Document Detail

The importance of hydrophobicity and electrophilicity descriptors in mechanistically-based QSARs for toxicological endpoints.
MedLine Citation:
PMID:  12074385     Owner:  NLM     Status:  MEDLINE    
Quantitative structure-activity relationship (QSAR) analysis of four toxicological data sets is described. The toxicological data include three data sets retrieved from the literature (the toxic and metabolic effects of 23 aliphatic alcohols on the perfused rat liver; the toxicity of 21 pyridines to mice; the lethality of 55 halogenated hydrocarbons to the mould Aspergillus nidulans). In addition, the toxicity of 13 mono- and di-substituted nitrobenzenes in a 15 min assay using the alga Chlorella vulgaris was analysed. QSARs were developed successfully using descriptors to describe uptake in the organism (i.e. hydrophobicity as quantified by the logarithm of the octanol-water partition coefficient, log P) and reactivity at the site of action (i.e. electrophilicity as quantified by the energy of the lowest unoccupied molecular orbital, E(LUMO)). A further parameter describing molecular branching as also required to model the data for the aliphatic alcohols. The results demonstrate that mechanistically based QSARs can be developed for these diverse endpoints which are, in terms of statistical quality as good as, if not better, than QSARs based on less mechanistically interpretable descriptors.
M T D Cronin; J C Dearden; J C Duffy; R Edwards; N Manga; A P Worth; A D P Worgan
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  SAR and QSAR in environmental research     Volume:  13     ISSN:  1062-936X     ISO Abbreviation:  SAR QSAR Environ Res     Publication Date:  2002 Mar 
Date Detail:
Created Date:  2002-06-20     Completed Date:  2002-10-16     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  9440156     Medline TA:  SAR QSAR Environ Res     Country:  England    
Other Details:
Languages:  eng     Pagination:  167-76     Citation Subset:  IM    
School of Pharmacy and Chemistry, Liverpool John Moores University, UK.
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MeSH Terms
Hydrocarbons, Halogenated / toxicity*
Models, Chemical*
Nitrobenzenes / toxicity*
Pyridines / toxicity*
Structure-Activity Relationship
Toxicity Tests
Reg. No./Substance:
0/Hydrocarbons, Halogenated; 0/Nitrobenzenes; 0/Pyridines

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