16α-LE2

16α-LE2
Identifiers
  • 3,17β-Dihydroxy-16α,21-epoxy-19-nor-17α-pregna-1,3,5(10)-trien-21-one
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC20H24O4
Molar mass328.408 g·mol−1
3D model (JSmol)
  • O=C1O[C@@]2([H])[C@]([C@@]3(C)CC[C@]4([H])C5=CC=C(C=C5CC[C@@]4([H])[C@]3([H])C2)O)(C1)O
  • InChI=InChI=1S/C20H24O4/c1-19-7-6-14-13-5-3-12(21)8-11(13)2-4-15(14)16(19)9-17-20(19,23)10-18(22)24-17/h3,5,8,14-17,21,23H,2,4,6-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20+/m1/s1
  • Key:NLUGVTJBNRSIKH-UQZPWQSVSA-N

16α-LE2, or 16α-lactone-estradiol, also known as 3,17β-dihydroxy-19-nor-17α-pregna-1,3,5-(10)-triene-21,16α-lactone, is a synthetic, steroidal estrogen featuring an estradiol core. It is a highly potent and selective agonist of the ERα that is used in scientific research to study the function of the ERα.[1][2] It has 265-fold higher potency in transactivation assays of the ERα relative to the ERβ and 70-fold preference in binding affinity for the ERα over the ERβ.[2]

In rodents, 16α-LE2 has no effect on ovarian follicle development, whereas the highly ERβ-selective agonist 8β-VE2 stimulates follicular growth and to a comparable extent as estradiol, 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]

See also

References

  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.
  2. ^ a b c d 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.
  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.
  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.
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