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New qsar models for polyhalogenated aromatics
Author(s) -
Nevalainen Tapio,
Kolehmainen Erkki
Publication year - 1994
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1002/etc.5620131020
Subject(s) - homo/lumo , chemistry , quantitative structure–activity relationship , molecular descriptor , binding energy , computational chemistry , polarizability , chlorine atom , molecule , stereochemistry , organic chemistry , medicinal chemistry , physics , nuclear physics
Abstract 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 ( E LUMO ), the energy of the highest occupied molecular orbital ( E HOMO ), the E LUMO ‐ E HOMO gap (d E ), 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 d E and Ah receptor binding affinities for PCDDs, PCDFs, and PCBs and for immunotoxicity of PCDEs A combination of descriptors E LUMO and the total number of chlorine atoms attached to a molecule ( n Cl ) 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