Template:Affinities of estrogen receptor ligands for the ERα and ERβ

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Affinities of estrogen receptor ligands for the ERα and ERβ

Ligand Other names Relative binding affinities (RBA, %)a Absolute binding affinities (Ki, nM)a Action
Template:No selflink Template:No selflink Template:No selflink Template:No selflink
Template:No selflink E2; 17β-Estradiol 100 100 Template:Median (0.04–0.24) Template:Median (0.10–2.08) Estrogen
Template:No selflink E1; 17-Ketoestradiol Template:Median (0.7–60) Template:Median (1.36–52) Template:Median (0.3–1.01) Template:Median (0.35–9.24) Estrogen
Template:No selflink E3; 16α-OH-17β-E2 Template:Median (4.03–56) Template:Median (14.0–44.6) Template:Median (0.35–1.4) Template:Median (0.63–0.7) Estrogen
Template:No selflink E4; 15α,16α-Di-OH-17β-E2 4.0 3.0 4.9 19 Estrogen
Template:No selflink 17α-Estradiol Template:Median (7–80.1) Template:Median (2–42) 0.2–0.52 0.43–1.2 Metabolite
Template:No selflink 16β-Hydroxy-17β-estradiol Template:Median (4.94–63) 50 ? ? Metabolite
Template:No selflink 16α-Hydroxy-17α-estradiol Template:Median (29–103) 79–80 ? ? Metabolite
Template:No selflink 16β-Hydroxy-17α-estradiol 1.0 13 ? ? Metabolite
Template:No selflink 2-OH-E2 Template:Median (7–81) 11–35 2.5 1.3 Metabolite
Template:No selflink 2-MeO-E2 0.0027–2.0 1.0 ? ? Metabolite
Template:No selflink 4-OH-E2 Template:Median (8–70) 7–56 1.0 1.9 Metabolite
Template:No selflink 4-MeO-E2 2.0 1.0 ? ? Metabolite
Template:No selflink 2-OH-E1 2.0–4.0 0.2–0.4 ? ? Metabolite
Template:No selflink 2-MeO-E1 <0.001–<1 <1 ? ? Metabolite
Template:No selflink 4-OH-E1 1.0–2.0 1.0 ? ? Metabolite
Template:No selflink 4-MeO-E1 <1 <1 ? ? Metabolite
Template:No selflink 16α-OH-E1; 17-Ketoestriol 2.0–6.5 35 ? ? Metabolite
Template:No selflink 2-OH-E3 2.0 1.0 ? ? Metabolite
Template:No selflink 4-MeO-E3 1.0 1.0 ? ? Metabolite
Template:No selflink E2S; Estradiol 3-sulfate <1 <1 ? ? Metabolite
Template:No selflink Estradiol 3,17β-disulfate 0.0004 ? ? ? Metabolite
Template:No selflink E2-3G 0.0079 ? ? ? Metabolite
Template:No selflink E2-17G 0.0015 ? ? ? Metabolite
Template:No selflink E2-3G-17S 0.0001 ? ? ? Metabolite
Template:No selflink E1S; Estrone 3-sulfate <1 <1 >10 >10 Metabolite
Template:No selflink EB; Estradiol 3-benzoate 10 ? ? ? Estrogen
Template:No selflink E2-17B 11.3 32.6 ? ? Estrogen
Template:No selflink Estrone 3-methyl ether 0.145 ? ? ? Estrogen
Template:No selflink 1-Estradiol 1.31–12.34 9.44–80.07 ? ? Estrogen
Template:No selflink 7-Dehydroestrone Template:Median (4.0–28.9) 13.0–49 0.79 0.36 Estrogen
Template:No selflink 6,8-Didehydroestrone 2.0–15 7.0–20 0.64 0.62 Estrogen
Template:No selflink 7-Dehydro-17β-estradiol 7.9–113 7.9–108 0.09 0.17 Estrogen
Template:No selflink 7-Dehydro-17α-estradiol Template:Median (18–41) 14–32 0.24 0.57 Estrogen
Template:No selflink 6,8-Didehydro-17β-estradiol 35–68 90–100 0.15 0.20 Estrogen
Template:No selflink 6,8-Didehydro-17α-estradiol 20 49 0.50 0.37 Estrogen
Template:No selflink 8,9-Dehydro-17β-estradiol 68 72 0.15 0.25 Estrogen
Template:No selflink 8,9-Dehydroestrone 19 32 0.52 0.57 Estrogen
Template:No selflink EE; 17α-Ethynyl-17β-E2 Template:Median (68.8–480) Template:Median (2.0–144) 0.02–0.05 0.29–0.81 Estrogen
Template:No selflink EE 3-methyl ether ? 2.5 ? ? Estrogen
Template:No selflink RU-2858; 11β-Methoxy-EE 35–43 5–20 0.5 2.6 Estrogen
Template:No selflink 17α-Methyl-17β-estradiol 70 44 ? ? Estrogen
Template:No selflink DES; Stilbestrol Template:Median (89.1–468) Template:Median (61.2–295) 0.04 0.05 Estrogen
Template:No selflink Dihydrodiethylstilbestrol Template:Median (31–302) 60–234 0.06 0.06 Estrogen
Template:No selflink Dehydrostilbestrol Template:Median (20.4–223) 56–404 0.05 0.03 Estrogen
Template:No selflink 114 ? ? ? Estrogen
Template:No selflink TACE 1.74 ? 15.30 ? Estrogen
Template:No selflink TPE 0.074 ? ? ? Estrogen
Template:No selflink TPBE 2.69 ? ? ? Estrogen
Template:No selflink ICI-46,474 Template:Median (0.1–47) Template:Median (0.28–6) 3.4–9.69 2.5 SERM
Template:No selflink 4-Hydroxytamoxifen; 4-OHT Template:Median (1.7–257) Template:Median (0.98–339) Template:Median (0.1–3.61) 0.04–4.8 SERM
Template:No selflink 4-Chlorotamoxifen; 4-CT ? ? 7.14–20.3 15.4 SERM
Template:No selflink MRL-41 Template:Median (19.2–37.2) 12 0.9 1.2 SERM
Template:No selflink F-6066; Sexovid 151–152 243 ? ? SERM
Template:No selflink U-11,000A 30.9–44 16 0.3 0.8 SERM
Template:No selflink Template:Median (7.8–69) Template:Median (0.54–16) 0.188–0.52 20.2 SERM
Template:No selflink LY-353,381 ? ? 0.179 ? SERM
Template:No selflink CP-336,156 10.2–166 19.0 0.229 ? SERM
Template:No selflink Centchroman ? ? 0.313 ? SERM
Template:No selflink 6720-CDRI; NNC-460,020 1.55 1.88 ? ? SERM
Template:No selflink Deaminohydroxytoremifene 2.63 1.22 ? ? SERM
Template:No selflink ? ? 0.053 ? SERM
Template:No selflink GW-5638 4.30 11.5 ? ? SERM
Template:No selflink Template:Median (3.70–97.7) 166 0.2 0.08 Antiestrogen
Template:No selflink ICI-182,780 Template:Median (9.4–325) Template:Median (2.05–40.5) 0.42 1.3 Antiestrogen
Template:No selflink PPT Template:Median (10.0–89.1) 0.12 0.40 92.8 ERα agonist
Template:No selflink 16α-Lactone-17β-estradiol 14.6–57 0.089 0.27 131 ERα agonist
Template:No selflink 16α-Iodo-17β-estradiol 30.2 2.30 ? ? ERα agonist
Template:No selflink MPP 11 0.05 ? ? ERα antagonist
Template:No selflink DPN 0.12–0.25 6.6–18 32.4 1.7 ERβ agonist
Template:No selflink 8β-Vinyl-17β-estradiol 0.35 22.0–83 12.9 0.50 ERβ agonist
Template:No selflink ERB-041; WAY-202,041 0.27 67–72 ? ? ERβ agonist
Template:No selflink WAY-202,196 ? 180 ? ? ERβ agonist
Template:No selflink SERBA-1; LY-500,307 ? ? 2.68 0.19 ERβ agonist
Template:No selflink ? ? 14.5 1.54 ERβ agonist
Template:No selflink Template:Median (0.0117–94) Template:Median (0.41–185) 0.14–80.0 0.07–27.0 Xenoestrogen
Template:No selflink Template:Median (0.0012–16) Template:Median (0.86–87) 2.6–126 0.3–12.8 Xenoestrogen
Template:No selflink 0.2–0.287 Template:Median (0.10–2.85) ? ? Xenoestrogen
Template:No selflink Template:Median (0.0018–9.3) Template:Median (0.04–17.1) 2.0 85.3 Xenoestrogen
Template:No selflink Template:Median (0.022–0.15) Template:Median (0.010–1.2) 174 8.9 Xenoestrogen
Template:No selflink Template:Median (0.029–0.10) Template:Median (0.002–3.00) ? ? Xenoestrogen
Template:No selflink Template:Median (<0.001–0.01) Template:Median (0.11–0.33) ? ? Xenoestrogen
Template:No selflink 8-PN 4.4 ? ? ? Xenoestrogen
Template:No selflink <0.001–0.01 0.002–0.040 ? ? Xenoestrogen
Template:No selflink <0.01 <0.01 ? ? Xenoestrogen
Template:No selflink 0.39 ? ? ? Xenoestrogen
Template:No selflink 2.0 ? ? ? Xenoestrogen
Template:No selflink <0.001–0.0875 <0.001–0.016 ? ? Xenoestrogen
Template:No selflink <0.001–0.0032 ? ? ? Xenoestrogen
Template:No selflink Template:Median (13–52.5) ? ? ? Xenoestrogen
Template:No selflink Template:Median (0.032–13) ? ? ? Xenoestrogen
Template:No selflink α-Zearalanol 48–111 ? ? ? Xenoestrogen
Template:No selflink β-Zearalanol Template:Median (13–17.8) 14 0.8 0.9 Xenoestrogen
Template:No selflink ZEN Template:Median (2.04–28) Template:Median (2.43–31.5) ? ? Xenoestrogen
Template:No selflink ZAN 0.51 ? ? ? Xenoestrogen
Template:No selflink BPA Template:Median (0.008–1.0) Template:Median (0.002–4.23) 195 35 Xenoestrogen
Template:No selflink EDS <0.001–<0.01 <0.01 ? ? Xenoestrogen
Template:No selflink Chlordecone 0.0069–0.2 ? ? ? Xenoestrogen
Template:No selflink 0.0073–0.4 ? ? ? Xenoestrogen
Template:No selflink Template:Median ? ? ? Xenoestrogen
Template:No selflink p,p'-Dimethoxy-DDT Template:Median (<0.001–0.02) 0.01–0.13 ? ? Xenoestrogen
Template:No selflink Hydroxychlor; p,p'-OH-DDT 1.2–1.7 ? ? ? Xenoestrogen
Template:No selflink T; 4-Androstenolone <0.0001–<0.01 <0.002–0.040 >5000 >5000 Androgen
Template:No selflink DHT; 5α-Androstanolone Template:Median (<0.001–0.05) 0.0059–0.17 221–>5000 73–1688 Androgen
Template:No selflink 19-Nortestosterone; 19-NT 0.01 0.23 765 53 Androgen
Template:No selflink DHEA; Prasterone Template:Median (<0.001–0.04) 0.019–0.07 245–1053 163–515 Androgen
Template:No selflink A5; Androstenediol 6 17 3.6 0.9 Androgen
Template:No selflink 0.5 0.6 23 19 Androgen
Template:No selflink A4; Androstenedione <0.01 <0.01 >10000 >10000 Androgen
Template:No selflink 3α-Adiol 0.07 0.3 260 48 Androgen
Template:No selflink 3β-Adiol 3 7 6 2 Androgen
Template:No selflink 5α-Androstanedione <0.01 <0.01 >10000 >10000 Androgen
Template:No selflink 5β-Androstanedione <0.01 <0.01 >10000 >10000 Androgen
Template:No selflink 17α-Methyltestosterone <0.0001 ? ? ? Androgen
Template:No selflink 17α-Ethynyl-3α-adiol 4.0 <0.07 ? ? Estrogen
Template:No selflink 17α-Ethynyl-3β-adiol 50 5.6 ? ? Estrogen
Template:No selflink P4; 4-Pregnenedione <0.001–0.6 <0.001–0.010 ? ? Progestogen
Template:No selflink NET; 17α-Ethynyl-19-NT Template:Median (0.0015–<0.1) Template:Median (0.01–0.3) 152 1084 Progestogen
Template:No selflink 5(10)-Norethisterone Template:Median (0.3–0.7) <0.1–0.22 14 53 Progestogen
Template:No selflink 7α-Methylnorethynodrel Template:Median (0.45–2.0) 0.2–0.076 ? ? Progestogen
Template:No selflink 7α-Methylnorethisterone 0.069–<0.1 0.027–<0.1 ? ? Progestogen
Template:No selflink Template:Median (1.06–5.0) 0.6–0.8 ? ? Progestogen
Template:No selflink Template:Median (0.75–1.9) 0.070–0.1 ? ? Progestogen
Footnotes: a = (1) Binding affinity values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of in-vitro systems with labeled estradiol and human ERα and ERβ proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ).

Sources: Kuiper et al. (1997, 1998),[1][2][3][4] Bolger et al. (1998),[5] Fritzemeier & Hegele-Hartung (1999),[6] Matthews et al. (2000),[7] Gutendorf & Westendorf (2001),[8] Han et al. (2002),[9][10] Harris et al. (2002),[11] Tamrazi et al. (2002),[12] de Gooyer et al. (2003),[13] Ohno & Suzuki et al. (2003),[14][15][16] Mueller et al. (2004),[17] Perez et al. (2004, 2005),[18][19][20] Chen et al. (2005),[21] Matsumura et al. (2005),[22] Veeneman (2005),[23] Escande et al. (2006),[24] Sonneveld et al. (2006),[25] Taneja et al. (2006),[26] Zhu et al. (2006),[27][28] Harris (2007),[29] Akahori et al. (2008),[30] Attardi et al. (2008),[31] Bhavnani, Tam, & Lu (2008),[32][33][3][34] NITE (2008),[35][36] Visser et al. (2008),[37] Escande et al. (2009),[38] Rider et al. (2009),[39][40] Shanle & Xu (2010),[41] Dang et al. (2010),[10] Toniti et al. (2011),[42] Ahlem et al. (2012),[43] Mizutani et al. (2012),[44] Durmaz et al. (2013),[45] Unkilaa et al. (2013),[46] and Perkins et al. (2018).[47][48] Other sources (not included due to (1) no ER subtype specificity; (2) non-human ERs; and/or (3) only estrogenic potencies without affinity values): [49][50][51][52][53][54][55][56][57][58][59][22][60][61][62][63]
Template documentation

See also

References

  1. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–70. doi:10.1210/endo.138.3.4979. PMID 9048584.
  2. Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (October 1998). "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta". Endocrinology. 139 (10): 4252–63. doi:10.1210/endo.139.10.6216. PMID 9751507.
  3. 3.0 3.1 Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
  4. Antonio R. Gargiulo (23 December 2017). Yen & Jaffe's Reproductive Endocrinology E-Book: Physiology, Pathophysiology, and Clinical Management. Elsevier Health Sciences. pp. 120–. ISBN 978-0-323-58232-2.
  5. Bolger R, Wiese TE, Ervin K, Nestich S, Checovich W (September 1998). "Rapid screening of environmental chemicals for estrogen receptor binding capacity". Environ. Health Perspect. 106 (9): 551–7. doi:10.1289/ehp.98106551. PMC 1533147. PMID 9721254.
  6. Fritzemeier, K.-H.; Hegele-Hartung, C. (1999). "In Vitro and In Vivo Models to Characterise Estrogens and Antiestrogens". In Michael Oettel; Ekkehard Schillinger (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. 135 / 2. Springer. pp. 3–94. doi:10.1007/978-3-642-60107-1_1. ISBN 978-3-642-60107-1. ISSN 0171-2004.
  7. Matthews J, Celius T, Halgren R, Zacharewski T (November 2000). "Differential estrogen receptor binding of estrogenic substances: a species comparison". J. Steroid Biochem. Mol. Biol. 74 (4): 223–34. doi:10.1016/s0960-0760(00)00126-6. PMID 11162928.
  8. Gutendorf B, Westendorf J (September 2001). "Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens". Toxicology. 166 (1–2): 79–89. doi:10.1016/s0300-483x(01)00437-1. PMID 11518614.
  9. Han DH, Denison MS, Tachibana H, Yamada K (July 2002). "Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids". Biosci. Biotechnol. Biochem. 66 (7): 1479–87. doi:10.1271/bbb.66.1479. PMID 12224631.
  10. 10.0 10.1 Dang Z (February 2010). "Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications". Toxicol. Lett. 192 (3): 298–315. doi:10.1016/j.toxlet.2009.11.004. PMID 19913605.
  11. Harris HA, Bapat AR, Gonder DS, Frail DE (April 2002). "The ligand binding profiles of estrogen receptors alpha and beta are species dependent". Steroids. 67 (5): 379–84. doi:10.1016/s0039-128x(01)00194-5. PMID 11958794.
  12. Tamrazi A, Carlson KE, Daniels JR, Hurth KM, Katzenellenbogen JA (December 2002). "Estrogen receptor dimerization: ligand binding regulates dimer affinity and dimer dissociation rate". Mol. Endocrinol. 16 (12): 2706–19. doi:10.1210/me.2002-0250. PMID 12456792.
  13. de Gooyer ME, Deckers GH, Schoonen WG, Verheul HA, Kloosterboer HJ (January 2003). "Receptor profiling and endocrine interactions of tibolone". Steroids. 68 (1): 21–30. doi:10.1016/s0039-128x(02)00112-5. PMID 12475720.
  14. Ohno K, Suzuki S, Fukushima T, Maeda M, Santa T, Imai K (August 2003). "Study on interactions of endocrine disruptors with estrogen receptor using fluorescence polarization". Analyst. 128 (8): 1091–6. doi:10.1039/b303985d. PMID 12964612.
  15. Suzuki S, Ohno K, Santa T, Imai K (August 2003). "Study on interactions of endocrine disruptors with estrogen receptor-beta using fluorescence polarization". Anal Sci. 19 (8): 1103–8. doi:10.2116/analsci.19.1103. PMID 12945660.
  16. Jin J, Wu P, Zhang X, Li D, Wong WL, Lu YJ, Sun N, Zhang K (2020). "Understanding the interaction of estrogenic ligands with estrogen receptors: a survey of the functional and binding kinetic studies". J Environ Sci Health C Toxicol Carcinog. 38 (2): 142–168. doi:10.1080/26896583.2020.1761204. PMID 32500833.
  17. Mueller SO, Simon S, Chae K, Metzler M, Korach KS (July 2004). "Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor alpha (ERalpha) and ERbeta in human cells". Toxicol. Sci. 80 (1): 14–25. doi:10.1093/toxsci/kfh147. PMID 15084758.
  18. Perez, E. J. (2004). Estratriene Neuroprotection through Antioxidant, Non-Estrogen Receptor Mediated Mechanisms (Doctoral). University of Florida.
  19. Perez, Evelyn; Cai, Zu Yun; Covey, Douglas F.; Simpkins, James W. (2005). "Neuroprotective effects of estratriene analogs: structure-activity relationships and molecular optimization". Drug Development Research. 66 (2): 78–92. doi:10.1002/ddr.20047. ISSN 0272-4391.
  20. Yi KD, Perez E, Yang S, Liu R, Covey DF, Simpkins JW (March 2011). "The assessment of non-feminizing estrogens for use in neuroprotection". Brain Res. 1379: 61–70. doi:10.1016/j.brainres.2010.11.058. PMC 3048764. PMID 21111714.
  21. Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, Moreno CT, Schmidt A, Harada S, Freedman LP, Reszka AA (November 2005). "Direct agonist/antagonist functions of dehydroepiandrosterone". Endocrinology. 146 (11): 4568–76. doi:10.1210/en.2005-0368. PMID 15994348.
  22. 22.0 22.1 Matsumura A, Ghosh A, Pope GS, Darbre PD (April 2005). "Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells". J. Steroid Biochem. Mol. Biol. 94 (5): 431–43. doi:10.1016/j.jsbmb.2004.12.041. PMID 15876408.
  23. Veeneman GH (2005). "Non-steroidal subtype selective estrogens". Curr. Med. Chem. 12 (9): 1077–136. doi:10.2174/0929867053764662. PMID 15892637.
  24. Escande A, Pillon A, Servant N, Cravedi JP, Larrea F, Muhn P, Nicolas JC, Cavaillès V, Balaguer P (2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". Biochem. Pharmacol. 71 (10): 1459–69. doi:10.1016/j.bcp.2006.02.002. PMID 16554039.
  25. Sonneveld E, Riteco JA, Jansen HJ, Pieterse B, Brouwer A, Schoonen WG, van der Burg B (January 2006). "Comparison of in vitro and in vivo screening models for androgenic and estrogenic activities". Toxicol. Sci. 89 (1): 173–87. doi:10.1093/toxsci/kfj009. PMID 16221957.
  26. Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA (March 2006). "Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy". Expert Opin Investig Drugs. 15 (3): 293–305. doi:10.1517/13543784.15.3.293. PMID 16503765.
  27. Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR (September 2006). "Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding". Endocrinology. 147 (9): 4132–50. doi:10.1210/en.2006-0113. PMID 16728493.
  28. Wang P, McInnes C, Zhu BT (2013). "Structural characterization of the binding interactions of various endogenous estrogen metabolites with human estrogen receptor α and β subtypes: a molecular modeling study". PLoS ONE. 8 (9): e74615. doi:10.1371/journal.pone.0074615. PMC 3786999. PMID 24098659.
  29. Harris HA (January 2007). "Estrogen receptor-beta: recent lessons from in vivo studies". Mol. Endocrinol. 21 (1): 1–13. doi:10.1210/me.2005-0459. PMID 16556737.
  30. Akahori Y, Nakai M, Yamasaki K, Takatsuki M, Shimohigashi Y, Ohtaki M (February 2008). "Relationship between the results of in vitro receptor binding assay to human estrogen receptor alpha and in vivo uterotrophic assay: comparative study with 65 selected chemicals". Toxicol In Vitro. 22 (1): 225–31. doi:10.1016/j.tiv.2007.08.004. PMID 17904329.
  31. Attardi BJ, Pham TC, Radler LC, Burgenson J, Hild SA, Reel JR (June 2008). "Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase". J. Steroid Biochem. Mol. Biol. 110 (3–5): 214–22. doi:10.1016/j.jsbmb.2007.11.009. PMC 2575079. PMID 18555683.
  32. Bhavnani BR, Tam SP, Lu X (October 2008). "Structure activity relationships and differential interactions and functional activity of various equine estrogens mediated via estrogen receptors (ERs) ERalpha and ERbeta". Endocrinology. 149 (10): 4857–70. doi:10.1210/en.2008-0304. PMID 18599548.
  33. Bhavnani BR (June 2003). "Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's". J. Steroid Biochem. Mol. Biol. 85 (2–5): 473–82. doi:10.1016/s0960-0760(03)00220-6. PMID 12943738.
  34. Atwood CS, Ekstein SF (January 2019). "Human versus non-human sex steroid use in hormone replacement therapies part 1: Preclinical data". Mol. Cell. Endocrinol. 480: 12–35. doi:10.1016/j.mce.2018.10.003. PMID 30308266.
  35. Liu ZH, Kanjo Y, Mizutani S (January 2009). "Removal mechanisms for endocrine disrupting compounds (EDCs) in wastewater treatment - physical means, biodegradation, and chemical advanced oxidation: a review". Sci. Total Environ. 407 (2): 731–48. doi:10.1016/j.scitotenv.2008.08.039. PMID 18992918.
  36. Liu ZH, Kanjo Y, Mizutani S (September 2009). "Urinary excretion rates of natural estrogens and androgens from humans, and their occurrence and fate in the environment: a review". Sci. Total Environ. 407 (18): 4975–85. doi:10.1016/j.scitotenv.2009.06.001. PMID 19559467.
  37. Visser M, Foidart JM, Coelingh Bennink HJ (2008). "In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism". Climacteric. 11 Suppl 1: 64–8. doi:10.1080/13697130802050340. PMID 18464025.
  38. Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T (August 2009). "Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites". J. Steroid Biochem. Mol. Biol. 116 (1–2): 8–14. doi:10.1016/j.jsbmb.2009.03.008. PMID 19464167.
  39. Rider CV, Hartig PC, Cardon MC, Wilson VS (October 2009). "Comparison of chemical binding to recombinant fathead minnow and human estrogen receptors alpha in whole cell and cell-free binding assays". Environ. Toxicol. Chem. 28 (10): 2175–81. doi:10.1897/09-018.1. PMID 19453209.
  40. Rider CV, Hartig PC, Cardon MC, Wilson VS (January 2009). "Development of a competitive binding assay system with recombinant estrogen receptors from multiple species". Toxicol. Lett. 184 (2): 85–9. doi:10.1016/j.toxlet.2008.10.015. PMID 19022364.
  41. Shanle EK, Xu W (October 2010). "Selectively targeting estrogen receptors for cancer treatment". Adv. Drug Deliv. Rev. 62 (13): 1265–76. doi:10.1016/j.addr.2010.08.001. PMC 2991615. PMID 20708050.
  42. Toniti W, Suthiyotha N, Puchadapirom P, Jenwitheesuk E (2011). "Binding capacity of ER-α ligands and SERMs: comparison of the human, dog and cat". Asian Pac. J. Cancer Prev. 12 (11): 2875–9. PMID 22393957.
  43. Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J (2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs. 30 (1): 59–78. doi:10.1007/s10637-010-9517-0. PMID 20814732.
  44. Mizutani MY, Takamatsu Y, Ichinose T, Itai A (2012). "Prediction of ligand binding affinity using a multiple-conformations-multiple-protonation scheme: application to estrogen receptor α". Chem. Pharm. Bull. 60 (2): 183–94. doi:10.1248/cpb.60.183. PMID 22293477.
  45. Durmaz V, Schmidt S, Sabri P, Piechotta C, Weber M (October 2013). "Hands-off linear interaction energy approach to binding mode and affinity estimation of estrogens". J Chem Inf Model. 53 (10): 2681–8. doi:10.1021/ci400392p. PMID 24063761.
  46. Unkila M, Kari S, Yatkin E, Lammintausta R (November 2013). "Vaginal effects of ospemifene in the ovariectomized rat preclinical model of menopause". J. Steroid Biochem. Mol. Biol. 138: 107–15. doi:10.1016/j.jsbmb.2013.04.004. PMID 23665515.
  47. Perkins MS, Louw-du Toit R, Africander D (November 2017). "A comparative characterization of estrogens used in hormone therapy via estrogen receptor (ER)-α and -β". J. Steroid Biochem. Mol. Biol. 174: 27–39. doi:10.1016/j.jsbmb.2017.07.022. PMID 28743541.
  48. Perkins, M. S. (2018). Investigating the mechanism of action of hormones used in hormone replacement therapy via estrogen receptor subtypes and the influence of the progesterone receptor (Doctoral). Stellenbosch, South Africa: Stellenbosch University.
  49. Anstead GM, Carlson KE, Katzenellenbogen JA (March 1997). "The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site". Steroids. 62 (3): 268–303. doi:10.1016/s0039-128x(96)00242-5. PMID 9071738.
  50. Legler J, Zeinstra LM, Schuitemaker F, Lanser PH, Bogerd J, Brouwer A, Vethaak AD, De Voogt P, Murk AJ, Van der Burg B (October 2002). "Comparison of in vivo and in vitro reporter gene assays for short-term screening of estrogenic activity". Environ. Sci. Technol. 36 (20): 4410–5. doi:10.1021/es010323a. PMID 12387416.
  51. Tong W, Perkins R, Strelitz R, Collantes ER, Keenan S, Welsh WJ, Branham WS, Sheehan DM (October 1997). "Quantitative structure-activity relationships (QSARs) for estrogen binding to the estrogen receptor: predictions across species". Environ. Health Perspect. 105 (10): 1116–24. doi:10.1289/ehp.971051116. PMC 1470374. PMID 9353176.
  52. Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM (March 2000). "The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands". Toxicol. Sci. 54 (1): 138–53. doi:10.1093/toxsci/54.1.138. PMID 10746941.
  53. Fang H, Tong W, Perkins R, Soto AM, Prechtl NV, Sheehan DM (August 2000). "Quantitative comparisons of in vitro assays for estrogenic activities". Environ. Health Perspect. 108 (8): 723–9. doi:10.1289/ehp.00108723. PMC 1638296. PMID 10964792.
  54. Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, Hass BS, Xie Q, Dial SL, Moland CL, Sheehan DM (March 2001). "Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens". Chem. Res. Toxicol. 14 (3): 280–94. doi:10.1021/tx000208y. PMID 11258977.
  55. Shi LM, Fang H, Tong W, Wu J, Perkins R, Blair RM, Branham WS, Dial SL, Moland CL, Sheehan DM (2001). "QSAR models using a large diverse set of estrogens". J Chem Inf Comput Sci. 41 (1): 186–95. doi:10.1021/ci000066d. PMID 11206373.
  56. Branham WS, Dial SL, Moland CL, Hass BS, Blair RM, Fang H, Shi L, Tong W, Perkins RG, Sheehan DM (April 2002). "Phytoestrogens and mycoestrogens bind to the rat uterine estrogen receptor". J. Nutr. 132 (4): 658–64. doi:10.1093/jn/132.4.658. PMID 11925457.
  57. Hu JY, Aizawa T (March 2003). "Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals". Water Res. 37 (6): 1213–22. doi:10.1016/S0043-1354(02)00378-0. PMID 12598185.
  58. Bovee TF, Helsdingen RJ, Rietjens IM, Keijer J, Hoogenboom RL (July 2004). "Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types". J. Steroid Biochem. Mol. Biol. 91 (3): 99–109. doi:10.1016/j.jsbmb.2004.03.118. PMID 15276617.
  59. Tong, W.; Fang, H.; Hong, H.; Xie, Q.; Perkins, R.; Sheehan, D. M. (10 May 2004). "Receptor-mediated toxicity: QSARs for estrogen receptor binding and priority setting of potential estrogenic endocrine disruptors". In Mark T.D. Cronin (ed.). Predicting Chemical Toxicity and Fate. CRC Press. pp. 285–. ISBN 978-0-203-64262-7.
  60. Liu H, Papa E, Gramatica P (February 2008). "Evaluation and QSAR modeling on multiple endpoints of estrogen activity based on different bioassays". Chemosphere. 70 (10): 1889–97. doi:10.1016/j.chemosphere.2007.07.071. PMID 17884132.
  61. Lóránd T, Vigh E, Garai J (2010). "Hormonal action of plant derived and anthropogenic non-steroidal estrogenic compounds: phytoestrogens and xenoestrogens". Curr. Med. Chem. 17 (30): 3542–74. doi:10.2174/092986710792927813. PMID 20738246.
  62. Dang Z, Ru S, Wang W, Rorije E, Hakkert B, Vermeire T (March 2011). "Comparison of chemical-induced transcriptional activation of fish and human estrogen receptors: regulatory implications". Toxicol. Lett. 201 (2): 152–75. doi:10.1016/j.toxlet.2010.12.020. PMID 21195753.
  63. Borgert CJ, Matthews JC, Baker SP (May 2018). "Human-relevant potency threshold (HRPT) for ERα agonism". Arch. Toxicol. 92 (5): 1685–1702. doi:10.1007/s00204-018-2186-z. PMC 5962616. PMID 29632997.