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IN VITRO
JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Assignment of anabolic-androgenic and antiandrogenic properties to some chlorine-substituted steroids on the basis of their binding characteristics to the androgen receptor of the rat seminal vesicle.
Experimental and Clinical Endocrinology 1986 July
In this study we investigated the affinity of several 4-chlorinated and 1-ene derivatives of 17 alpha-methyltestosterone (MT) and 17 alpha-methyl-5 alpha-dihydrotestosterone (MDHT) to the androgen receptor, and, additionally, the effect of a few MT-derived steroids on the activity of the 5 alpha-reductase enzyme present in the rat seminal vesicle. From our results we conclude, that delta 1 or/and delta 4 double bonds in ring A counteract the inhibition of receptor-binding caused by chlorine-substitution at C4; the dissociation of myotropic and androgenic effects [= M/A dissociation] of 4-chloro-MT (as compared to MT) is due to its inactivation by 5 alpha-reductase in androgen target organs and/or to the inhibition of the conversion of endogenous testosterone to DHT; the M/A dissociation of 1-ene-MT and 4-chloro-1-ene-MT may be explained by their inability to be activated by 5 alpha-reductase; for the same reason, M/A dissociation can be assigned to the effects of 4 alpha-chloro-1-ene-DHT. We determined the short-term and long-term competition of cyproterone acetate and chlormadinone acetate with [3H]DHT for receptor binding at 0 degrees C and showed, that the complexes formed by these antiandrogens with the androgen receptor have equally reduced stabilities compared to the DHT-receptor complex.
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