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大黄酸膦酸酯衍生物作为抗肿瘤药物的合成、细胞毒性、DNA结合及凋亡作用

Synthesis, cytotoxicity, DNA binding and apoptosis of rhein-phosphonate derivatives as antitumor agents.

作者信息

Ye Man-Yi, Yao Gui-Yang, Wei Jing-Chen, Pan Ying-Ming, Liao Zhi-Xin, Wang Heng-Shan

机构信息

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.

出版信息

Int J Mol Sci. 2013 Apr 29;14(5):9424-39. doi: 10.3390/ijms14059424.

DOI:10.3390/ijms14059424
PMID:23629673
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3676791/
Abstract

Several rhein-phosphonate derivatives (5a-c) 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.

摘要

合成了几种大黄酸膦酸酯衍生物（5a - c），并评估了它们对HepG - 2、CNE、Spca - 2、Hela和Hct - 116细胞系的体外细胞毒性。一些化合物表现出相对较高的细胞毒性。特别是化合物5b对HepG - 2和Spca - 2细胞表现出最强的细胞毒性（IC50分别为8.82和9.01 µM）。所有合成的化合物对HUVEC细胞表现出低细胞毒性。进一步的实验证明5b可干扰HepG - 2细胞的细胞周期并诱导凋亡。此外，通过紫外可见光谱、荧光光谱、圆二色光谱等方法研究了模型共轭物5b与DNA的结合特性。结果表明5b与ct - DNA有中等程度的相互作用能力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b3c5/3676791/b89fa120cc9a/ijms-14-09424f6.jpg
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2
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J Med Chem. 2011 Sep 8;54(17):5955-80. doi: 10.1021/jm200587f. Epub 2011 Aug 5.
3
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4
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