Abstract
In this study, a chlorophenol (CP) 3D-QSAR model with a double activity (bioaccumulation and degradation) combination was established. 19 CPs were divided into a training set and test set according to the ratio of 4:1. The cross-validation coefficient (q2) and non-cross-validation coefficient (R2) of the model were 0.803 (> 0.5) and 0.925 (> 0.9), respectively, indicating a good stability and predictive ability of the 3D-QSAR. 2,4,6-trichlorophenol (2,4,6-TCP) was used as a target molecule, and 46 derivatives with low comprehensive effects were designed. Out of the 46 derivatives, 11 derivatives were screened to have the good insecticidal and preservative properties. From the perspective of the toxicity of zebrafish, 4 out of the 11 derivatives were found to have lower aquatic toxicity effects. Through the food chain simulation of cyanobacteria-daphnia-swamp-mandarin fish, it was found that the bioaccumulation effect of the four derivatives was lower than that of 2,4, 6-TCP. Finally, molecular dynamics simulation was conducted using 2-CH2NH2 substituted derivatives, and it was found that the degradation effect by laccase (white rot fungi) was significantly improved in the presence of violuric acid, hydroxybenzotriazole, and syringaldehyde. This study can provide theoretical support for the development of environment-friendly technology for emerging pollutants.
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Acknowledgements
The authors would like to thank Prof. Zhao Wenjin from Jilin University for providing the Discovery Studio 2020 software to compute the molecular docking.
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Conceptualization: Shuhai Sun, Zeyang Liu, Qing Li, Yu Li; methodology: Shuhai Sun, Zeyang Liu, Qing Li; formal analysis and investigation: Shuhai Sun, Zeyang Liu, Qing Li; writing—original draft: Shuhai Sun, Zeyang Liu, Qing Li; supervision: Yu Li; resources: Shuhai Sun, Zeyang Liu; visualization: Qing Li; validation: Yu Li; writing—review & editing: Yu Li.
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Sun, S., Liu, Z., Li, Q. et al. Molecular design of environment-friendly chlorophenol (CP) derivatives based on 3D-QSAR assisted with a comprehensive evaluation method combining bioaccumulation and degradation. Environ Sci Pollut Res 30, 83643–83656 (2023). https://doi.org/10.1007/s11356-023-28322-1
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DOI: https://doi.org/10.1007/s11356-023-28322-1