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Title: New QSAR models for polyhalogenated aromatics

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 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.

Authors:
;  [1]
  1. Univ. of Jyvaeskylae (Finland). Dept. of Chemistry
Publication Date:
OSTI Identifier:
6868232
Resource Type:
Journal Article
Journal Name:
Environmental Toxicology and Chemistry; (United States)
Additional Journal Information:
Journal Volume: 13:10; Journal ID: ISSN 0730-7268
Country of Publication:
United States
Language:
English
Subject:
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.; 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

Citation Formats

Nevalainen, T, and Kolehmainen, E. New QSAR models for polyhalogenated aromatics. United States: N. p., 1994. Web. doi:10.1002/etc.5620131020.
Nevalainen, T, & Kolehmainen, E. New QSAR models for polyhalogenated aromatics. United States. https://doi.org/10.1002/etc.5620131020
Nevalainen, T, and Kolehmainen, E. 1994. "New QSAR models for polyhalogenated aromatics". United States. https://doi.org/10.1002/etc.5620131020.
@article{osti_6868232,
title = {New QSAR models for polyhalogenated aromatics},
author = {Nevalainen, T and Kolehmainen, E},
abstractNote = {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.},
doi = {10.1002/etc.5620131020},
url = {https://www.osti.gov/biblio/6868232}, journal = {Environmental Toxicology and Chemistry; (United States)},
issn = {0730-7268},
number = ,
volume = 13:10,
place = {United States},
year = {Sat Oct 01 00:00:00 EDT 1994},
month = {Sat Oct 01 00:00:00 EDT 1994}
}