FLUORINATED ANDROGENS AND PROGESTINS - MOLECULAR PROBES FOR ANDROGEN AND PROGESTERONE RECEPTORS WITH POTENTIAL USE IN POSITRON EMISSION TOMOGRAPHY

  • 1 September 1987
    • journal article
    • research article
    • Vol. 32  (3) , 391-403
Abstract
In order to develop imaging agents for receptor-positive tumors of the breast and prostate, we have investigated the binding affinity of several fluorine-substituted steroids in the testosterone and nortestosterone series for the androgen receptor and the progesterone receptor. The 6.alpha.- and 11.beta.-fluoro-, and 16.alpha.-fluoroalkyl-substituted steroids were prepared by an olefin bromofluorination reaction followed by dehydrobromination or reductive debromination. The 17.alpha.-fluoromethyl derivatives were prepared by fluoride ion attack on the 17-spiroepoxide or 17-spiro sulfate and the 17.alpha.-fluoropropynyl derivative, by reaction of a propargyl alcohol precursor with diethylaminosulfur trifluoride. Of the compounds synthesized, 17.alpha.-(3-fluoro-1-propynyl)nortestosterone was found to possess the highest binding affinity and selectivity for the progesterone receptor, and 11.beta.-fluoronordihydrotestosterone had the greatest affinity for the androgen receptor. Both receptor systems seem to tolerate reasonably well the substitution of fluorine for hydrogen.

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