New QSAR models for polyhalogenated aromatics
- Univ. of Jyvaeskylae (Finland). Dept. of Chemistry
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 AM 1 method. The calculated electronic descriptions--the energy of the lowest unoccupied molecular orbital (E[sub LUMO]), the energy of the highest occupied molecular orbital (E[sub HOMO]), the E[sub LUMO]-E[sub HOMO] 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 E[sub LUMO] and the total number of chlorine atoms attached to a molecule (n[sub 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.
- OSTI ID:
- 6868232
- Journal Information:
- Environmental Toxicology and Chemistry; (United States), Vol. 13:10; ISSN 0730-7268
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
DIOXIN
STRUCTURE-ACTIVITY RELATIONSHIPS
POLYCHLORINATED BIPHENYLS
BIOLOGICAL EFFECTS
FORECASTING
MATHEMATICAL MODELS
AROMATICS
CHLORINATED AROMATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
560300* - Chemicals Metabolism & Toxicology