Relationships of the molecular structure of aldosterone derivatives with their binding affinity for mineralocorticoid receptor

M Yamakawa, K Ezumi, M Shiro, H Nakai, S Kamata, T Matsui and N Haga

The molecular structures of 19-nor-11-deoxycorticosterone (III) and 21- hydroxypregna-4,11-diene-3,20-dione (IV) were determined by X-ray crystallographic analysis and the factors affecting the binding affinities for the mineralocorticoid receptor were examined with six aldosterone derivatives (I-VI) containing these two compounds. The most important factor was found to be the steric one; affinity increased with increasing flatness of the structure. The electronic factor may be a minor influence although a good relationship was found between the affinity and the 13C-NMR chemical shift of the C(5) atom. The factor playing no role in the binding is the hydrophobic one.

Volume 30, Issue 6, pp. 585-589, 12/01/1986
Copyright © 1986 by American Society for Pharmacology and Experimental Therapeutics

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