(R,R)-Tetrahydrochrysene

(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]

(R,R)-Tetrahydrochrysene
Identifiers
IUPAC name
  • (5R,11R)-5,11-Diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC22H24O2
Molar mass320.432 g·mol−1
3D model (JSmol)
SMILES
  • CCC1CC2=C(C=CC(=C2)O)C3=C1C4=C(CC3CC)C=C(C=C4)O
InChI
  • 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

(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]

See also

References
  1. Ying Chen (2008). The Role of Steroids in the Regulation of Oocyte Cyst Breakdown and Primordial Follicle Assembly in the Neonatal Mouse Ovary. pp. 101–. ISBN 978-0-549-74620-1.
  2. 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.
  3. 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.


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