(R,R)-Tetrahydrochrysene

(R,R)-Tetrahydrochrysene
Identifiers
IUPAC name
  • (5R,11R)-5,11-Diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol
CAS Number
PubChem CID
ChemSpider
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

(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]

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. 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. 1 2 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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