8β-VE2

8β-VE2
Clinical data
Other names	8β-Vinylestradiol; 8β-Vinylestra-1,3,5(10)-triene-3β,17β-diol
Identifiers
	IUPAC name 8β-Vinylestra-1,3,5(10)-triene-3,17β-diol;
CAS Number	367929-02-0 ;
ChemSpider	8007830;
UNII	D5KU4JGS7Y;
Chemical and physical data
Formula	C20H26O2
Molar mass	298.426 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C=C[C@@]12CCC3=CC(O)=CC=C3[C@@]1([H])CC[C@]4([C@@]2([H])CC[C@]4([H])O)C;
	InChI InChI=1S/C20H26O2/c1-3-20-11-8-13-12-14(21)4-5-15(13)16(20)9-10-19(2)17(20)6-7-18(19)22/h3-5,12,16-18,21-22H,1,6-11H2,2H3/t16-,17-,18+,19+,20-/m1/s1; Key:NMCRWZRLOOYKTG-SWBPCFCJSA-N;

8β-VE2, or 8β-vinylestradiol, also known as 8β-vinylestra-1,3,5(10)-triene-3β,17β-diol, is a synthetic estrogen featuring an estradiol core.^[1]^[2] It is a highly potent and selective agonist of the ERβ that is used in scientific research to study the function of the ERβ.^[1]^[2] It has 190-fold higher potency in transactivation assays of the ERβ relative to the ERα and 93- (rat) and 180-fold (human) preference in binding affinity for the ERβ over the ERα.^[2]

In rodents, 8β-VE2 stimulates follicular growth and to a comparable extent as estradiol, whereas the highly ERα-selective agonist 16α-LE2 has no effect on ovarian follicle development, indicating that the ERβ and not the ERα is involved in the effects of estrogen on ovarian follicles.^[2]^[3] In contrast, 16α-LE2 stimulates uterine weight, whereas 8β-VE2 has no effect, indicating that the ERα and not the ERβ is involved in the effects of estrogen on the uterus.^[2]

Research has determined through experimental rodent studies with estradiol, 16α-LE2, and 8β-VE2 that the positive, protective effects of estrogens on bone formation resorption and bone mineral density are mediated via the ERα, whereas the ERβ does not appear to be involved.^[4] On the other hand, while both ERα and ERβ are expressed in skeletal muscle, it was found that ERβ is the predominant ER subtype that is responsible for estrogen stimulation of skeletal muscle growth and regeneration.^[5] Moreover, similarly to testosterone, 8β-VE2 has anabolic effects in skeletal muscle and significantly increases muscle mass as well as produces muscle hypertrophy in rats.^[5] In contrast to testosterone however, 8β-VE2 shows no androgenic effects.^[5] The effects of 8β-VE2 and ERβ may be mediated, in part, by local stimulation of insulin-like growth factor 1 (IGF-1)-induced myogenic protein synthesis, as 8β-VE2 has been found to strongly induce expression of IGF-1 in the rat levator ani muscle.^[5]

References

^ ^a ^b Pakdel F, Kah O, Jégou B (31 March 2009). "Mechanisms of action of particular endocrine-disrupting chemicals". In Shaw I (ed.). Endocrine-Disrupting Chemicals in Food. Elsevier. pp. 550–. ISBN 978-1-84569-574-3.
^ ^a ^b ^c ^d ^e Hegele-Hartung C, Siebel P, Peters O, Kosemund D, Müller G, Hillisch A, et al. (April 2004). "Impact of isotype-selective estrogen receptor agonists on ovarian function". Proceedings of the National Academy of Sciences of the United States of America. 101 (14): 5129–5134. Bibcode:2004PNAS..101.5129H. doi:10.1073/pnas.0306720101. PMC 387385. PMID 15037755.
^ Binder K, Winuthayanon W, Hewitt SC, Couse JF, Korach KS (15 November 2014). "Steroid Receptors in the Uterus and Ovary". In Plant TM, Zeleznik AJ (eds.). Knobil and Neill's Physiology of Reproduction. Academic Press. pp. 1150–. ISBN 978-0-12-397769-4.
^ Hertrampf T, Schleipen B, Velders M, Laudenbach U, Fritzemeier KH, Diel P (September 2008). "Estrogen receptor subtype-specific effects on markers of bone homeostasis" (PDF). Molecular and Cellular Endocrinology. 291 (1–2): 104–108. doi:10.1016/j.mce.2008.03.003. PMID 18433985. S2CID 1774519.
^ ^a ^b ^c ^d Velders M, Schleipen B, Fritzemeier KH, Zierau O, Diel P (May 2012). "Selective estrogen receptor-β activation stimulates skeletal muscle growth and regeneration". FASEB Journal. 26 (5): 1909–1920. doi:10.1096/fj.11-194779. PMID 22278942. S2CID 39692168.

[Shaw2009-1] Pakdel F, Kah O, Jégou B (31 March 2009). "Mechanisms of action of particular endocrine-disrupting chemicals". In Shaw I (ed.). Endocrine-Disrupting Chemicals in Food. Elsevier. pp. 550–. ISBN 978-1-84569-574-3.

[pmid15037755-2] Hegele-Hartung C, Siebel P, Peters O, Kosemund D, Müller G, Hillisch A, et al. (April 2004). "Impact of isotype-selective estrogen receptor agonists on ovarian function". Proceedings of the National Academy of Sciences of the United States of America. 101 (14): 5129–5134. Bibcode:2004PNAS..101.5129H. doi:10.1073/pnas.0306720101. PMC 387385. PMID 15037755.

[PlantZeleznik2014-3] Binder K, Winuthayanon W, Hewitt SC, Couse JF, Korach KS (15 November 2014). "Steroid Receptors in the Uterus and Ovary". In Plant TM, Zeleznik AJ (eds.). Knobil and Neill's Physiology of Reproduction. Academic Press. pp. 1150–. ISBN 978-0-12-397769-4.

[pmid18433985-4] Hertrampf T, Schleipen B, Velders M, Laudenbach U, Fritzemeier KH, Diel P (September 2008). "Estrogen receptor subtype-specific effects on markers of bone homeostasis" (PDF). Molecular and Cellular Endocrinology. 291 (1–2): 104–108. doi:10.1016/j.mce.2008.03.003. PMID 18433985. S2CID 1774519.

[pmid22278942-5] Velders M, Schleipen B, Fritzemeier KH, Zierau O, Diel P (May 2012). "Selective estrogen receptor-β activation stimulates skeletal muscle growth and regeneration". FASEB Journal. 26 (5): 1909–1920. doi:10.1096/fj.11-194779. PMID 22278942. S2CID 39692168.

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See also

References