Synthesis, antioxidant and anticancer screenings of berberine–indole conjugates

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• 作者：Bhupendra Mistry ; Young-Soo Keum ; Doo Hwan Kim
• 关键词：Berberine ; Indole ; Antioxidant ; Anticancer ; Cervical cancer ; Natural product derivatives ; Alkaloids
• 刊名：Research on Chemical Intermediates
• 出版年：2016
• 出版时间：April 2016
• 年：2016
• 卷：42
• 期：4
• 页码：3241-3256
• 全文大小：500 KB
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• 作者单位：Bhupendra Mistry (1)
  Young-Soo Keum (1)
  Doo Hwan Kim (1)
  
  1. Organic Research Laboratory, Department of Bioresources and Food Sciences, College of Life and Environmental Sciences, Konkuk University, Seoul, South Korea
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Catalysis
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1568-5675

文摘

A variety of heterocyclic nitrogen cores in the form of indole moieties were linked to the natural isoquinoline alkaloid molecule berberine to achieve anticipated antioxidant and anticancer properties. An efficient synthetic pathway afforded final compounds 5a–j, which were tested in vitro for antioxidant potency using 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radical (ABTS) bioassays, and for anticancer activity using sulforhodamine B (SRB) assay against HeLa and Caski cancer cell lines. Moreover, the toxic nature of the resultant molecules was investigated using Madin–Darby canine kidney cells. The therapeutic indices of 5a–j were more appreciable against the Caski than HeLa cell line, in which compounds with electron-releasing alkyl or alkoxy functional group on indole entity as well as azaindole derivative performed well. In addition, these compounds were well endowed with antioxidant properties, in addition to the equal antioxidant effect of the compound with electron-withdrawing chlorine atom within indole entity. Adequate confirmation of the structure of the final analogues was achieved using Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), and mass spectroscopy and elemental (CHN) analysis.