Binding of some dioxins and dibenzofurans to the Ah receptor. A QSAR model based on comparative molecular field analysis (CoMFA)

Abstract

Based on comparative molecular field analysis (CoMFA), a quantitative structure-activity relationship, model for the cytosolic aryl hydrocarbon (Ah) receptor binding affinity of 50 chlorinated dibenzo- para-dioxin and dibenzofuran analogues is presented. The electronic structures of these compounds were calculated using the semiempirical AM1 method. Their extreme stabilities were rationalized using the frontier molecular orbital theory. The results indicate that their binding affinity was mainly influenced by steric and electrostatic interactions, whereas charge-transfer and hydrogen bonding mechanisms are probably of minor importance.