Imazamox (IMX), a chiral herbicide used in cereals and oilseed crops to control weeds, is commonly sold as a racemic mixture. Its enantiomers, being chiral compounds, may exhibit unique properties when exposed to chiral environments. While IMX enantiomers have been reported to degrade differently in soil and be toxic to some species, their effects on human systems remain poorly understood. This study utilized Caco‐2 (human colon adenocarcinoma cell line) cells to assess the in vitro permeability of a racemic mixture of IMX and its isolated enantiomers. Additionally, the study aimed to evaluate whether the metabolite imazamox‐O‐desmethyl (IMX‐D) forms during the permeability process. An enantioselective chromatographic method was developed, fully validated, and the apparent permeability values were obtained. The apparent permeability of rac‐IMX, (+)‐IMX, and (−)‐IMX was determined to be 4.15 × 10–5, 5.78 × 10–5, and 7.33 × 10–5 cm s–1, respectively. These findings suggest that IMX exhibits high intestinal permeability, with an enantioselective absorption for (–)‐IMX as compared to (+)‐IMX. Finally, the permeability study in Caco‐2 cells revealed that the metabolite IMX‐D was not generated.

中文翻译：

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Caco-2 细胞体外渗透性研究后农药甲氧咪草烟的对映选择性分析

甲咪草烟 (IMX) 是一种手性除草剂，用于谷物和油籽作物中控制杂草，通常作为外消旋混合物出售。其对映体是手性化合物，当暴露于手性环境时可能表现出独特的性质。据报道，IMX 对映体在土壤中会以不同方式降解，并对某些物种有毒，但它们对人体系统的影响仍知之甚少。本研究利用 Caco-2（人结肠腺癌细胞系）细胞来评估 IMX 及其分离对映体的外消旋混合物的体外渗透性。此外，该研究旨在评估代谢物 imazamox-O-desmethyl (IMX-D) 是否在渗透过程中形成。开发了一种对映选择性色谱方法，经过充分验证，并获得了表观渗透率值。表观渗透率拉克‐IMX、(+)‐IMX 和 (−)‐IMX 确定为 4.15 × 10–5, 5.78 × 10–5, 和 7.33 × 10–5厘米–1， 分别。这些发现表明，IMX 表现出高肠道渗透性，与 (+)-IMX 相比，(-)-IMX 具有对映选择性吸收。最后，Caco-2 细胞的渗透性研究表明，代谢物 IMX-D 并未生成。