• DOI:10.1039/c8ob00677f
• Corpus ID: 4728907

Design and synthesis of novel monoterpenoid indole alkaloid-like analogues and their antitumour activities in vitro.

@article{Fang2018DesignAS,
  title={Design and synthesis of novel monoterpenoid indole alkaloid-like analogues and their antitumour activities in vitro.},
  author={Jia-qi Fang and Tao Huang and Meng-yuan Xia and Lu-lu Deng and Xiaojiang Hao and Yuehu Wang and Shu-zhen Mu},
  journal={Organic \& biomolecular chemistry},
  year={2018},
  volume={16 16},
  pages={
          3026-3037
        }
}

• Jia-qi Fang, Tao Huang, +4 authors S. Mu
• Published 25 April 2018
• Chemistry, Biology
• Organic & biomolecular chemistry

A biomimetic synthetic strategy and combinatorial chemistry were used to synthesize 34 novel monoterpenoid indole alkaloid (MIA) analogues, and their cytotoxic activities against five cancer cell lines (SW-480, A-549, HL-60, SMMC-7721, and MCF-7) were determined using the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) assay. Fourteen of these analogues (7, 16-18, and 23-32) showed significantly greater inhibition of tumour cell proliferation than cisplatin. Compounds 17 and 18 showed the highest cytotoxic activity against the HL-60 cell line with IC50 values of 0.90 μM and 0.43 μM, respectively. Compound 18 slightly induced apoptosis and arrested the cell cycle in SW-480, A-549, HL-60, SMMC-7721, and MCF-7 cells. Analysis of the primary structure-activity relationships reveals that the introduction of different substituent groups at the C-3, C-5, and C-6 positions of the indole moiety and the C-10 position of the genipin moiety might have an effect on the antitumour activity of the resulting compounds.