New QSAR models for polyhalogenated aromatics

Journal Article · Sat Oct 01 04:00:00 EDT 1994 · Environmental Toxicology and Chemistry; (United States)

DOI:https://doi.org/10.1002/etc.5620131020· OSTI ID:6868232

Nevalainen, T; Kolehmainen, E ^[1]

---

1. 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), Journal Name: Environmental Toxicology and Chemistry; (United States) Vol. 13:10; ISSN ETOCDK; ISSN 0730-7268
• Country of Publication: United States
• Language: English

Related Subjects

560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
BIOLOGICAL EFFECTS
CHLORINATED AROMATIC HYDROCARBONS
DIOXIN
FORECASTING
HALOGENATED AROMATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
MATHEMATICAL MODELS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYCHLORINATED BIPHENYLS
STRUCTURE-ACTIVITY RELATIONSHIPS