Enantioselective in vitro metabolism of the herbicide diclofop-methyl: Prediction of toxicokinetic parameters and reaction phenotyping

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Autor(es): dc.contributorUniversidade de São Paulo (USP)-
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.creatorBarbetta, Maike Felipe Santos-
Autor(es): dc.creatorPerovani, Icaro Salgado-
Autor(es): dc.creatorDuarte, Leandro Oka-
Autor(es): dc.creatorde Oliveira, Anderson Rodrigo Moraes-
Data de aceite: dc.date.accessioned2025-08-21T20:00:07Z-
Data de disponibilização: dc.date.available2025-08-21T20:00:07Z-
Data de envio: dc.date.issued2025-04-29-
Data de envio: dc.date.issued2023-10-24-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1016/j.jpba.2023.115639-
Fonte completa do material: dc.identifierhttps://hdl.handle.net/11449/297362-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/297362-
Descrição: dc.descriptionHuman exposure to contaminants of emerging concern, like pesticides, has increased in the past decades. Diclofop-methyl (DFM) is a chiral herbicide that is employed as a racemic mixture (rac-DFM) in soybean and other crops against wild oats. Studies have shown that DFM has enantioselective action (higher for R-DFM), degradation (faster for S-DFM), and metabolism, producing diclofop (DF) which is also a pesticide. Although toxic effects have been reported for DFM, information regarding how DFM affects humans is lacking, especially when its chirality is concerned. In this study, the in vitro metabolism of rac-DFM and its isolated enantiomers was assessed by using a human model based on human liver microsomes. The kinetic model and parameters were obtained, and the hepatic clearance (CLH) and hepatic extraction ratio (EH) were estimated. Enzyme phenotyping was carried out by employing carboxylesterase isoforms (CES 1 and CES 2). DFM was metabolized through positive homotropic cooperativity with slight preference for (−)-DFM metabolism to (−)-DF. CLH and EH were above 19.60 mL min−1 kg−1 and 98 % for all the monitored reactions, respectively, and CES 1 was the main enzyme underlying the metabolism. These findings point out that liver contributes to DFM metabolism, which is fast, resulting in nearly complete conversion to DF after exposition to DFM.-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionDepartamento de Química Faculdade de Filosofia Ciências e Letras de Ribeirão Preto Universidade de São Paulo, SP-
Descrição: dc.descriptionNational Institute for Alternative Technologies of Detection Toxicological Evaluation and Removal of Micropollutants and Radioactives (INCT–DATREM) Unesp Institute of Chemistry, P.O. Box 355, SP-
Descrição: dc.descriptionNational Institute for Alternative Technologies of Detection Toxicological Evaluation and Removal of Micropollutants and Radioactives (INCT–DATREM) Unesp Institute of Chemistry, P.O. Box 355, SP-
Descrição: dc.descriptionFAPESP: 2014/50945-4-
Descrição: dc.descriptionFAPESP: 2018/07534-4-
Descrição: dc.descriptionFAPESP: 2021/10098-4-
Idioma: dc.languageen-
Relação: dc.relationJournal of Pharmaceutical and Biomedical Analysis-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectChiral analysis-
Palavras-chave: dc.subjectin vitro metabolism-
Palavras-chave: dc.subjectin vitro-in vivo extrapolation-
Palavras-chave: dc.subjectPesticide-
Título: dc.titleEnantioselective in vitro metabolism of the herbicide diclofop-methyl: Prediction of toxicokinetic parameters and reaction phenotyping-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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