Synthesis and receptor-binding examination of 16-hydroxymethyl-3,17-estradiol stereoisomers.
The four 16-hydroxymethylestra-1,3,5(10)-triene-3,17-diol isomers were synthesized and tested in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities are lower than 2.0% relative to that of the reference molecule estra-1,3,5(10)-triene-3,17beta-diol. The affinities of the tested compounds for the androgen and progesterone receptors are very low (K(i)> 100 microm and 1 microM, respectively). The prepared 16-hydroxymethylestra-1,3,5(10)-triene-3,17-diol isomers are therefore estrogen receptor-selective molecules.
Tapolcsányi
Pál
P
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Wölfling
János
J
Falkay
George
G
Márki
Arpád
A
Minorics
Renáta
R
Schneider
Gyula
G
D000818:Animals; D004958:Estradiol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism*; D005260:Female; D008297:Male; D011817:Rabbits; D011869:Radioligand Assay; D051381:Rats; D011944:Receptors, Androgen / Q000378:metabolism; D011960:Receptors, Estrogen / Q000378:metabolism*; D011980:Receptors, Progesterone / Q000378:metabolism; D013237:Stereoisomerism
C464426:16-hydroxymethylestra-1,3,5(10)-triene-3,17-diol; D011944:Receptors, Androgen; D011960:Receptors, Estrogen; D011980:Receptors, Progesterone; D004958:Estradiol