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Int. J. Mol. Sci. 2013, 14(5), 9424-9439; doi:10.3390/ijms14059424

Synthesis, Cytotoxicity, DNA Binding and Apoptosis of Rhein-Phosphonate Derivatives as Antitumor Agents

1,* , 3
1 State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, China 2 College of Pharmacy, Guilin Medical University, Guilin 541004, China 3 Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 31 January 2013 / Revised: 12 April 2013 / Accepted: 15 April 2013 / Published: 29 April 2013
(This article belongs to the Section Biochemistry, Molecular Biology and Biophysics)
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Several rhein-phosphonate derivatives (5ac) were synthesized and evaluated for in vitro cytotoxicity against HepG-2, CNE, Spca-2, Hela and Hct-116 cell lines. Some compounds showed relatively high cytotoxicity. Especially compounds 5b exhibited the strongest cytotoxicity against HepG-2 and Spca-2 cells (IC50 was 8.82 and 9.01 µM), respectively. All the synthesized compounds exhibited low cytotoxicity against HUVEC cells. Further experiments proved that 5b could disturb the cell cycle in HepG-2 cells and induce apoptosis. In addition, the binding properties of a model conjugate 5b to DNA were investigated by methods (UV-Vis, fluorescence, CD spectroscopy). Results indicated that 5b showed moderate ability to interact ct-DNA.
Keywords: rhein; phosphonate; synthesis; cytotoxicity; apoptosis; DNA binding rhein; phosphonate; synthesis; cytotoxicity; apoptosis; DNA binding
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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Ye, M.-Y.; Yao, G.-Y.; Wei, J.-C.; Pan, Y.-M.; Liao, Z.-X.; Wang, H.-S. Synthesis, Cytotoxicity, DNA Binding and Apoptosis of Rhein-Phosphonate Derivatives as Antitumor Agents. Int. J. Mol. Sci. 2013, 14, 9424-9439.

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