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Design, Synthesis, Docking Study, Α-Glucosidase Inhibition, and Cytotoxic Activities of Acridine Linked to Thioacetamides As Novel Agents in Treatment of Type 2 Diabetes Publisher Pubmed



Mohammadikhanaposhtani M1 ; Rezaei S2 ; Khalifeh R2 ; Imanparast S3 ; Faramarzi MA3 ; Bahadorikhalili S4 ; Safavi M5 ; Bandarian F6 ; Nasli Esfahani E6 ; Mahdavi M6 ; Larijani B7
Authors
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Authors Affiliations
  1. 1. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  2. 2. Department of Chemistry, Shiraz University of Technology, Shiraz, Iran
  3. 3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Iran
  4. 4. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  5. 5. Department of Biotechnology, Iranian Research Organization for Science and Technology (IROST), Tehran, Iran
  6. 6. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  7. 7. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2018


Abstract

A novel series of acridine linked to thioacetamides 9a–o were synthesized and evaluated for their α-glucosidase inhibitory and cytotoxic activities. All the synthesized compounds exhibited excellent α-glucosidase inhibitory activity in the range of IC 50 = 80.0 ± 2.0–383.1 ± 2.0 µM against yeast α-glucosidase, when compared to the standard drug acarbose (IC 50 = 750.0 ± 1.5 µM). Among the synthesized compounds, 2-((6-chloro-2-methoxyacridin-9-yl)thio)-N-(p-tolyl) acetamide 9b displayed the highest α-glucosidase inhibitory activity (IC 50 = 80.0 ± 2.0 μM). The in vitro cytotoxic assay of compounds 9a–o against MCF-7 cell line revealed that only the compounds 9d, 9c, and 9n exhibited cytotoxic activity. Cytotoxic compounds 9d, 9c, and 9n did not show cytotoxic activity against the normal human cell lines HDF. Kinetic study revealed that the most potent compound 9b is a competitive inhibitor with a K i of 85 μM. Furthermore, the interaction modes of the most potent compounds 9b and 9f with α-glucosidase were evaluated through the molecular docking studies. © 2018
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