger, B.A., Callard, G.V. Biol. Reprod. (1989) [Pubmed]
  11. Anorectic estrogen mimics leptin's effect on the rewiring of melanocortin cells and Stat3 signaling in obese animals. Gao, Q., Mezei, G., Nie, Y., Rao, Y., Choi, C.S., Bechmann, I., Leranth, C., Toran-Allerand, D., Priest, C.A., Roberts, J.L., Gao, X.B., Mobbs, C., Shulman, G.I., Diano, S., Horvath, T.L. Nat. Med. (2007) [Pubmed]
  12. Genetic variation in susceptibility to endocrine disruption by estrogen in mice. Spearow, J.L., Doemeny, P., Sera, R., Leffler, R., Barkley, M. Science (1999) [Pubmed]
  13. Induction of abnormal epithelial changes by estrogen in neonatal mouse vaginal transplants. Iguchi, T., Ostrander, P.L., Mills, K.T., Bern, H.A. Cancer Res. (1985) [Pubmed]
  14. Gene expression preferentially regulated by tamoxifen in breast cancer cells and correlations with clinical outcome. Frasor, J., Chang, E.C., Komm, B., Lin, C.Y., Vega, V.B., Liu, E.T., Miller, L.D., Smeds, J., Bergh, J., Katzenellenbogen, B.S. Cancer Res. (2006) [Pubmed]
  15. Interactive effects of unleaded gasoline and estrogen on liver tumor promotion in female B6C3F1 mice. Standeven, A.M., Wolf, D.C., Goldsworthy, T.L. Cancer Res. (1994) [Pubmed]
  16. Overexpression of estrogen receptor in HTB 96 human osteosarcoma cells results in estrogen-induced growth inhibition and receptor cross talk. Watts, C.K., King, R.J. J. Bone Miner. Res. (1994) [Pubmed]
  17. Origin of estrogen in normal men and in women with testicular feminization. MacDonald, P.C., Madden, J.D., Brenner, P.F., Wilson, J.D., Siiteri, P.K. J. Clin. Endocrinol. Metab. (1979) [Pubmed]
  18. A cell-type-specific transcriptional network required for estrogen regulation of cyclin D1 and cell cycle progression in breast cancer. Eeckhoute, J., Carroll, J.S., Geistlinger, T.R., Torres-Arzayus, M.I., Brown, M. Genes Dev. (2006) [Pubmed]
  19. Induction by estrogen metabolite 16 alpha-hydroxyestrone of genotoxic damage and aberrant proliferation in mouse mammary epithelial cells. Telang, N.T., Suto, A., Wong, G.Y., Osborne, M.P., Bradlow, H.L. J. Natl. Cancer Inst. (1992) [Pubmed]
  20. Growth regulation of estrogen receptor-negative breast cancer cells transfected with complementary DNAs for estrogen receptor. Jiang, S.Y., Jordan, V.C. J. Natl. Cancer Inst. (1992) [Pubmed]
  21. Estrogen receptor alpha mediates the nongenomic activation of endothelial nitric oxide synthase by estrogen. Chen, Z., Yuhanna, I.S., Galcheva-Gargova, Z., Karas, R.H., Mendelsohn, M.E., Shaul, P.W. J. Clin. Invest. (1999) [Pubmed]
  22. Estrogen-dependent Leydig cell protein recognized by monoclonal antibody to MCF-7 cell line. Ciocca, D.R., Dufau, M.L. Science (1984) [Pubmed]
  23. Genetic deletion of the repressor of estrogen receptor activity (REA) enhances the response to estrogen in target tissues in vivo. Park, S.E., Xu, J., Frolova, A., Liao, L., O'Malley, B.W., Katzenellenbogen, B.S. Mol. Cell. Biol. (2005) [Pubmed]
  24. Estrogen enhances dietary cholesterol induction of saturated bile in the hamster. Coyne, M.J., Bonorris, G.G., Chung, A., Winchester, R., Schoenfield, L.J. Gastroenterology (1978) [Pubmed]
  25. Analysis of estrogen receptor transcriptional enhancement by a nuclear hormone receptor coactivator. McInerney, E.M., Tsai, M.J., O'Malley, B.W., Katzenellenbogen, B.S. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  26. Hormonal control of plasma renin substrate; (angiotensinogen). Krakoff, L.R., Eisenfeld, A.J. Circ. Res. (1977) [Pubmed]
  27. Estrogen and sex hormone-binding globulin levels in nulliparous and parous women. Bernstein, L., Pike, M.C., Ross, R.K., Judd, H.L., Brown, J.B., Henderson, B.E. J. Natl. Cancer Inst. (1985) [Pubmed]
  28. Dominant activity of activation function 1 (AF-1) and differential stoichiometric requirements for AF-1 and -2 in the estrogen receptor alpha-beta heterodimeric complex. Tremblay, G.B., Tremblay, A., Labrie, F., Giguère, V. Mol. Cell. Biol. (1999) [Pubmed]
  29. The aryl hydrocarbon receptor mediates degradation of estrogen receptor alpha through activation of proteasomes. Wormke, M., Stoner, M., Saville, B., Walker, K., Abdelrahim, M., Burghardt, R., Safe, S. Mol. Cell. Biol. (2003) [Pubmed]
  30. Rapid estrogen-induced phosphorylation of the SRC-3 coactivator occurs in an extranuclear complex containing estrogen receptor. Zheng, F.F., Wu, R.C., Smith, C.L., O'Malley, B.W. Mol. Cell. Biol. (2005) [Pubmed]
  31. Estrogen maintains trabecular bone volume in rats not only by suppression of bone resorption but also by stimulation of bone formation. Chow, J., Tobias, J.H., Colston, K.W., Chambers, T.J. J. Clin. Invest. (1992) [Pubmed]
  32. From the Cover: Location analysis of estrogen receptor alpha target promoters reveals that FOXA1 defines a domain of the estrogen response. Laganière, J., Deblois, G., Lefebvre, C., Bataille, A.R., Robert, F., Giguère, V. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  33. Direct arterial vascularization of estrogen-induced prolactin-secreting anterior pituitary tumors. Elias, K.A., Weiner, R.I. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  34. Estrogenic and antiestrogenic properties of resveratrol in mammary tumor models. Bhat, K.P., Lantvit, D., Christov, K., Mehta, R.G., Moon, R.C., Pezzuto, J.M. Cancer Res. (2001) [Pubmed]
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