Molecular design of 1,3,5,7-TetraCN derivatives with reduced bioconcentration using 3D-QSAR modeling, full factorial design, and molecular docking

Journal of Molecular Graphics & Modelling
Yuanyuan ZhaoYu Li

Abstract

Three-dimensional quantitative structure-activity relationship (3D-QSAR) models were established for polychlorinated naphthalenes (PCNs) using the logarithms of experimental bioconcentration factors of 10 PCNs in fish as the dependent variable and their molecular structures as the independent variable. The models were used to design PCN derivatives with lower bioconcentration than the parent compounds. The contour maps from the 3D-QSAR models were used to evaluate sites and different substituents for monosubstitution. A full factorial experiment based on the target molecule (1,3,5,7-tetraCN, CN-42) was used to evaluate sites for disubstitution. The established 3D-QSAR models had good predictive abilities for the remaining 65 PCN congeners. Comparative molecular field analysis and comparative molecular similarity indices analysis models showed that PCN bioconcentration was dominated by the electrostatic field. Taking CN-42 as a template, 15 new monosubstituted compounds and 19 new disubstituted compounds with lower bioconcentration than CN-42 were designed using the 3D-QSAR model and full factorial design, respectively. Furthermore, the persistent organic pollutant properties and the practicability of these compounds were evalua...Continue Reading

Citations

Oct 31, 2019·International Journal of Environmental Research and Public Health·Meijin DuYu Li
Jan 17, 2020·Molecular Informatics·Alla P ToropovaAndrey A Toropov
May 10, 2020·International Journal of Environmental Research and Public Health·Xixi LiBing Chen
Jun 30, 2019·Environmental Science and Pollution Research International·Wenwen GuYu Li
Jun 6, 2021·Environmental Science and Pollution Research International·Xixi LiBaiyu Zhang
Jun 3, 2021·International Journal of Environmental Research and Public Health·Wei HeYu Li

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