6533b7d8fe1ef96bd126a113

RESEARCH PRODUCT

New qsar models for polyhalogenated aromatics

Tapio NevalainenErkki Kolehmainen

subject

Quantitative structure–activity relationshipComputational chemistryPolychlorinated Dibenzo-p-dioxinsChemistryStereochemistryHealth Toxicology and MutagenesisChlorine atomEnvironmental ChemistryHOMO/LUMOPolychlorinated dibenzofuransPolychlorinated diphenyl ethersBinding affinitiesElectronic properties

description

Electronic properties of polychlorinated dibenzo p dioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), polychlorinated biphenyls (PCBs), and polychlorinated diphenyl ethers (PCDEs) were calculated using the semi-empirical AM1 method The calculated electronic descriptors — the energy of the lowest unoccupied molecular orbital (ELUMO), the energy of the highest occupied molecular orbital (EHOMO), the ELUMO-EHOMO gap (dE), and molecular polarizability — are related to the Ah receptor binding affinity values of PCDDs, PCDFs, and PCBs and immunotoxicity values for PCDEs The quantitative structure activity relationships (QSARs) based on chlorine substitution patterns were also constructed, and they proved to be very predictive for Ah receptor binding Significant correlations of the electronic factors were found between the dE and Ah receptor binding affinities for PCDDs, PCDFs, and PCBs and for immunotoxicity of PCDEs A combination of descriptors ELUMO and the total number of chlorine atoms attached to a molecule (nCl) gives significant correlation for the Ah receptor binding of PCDFs and for immunotoxicity of PCDEs Hydrophobicity values taken from the literature were shown to be non-significant for toxicity prediction of these polychlorinated compounds

yearjournalcountryeditionlanguage
1994-10-01Environmental Toxicology and Chemistry
https://doi.org/10.1002/etc.5620131020