高级检索+

脱氢枞基苯并咪唑希夫碱和酰腙衍生物与DNA作用的比较研究

Comparation Study of DNA Binding Property with Dehydrobietic Benzimidazole Schiff Base and Hydrazone Derivatives

  • 摘要: 合成了脱氢枞胺和脱氢枞酸的衍生物脱氢枞基-1-甲基苯并咪唑希夫碱( 1 )和脱氢枞基-1-甲基苯并咪唑酰腙( 2 ),并通过红外、质谱、元素分析和核磁等方法对其进行了表征。运用荧光光谱,黏度分析和图二色(CD)光谱等方法研究了化合物 1、2 和鲑鱼精DNA的相互作用,在荧光光谱中,通过在DNA-溴化乙锭(EB)体系中加入不同浓度的 1 和 2 ,随着化合物浓度的增加,DNA-EB体系的荧光强度发生了明显的猝灭效应,由此推测化合物可能与EB一样插入到了DNA的碱基对中,再根据Stern-Volmer方程分析得出,化合物 1 与DNA作用强于 2 ;黏度分析中,随着化合物 1 和 2 浓度的增加,DNA的黏度逐渐增加,且化合物 1 增加的幅度大于 2 ;CD光谱中,相同浓度的不同化合物使DNA的CD信号的改变量不同,并且化合物 1 对DNA构型的影响要强于 2 ,三者的实验结果均表明化合物以插入作用的方式与DNA作用。凝胶电泳实验表明,在抗坏血酸(Vc)存在的条件下,化合物 1 和 2 均能够对PBR322 DNA质粒进行单股切割,在Vc不存在的条件下, 1 能够对DNA质粒进行单股切割。结果表明:化合物 1 具有更强的与DNA作用的能力。

     

    Abstract: Two derivatives of dehydroabietylamine and dehydroabietic acid, i.e., dehydroabietic-1-methyl benzoimidazol Schiff base ( 1 ) and dehydroabietic-1-methyl benzoimidazol hydrazone ( 2 ) were synthesized and characterized by FT-IR, MS, elemental analysis and 1H NMR. Their interactions with salmon sperm DNA were investigated by fluorescence spectra, viscosity analysis and circular dichronism spectra. In fluorescence spectra, different concentrations of compounds 1 and 2 were added into DNA-EB system, and with the increase of concentration, the quenching effect of fluorescence intensity of DNA-EB system was obviously occurred. The results suggested that the compounds might be inserted into the base pairs of DNA, just like EB. According to Stern-Volmer equation analysis, the interaction of compound 1 and DNA was better than that of compound 2 . With the increase of concentration of compounds 1 and 2 , the viscosity of DNA increased gradually, and the increase amplitude of compound 1 was greater than that of compound 2 . CD spectra showed that the same concentration of different compounds could make different changes of the CD signal quantity of the DNA, and the influence of compound 1 on the conformation of DNA was greater than compound 2 . The three experimental results indicated that the two compounds bound to DNA by intercalation mode. The results of agarose gel electrophoresis suggested that compounds 1 and 2 could cleave PBR322 plasmid DNA by single strand in the presence of ascorbic acid. While in the absence of ascorbic acid, only compound 1 showed the same activity. All the data showed that Schiff base had stronger DNA binding ability.

     

/

返回文章
返回