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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\u20102 (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\u2010O\u2010desmethyl (IMX\u2010D) forms during the permeability process. An enantioselective chromatographic method was developed, fully validated, and the apparent permeability values were obtained. The apparent permeability of <jats:italic>rac<\/jats:italic>\u2010IMX, (+)\u2010IMX, and (\u2212)\u2010IMX was determined to be 4.15\u00a0\u00d7\u00a010<jats:sup>\u20135<\/jats:sup>, 5.78\u00a0\u00d7\u00a010<jats:sup>\u20135<\/jats:sup>, and 7.33\u00a0\u00d7\u00a010<jats:sup>\u20135\u00a0<\/jats:sup>cm s<jats:sup>\u20131<\/jats:sup>, respectively. These findings suggest that IMX exhibits high intestinal permeability, with an enantioselective absorption for (\u2013)\u2010IMX as compared to (+)\u2010IMX. Finally, the permeability study in Caco\u20102 cells revealed that the metabolite IMX\u2010D was not generated.<\/jats:p>","DOI":"10.1002\/elps.202300193","type":"journal-article","created":{"date-parts":[[2024,3,8]],"date-time":"2024-03-08T05:46:43Z","timestamp":1709876803000},"page":"1033-1040","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Enantioselective analysis of the pesticide imazamox after in vitro permeability study in Caco\u20102 cells"],"prefix":"10.1002","volume":"45","author":[{"given":"Carolina Oliveira","family":"Serpellone","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Faculdade de Filosofia Ci\u00eancias e Letras de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  Ribeir\u00e3o Preto Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maike Felipe Santos","family":"Barbetta","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Faculdade de Filosofia Ci\u00eancias e Letras de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  Ribeir\u00e3o Preto Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Icaro Salgado","family":"Perovani","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Faculdade de Filosofia Ci\u00eancias e Letras de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  Ribeir\u00e3o Preto Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Giulia","family":"Ballestero","sequence":"additional","affiliation":[{"name":"Laboratory of Research Development and Innovation ELEVE Science  Ribeir\u00e3o Preto S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nayara Cristina Perez","family":"de Albuquerque","sequence":"additional","affiliation":[{"name":"Laboratory of Research Development and Innovation ELEVE Science  Ribeir\u00e3o Preto S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5305-8957","authenticated-orcid":false,"given":"Anderson Rodrigo Moraes","family":"de Oliveira","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Faculdade de Filosofia Ci\u00eancias e Letras de Ribeir\u00e3o Preto Universidade de S\u00e3o Paulo  Ribeir\u00e3o Preto Brazil"},{"name":"National Institute for Alternative Technologies of Detection Toxicological Evaluation and Removal of Micropollutants and Radioactives (INCT\u2010DATREM), Unesp Institute of Chemistry  Araraquara S\u00e3o Paulo Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,3,8]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijerph18031112"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1080\/10937404.2012.632358"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00401-019-02033-9"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/em.22355"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2020.142630"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fct.2019.04.009"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx500481n"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2017.08.011"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b01139"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tiv.2020.104887"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1012102522787"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants9080981"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.2903\/j.efsa.2016.4432"},{"key":"e_1_2_9_15_1","unstructured":"EPA U.Imazamox technical. 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