Template:Affinities_of_estrogen_receptor_ligands_for_the_ERα_and_ERβ

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 (K_i, nM)^a		Action
Ligand	Other names	ERα	ERβ	ERα	ERβ	Action
Estradiol	E2; 17β-Estradiol	100	100	0.115 (0.04–0.24)	0.15 (0.10–2.08)	Estrogen
Estrone	E1; 17-Ketoestradiol	16.39 (0.7–60)	6.5 (1.36–52)	0.445 (0.3–1.01)	1.75 (0.35–9.24)	Estrogen
Estriol	E3; 16α-OH-17β-E2	12.65 (4.03–56)	26 (14.0–44.6)	0.45 (0.35–1.4)	0.7 (0.63–0.7)	Estrogen
Estetrol	E4; 15α,16α-Di-OH-17β-E2	4.0	3.0	4.9	19	Estrogen
Alfatradiol	17α-Estradiol	20.5 (7–80.1)	8.195 (2–42)	0.2–0.52	0.43–1.2	Metabolite
16-Epiestriol	16β-Hydroxy-17β-estradiol	7.795 (4.94–63)	50	?	?	Metabolite
17-Epiestriol	16α-Hydroxy-17α-estradiol	55.45 (29–103)	79–80	?	?	Metabolite
16,17-Epiestriol	16β-Hydroxy-17α-estradiol	1.0	13	?	?	Metabolite
2-Hydroxyestradiol	2-OH-E2	22 (7–81)	11–35	2.5	1.3	Metabolite
2-Methoxyestradiol	2-MeO-E2	0.0027–2.0	1.0	?	?	Metabolite
4-Hydroxyestradiol	4-OH-E2	13 (8–70)	7–56	1.0	1.9	Metabolite
4-Methoxyestradiol	4-MeO-E2	2.0	1.0	?	?	Metabolite
2-Hydroxyestrone	2-OH-E1	2.0–4.0	0.2–0.4	?	?	Metabolite
2-Methoxyestrone	2-MeO-E1	<0.001–<1	<1	?	?	Metabolite
4-Hydroxyestrone	4-OH-E1	1.0–2.0	1.0	?	?	Metabolite
4-Methoxyestrone	4-MeO-E1	<1	<1	?	?	Metabolite
16α-Hydroxyestrone	16α-OH-E1; 17-Ketoestriol	2.0–6.5	35	?	?	Metabolite
2-Hydroxyestriol	2-OH-E3	2.0	1.0	?	?	Metabolite
4-Methoxyestriol	4-MeO-E3	1.0	1.0	?	?	Metabolite
Estradiol sulfate	E2S; Estradiol 3-sulfate	<1	<1	?	?	Metabolite
Estradiol disulfate	Estradiol 3,17β-disulfate	0.0004	?	?	?	Metabolite
Estradiol 3-glucuronide	E2-3G	0.0079	?	?	?	Metabolite
Estradiol 17β-glucuronide	E2-17G	0.0015	?	?	?	Metabolite
Estradiol 3-gluc. 17β-sulfate	E2-3G-17S	0.0001	?	?	?	Metabolite
Estrone sulfate	E1S; Estrone 3-sulfate	<1	<1	>10	>10	Metabolite
Estradiol benzoate	EB; Estradiol 3-benzoate	10	?	?	?	Estrogen
Estradiol 17β-benzoate	E2-17B	11.3	32.6	?	?	Estrogen
Estrone methyl ether	Estrone 3-methyl ether	0.145	?	?	?	Estrogen
ent-Estradiol	1-Estradiol	1.31–12.34	9.44–80.07	?	?	Estrogen
Equilin	7-Dehydroestrone	13 (4.0–28.9)	13.0–49	0.79	0.36	Estrogen
Equilenin	6,8-Didehydroestrone	2.0–15	7.0–20	0.64	0.62	Estrogen
17β-Dihydroequilin	7-Dehydro-17β-estradiol	7.9–113	7.9–108	0.09	0.17	Estrogen
17α-Dihydroequilin	7-Dehydro-17α-estradiol	18.6 (18–41)	14–32	0.24	0.57	Estrogen
17β-Dihydroequilenin	6,8-Didehydro-17β-estradiol	35–68	90–100	0.15	0.20	Estrogen
17α-Dihydroequilenin	6,8-Didehydro-17α-estradiol	20	49	0.50	0.37	Estrogen
Δ⁸-Estradiol	8,9-Dehydro-17β-estradiol	68	72	0.15	0.25	Estrogen
Δ⁸-Estrone	8,9-Dehydroestrone	19	32	0.52	0.57	Estrogen
Ethinylestradiol	EE; 17α-Ethynyl-17β-E2	120.9 (68.8–480)	44.4 (2.0–144)	0.02–0.05	0.29–0.81	Estrogen
Mestranol	EE 3-methyl ether	?	2.5	?	?	Estrogen
Moxestrol	RU-2858; 11β-Methoxy-EE	35–43	5–20	0.5	2.6	Estrogen
Methylestradiol	17α-Methyl-17β-estradiol	70	44	?	?	Estrogen
Diethylstilbestrol	DES; Stilbestrol	129.5 (89.1–468)	219.63 (61.2–295)	0.04	0.05	Estrogen
Hexestrol	Dihydrodiethylstilbestrol	153.6 (31–302)	60–234	0.06	0.06	Estrogen
Dienestrol	Dehydrostilbestrol	37 (20.4–223)	56–404	0.05	0.03	Estrogen
Benzestrol (B2)	–	114	?	?	?	Estrogen
Chlorotrianisene	TACE	1.74	?	15.30	?	Estrogen
Triphenylethylene	TPE	0.074	?	?	?	Estrogen
Triphenylbromoethylene	TPBE	2.69	?	?	?	Estrogen
Tamoxifen	ICI-46,474	3 (0.1–47)	3.33 (0.28–6)	3.4–9.69	2.5	SERM
Afimoxifene	4-Hydroxytamoxifen; 4-OHT	100.1 (1.7–257)	10 (0.98–339)	2.3 (0.1–3.61)	0.04–4.8	SERM
Toremifene	4-Chlorotamoxifen; 4-CT	?	?	7.14–20.3	15.4	SERM
Clomifene	MRL-41	25 (19.2–37.2)	12	0.9	1.2	SERM
Cyclofenil	F-6066; Sexovid	151–152	243	?	?	SERM
Nafoxidine	U-11,000A	30.9–44	16	0.3	0.8	SERM
Raloxifene	–	41.2 (7.8–69)	5.34 (0.54–16)	0.188–0.52	20.2	SERM
Arzoxifene	LY-353,381	?	?	0.179	?	SERM
Lasofoxifene	CP-336,156	10.2–166	19.0	0.229	?	SERM
Ormeloxifene	Centchroman	?	?	0.313	?	SERM
Levormeloxifene	6720-CDRI; NNC-460,020	1.55	1.88	?	?	SERM
Ospemifene	Deaminohydroxytoremifene	0.82–2.63	0.59–1.22	?	?	SERM
Bazedoxifene	–	?	?	0.053	?	SERM
Etacstil	GW-5638	4.30	11.5	?	?	SERM
ICI-164,384	–	63.5 (3.70–97.7)	166	0.2	0.08	Antiestrogen
Fulvestrant	ICI-182,780	43.5 (9.4–325)	21.65 (2.05–40.5)	0.42	1.3	Antiestrogen
Propylpyrazoletriol	PPT	49 (10.0–89.1)	0.12	0.40	92.8	ERα agonist
16α-LE2	16α-Lactone-17β-estradiol	14.6–57	0.089	0.27	131	ERα agonist
16α-Iodo-E2	16α-Iodo-17β-estradiol	30.2	2.30	?	?	ERα agonist
Methylpiperidinopyrazole	MPP	11	0.05	?	?	ERα antagonist
Diarylpropionitrile	DPN	0.12–0.25	6.6–18	32.4	1.7	ERβ agonist
8β-VE2	8β-Vinyl-17β-estradiol	0.35	22.0–83	12.9	0.50	ERβ agonist
Prinaberel	ERB-041; WAY-202,041	0.27	67–72	?	?	ERβ agonist
ERB-196	WAY-202,196	?	180	?	?	ERβ agonist
Erteberel	SERBA-1; LY-500,307	?	?	2.68	0.19	ERβ agonist
SERBA-2	–	?	?	14.5	1.54	ERβ agonist
Coumestrol	–	9.225 (0.0117–94)	64.125 (0.41–185)	0.14–80.0	0.07–27.0	Xenoestrogen
Genistein	–	0.445 (0.0012–16)	33.42 (0.86–87)	2.6–126	0.3–12.8	Xenoestrogen
Equol	–	0.2–0.287	0.85 (0.10–2.85)	?	?	Xenoestrogen
Daidzein	–	0.07 (0.0018–9.3)	0.7865 (0.04–17.1)	2.0	85.3	Xenoestrogen
Biochanin A	–	0.04 (0.022–0.15)	0.6225 (0.010–1.2)	174	8.9	Xenoestrogen
Kaempferol	–	0.07 (0.029–0.10)	2.2 (0.002–3.00)	?	?	Xenoestrogen
Naringenin	–	0.0054 (<0.001–0.01)	0.15 (0.11–0.33)	?	?	Xenoestrogen
8-Prenylnaringenin	8-PN	4.4	?	?	?	Xenoestrogen
Quercetin	–	<0.001–0.01	0.002–0.040	?	?	Xenoestrogen
Ipriflavone	–	<0.01	<0.01	?	?	Xenoestrogen
Miroestrol	–	0.39	?	?	?	Xenoestrogen
Deoxymiroestrol	–	2.0	?	?	?	Xenoestrogen
β-Sitosterol	–	<0.001–0.0875	<0.001–0.016	?	?	Xenoestrogen
Resveratrol	–	<0.001–0.0032	?	?	?	Xenoestrogen
α-Zearalenol	–	48 (13–52.5)	?	?	?	Xenoestrogen
β-Zearalenol	–	0.6 (0.032–13)	?	?	?	Xenoestrogen
Zeranol	α-Zearalanol	48–111	?	?	?	Xenoestrogen
Taleranol	β-Zearalanol	16 (13–17.8)	14	0.8	0.9	Xenoestrogen
Zearalenone	ZEN	7.68 (2.04–28)	9.45 (2.43–31.5)	?	?	Xenoestrogen
Zearalanone	ZAN	0.51	?	?	?	Xenoestrogen
Bisphenol A	BPA	0.0315 (0.008–1.0)	0.135 (0.002–4.23)	195	35	Xenoestrogen
Endosulfan	EDS	<0.001–<0.01	<0.01	?	?	Xenoestrogen
Kepone	Chlordecone	0.0069–0.2	?	?	?	Xenoestrogen
o,p'-DDT	–	0.0073–0.4	?	?	?	Xenoestrogen
p,p'-DDT	–	0.03	?	?	?	Xenoestrogen
Methoxychlor	p,p'-Dimethoxy-DDT	0.01 (<0.001–0.02)	0.01–0.13	?	?	Xenoestrogen
HPTE	Hydroxychlor; p,p'-OH-DDT	1.2–1.7	?	?	?	Xenoestrogen
Testosterone	T; 4-Androstenolone	<0.0001–<0.01	<0.002–0.040	>5000	>5000	Androgen
Dihydrotestosterone	DHT; 5α-Androstanolone	0.01 (<0.001–0.05)	0.0059–0.17	221–>5000	73–1688	Androgen
Nandrolone	19-Nortestosterone; 19-NT	0.01	0.23	765	53	Androgen
Dehydroepiandrosterone	DHEA; Prasterone	0.038 (<0.001–0.04)	0.019–0.07	245–1053	163–515	Androgen
5-Androstenediol	A5; Androstenediol	6	17	3.6	0.9	Androgen
4-Androstenediol	–	0.5	0.6	23	19	Androgen
4-Androstenedione	A4; Androstenedione	<0.01	<0.01	>10000	>10000	Androgen
3α-Androstanediol	3α-Adiol	0.07	0.3	260	48	Androgen
3β-Androstanediol	3β-Adiol	3	7	6	2	Androgen
Androstanedione	5α-Androstanedione	<0.01	<0.01	>10000	>10000	Androgen
Etiocholanedione	5β-Androstanedione	<0.01	<0.01	>10000	>10000	Androgen
Methyltestosterone	17α-Methyltestosterone	<0.0001	?	?	?	Androgen
Ethinyl-3α-androstanediol	17α-Ethynyl-3α-adiol	4.0	<0.07	?	?	Estrogen
Ethinyl-3β-androstanediol	17α-Ethynyl-3β-adiol	50	5.6	?	?	Estrogen
Progesterone	P4; 4-Pregnenedione	<0.001–0.6	<0.001–0.010	?	?	Progestogen
Norethisterone	NET; 17α-Ethynyl-19-NT	0.085 (0.0015–<0.1)	0.1 (0.01–0.3)	152	1084	Progestogen
Norethynodrel	5(10)-Norethisterone	0.5 (0.3–0.7)	<0.1–0.22	14	53	Progestogen
Tibolone	7α-Methylnorethynodrel	0.5 (0.45–2.0)	0.2–0.076	?	?	Progestogen
Δ⁴-Tibolone	7α-Methylnorethisterone	0.069–<0.1	0.027–<0.1	?	?	Progestogen
3α-Hydroxytibolone	–	2.5 (1.06–5.0)	0.6–0.8	?	?	Progestogen
3β-Hydroxytibolone	–	1.6 (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] Qu et al. (2000),^[8] Gutendorf & Westendorf (2001),^[9] Han et al. (2002),^[10]^[11] Harris et al. (2002),^[12] Tamrazi et al. (2002),^[13] de Gooyer et al. (2003),^[14] Ohno & Suzuki et al. (2003),^[15]^[16]^[17] Mueller et al. (2004),^[18] Perez et al. (2004, 2005),^[19]^[20]^[21] Chen et al. (2005),^[22] Matsumura et al. (2005),^[23] Veeneman (2005),^[24] Escande et al. (2006),^[25] Sonneveld et al. (2006),^[26] Taneja et al. (2006),^[27] Zhu et al. (2006),^[28]^[29] Harris (2007),^[30] Akahori et al. (2008),^[31] Attardi et al. (2008),^[32] Bhavnani, Tam, & Lu (2008),^[33]^[34]^[3]^[35] NITETooltip National Institute of Technology and Evaluation (2008),^[36]^[37] Visser et al. (2008),^[38] Escande et al. (2009),^[39] Rider et al. (2009),^[40]^[41] Shanle & Xu (2010),^[42] Dang et al. (2010),^[11] Toniti et al. (2011),^[43] Ahlem et al. (2012),^[44] Mizutani et al. (2012),^[45] Durmaz et al. (2013),^[46] Unkilaa et al. (2013),^[47] and Perkins et al. (2018).^[48]^[49] Other sources (not included due to (1) no ER subtype specificity; (2) non-human ERs; and/or (3) only estrogenic potencies without affinity values): ^[50]^[51]^[52]^[53]^[54]^[55]^[56]^[57]^[58]^[59]^[60]^[23]^[61]^[62]^[63]^[64]

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[pmid9048584-1] [1]
Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (March 1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–870. doi:10.1210/endo.138.3.4979. PMID 9048584. S2CID 142569.

[pmid9751507-2] [2]
Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, et al. (October 1998). "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta". Endocrinology. 139 (10): 4252–4263. doi:10.1210/endo.139.10.6216. PMID 9751507.

[pmid16112947-3] [3]
Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.

[Gargiulo2017-4] [4]
Gargiulo AR (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.

[pmid9721254-5] [5]
Bolger R, Wiese TE, Ervin K, Nestich S, Checovich W (September 1998). "Rapid screening of environmental chemicals for estrogen receptor binding capacity". Environmental Health Perspectives. 106 (9): 551–557. doi:10.1289/ehp.98106551. PMC 1533147. PMID 9721254.

[FritzemeierHegele-Hartung1999-6] [6]
Fritzemeier KH, Hegele-Hartung C (1999). "In Vitro and In Vivo Models to Characterise Estrogens and Antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer. pp. 3–94. doi:10.1007/978-3-642-60107-1_1. ISBN 978-3-642-60107-1. ISSN 0171-2004.

[pmid11162928-7] [7]
Matthews J, Celius T, Halgren R, Zacharewski T (November 2000). "Differential estrogen receptor binding of estrogenic substances: a species comparison". The Journal of Steroid Biochemistry and Molecular Biology. 74 (4): 223–234. doi:10.1016/s0960-0760(00)00126-6. PMID 11162928. S2CID 1979844.

[pmid10650964-8] [8]
Qu Q, Zheng H, Dahllund J, Laine A, Cockcroft N, Peng Z, et al. (February 2000). "Selective estrogenic effects of a novel triphenylethylene compound, FC1271a, on bone, cholesterol level, and reproductive tissues in intact and ovariectomized rats". Endocrinology. 141 (2): 809–820. doi:10.1210/endo.141.2.7342. PMID 10650964.

[pmid11518614-9] [9]
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.

[pmid12224631-10] [10]
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". Bioscience, Biotechnology, and Biochemistry. 66 (7): 1479–1487. doi:10.1271/bbb.66.1479. PMID 12224631. S2CID 25774763.

[pmid19913605-11] [11]
Dang Z (February 2010). "Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications". Toxicology Letters. 192 (3): 298–315. doi:10.1016/j.toxlet.2009.11.004. PMID 19913605.

[pmid11958794-12] [12]
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): 379–384. doi:10.1016/s0039-128x(01)00194-5. PMID 11958794. S2CID 54270380.

[pmid12456792-13] [13]
Tamrazi A, Carlson KE, Daniels JR, Hurth KM, Katzenellenbogen JA (December 2002). "Estrogen receptor dimerization: ligand binding regulates dimer affinity and dimer dissociation rate". Molecular Endocrinology. 16 (12): 2706–2719. doi:10.1210/me.2002-0250. PMID 12456792. S2CID 317180.

[pmid12475720-14] [14]
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. S2CID 40426061.

[pmid12964612-15] [15]
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". The Analyst. 128 (8): 1091–1096. Bibcode:2003Ana...128.1091O. doi:10.1039/b303985d. PMID 12964612. S2CID 28000543.

[pmid12945660-16] [16]
Suzuki S, Ohno K, Santa T, Imai K (August 2003). "Study on interactions of endocrine disruptors with estrogen receptor-beta using fluorescence polarization". Analytical Sciences. 19 (8): 1103–1108. doi:10.2116/analsci.19.1103. PMID 12945660. S2CID 44528583.

[pmid32500833-17] [17]
Jin J, Wu P, Zhang X, Li D, Wong WL, Lu YJ, et al. (2020). "Understanding the interaction of estrogenic ligands with estrogen receptors: a survey of the functional and binding kinetic studies". Journal of Environmental Science and Health. Part C, Toxicology and Carcinogenesis. 38 (2): 142–168. doi:10.1080/26896583.2020.1761204. PMID 32500833. S2CID 218934332.

[pmid15084758-18] [18]
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". Toxicological Sciences. 80 (1): 14–25. doi:10.1093/toxsci/kfh147. PMID 15084758.

[Perez2004-19] [19]
Perez EJ (2004). Estratriene Neuroprotection through Antioxidant, Non-Estrogen Receptor Mediated Mechanisms (Doctoral). University of Florida.

[PerezCai2005-20] [20]
Perez E, Cai ZY, Covey DF, Simpkins JW (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. S2CID 86133327.

[pmid21111714-21] [21]
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 Research. 1379: 61–70. doi:10.1016/j.brainres.2010.11.058. PMC 3048764. PMID 21111714.

[pmid15994348-22] [22]
Chen F, Knecht K, Birzin E, Fisher J, Wilkinson H, Mojena M, et al. (November 2005). "Direct agonist/antagonist functions of dehydroepiandrosterone". Endocrinology. 146 (11): 4568–4576. doi:10.1210/en.2005-0368. PMID 15994348. S2CID 15150213.

[pmid15876408-23] [23]
Matsumura A, Ghosh A, Pope GS, Darbre PD (April 2005). "Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells". The Journal of Steroid Biochemistry and Molecular Biology. 94 (5): 431–443. doi:10.1016/j.jsbmb.2004.12.041. PMID 15876408. S2CID 25341363.

[pmid15892637-24] [24]
Veeneman GH (2005). "Non-steroidal subtype selective estrogens". Current Medicinal Chemistry. 12 (9): 1077–1136. doi:10.2174/0929867053764662. PMID 15892637.

[pmid16554039-25] [25]
Escande A, Pillon A, Servant N, Cravedi JP, Larrea F, Muhn P, et al. (May 2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". Biochemical Pharmacology. 71 (10): 1459–1469. doi:10.1016/j.bcp.2006.02.002. PMID 16554039.

[pmid16221957-26] [26]
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". Toxicological Sciences. 89 (1): 173–187. doi:10.1093/toxsci/kfj009. PMID 16221957.

[pmid16503765-27] [27]
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 Opinion on Investigational Drugs. 15 (3): 293–305. doi:10.1517/13543784.15.3.293. PMID 16503765. S2CID 29510508.

[pmid16728493-28] [28]
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): 4132–4150. doi:10.1210/en.2006-0113. PMID 16728493.

[pmid24098659-29] [29]
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. Bibcode:2013PLoSO...874615W. doi:10.1371/journal.pone.0074615. PMC 3786999. PMID 24098659.

[pmid16556737-30] [30]
Harris HA (January 2007). "Estrogen receptor-beta: recent lessons from in vivo studies". Molecular Endocrinology. 21 (1): 1–13. doi:10.1210/me.2005-0459. PMID 16556737.

[pmid17904329-31] [31]
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". Toxicology in Vitro. 22 (1): 225–231. doi:10.1016/j.tiv.2007.08.004. PMID 17904329.

[pmid18555683-32] [32]
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". The Journal of Steroid Biochemistry and Molecular Biology. 110 (3–5): 214–222. doi:10.1016/j.jsbmb.2007.11.009. PMC 2575079. PMID 18555683.

[pmid18599548-33] [33]
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): 4857–4870. doi:10.1210/en.2008-0304. PMID 18599548.

[pmid12943738-34] [34]
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". The Journal of Steroid Biochemistry and Molecular Biology. 85 (2–5): 473–482. doi:10.1016/s0960-0760(03)00220-6. PMID 12943738. S2CID 45552896.

[pmid30308266-35] [35]
Atwood CS, Ekstein SF (January 2019). "Human versus non-human sex steroid use in hormone replacement therapies part 1: Preclinical data". Molecular and Cellular Endocrinology. 480: 12–35. doi:10.1016/j.mce.2018.10.003. PMID 30308266. S2CID 52961862.

[pmid18992918-36] [36]
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". The Science of the Total Environment. 407 (2): 731–748. Bibcode:2009ScTEn.407..731L. doi:10.1016/j.scitotenv.2008.08.039. PMID 18992918.

[pmid19559467-37] [37]
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". The Science of the Total Environment. 407 (18): 4975–4985. Bibcode:2009ScTEn.407.4975L. doi:10.1016/j.scitotenv.2009.06.001. PMID 19559467.

[pmid18464025-38] [38]
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): 64–68. doi:10.1080/13697130802050340. PMID 18464025. S2CID 11027782.

[pmid19464167-39] [39]
Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, et al. (August 2009). "Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites" (PDF). The Journal of Steroid Biochemistry and Molecular Biology. 116 (1–2): 8–14. doi:10.1016/j.jsbmb.2009.03.008. PMID 19464167. S2CID 18346113.

[pmid19453209-40] [40]
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". Environmental Toxicology and Chemistry. 28 (10): 2175–2181. doi:10.1897/09-018.1. PMID 19453209. S2CID 41769636.

[pmid19022364-41] [41]
Rider CV, Hartig PC, Cardon MC, Wilson VS (January 2009). "Development of a competitive binding assay system with recombinant estrogen receptors from multiple species". Toxicology Letters. 184 (2): 85–89. doi:10.1016/j.toxlet.2008.10.015. PMID 19022364.

[pmid20708050-42] [42]
Shanle EK, Xu W (October 2010). "Selectively targeting estrogen receptors for cancer treatment". Advanced Drug Delivery Reviews. 62 (13): 1265–1276. doi:10.1016/j.addr.2010.08.001. PMC 2991615. PMID 20708050.

[pmid22393957-43] [43]
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 Pacific Journal of Cancer Prevention. 12 (11): 2875–2879. PMID 22393957.

[pmid20814732-44] [44]
Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, et al. (February 2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Investigational New Drugs. 30 (1): 59–78. doi:10.1007/s10637-010-9517-0. PMID 20814732. S2CID 24785562.

[pmid22293477-45] [45]
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". Chemical & Pharmaceutical Bulletin. 60 (2): 183–194. doi:10.1248/cpb.60.183. PMID 22293477.

[pmid24063761-46] [46]
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". Journal of Chemical Information and Modeling. 53 (10): 2681–2688. doi:10.1021/ci400392p. PMID 24063761.

[pmid23665515-47] [47]
Unkila M, Kari S, Yatkin E, Lammintausta R (November 2013). "Vaginal effects of ospemifene in the ovariectomized rat preclinical model of menopause". The Journal of Steroid Biochemistry and Molecular Biology. 138: 107–115. doi:10.1016/j.jsbmb.2013.04.004. PMID 23665515. S2CID 20363618.

[pmid28743541-48] [48]
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". The Journal of Steroid Biochemistry and Molecular Biology. 174: 27–39. doi:10.1016/j.jsbmb.2017.07.022. PMID 28743541. S2CID 36935474.

[Perkins2018-49] [49]
Perkins MS (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.

[pmid9071738-50] [50]
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. S2CID 10080044.

[pmid12387416-51] [51]
Legler J, Zeinstra LM, Schuitemaker F, Lanser PH, Bogerd J, Brouwer A, et al. (October 2002). "Comparison of in vivo and in vitro reporter gene assays for short-term screening of estrogenic activity". Environmental Science & Technology. 36 (20): 4410–4415. Bibcode:2002EnST...36.4410L. doi:10.1021/es010323a. PMID 12387416.

[pmid9353176-52] [52]
Tong W, Perkins R, Strelitz R, Collantes ER, Keenan S, Welsh WJ, et al. (October 1997). "Quantitative structure-activity relationships (QSARs) for estrogen binding to the estrogen receptor: predictions across species". Environmental Health Perspectives. 105 (10): 1116–1124. doi:10.1289/ehp.971051116. PMC 1470374. PMID 9353176.

[pmid10746941-53] [53]
Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, et al. (March 2000). "The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands". Toxicological Sciences. 54 (1): 138–153. doi:10.1093/toxsci/54.1.138. PMID 10746941.

[pmid10964792-54] [54]
Fang H, Tong W, Perkins R, Soto AM, Prechtl NV, Sheehan DM (August 2000). "Quantitative comparisons of in vitro assays for estrogenic activities". Environmental Health Perspectives. 108 (8): 723–729. doi:10.1289/ehp.00108723. PMC 1638296. PMID 10964792.

[pmid11258977-55] [55]
Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, et al. (March 2001). "Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens". Chemical Research in Toxicology. 14 (3): 280–294. doi:10.1021/tx000208y. PMID 11258977.

[pmid11206373-56] [56]
Shi LM, Fang H, Tong W, Wu J, Perkins R, Blair RM, et al. (2001). "QSAR models using a large diverse set of estrogens". Journal of Chemical Information and Computer Sciences. 41 (1): 186–195. doi:10.1021/ci000066d. PMID 11206373.

[pmid11925457-57] [57]
Branham WS, Dial SL, Moland CL, Hass BS, Blair RM, Fang H, et al. (April 2002). "Phytoestrogens and mycoestrogens bind to the rat uterine estrogen receptor". The Journal of Nutrition. 132 (4): 658–664. doi:10.1093/jn/132.4.658. PMID 11925457.

[pmid12598185-58] [58]
Hu JY, Aizawa T (March 2003). "Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals". Water Research. 37 (6): 1213–1222. Bibcode:2003WatRe..37.1213H. doi:10.1016/S0043-1354(02)00378-0. PMID 12598185.

[pmid15276617-59] [59]
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". The Journal of Steroid Biochemistry and Molecular Biology. 91 (3): 99–109. doi:10.1016/j.jsbmb.2004.03.118. PMID 15276617. S2CID 54320898.

[Cronin2004-60] [60]
Tong W, Fang H, Hong H, Xie Q, Perkins R, Sheehan DM (10 May 2004). "Receptor-mediated toxicity: QSARs for estrogen receptor binding and priority setting of potential estrogenic endocrine disruptors". In Cronin MT (ed.). Predicting Chemical Toxicity and Fate. CRC Press. pp. 285–. ISBN 978-0-203-64262-7.

[pmid17884132-61] [61]
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): 1889–1897. Bibcode:2008Chmsp..70.1889L. doi:10.1016/j.chemosphere.2007.07.071. PMID 17884132.

[pmid20738246-62] [62]
Lóránd T, Vigh E, Garai J (2010). "Hormonal action of plant derived and anthropogenic non-steroidal estrogenic compounds: phytoestrogens and xenoestrogens". Current Medicinal Chemistry. 17 (30): 3542–3574. doi:10.2174/092986710792927813. PMID 20738246.

[pmid21195753-63] [63]
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". Toxicology Letters. 201 (2): 152–175. doi:10.1016/j.toxlet.2010.12.020. PMID 21195753.

[pmid29632997-64] [64]
Borgert CJ, Matthews JC, Baker SP (May 2018). "Human-relevant potency threshold (HRPT) for ERα agonism". Archives of Toxicology. 92 (5): 1685–1702. doi:10.1007/s00204-018-2186-z. PMC 5962616. PMID 29632997.

[1]

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[3]

[4]

[5]

[6]

[7]

[8]

[9]

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[14]

[15]

[16]

[17]

[18]

[19]

[20]

[21]

[22]

[23]

[24]

[25]

[26]

[27]

[28]

[29]

[30]

[31]

[32]

[33]

[34]

[35]

[36]

[37]

[38]

[39]

[40]

[41]

[42]

[43]

[44]

[45]

[46]

[47]

[48]

[49]

[50]

[51]

[52]

[53]

[54]

[55]

[56]

[57]

[58]

[59]

[60]

[61]

[62]

[63]

[64]

Template:Affinities_of_estrogen_receptor_ligands_for_the_ERα_and_ERβ

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

See also

References

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