Alan G. MacDiarmid Institute, College of Chemistry, Jilin University, Changchun 130012, China.
Int J Environ Res Public Health. 2020 Jul 23;17(15):5299. doi: 10.3390/ijerph17155299.
A phthalic acid ester's (PAEs) comprehensive biodegradability three-dimensional structure-activity relationship (3D-QSAR) model was established, to design environmentally friendly PAE derivatives, which could be simultaneously degraded by plasticizer-degrading bacteria, such as , , and . Only three derivatives of diethyl phthalate (DEP (DEP-27, DEP-28 and DEP-29)) were suited for their functionality and environmental friendliness, which had an improved stability in the environment and improved the characteristics (bio-toxicity, bioaccumulation, persistence, and long-range migration) of the persistent organic pollutants (POPs). The simulation inference of the microbial degradation path before and after DEP modification and the calculation of the reaction energy barrier exhibited the energy barrier for degradation being reduced after DEP modification and was consistent with the increased ratio of comprehensive biodegradability. This confirmed the effectiveness of the comparative molecular similarity index analysis (CoMSIA) model of the PAE's comprehensive biodegradability. In addition, a molecular dynamics simulation revealed that the binding of the DEP-29 derivative with the three plasticizer-degradation enzymes increased significantly. DEP-29 could be used as a methyl phthalate derivative that synergistically degrades with microplastics, providing directional selection and theoretical designing for plasticizer replacement.
建立了邻苯二甲酸酯（PAEs）的综合生物降解性三维结构-活性关系（3D-QSAR）模型，以设计同时可被增塑剂降解菌如 、 、 等降解的环保型 PAE 衍生物。只有邻苯二甲酸二乙酯（DEP）的三个衍生物（DEP-27、DEP-28 和 DEP-29）适合其功能和环境友好性，在环境中具有更高的稳定性，并改善了持久性有机污染物（POPs）的特性（生物毒性、生物蓄积性、持久性和长距离迁移性）。DEP 修饰前后微生物降解途径的模拟推断和反应能垒的计算表明，DEP 修饰后降解的能垒降低，与综合生物降解性的增加比例一致，这证实了 PAE 综合生物降解性的比较分子相似性指数分析（CoMSIA）模型的有效性。此外，分子动力学模拟表明，DEP-29 衍生物与三种增塑剂降解酶的结合显著增加。DEP-29 可用作与微塑料协同降解的邻苯二甲酸二甲酯衍生物，为增塑剂替代提供了定向选择和理论设计。
