高等学校化学学报

高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (02): 292.doi: 10.3969/j.issn.0251-0790.2012.02.014

• 有机化学 • 上一篇    下一篇

紫精与八元瓜环的超分子组装及光切割质粒DNA

张同艳1, 孙世国1, 彭孝军1, 陶彬彬2   

  1. 1. 大连理工大学精细化工国家重点实验室, 大连 116024;
    2. 浙江闰土股份有限公司, 上虞 312368
  • 收稿日期:2011-03-10 出版日期:2012-02-10 发布日期:2012-01-13
  • 通讯作者: 孙世国, 男, 博士, 副教授, 主要从事功能染料分子及其光电化学研究. E-mail: shiguo@dlut.edu.cn 彭孝军, 男, 博士, 教授, 博士生导师, 主要从事功能性染料及其工业应用研究. E-mail: pengxj@dlut.edu.cn E-mail:shiguo@dlut.edu.cn;pengxj@dlut.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 21072024, 20872012)资助.

Supramolecular Self-assembly Between Viologen and Cucurbit[8]uril and Its Application for the DNA Photocleavage

ZHANG Tong-Yan1, SUN Shi-Guo1, PENG Xiao-Jun1, TAO Bin-Bin2   

  1. 1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China;
    2. Zhejiang Runtu Co. Ltd., Shangyu 312368, China
  • Received:2011-03-10 Online:2012-02-10 Published:2012-01-13

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被引次数

10

摘要： 利用紫精可以活化水中溶解氧的特性, 设计合成了苯-紫精化合物(BEV). 利用紫外吸收、电化学及核磁等方法研究了BEV与八元瓜环CB[8] 之间的相互作用. 实验结果表明, 2种化合物可以进行主客体超分子自组装形成1∶ 1的二元包合物BEV-CB[8]. 同时, 分别考察了化合物BEV和BEV-CB[8]与小牛胸腺DNA的相互作用, 并采用琼脂糖凝胶电泳研究了氙灯光照下化合物对pBR322 DNA的切割能力. 结果表明, CB[8]的引入改变了化合物BEV与DNA的作用方式, 使嵌入作用和静电作用增强. 光照结果说明只有超分子BEV-CB[8]在光照下可以完全切割质粒DNA, 即CB[8]的存在明显提高了BEV对质粒DNA的切割效率.

关键词: 八元瓜环, 紫精, 超分子组装, 光切割DNA

Abstract: Combining supramolecular chemistry with biochemistry was a new research direction. In this paper, self-assembly between a host compound CB[8] with a guest molecule benzyl viologen(BEV) was examined by UV absorption measurement, cyclic voltammetric method and 1H NMR technique. The experimental results revealed that CB[8] included benzyl and part of pyridinum of BEV to form binary compounds BEV-CB[8], and when BEV2+ was reduced to BEV+·, a new stable ternary complex (BEV+·)2/CB[8] would be formed. The two kinds of viologens, BEV and BEV-CB[8], were used for DNA photocleavage stu-dies in physiological environment following the research results that CB[8] could enhance the interaction between BEV and CT DNA with intercalation and electrostatic interaction. Only 50 μmol/L of the complex BEV-CB[8] could cleave SC pBR 322 DNA completely compared with BEV, which showed no ability for DNA clea-vage under the irradiation of Xe lamp. The main reason was that BEV2+ was reduced to BEV+· under irradiation and CB[8] bound BEV+· tightly to form (BEV+·)2/CB[8], which prolonged the lifetime of viologen radical BEV+·, causing the dissolved oxygen in water activation and the reactive oxygen species, · OH and O2-·, could cleave SC pBR 322 DNA. The results indicate an important application by host molecule CB in supramolecular chemistry, which gives an obviously evidence for the field of DNA cleavage.

Key words: Cucurbit[8]uril, Viologen, Supramolecular self-assembly, DNA photocleavage

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