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Synthesis and antitumor properties of novel curcumin analogs

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Abstract

A series of novel curcumin (CC) analogs were synthesized by reacting substituted aldehydes with intermediates 4a and 4b. The inhibitory activities of these CC analogs were investigated on human cancer cells PC3, Bcap-37, and MGC-803 in vitro by MTT assay. The results showed that most of the title compounds displayed moderate to high levels of antitumor activities. Compound 5f, the most active CC analogs, has the IC50 values of 1.34 ± 0.28, 3.90 ± 0.36, and 0.86 ± 0.44 μM against the three human cancer cells assayed, respectively. Furthermore, subsequent fluorescence staining and flow cytometry analysis indicated compound 5f could induce apoptosis in PC3, Bcap-37, and MGC-803 cells, and the apoptosis ratio reachs the peak (27.1 %) in MGC-803 cells at 24 h after treatment at 10 μM.

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Abbreviations

ADM:

Adriamycin

AO/EB:

Acridine orange/ethidium bromide

CC:

Curcumin

13C NMR:

13C nuclear magnetic resonance

DMSO:

Dimethyl sulfoxide

FCM:

Flow cytometry

HCPT:

10-Hydroxyl camptothecine

1H NMR:

Proton nuclear magnetic resonance

IR:

Infra-red

MTT:

3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

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Acknowledgments

The authors wish to thank the Guizhou Province Production Technology & Innovation Capacity Building for Fine Fruits (No. 20104009) and the Science and Technology Major Specialized Projects for “Significant New Drugs Creation” of the 12th 5-year Plan (2012ZX09101231-004) for the financial support.

Conflict of interest

None.

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Authors and Affiliations

  1. Guizhou Fruit Institute, Guizhou Academy of Agricultural Sciences, Guiyang, 550006, People’s Republic of China

    Hui Luo

  2. Research Institute of Traditional Chinese Medicine, Yangtze River Pharmaceutical Group Co., Ltd, Taizhou, 225321, People’s Republic of China

    Shengjie Yang

  3. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, 550025, People’s Republic of China

    Hui Luo, Shengjie Yang, Qi Zhao & Hongmei Xiang

  4. Ctr for R&D of Fine Chemicals, Guizhou University, Huaxi St, Guiyang, 550025, People’s Republic of China

    Hui Luo, Shengjie Yang, Qi Zhao & Hongmei Xiang

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  1. Hui Luo
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  2. Shengjie Yang
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  3. Qi Zhao
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  4. Hongmei Xiang
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Corresponding author

Correspondence to Hui Luo.

Additional information

Hui Luo and Shengjie Yang have contributed equally to this study.

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Luo, H., Yang, S., Zhao, Q. et al. Synthesis and antitumor properties of novel curcumin analogs. Med Chem Res 23, 2584–2595 (2014). https://doi.org/10.1007/s00044-013-0854-3

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  • DOI: https://doi.org/10.1007/s00044-013-0854-3

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