Abstract:
:The relative toxicity (log IGC-1(50)) of 54 selected alkanones, both aliphatic and aromatic, as well as, alkenones and alkynones was evaluated in the static Tetrahymena pyriformis population growth assay. Excess toxicity, an indicator of bioreactivity, was associated only with the alpha-beta unsaturated alkenones and alkynones. Moreover, the alkynones were found to be more toxic than corresponding alkenones. A high quality 1-octanol/water partition coefficient (log Kow) dependent structure-toxicity relationship, log IGC-1(50) = 0.86 (log Kow) - 2.27; r2 = 0.955, was developed for alkanones. This QSAR represented the nonpolar narcosis mechanism of toxic action. Toxicity of alkenones was predicted by the highest-occupied-molecular-orbital energy (HOMO), log IGC-1(50) = -3.474 (HOMO) -35.357; r2 = 0.897, and the difference between HOMO and the lowest-unoccupied-molecular-orbital energy (LUMO), log IGC-1(50) = -3.559 (HOMO-LUMO gap) - 36.106; r2 = 0.903. The alpha-beta unsaturated ketones are considered soft electrophiles. Moreover, the toxicity of the aliphatic alkanones and alkenones was predicted by log Kow and LUMO, log IGC-1(50) = 0.69 (log Kow) - 2.55 (LUMO) + 0.05; r2 = 0.852.
journal_name
SAR QSAR Environ Resjournal_title
SAR and QSAR in environmental researchauthors
Schultz TW,Sinks GD,Hunter RSdoi
10.1080/10629369508233991subject
Has Abstractpub_date
1995-01-01 00:00:00pages
27-36issue
1eissn
1062-936Xissn
1029-046Xjournal_volume
3pub_type
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