Predicting aquatic toxicity of anionic hydrocarbon and perfluorinated surfactants using membrane-water partition coefficients from coarse-grained simulations†

Anionic surfactants are widely used in commercial and industrial applications. For assessment of their environmental fate and effects, it is highly desirable to quantify the membrane-water partition/distribution coefficient (K_mw/D_mw). Here, we further develop a computational route to D_mw for anionic surfactants based on coarse-grained molecular dynamics simulations, validating it against new and existing experimental measurements. Having parameterised molecular fragments for the coarse-grained models, the simulations are used to predict D_mw for molecules where no experimental values are available. This expanded set of simulated D_mw values is then used to derive QSARs for acute toxicity of mono-constituent anionic surfactants in daphnids and fish, allowing for extrapolation to similar compounds without experimental D_mw values. For this study, we have selected hydrocarbon-based (HC) surfactants because of their widespread use, and perfluorinated (FC) surfactants as a challenging case study. Separate daphnid and fish QSARs demonstrate good fits, robustness and predictivity, and highlight differing toxicity relationships for HC and FC surfactants in daphnids. Overall, the combined use of simulated D_mw and derived QSARs is a promising approach for ecotoxicity screening of surfactants.