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Chemical compound
8β-VE2 Other names 8β-Vinylestradiol; 8β-Vinylestra-1,3,5(10)-triene-3β,17β-diol
8β-Vinylestra-1,3,5(10)-triene-3,17β-diol
CAS Number ChemSpider UNII Formula C 20 H 26 O 2 Molar mass 298.426 g·mol−1 3D model (JSmol )
C=C[C@@]12CCC3=CC(O)=CC=C3[C@@]1([H])CC[C@]4([C@@]2([H])CC[C@]4([H])O)C
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]
^ 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
ER Tooltip Estrogen receptor
Agonists
Steroidal: 2-Hydroxyestradiol
2-Hydroxyestrone
3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
3β,5α-Dihydrolevonorgestrel
3α-Hydroxytibolone
3β-Hydroxytibolone
3β-Androstanediol
4-Androstenediol
4-Androstenedione
4-Fluoroestradiol
4-Hydroxyestradiol
4-Hydroxyestrone
4-Methoxyestradiol
4-Methoxyestrone
5-Androstenediol
7-Oxo-DHEA
7α-Hydroxy-DHEA
7α-Methylestradiol
7β-Hydroxyepiandrosterone
8,9-Dehydroestradiol
8,9-Dehydroestrone
8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
11β-Methoxyestradiol
15α-Hydroxyestradiol
16-Ketoestradiol
16-Ketoestrone
16α-Fluoroestradiol
16α-Hydroxy-DHEA
16α-Hydroxyestrone
16α-Iodoestradiol
16α-LE2
16β-Hydroxyestrone
16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
17α-Estradiol (alfatradiol )
17α-Dihydroequilenin
17α-Dihydroequilin
17α-Epiestriol (16α-hydroxy-17α-estradiol)
17α-Ethynyl-3α-androstanediol
17α-Ethynyl-3β-androstanediol
17β-Dihydroequilenin
17β-Dihydroequilin
17β-Methyl-17α-dihydroequilenin
Abiraterone
Abiraterone acetate
Alestramustine
Almestrone
Anabolic steroids (e.g., testosterone and esters , methyltestosterone , metandienone (methandrostenolone) , nandrolone and esters , many others; via estrogenic metabolites)
Atrimustine
Bolandiol
Bolandiol dipropionate
Butolame
Clomestrone
Cloxestradiol
Conjugated estriol
Conjugated estrogens
Cyclodiol
Cyclotriol
DHEA
DHEA-S
ent -Estradiol
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
Epimestrol
Equilenin
Equilin
ERA-63 (ORG-37663)
Esterified estrogens
Estetrol
Estradiol
Estramustine
Estramustine phosphate
Estrapronicate
Estrazinol
Estriol
Estrofurate
Estrogenic substances
Estromustine
Estrone
Etamestrol (eptamestrol)
Ethinylandrostenediol
Ethinylestradiol
Ethinylestriol
Ethylestradiol
Etynodiol
Etynodiol diacetate
Hexolame
Hippulin
Hydroxyestrone diacetate
Lynestrenol
Lynestrenol phenylpropionate
Mestranol
Methylestradiol
Moxestrol
Mytatrienediol
Nilestriol
Norethisterone
Noretynodrel
Orestrate
Pentolame
Prodiame
Prolame
Promestriene
RU-16117
Quinestradol
Quinestrol
Tibolone
Xenoestrogens: Anise -related (e.g., anethole , anol , dianethole , dianol , photoanethole )
Chalconoids (e.g., isoliquiritigenin , phloretin , phlorizin (phloridzin) , wedelolactone )
Coumestans (e.g., coumestrol , psoralidin )
Flavonoids (incl. 7,8-DHF , 8-prenylnaringenin , apigenin , baicalein , baicalin , biochanin A , calycosin , catechin , daidzein , daidzin , ECG , EGCG , epicatechin , equol , formononetin , glabrene , glabridin , genistein , genistin , glycitein , kaempferol , liquiritigenin , mirificin , myricetin , naringenin , penduletin , pinocembrin , prunetin , puerarin , quercetin , tectoridin , tectorigenin )
Lavender oil
Lignans (e.g., enterodiol , enterolactone , nyasol (cis -hinokiresinol) )
Metalloestrogens (e.g., cadmium )
Pesticides (e.g., alternariol , dieldrin , endosulfan , fenarimol , HPTE , methiocarb , methoxychlor , triclocarban , triclosan )
Phytosteroids (e.g., digitoxin (digitalis ), diosgenin , guggulsterone )
Phytosterols (e.g., β-sitosterol , campesterol , stigmasterol )
Resorcylic acid lactones (e.g., zearalanone , α-zearalenol , β-zearalenol , zearalenone , zeranol (α-zearalanol) , taleranol (teranol, β-zearalanol) )
Steroid -like (e.g., deoxymiroestrol , miroestrol )
Stilbenoids (e.g., resveratrol , rhaponticin )
Synthetic xenoestrogens (e.g., alkylphenols , bisphenols (e.g., BPA , BPF , BPS ), DDT , parabens , PBBs , PHBA , phthalates , PCBs )
Others (e.g., agnuside , rotundifuran )
Mixed (SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown