Quantitative structure-toxicity relationships for halogenated substituted-benzenes to Vibrio fischeri, using atom-based semi-empirical molecular-orbital descriptors.
Chemosphere
; 38(14): 3357-82, 1999 Jun.
Article
em En
| MEDLINE
| ID: mdl-10390847
ABSTRACT
Quantitative structure-toxicity relationships (QSTR's) are derived for an extensive series of halogenated benzenes, anilines, phenols, nitrobenzenes, toluenes and other substituted benzenes against Vibrio fischeri using a wide range of whole molecule and atom-based descriptors derived from semi-empirical molecular-orbital calculations. In terms of direct statistical correlation with toxicity it was found that the molar refractivity was the most important parameter, closely followed by the solvent accessible surface area of the compound. The accuracy of these descriptors in fitting the numerous fluoro- and chloro-mono-aromatic compounds was compared with bromine and iodine analogues, where the 'best' descriptors for the former were found in general to be less accurate for the latter in the case of multi-halogen substitution. The equations obtained were also used to classify the compounds into narcosis-based mechanisms of toxicity and those with respiratory uncoupling potential. A combination of the molar refractivity and the nucleophilic susceptibility of one of the meta ring carbons predicted the toxicity of the halo-benzenes and toluenes, along with anisoles, benzonitriles, nitrobenzenes and most of the anilines. The relevance of these descriptors to developing coherent and more generally applicable models for QSTR's of mono-aromatic compounds to other species in environmental toxicology is discussed.
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Base de dados:
MEDLINE
Assunto principal:
Vibrio
/
Derivados de Benzeno
/
Testes de Toxicidade
/
Hidrocarbonetos Halogenados
Tipo de estudo:
Prognostic_studies
Idioma:
En
Revista:
Chemosphere
Ano de publicação:
1999
Tipo de documento:
Article
País de afiliação:
Reino Unido