Publication Details
Category Text Publication
Reference Category Journals
DOI 10.1002/qsar.200330816
Title (Primary) Structure-activity relationships for the toxicity of substituted poly-hydroxylated benzenes to Tetrahymena pyriformis: influence of free radical formation
Author Netzeva, T.I.; Aptula, A.O.; Chaudary, S.H.; Duffy, J.C.; Schultz, T.W.; Schüürmann, G.; Cronin, M.T.D.
Journal QSAR & Combinatorial Science
Year 2003
Department OEC; COE
Volume 22
Issue 6
Page From 575
Page To 582
Language englisch
Keywords hydroquinones; free radicals; distribution coefficient; bond dissociation energy; absolute hardness
Abstract The aim of this study was to develop quantitative structure-activity relationships for the toxicity to Tetrahymena pyriformis of 30 substituted poly-hydroxylated benzenes. Physico-chemical descriptors for the expression of free radical formation, associated with the OH moiety on the aromatic ring, were calculated. These included one-electron equilibrium constants that did and did not account for the oxidation of an OH-group, homolytic bond dissociation energy (BDE), electronegativity (EN) and absolute hardness (AH), in addition to the distribution coefficient (log D) as a measure of hydrophobicity. The reactivity descriptors were calculated using the semi-empirical AM1 Hamiltonian in the MOPAC molecular orbital software. Statistically significant two-parameter QSARs for toxicity were obtained by combination of log D with either BDE or AH. The QSARs suggested that toxicity is associated with hydrophobicity and the probability of radical formation.
Persistent UFZ Identifier https://www.ufz.de/index.php?en=20939&ufzPublicationIdentifier=5092
Netzeva, T.I., Aptula, A.O., Chaudary, S.H., Duffy, J.C., Schultz, T.W., Schüürmann, G., Cronin, M.T.D. (2003):
Structure-activity relationships for the toxicity of substituted poly-hydroxylated benzenes to Tetrahymena pyriformis: influence of free radical formation
QSAR Comb. Sci. 22 (6), 575 - 582