Calculation of Lipophilicity of Organophosphate Pesticides Using Density Functional Theory

Membranes (Basel). 2022 Jun 19;12(6):632. doi: 10.3390/membranes12060632.

Abstract

Higher lipophilicity facilitates the passage of a substance across lipid cell membranes, the blood-brain barrier and protein binding, and may also indicate its toxicity. We proposed eight methods for predicting the lipophilicity of the 22 most commonly used organophosphate pesticides. In this work, to determine the lipophilicity and thermodynamic parameters of the solvation of pesticides, we used methods of density functional theory with various basis sets, as well as modern Grimm methods. The prediction models were evaluated and compared against eight performance statistics, as well as time and RAM used in the calculation. The results show that the PBE-SVP method provided the best of the proposed predictive capabilities. In addition, this method consumes relatively less CPU and RAM resources. These methods make it possible to reliably predict the ability of pesticide molecules to penetrate cell membranes and have a negative effect on cells and the organism as a whole.

Keywords: DFT; extraction; lipophilicity; logP; membrane; organophosphate pesticides; partition coefficient; toxicity.