Template:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors
Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
More information Estrogen, Other names ...
| Estrogen | Other names | RBATooltip Relative binding affinity (%)a | REP (%)b | |||
|---|---|---|---|---|---|---|
| ER | ERα | ERβ | ||||
| Estradiol | E2 | 100 | 100 | 100 | ||
| Estradiol 3-sulfate | E2S; E2-3S | ? | 0.02 | 0.04 | ||
| Estradiol 3-glucuronide | E2-3G | ? | 0.02 | 0.09 | ||
| Estradiol 17β-glucuronide | E2-17G | ? | 0.002 | 0.0002 | ||
| Estradiol benzoate | EB; Estradiol 3-benzoate | 10 | 1.1 | 0.52 | ||
| Estradiol 17β-acetate | E2-17A | 31–45 | 24 | ? | ||
| Estradiol diacetate | EDA; Estradiol 3,17β-diacetate | ? | 0.79 | ? | ||
| Estradiol propionate | EP; Estradiol 17β-propionate | 19–26 | 2.6 | ? | ||
| Estradiol valerate | EV; Estradiol 17β-valerate | 2–11 | 0.04–21 | ? | ||
| Estradiol cypionate | EC; Estradiol 17β-cypionate | ?c | 4.0 | ? | ||
| Estradiol palmitate | Estradiol 17β-palmitate | 0 | ? | ? | ||
| Estradiol stearate | Estradiol 17β-stearate | 0 | ? | ? | ||
| Estrone | E1; 17-Ketoestradiol | 11 | 5.3–38 | 14 | ||
| Estrone sulfate | E1S; Estrone 3-sulfate | 2 | 0.004 | 0.002 | ||
| Estrone glucuronide | E1G; Estrone 3-glucuronide | ? | <0.001 | 0.0006 | ||
| Ethinylestradiol | EE; 17α-Ethynylestradiol | 100 | 17–150 | 129 | ||
| Mestranol | EE 3-methyl ether | 1 | 1.3–8.2 | 0.16 | ||
| Quinestrol | EE 3-cyclopentyl ether | ? | 0.37 | ? | ||
| Footnotes: a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented.[1][2] b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC50) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assays in yeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters.[3] c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure).[4] Sources: Affinities: [1][2][5][6][7] Estrogenic potencies: [8][9][10][11] Additional: [4][3][12] | ||||||
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References
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- Kuhl, Herbert; Taubert, Hans-Dieter (1987). Das Klimakterium – Pathophysiologie, Klinik, Therapie [The Climacteric – Pathophysiology, Clinic, Therapy] (in German). Stuttgart, Germany: Thieme Verlag. p. 122. ISBN 978-3137008019.
- 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.
- 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.
- Mu Y, Peng S, Zhang A, Wang L (February 2011). "Role of pocket flexibility in the modulation of estrogen receptor alpha by key residue arginine 394". Environ. Toxicol. Chem. 30 (2): 330–6. doi:10.1002/etc.389. PMID 21038436.
- Yang R, Li N, Ma M, Wang Z (November 2014). "Combined effects of estrogenic chemicals with the same mode of action using an estrogen receptor binding bioassay". Environ. Toxicol. Pharmacol. 38 (3): 829–37. doi:10.1016/j.etap.2014.10.001. PMID 25461542.
- Luo J, Lei B, Ma M, Zha J, Wang Z (July 2011). "Identification of estrogen receptor agonists in sediments from Wenyu River, Beijing, China". Water Res. 45 (13): 3908–14. doi:10.1016/j.watres.2011.04.045. PMID 21621810.
- Rutishauser BV, Pesonen M, Escher BI, Ackermann GE, Aerni HR, Suter MJ, Eggen RI (April 2004). "Comparative analysis of estrogenic activity in sewage treatment plant effluents involving three in vitro assays and chemical analysis of steroids". Environ. Toxicol. Chem. 23 (4): 857–64. doi:10.1897/03-286. PMID 15095880.
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