Journal of Guangxi Normal University(Natural Science Edition) ›› 2014, Vol. 32 ›› Issue (3): 65-73.

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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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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

CLC Number: 

  • O641.4
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