广西师范大学学报（自然科学版） ›› 2014, Vol. 32 ›› Issue (3): 65-73.

• • 上一篇    下一篇

邻香草醛缩胡椒乙胺席夫碱锌(Ⅱ)配合物的研究

霍红月1,2, 李仲庆1,2, 覃其品1,2, 刘延成1,2, 陈振锋1,2   

  1. 1.广西师范大学化学与药学学院,广西桂林541004;
    2.广西师范大学药用资源化学与药物分子工程国家重点实验室培育基地,广西桂林541004
  • 收稿日期:2014-05-16 出版日期:2014-09-25 发布日期:2018-09-25
  • 通讯作者: 刘延成(1977—),男,河北文安人,广西师范大学副教授,博士;ycliugxnu@aliyun.com
  • 基金资助:
    国家自然科学基金资助项目(21271051,21261025);广西自然科学基金资助项目(2013GXNSFAA019044);药用资源化学与药物分子工程教育部重点实验室基金项目(CMEMR2012-A11,CMEMR2013-C05)

Crystal Structure and Antitumor Activity of Zinc(Ⅱ) Complex with Schiff Bases Derived from 2-Hydroxy-3-methoxybenzaldehyde and 2-(3,4-Methylenedioxyphenyl) ethylamine

HUO Hong-yue1,2, LI Zhong-qing1,2, QIN Qi-pin1,2, LIU Yan-cheng1,2, CHEN Zhen-feng1,2   

  1. 1.College of Chemistry and Pharmaceutical Sciences,Guangxi Normal University, Guilin Guangxi 541004, China;
    2.State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin Guangxi 541004, China
  • Received:2014-05-16 Online:2014-09-25 Published:2018-09-25

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摘要： 本文以邻香草醛缩胡椒乙胺席夫碱(L)为配体,合成一种新的席夫碱-锌(Ⅱ)双核配合物[Zn2(L)2Cl2](1),并通过谱学分析及X射线单晶衍射分析对配合物1进行结构表征,通过MTT法测试配合物1及L对6种人肿瘤细胞株和人正常肝细胞株HL-7702的体外增殖抑制活性。结果显示,配合物1对所有肿瘤株的增殖抑制率均高于配体,但低于顺铂;对HL-7702,其细胞毒性也远低于顺铂,且略低于配体,表现出一定的细胞毒性选择性。在分子水平上,通过荧光光谱法和凝胶电泳实验研究配合物1及L与DNA的作用机制。结果显示,配合物1以经典插入方式与DNA结合,而L对DNA的插入作用弱,表明柔性配体L与锌(Ⅱ)配位后,芳香平面结构刚性增强,使配合物1对DNA插入作用增强,从而能够通过阻碍肿瘤细胞DNA复制而表现显著高于L的抗肿瘤活性。

关键词: 席夫碱, 锌(Ⅱ)配合物, 晶体结构, 抗肿瘤活性, DNA结合

Abstract: 2-(3,4-Methylenedioxyphenyl)ethylamine and 2-hydroxy-3-methoxybenzaldehyde were selected to synthesize a new Schiff base (L) as bioactive ligand. The reaction of L with ZnCl2·2H2O afforded the binuclear zinc(Ⅱ) complex (1), which was structurally characterized by IR, elemental analysis, ESI-MS, and single crystal X-ray diffraction analysis. The in vitro cytotoxicity of 1against six human tumor cell lines (A549, MDA-MB-231, HeLa229, MGC80-3, A375, BEL-7404) and HL-7702 normal liver cell line was screened by MTT assay. The growth inhibition ratios of 1were found to be higher than those of L against all the tumor cell lines, but lower than those of cisplatin. However, the cytotoxicity of 1against HL-7702 was much lower than those of cisplatin, suggesting the cytotoxic selectivity of 1. On the molecular level, the DNA binding property of 1as well as L was studied by fluorescence spectroscopy and gel electrophoresis assay. The results indicated that complex 1intercalatively bound with DNA, while the intercalative binding ability of L was very weak. It may be ascribed to the much more rigid aromatic planar structure of 1than L, which will facilitate the intercalative binding of 1with DNA to effectively block the DNA replications in tumor cells, and higher antitumor activity of 1can be obtained than L.

Key words: Schiff base, zinc(Ⅱ) complex, crystal structure, antitumor activity, DNA binding

中图分类号: 

  • O641.4
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