MOE Key Laboratory of Resources and Environmental Systems Optimization, North China Electric Power University, Beijing, China.
College of Environmental Science and Engineering, North China Electric Power University, Beijing, China.
J Environ Sci Health A Tox Hazard Subst Environ Eng. 2021;56(3):361-378. doi: 10.1080/10934529.2021.1881352. Epub 2021 Feb 9.
The objective of this study was to investigate 13 phthalic acid esters (PAEs) with medium or long straight-alkyl-chain, branching or unsaturated side chains, because their structural characteristics make them difficult to biodegrade or highly toxic. A biodegradability and biotoxicity multi-effect pharmacophore model was built using comprehensive evaluation method. The results suggested that introducing hydrophobic groups to the side chains of the PAEs could improve the molecules' biodegradability and biotoxicity effects simultaneously. Thus, 40 target PAE (HEHP, DNOP, DUP) derivatives were designed. Two environmentally friendly PAE derivatives (HEHP-Anthryl and HEHP-Naphthyl) were screened via the test of environmental friendliness and functionality. In addition, the biodegradation and biotoxicity of derivatives were found to have improved as a result of the change in van der Waals forces between molecules and their corresponding proteins. Moreover, the environmental safety of the screened PAE derivatives was confirmed by predicting the toxicity of their intermediates and calculating the energy barrier values for biodegradation and metabolic pathways. This study could provide theoretical guidance for the practical development of environmentally friendly plasticizer.
本研究旨在探讨 13 种具有中长直烷基链、支链或不饱和侧链的邻苯二甲酸酯（PAE），因为其结构特征使其难以生物降解或具有高毒性。采用综合评价方法构建了可生物降解性和生物毒性多效药效团模型。结果表明，在 PAE 的侧链上引入疏水性基团可以同时提高分子的可生物降解性和生物毒性效应。因此，设计了 40 种目标 PAE（HEHP、DNOP、DUP）衍生物。通过环境友好性和功能性测试筛选出两种环保型 PAE 衍生物（HEHP-蒽基和 HEHP-萘基）。此外，由于分子与其相应蛋白质之间范德华力的变化，衍生物的生物降解性和生物毒性得到了改善。此外，通过预测中间体的毒性和计算生物降解和代谢途径的能量障碍值，证实了筛选出的 PAE 衍生物的环境安全性。本研究可为环保型增塑剂的实际开发提供理论指导。
