title: Toxicity of substituted anilines to Pseudokirchneriella subcapitata and quantitative structure-activity relationship analysis for polar narcotics.
abstract: This study evaluated the toxic effects of substituted anilines on Pseudokirchneriella subcapitata with the use of a closed algal toxicity testing technique with no headspace. Two response endpoints (i.e., dissolved oxygen production [DO] and algal growth rate) were used to evaluate the toxicity of anilines. Both DO and growth rate endpoints revealed similar sensitivity to the effects of anilines. However, trichloroanilines showed stronger inhibitory effects on microalgal photosynthetic reactions than that on algal growth. For various aquatic organisms, the relative sensitivity relationship for anilines is Daphnia magna > luminescent bacteria (Microtox) > or = Pocelia reticulata > or = Pseudokirchneriella subcapitata > or = fathead minnow > Tetrahymena pyriformis. The susceptibility of P. subcapitata to anilines is similar to fish, but P. subcapitata is apparently less sensitive than the water flea. The lack of correlation between the toxicity revealed by different aquatic organisms (microalgae, D. magna, luminescent bacteria, and P. reticulata) suggests that anilines might have different metabolic routes in these organisms. Both hydrogen bonding donor capacity (the lowest unoccupied molecular orbital energy, Elumo) and hydrophobicity (1-octanol:water partition coefficient, Kow) were found to provide satisfactory descriptions for the toxicity of polar narcotics (substituted anilines and chlorophenols). Quantitative structure-activity relationships (QSARs) based on Elumo, log Kow, or both values were established with r2 values varying from 0.75 to 0.92. The predictive power for the QSAR models were found to be satisfactory through leave-one-out cross-validation. Such relationships could provide useful information for the estimation of toxicity for other polar narcotic compounds.
authors.affiliation: Institute of Environmental Engineering, National Chiao Tung University 75, Po-Ai Street, Hsinchu, Taiwan 300, Republic of China. cychen1@cc.nctu.edu.tw
authors.forename: Chung-Yuan
authors.initials: CY
authors.lastname: Chen
authors.forename: Chia-Wen
authors.initials: CW
authors.lastname: Ko
authors.forename: Po-I
authors.initials: PI
authors.lastname: Lee
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry / Q000633:toxicity*; D000818:Animals; D056890:Eukaryota / Q000187:drug effects* / Q000254:growth & development / Q000502:physiology; D009294:Narcotics / Q000737:chemistry / Q000633:toxicity*; D010100:Oxygen / Q000378:metabolism; D010788:Photosynthesis; D021281:Quantitative Structure-Activity Relationship; D013045:Species Specificity
chemical_list: D000814:Aniline Compounds; D009294:Narcotics; D010100:Oxygen; C023650:aniline