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Synthesis, Cytotoxicity, DNA Binding, and Apoptosis of Alizarin 2-O-Side-Chain Derivatives

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Chemistry of Natural Compounds Aims and scope

Eleven new 2-O-side-chain derivatives of alizarin were synthesized via esterification, substitution, hydrolysis, or elimination reactions. The structures of all the products were confirmed by 1H NMR, MS, and elemental analysis. Compared with alizarin, most of the derivatives had significantly higher DNA binding affinity based on interaction with ct-DNA. In particular, compound 8 exhibited the best cytotoxicity against HeLa cells with IC50 20 μM and could induce HeLa cells apoptosis.

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Acknowledgment

This study was supported by the 973 project (No. 2011CB512005, 2012CB723501), the National Natural Science Foundation of China (No. 81260472, 21101035), the Guangxi Natural Science Foundation of China (2011GXNSFD018010 and No. 2010GXNSFF013001), the Bagui Scholar project, and the Foundation of Ministry of Education Innovation Team (No. IRT1225).

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Authors and Affiliations

  1. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Pharmaceutical Science of Guangxi Normal University, 541004, Guilin, P. R. China

    Guiyang Yao, Manyi Ye, Weilong Dai, Yingming Pan & Hengshan Wang

  2. Youjiang Medical University for Nationalities, 533000, Baise, P. R. China

    Xilin Ouyang

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  1. Guiyang Yao
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  2. Manyi Ye
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  3. Weilong Dai
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  4. Yingming Pan
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  5. Xilin Ouyang
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  6. Hengshan Wang
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Corresponding authors

Correspondence to Yingming Pan or Hengshan Wang.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2014, pp. 215–218.

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Yao, G., Ye, M., Dai, W. et al. Synthesis, Cytotoxicity, DNA Binding, and Apoptosis of Alizarin 2-O-Side-Chain Derivatives. Chem Nat Compd 50, 242–246 (2014). https://doi.org/10.1007/s10600-014-0922-z

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  • DOI: https://doi.org/10.1007/s10600-014-0922-z

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