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Synthesis, in Vitro Α-Glucosidase Inhibitory Activities, and Molecular Dynamic Simulations of Novel 4-Hydroxyquinolinone-Hydrazones As Potential Antidiabetic Agents Publisher Pubmed



Shayegan N1 ; Haghipour S1 ; Tanideh N2 ; Moazzam A1 ; Mojtabavi S3 ; Faramarzi MA3 ; Irajie C4 ; Parizad S5 ; Ansari S1 ; Larijani B1 ; Hosseini S1 ; Iraji A2, 6 ; Mahdavi M1
Authors
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Authors Affiliations
  1. 1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  3. 3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, Shiraz, Iran
  5. 5. Student Research Committee, Shiraz University of Medical Sciences, Shiraz, Iran
  6. 6. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran

Source: Scientific Reports Published:2023


Abstract

In the present study, new structural variants of 4-hydroxyquinolinone-hydrazones were designed and synthesized. The structure elucidation of the synthetic derivatives 6a–o was carried out using different spectroscopic techniques including FTIR, 1H-NMR, 13C-NMR, and elemental analysis, and their α-glucosidase inhibitory activity was also determined. The synthetic molecules 6a–o exhibited good α-glucosidase inhibition with IC50 values ranging between 93.5 ± 0.6 to 575.6 ± 0.4 µM as compared to the standard acarbose (IC50 = 752.0 ± 2.0 µM). Structure–activity relationships of this series were established which is mainly based on the position and nature of the substituent on the benzylidene ring. A kinetic study of the active compounds 6l and 6m as the most potent derivatives were also carried out to confirm the mode of inhibition. The binding interactions of the most active compounds within the active site of the enzyme were determined by molecular docking and molecular dynamic simulations. © 2023, The Author(s).
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