Quantitative Structure-Activity Relationships of Environmental Pollutants

Hermens, Joop L. M.

doi:10.1007/978-3-540-46161-6_3

Cited by 99 publications

(83 citation statements)

References 129 publications

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“…The octanol-water partition coefficient, K ow , is the most widely used descriptor of hydrophobicity in quantitative structure-activity relationships (QSAR), which are used to describe sorption to organic matter, soil, and sediments [15], bioaccumulation [104], and toxicity [105][106][107]. Octanol is an amphiphilic bulk solvent with a molar volume of 0:12 dm 3 mol À1 when saturated with water.…”

Section: Octanolmentioning

confidence: 99%

Chemical Speciation of Organics and of Metals at Biological Interphases

Escher

Sigg

2004

Physicochemical Kinetics and Transport at Biointerfaces

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Section: Octanolmentioning

confidence: 99%

Chemical Speciation of Organics and of Metals at Biological Interphases

Escher

Sigg

2004

Physicochemical Kinetics and Transport at Biointerfaces

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“…They have been used for a number of applications, e.g. the prediction of bioaccumulation potential of chemicals in aquatic organisms (Mackay 1982), ecotoxicity thresholds or endpoints (Hermens 1989;Lipnick 1989), and for filling data gaps, or establishing priorities for testing untested chemicals to meet regulatory requirements (Lipnick 1985).…”

Section: Introductionmentioning

confidence: 99%

Comparative toxicity of four microcystins of different hydrophobicities to the protozoan,Tetrahymena pyriformis

Ward

Codd

1999

Journal of Applied Microbiology

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Microcystins (MC) are a group of over 60 cyclic heptapeptide hepatotoxins produced by cyanobacteria. The 1-octanol/water partition coefficients (log P) of MC-LR, -LY, -LW and -LF have been estimated by HPLC to be 2·16, 2·92, 3·46 and 3·56, respectively. Their in vivo toxicities to Tetrahymena pyriformis was also investigated. Twenty-four hour LC 50 values followed the order MC-LR×-LY×-LW ¼ -LF. The LC 50 values of MC-LR and -LY were significantly reduced in the presence of 1% (v/v) dimethylsulphoxide, although no significant effect occurred with MC-LW or -LF. Tetrahymena pyriformis respiration rates were inhibited by MC-LR in both a time-and dose-dependent manner. Increasing log P of the MC used caused a significantly greater inhibition of respiration. Population growth rate and maximum culture density were inhibited by all MC variants in proportion to log P. Positive correlations between all toxicological endpoints and log P occurred, with the most hydrophobic toxin, MC-LF, being 1·4 to 3·5 times more toxic than MC-LR. MC-LW had a similar toxicity to MC-LF, while MC-LY toxicity was intermediate between that of MC-LR and -LF. Implications of this positive relationship between in vivo toxicity and hydrophobicity for the toxicity of MC to aquatic organisms, and the potential for using log P as a descriptor in a quantitative structureactivity relationship for MC, are discussed.

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“…Especially important are toxicants expected to work as electrophiles which can react with nucleophilic groups such as NH2, OH, and SH in deoxyribonucleic acid (DNA) and proteins. Hermens (1989) classified the reaction mechanisms of nucleophilic groups in biological systems with electrophilic toxicants into (a) nucleophilic displacement reaction, (b) addition to carbon-oxygen double bonds, and (c) addition to activated carbon-carbon double bonds (the Michael-type addition). He also surveyed various molecular substructures present in possible toxicants where these types of reactions might be responsible for their unwanted activity (Hermens, 1990).…”

Section: Aquatic Toxicitymentioning

confidence: 99%