(R,R)-Tetrahydrochrysene

From Wikipedia, the free encyclopedia
  (Redirected from (R,R)-tetrahydrochrysene)
Jump to: navigation, search
(R,R)-Tetrahydrochrysene
Tetrahydrochrysene.svg
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C22H24O2
Molar mass 320.42476 g/mol
3D model (JSmol)

(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[edit]

References[edit]

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