高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (12): 2663.doi: 10.7503/cjcu20120539

• 有机化学 • 上一篇    下一篇

钌-菲罗啉卟啉的合成及与DNA的相互作用

王凯1, 林笑1, 万幸1, 贾涛2, 张秀兰1, 张珩1, 巨修练1   

  1. 1. 武汉工程大学绿色化工过程省部共建教育部重点实验室, 武汉 430074;
    2. 武汉大学药学院, 武汉 430072
  • 收稿日期:2012-06-05 出版日期:2012-12-10 发布日期:2012-11-20
  • 通讯作者: 王凯,男,博士,副教授,主要从事抗肿瘤药物研究.E-mail:gmn424@163.com E-mail:gmn424@163.com
  • 基金资助:

    国家自然科学基金(批准号: 20902071, 21002074)和武汉工程大学科学研究基金(批准号: 10122021)资助.

Synthesis of Ruthenium-phenanthroline Porphyrins Interacting with DNA

WANG Kai1, LIN Xiao1, WAN Xing1, JIA Tao2, ZHANG Xiu-Lan1, ZHANG Heng1, JU Xiu-Lian1   

  1. 1. Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430074, China;
    2. School of Pharmaceutical Sciences, Wuhan University, Wuhan 430072, China
  • Received:2012-06-05 Online:2012-12-10 Published:2012-11-20

摘要:

以5-(4-羟基苯基)-10,15,20-三苯基卟啉和钌-菲罗啉衍生物为原料, 合成了3个两亲性钌-菲罗啉卟啉化合物, 并通过核磁共振波谱、红外光谱、紫外-可见光谱、质谱和元素分析等对化合物的结构进行了确证. 采用紫外-可见光谱、 荧光发射光谱和圆二色光谱考察了目标化合物与ct-DNA的相互作用, 研究了它们与DNA的结合模式. 实验结果表明, Por1, Por2和Por3与DNA的结合常数分别为1.46×105, 2.75×105和5.69×105 L/mol. 此外, 在不同DNA浓度下, Por1和Por2与DNA的结合模式为插入模式和外部结合模式共存, Por3与DNA的结合模式主要为自堆积的外部键合和静电作用. 结果表明, 钌-菲罗啉卟啉化合物是新型的光动力治疗试剂.

关键词: 卟啉, 钌-菲罗啉卟啉, ct-DNA, 结合模式

Abstract:

Porphyrin compounds have important research value and significance in photodynamic therapy against tumor diseases. In this work, 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin and ruthenium-phenanthroline derivates as starting materials, three amphiphilic ruthenium-phenanthroline porphyrins were prepared and confirmed by 1H NMR, IR, UV-Vis, MS and elemental analysis. Through UV-visible spectro-scopy, fluorescence spectroscopy and circular dichroism, the interactions of calf thymus DNA with these porphyrins were investigated and the binding modes of them were obtained. The binding constants of Por1, Por2 and Por3 were 1.46×105, 2.75×105 and 5.69×105 L/mol, respectively. Additionally, Por1 and Por2 showed intercalative interaction and outside groove-face binding with DNA, but Por3 interacted DNA with outside sta-cking and the electrostatic modes in presence of different DNA concentrations. The research results suggest these porphyrins are promising new photodynamic therapeutic agents.

Key words: Porphyrin, Ruthenium-phenanthroline porphyrin, ct-DNA, Binding mode

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