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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 3.0).

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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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