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J Pharm Pharmacol ; 72(10): 1412-1426, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-32639035

RESUMO

OBJECTIVES: This study was done to synthesize a novel Zn(II)-gallic acid complex with improved antidiabetic and antioxidative properties. METHODS: The complex was synthesized and characterized using Fourier Transform Infrared (FT-IR) and 1 H NMR. Cytotoxicity was evaluated using Chang liver cells and L6 myotubes. Radical scavenging and Fe3+ -reducing, as well as α-glucosidase, α-amylase and glycation inhibitory properties were measured. Glucose uptake was measured in L6 myotubes, while the complex was docked against glucose transporter type 4 (GLUT-4) and protein kinase B (PKB). KEY FINDINGS: Analysis showed that complexation occurred through a Zn(O4 ) coordination; thus, the complex acquired two moieties of gallic acid, which suggests why complexation increased the DPPH (IC50  = 48.2 µm) and ABTS (IC50  = 12.7 µm) scavenging and α-glucosidase inhibitory (IC50  = 58.5 µm) properties of gallic acid by several folds (5.5, 3.6 and 2.7 folds; IC50  = 8.79, 3.51 and 21.5 µm, respectively). Zn(II) conferred a potent dose-dependent glucose uptake activity (EC50  = 9.17 µm) on gallic acid, without reducing the viability of L6 myotubes and hepatocytes. Docking analysis showed the complex had stronger interaction with insulin signalling proteins (GLUT-4 and PKB) than its precursor. CONCLUSIONS: Data suggest that complexation of Zn(II) with gallic acid resulted in a complex with improved and multi-facet antioxidative and glycaemic control properties.


Assuntos
Antioxidantes/síntese química , Ácido Gálico/síntese química , Hipoglicemiantes/síntese química , Zinco/química , Antioxidantes/farmacologia , Linhagem Celular , Avaliação Pré-Clínica de Medicamentos/métodos , Ácido Gálico/farmacologia , Hepatócitos/efeitos dos fármacos , Hepatócitos/metabolismo , Humanos , Hipoglicemiantes/farmacologia , Estrutura Secundária de Proteína , Estrutura Terciária de Proteína , Espectroscopia de Infravermelho com Transformada de Fourier/métodos , Zinco/farmacologia
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