Abstract
The mechanism of the interaction of the D-ring of androgens with their intracellular receptor protein has been investigated. The study is based on the relationship between the receptor binding properties of a series of steroids, their structures determined by complete geometry optimisation, and some of their spectroscopic properties. The data are compatible with the occurrence of a specific H-bond between the receptor and the 17β-hydroxyl of the steroid. It is proposed that the hydroxyl acts as an acceptor and that a receptor proton is donated to the hydroxylic oxygen of the steroid in an equatorial direction pointing towards the C-12 atom. This model also provides for androgen receptor binding of progesterone and its analogues through the π-orbital of the pregnane side-chain. The possible role of D-ring binding in assigning androgenic agonist or antagonist activity is discussed.
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