title: QSAR study of the toxicity of benzoic acids to Vibrio fischeri, Daphnia magna and carp.
abstract: The toxicities of benzoic acids to Vibrio fischeri, Daphnia magna and carp were measured. The results showed that the toxicity to V. fischeri and Daphnia decreased in the order of bromo > chloro > fluoro approximately equal to aminobenzoic acids. The toxicity of substituted benzoic acids to carp and Daphnia was much lower that to V. fischeri. The results also showed that the toxicity of benzoic acids to Daphnia decreased as the pH increased. It is suggested that ionized and non-ionized forms have different toxic responses. The non-ionized form may play an important role in toxicity because the toxicity of benzoic acids to Daphnia greatly decreases as the pH increases. The toxicity of benzoic acids to Daphnia may operate through non-polar narcosis, based on the regression results between the toxicities and partition coefficients (log P) and apparent partition coefficients (log D). However, toxicity cannot be predicted from non-polar baseline models because the ionized and non-ionized form of benzoic acids have different contributions to toxicity. Compared with the single descriptors, the prediction of toxicity of the benzoic acids was improved remarkably by using log P with pKa and log P with ELUMO. For the toxicity of benzoic acids to V. fischeri, it is suggested that the toxic mechanism may be different from the mechanism in Daphnia and carp. A probable reason is that V. fischeri is a unicellular organism with low lipid content, and hence both ionized and non-ionized forms of benzoic acids can easily cross the cell membrane and contribute to toxicity.
authors.affiliation: Department of Environmental Sciences, Northeast Normal University, Changchun, People's Republic of China.
authors.forename: Y H
authors.initials: YH
authors.lastname: Zhao
authors.forename: G D
authors.initials: GD
authors.lastname: Ji
authors.forename: M T
authors.initials: MT
authors.lastname: Cronin
authors.forename: J C
authors.initials: JC
authors.lastname: Dearden
mesh_terms: D000818:Animals; D001565:Benzoates / Q000737:chemistry / Q000493:pharmacokinetics / Q000633:toxicity*; D002347:Carps / Q000378:metabolism; D002462:Cell Membrane / Q000378:metabolism; D003621:Daphnia / Q000187:drug effects* / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D007477:Ions; D050356:Lipid Metabolism; D013045:Species Specificity; D013329:Structure-Activity Relationship; D014733:Vibrio / Q000187:drug effects* / Q000378:metabolism
chemical_list: D001565:Benzoates; D007477:Ions