Potential organ or tumor imaging agents. 16. Fluorinated androstanes and the prostate.
A series of substituted 5alpha-androstan-17beta-ols was synthesized and evaluated for their potential use in the development of a prostate imaging agent. The ability of the synthesized compounds to compete with [3H]-5alpha-dihydrotestosterone for rat prostate androgen receptor protein served as the screening assay. For 3-substituted derivatives, the order of binding to the androgen receptor protein was =O greater than -OH greater than H approximately or equal to F. 3beta-Fluoro-5alpha-androstan-17beta-ol was found to have approximately 5% the androgenic activity of testosterone propionate in the castrated rat. The low biological activity for the 3beta-fluoro derivatives, coupled with the synthetic obstacles associated with introducing fluorine-18, has led us to search for more suitable halo steroids as potential radiodiagnostics.
D000731:Androstanes / Q000138:chemical synthesis* / Q000378:metabolism; D000818:Animals; D001667:Binding, Competitive; D013196:Dihydrotestosterone / Q000378:metabolism; D066298:In Vitro Techniques; D008297:Male; D011467:Prostate / Q000000981:diagnostic imaging*; D011877:Radionuclide Imaging; D051381:Rats; D011944:Receptors, Androgen / Q000378:metabolism
D000731:Androstanes; D011944:Receptors, Androgen; D013196:Dihydrotestosterone