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林产化学与工业 ›› 2016, Vol. 36 ›› Issue (3): 81-87.doi: 10.3969/j.issn.0253-2417.2016.03.012

• 研究报告 • 上一篇    下一篇

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

殷彬1, 徐武双1, 解静聪1, 张瑜1, 刘庆波2, 龙剑英2, 费宝丽1   

  1. 1. 南京林业大学化学工程学院, 江苏 南京 210037;
    2. 南京林业大学理学院, 江苏 南京 210037
  • 收稿日期:2015-06-23 出版日期:2016-06-25 发布日期:2016-07-07
  • 通讯作者: 费宝丽(1971-),女,黑龙江齐齐哈尔人,副教授,博士,主要从事功能配合物和林产配位化学的研究;E-mail:baolifei@yahoo.com。 E-mail:baolifei@yahoo.com
  • 作者简介:殷彬(1992-),男,安徽池州人,硕士生,从事功能配合物和林产配位化学的研究;E-mail:1282341685@qq.com
  • 基金资助:
    南京大学配位化学国家重点实验室开放基金(无编号);江苏省高校自然科学研究面上项目(13KJB220006);江苏省普通高校研究生科研创新计划(CXLX13_517)

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

YIN Bin1, XU Wu-shuang1, XIE Jing-cong1, ZHANG Yu1, LIU Qing-bo2, LONG Jian-ying2, FEI Bao-li1   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    2. College of Science, Nanjing Forestry University, Nanjing 210037, China
  • Received:2015-06-23 Online:2016-06-25 Published:2016-07-07

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12,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12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12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。

关键词: 脱氢枞酸, 脱氢枞胺, 苯并咪唑, 希夫碱, 酰腙, DNA

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.

Key words: dehydroabietic acid, dehydroabietylamine, benzimidazole, schiff base, hydrazone, DNA

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