Activity, toxicity, molecular docking, and environmental effects of three imidazolinone herbicides enantiomers.
Activity, toxicity, molecular docking, and environmental effects of three imidazolinone herbicides enantiomers.
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DOI：
10.1016/j.scitotenv.2017.11.333
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发表时间：
2018-05
期刊：
影响因子：
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通讯作者：
Jingqian Xie;Lu Zhao;Kai Liu;Fangjie Guo;Lidi Gao;Weiping Liu
中科院分区：
文献类型：
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作者：
Jingqian Xie;Lu Zhao;Kai Liu;Fangjie Guo;Lidi Gao;Weiping Liu
所有咪唑啉酮（IMI）除草剂都是手性的，由两个对映体组成；然而，对它们相互作用的对映选择性的研究是有限的。本研究对IMI除草剂的对映体和外消旋物进行了系统的评估，包括半制备和绝对构型的测定，对靶生物的立体选择性生物活性（Echinochloa - crusu -galliand microcystisaeruginosa），以及对密歇根癌症基金会-7 （MCF-7）细胞的毒性。r -咪唑啉酮在抑制靶生物方面比ans - imis更有活性，而且这两种对映体都没有雌激素活性。此外，还研究了分子结构与IMI除草剂对目标生长抑制效果的关系。分子模拟为IMIs乙酰羟基酸合酶活性的对映选择性提供了合理的结构依据。这些发现鼓励应用对映异构物- imi除草剂，以利用其优于外消旋物的优势。
All imidazolinone (IMI) herbicides are chiral consisting of two enantiomers; however, studies on the enantioselectivities of their interactions are limited. This study is a systematic assessment of the enantiomers and racemates of IMI herbicides, including semi-preparation and determination of absolute configurations, stereoselective bioactivity toward target organisms (Echinochloa crus-galliandMicrocystisaeruginosa), and toxicity toward Michigan Cancer Foundation-7 (MCF-7) cells.R-imidazolinones were found to be more active thanS-IMIs in the inhibition of target organisms, and neither enantiomer had estrogenic activity. Moreover, the relationship between the molecular structures and the efficiency of target growth inhibition by the IMI herbicides was investigated. Molecular modeling provided the rational structural basis for the enantioselectivity of the acetohydroxyacid synthase (AHAS) activity of the IMIs. These findings encourage the application of enantiopureR-IMI herbicides to capitalize on their advantages over the racemates.