Affiliation:
1. Departamento de Química Faculdade de Filosofia Ciências e Letras de Ribeirão Preto Universidade de São Paulo Ribeirão Preto Brazil
2. Laboratory of Research Development and Innovation ELEVE Science Ribeirão Preto São Paulo Brazil
3. National Institute for Alternative Technologies of Detection Toxicological Evaluation and Removal of Micropollutants and Radioactives (INCT‐DATREM), Unesp Institute of Chemistry Araraquara São Paulo Brazil
Abstract
AbstractImazamox (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.
Funder
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
Fundação de Amparo à Pesquisa do Estado de São Paulo
Conselho Nacional de Desenvolvimento Científico e Tecnológico