83274-63-9Relevant academic research and scientific papers
Novel estradiol derivatives labeled with Ru, W, and Co complexes. Influence on hormone-receptor affinity of several organometallic groups at the 17α position
Top, Siden,El Hafa, Hassane,Vessieres, Anne,Huche, Michel,Vaissermann, Jacqueline,Jaouen, Gerard
, p. 5241 - 5249 (2002)
In order to elucidate the extent to which recognition of the estrogen receptor is influenced by addition of an organometallic substituent at the 17α position, modification of 17β-estradiol at this position was carried out by using the organometallic groups -C≡C-(η5-C5H4)RuCp, CH2-(η5-C5H4)RuCp, -C≡C-(η5-C5H4)- W(CO)3(Me), -(C≡CCHO)Co2(CO)6, and -(C≡CCH2OH)Co2(CO)6. The relative binding affinity (RBA) values for estradiol receptor alpha showed that recognition was good (RBA between 20 and 13.5%) when the organometallic moiety was attached at the end of a rigid alkyne spacer. However, the affinity of the modified hormone for the receptor was severely reduced. (RBA = 1 %) for a substituent such as -CH2-(η5-C5H4)- RuCp, in which the spacer is reduced to a single flexible sp3 carbon atom, allowing the organometallic moiety greater freedom of movement around the attachment point. The RBA values found were in agreement with results obtained from a molecular-modeling study in which 5, an organometallic hormone with a rigid spacer, or 7, a molecule with a flexible spacer, was inserted into the cavity of the recently characterized Ligand-Binding Domain of estrogen receptor alpha.
