Chemical compound
(R ,R )-Tetrahydrochrysene
(5R ,11R )-5,11-Diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol
CAS Number PubChem CID ChemSpider UNII ChEBI Formula C 22 H 24 O 2 Molar mass 320.432 g·mol−1 3D model (JSmol )
CCC1CC2=C(C=CC(=C2)O)C3=C1C4=C(CC3CC)C=C(C=C4)O
InChI=1S/C22H24O2/c1-3-13-9-15-11-17(23)6-8-20(15)22-14(4-2)10-16-12-18(24)5-7-19(16)21(13)22/h5-8,11-14,23-24H,3-4,9-10H2,1-2H3/t13-,14-/m1/s1
Key:MASYAWHPJCQLSW-ZIAGYGMSSA-N
(R ,R )-Tetrahydrochrysene ((R ,R )-THC ) is a drug used to study the estrogen receptors (ERs) in scientific research . It is an ERβ antagonist and an ERα agonist with 10-fold higher affinity for ERβ relative to ERα.[ 1] [ 2] (R ,R )-THC is a silent antagonist of ERβ,[ 3] and, uniquely relative to other known ERβ antagonists, a passive antagonist of the receptor.[ 2]
(S ,S )-Tetrahydrochrysene ((S ,S )-THC) also binds to the ERs, but in contrast to (R ,R )-THC, (S ,S )-THC is an agonist of both ERα and ERβ and has 20-fold lower affinity for ERβ relative to (R ,R )-THC.[ 3]
^ Ying Chen (2008). The Role of Steroids in the Regulation of Oocyte Cyst Breakdown and Primordial Follicle Assembly in the Neonatal Mouse Ovary . Syracuse University. pp. 101–. ISBN 978-0-549-74620-1 .
^ a b Shiau AK, Barstad D, Radek JT, Meyers MJ, Nettles KW, Katzenellenbogen BS, Katzenellenbogen JA, Agard DA, Greene GL (2002). "Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism". Nat. Struct. Biol . 9 (5): 359–64. doi :10.1038/nsb787 . PMID 11953755 . S2CID 452305 .
^ a b Sun J, Meyers MJ, Fink BE, Rajendran R, Katzenellenbogen JA, Katzenellenbogen BS (1999). "Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta" . Endocrinology . 140 (2): 800–4. doi :10.1210/endo.140.2.6480 . PMID 9927308 .