Quantitative structure-activity analyses of nitrobenzene toxicity to Tetrahymena pyriformis. 1998

M T Cronin, and B W Gregory, and T W Schultz
School of Pharmacy and Chemistry, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, England. m.t.cronin@livjm.ac.uk

Toxicity data for the 50% growth inhibitory concentration against Tetrahymena pyriformis (log (IGC50-1)) for 42 alkyl- and halogen-substituted nitro- and dinitrobenzenes were obtained experimentally. Log (IGC50-1) along with the hydrophobicity, the logarithm of the 1-octanol/water partition coefficient (log Kow), and the molecular orbital properties, the lowest unoccupied molecular orbital energy (Elumo) and maximum acceptor superdelocalizability (Amax), were used to develop quantitative structure-activity relationships (QSARs). All the nitroaromatic compounds tested had toxicity in excess of baseline, nonpolar narcosis. The nitrobenzenes were thought to elicit their toxic response through multiple (and mixed) mechanisms. No high-quality relationship was observed between toxicity and hydrophobicity, or Elumo, individually. However, a strong relationship ¿log (IGC50-1) = 16.4(Amax) - 4.64; n = 42, r2 = 0.847, s = 0.279, F = 229¿ was obtained. In an effort to improve predictability, two-parameter QSAR, or response surface, analyses were performed. These analyses resulted in the following QSARs: ¿log (IGC50-1) = 0.206(log Kow) - 16.0(Amax) - 5.04; n = 42, r2 = 0.897, s = 0.229, F = 180¿ and ¿log (IGC50-1) = 0.467(log Kow) - 1.60(Elumo) - 2.55; n = 42, r2 = 0.881, s = 0.246, F = 154¿.

UI MeSH Term Description Entries
D008956 Models, Chemical Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment. Chemical Models,Chemical Model,Model, Chemical
D009578 Nitrobenzenes BENZENE derivatives carrying nitro group substituents.
D004785 Environmental Pollutants Substances or energies, for example heat or light, which when introduced into the air, water, or land threaten life or health of individuals or ECOSYSTEMS. Environmental Pollutant,Pollutant,Pollutants,Pollutants, Environmental,Pollutant, Environmental
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013769 Tetrahymena pyriformis A species of ciliate protozoa used extensively in genetic research. Tetrahymena pyriformi,pyriformi, Tetrahymena

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