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Anti-Cancer, Anti-Oxidant and Molecular Docking Studies of Thiosemicarbazone Indole-Based Derivatives Publisher



Bakherad Z1 ; Safavi M2 ; Fassihi A1 ; Sadeghialiabadi H1 ; Bakherad M3 ; Rastegar H4 ; Ghasemi JB5 ; Sepehri S6 ; Saghaie L1 ; Mahdavi M7
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, 81746-73461, Iran
  2. 2. Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, 33535-111, Iran
  3. 3. School of Chemistry, Shahrood University of Technology, Shahrood, Iran
  4. 4. Food and Drug Control Laboratories, Food and Drug Laboratory Research Center, MOE and ME, Tehran, Iran
  5. 5. Drug Design in Silico Lab, Chemistry Faculty, School of Sciences, University of Tehran, Teheran, Iran
  6. 6. Department of Medicinal Chemistry, School of Pharmacy, Ardabil University of Medical Sciences, Ardabil, 5618953141, Iran
  7. 7. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Research Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Research on Chemical Intermediates Published:2019


Abstract

Based on the structural elements of bioactive 3-substituted indoles, a new series of indole–thiosemicarbazone hybrid derivatives were designed, synthesized, and well-characterized using different spectral techniques. The intended scaffolds were screened for their in vitro anti-proliferative activities against breast cancer (MCF-7), lung cancer (A-549), and liver cancer (Hep-G2) cell lines, as well as their anti-oxidant properties. Cytotoxicity studies revealed that compound 6n was the most potent, at least threefold more potent than the commercially available reference drug etoposide, against A-549. In addition, morphological analysis by the acridine orange/ethidium bromide double staining test and flow cytometry analysis confirmed induction of apoptosis in the A-549 cells by compound 6n. In order to validate the experimental results, molecular studies were performed to achieve the possible binding interactions of the most potent compound (6n) and colchicine with tubulin as well as ANP with ATPase domain of topoisomerase IIα active sites. Moreover, the radical scavenging potential of the final derivatives was found to be excellent with the range of 0.015–0.630 µM, comparable to the standard ascorbic acid (0.655 µM). © 2019, Springer Nature B.V.
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