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Madrigal-Angulo, José Luis; Ménez-Guerrero, Carlos; Estrada-Soto, Samuel; Ramírez-Espinosa, Juan José; Almanza-Pérez, Julio César; León-Rivera, Ismael; Hernández-Núñez, Emanuel; Aguirre-Vidal, Yoshajandith; Flores-León, Carlos D.; Aguayo-Ortíz, Rodrigo; Navarrete-Vazquez, Gabriel
Bioorganic & medicinal chemistry letters, 08/2022, Volume: 70Journal Article
Display omitted In current work, we prepared a series of nine 4-benzyloxy-5-benzylidene-1,3-thiazolidine-2,4-diones using a two-step pathway. Compounds 1–9 were tested in vitro using a set of three proteins recognized as important targets in diabetes and related diseases: PPARα, PPARγ, and GLUT-4. Compounds 1–3, 5, and 7 showed significant increases in the mRNA expression of PPARγ and GLUT-4, whereas compounds 1–3 did it over PPARα. Compounds 1–3 were identified as a dual PPAR α/γ modulators and were selected for evaluating the in vivo antidiabetic action at 100 mg/kg dose, being orally actives and decreasing blood glucose concentration in a hyperglycemic mice model, as well as reducing the triacylglycerides levels in normolipidemic rats. Docking and molecular dynamics studies were conducted to clarify the dual effect and binding mode of compounds 1–3 on both PPARs. Compounds 2 and 3 exhibited robust in vitro and in vivo efficacy and could be considered dual PPAR modulators with antidiabetic and antidyslipidemic effects.
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