STRUCTURAL AND ELECTRONIC-PROPERTIES OF MX COMPOUNDS RELATED TO TA100 MUTAGENICITY - A SEMIEMPIRICAL MOLECULAR-ORBITAL QSAR STUDY

The structural and electronic properties of chlorofuranones including MX and its anhydride were calculated using the semi-empirical AMI method to elucidate the key features related to the strong mutagenic activity of MX. Significant correlations were found between Ames TA100 mutagenicity and the following electronic parameters of chlorofuranones: LUMO energy (r = 0.9607, n = 17), electron affinity (r = 0.9557), LUMO electron density at the alpha-carbon (r = 0.8855) and partial charge of the alpha-carbon (r = 0.8812). Based on these results, a molecular orbital QSAR model for the mutagenic activity of 17 MX analogues is presented. The controversial role of the open-chain tautomers of MX compounds, chlorinated butenoic acids, is discussed briefly.