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Open AccessArticle

Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents

1,†, 1,†, 2, 2, 2 and 1,*
1
School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832003, China
2
Xinjiang Huashidan Pharmaceutical Research Co. Ltd., 175 He Nan East Road, Urumqi 830011, China
*
Author to whom correspondence should be addressed.
These authors contributed equally to the work.
Molecules 2019, 24(16), 2950; https://doi.org/10.3390/molecules24162950
Received: 21 July 2019 / Revised: 7 August 2019 / Accepted: 8 August 2019 / Published: 14 August 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
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Abstract

Utilizing a pharmacophore hybridization approach, we have designed and synthesized a novel series of 28 new heterobivalent β-carbolines. The in vitro cytotoxic potential of each compound was evaluated against the five cancer cell lines (LLC, BGC-823, CT-26, Bel-7402, and MCF-7) of different origin—murine and human, with the aim of determining the potency and selectivity of the compounds. Compound 8z showed antitumor activities with half-maximal inhibitory concentration (IC50) values of 9.9 ± 0.9, 8.6 ± 1.4, 6.2 ± 2.5, 9.9 ± 0.5, and 5.7 ± 1.2 µM against the tested five cancer cell lines. Moreover, the effect of compound 8z on the angiogenesis process was investigated using a chicken chorioallantoic membrane (CAM) in vivo model. At a concentration of 5 μM, compound 8z showed a positive effect on angiogenesis. The results of this study contribute to the further elucidation of the biological regulatory role of heterobivalent β-carbolines and provide helpful information on the development of vascular targeting antitumor drugs. View Full-Text
Keywords: asymmetric dimeric β-carboline; acylhydrazone group; cytotoxic; antitumor; structure–activity relationship asymmetric dimeric β-carboline; acylhydrazone group; cytotoxic; antitumor; structure–activity relationship
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Chen, X.; Guo, L.; Ma, Q.; Chen, W.; Fan, W.; Zhang, J. Design, Synthesis, and Biological Evaluation of Novel N-Acylhydrazone Bond Linked Heterobivalent β-Carbolines as Potential Anticancer Agents. Molecules 2019, 24, 2950.

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