影像科学与光化学 ›› 2017, Vol. 35 ›› Issue (4): 546-551.DOI: 10.7517/j.issn.1674-0475.2017.04.016

• 论文 • 上一篇    下一篇

基于新型不对称BODIPY的GSH荧光探针

费强, 安建才, 赵春常   

  1. 华东理工大学 化学与分子工程学院 精细化工研究所, 上海 200237
  • 收稿日期:2017-05-26 修回日期:2017-06-05 出版日期:2017-07-15 发布日期:2017-07-15
  • 通讯作者: 赵春常
  • 基金资助:

    国家自然科学基金项目(21372083,21672062)资助

A BODIPY-based Fluorescent Probe for Selective Detection of GSH

FEI Qiang, AN Jiancai, ZHAO Chunchang   

  1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. China
  • Received:2017-05-26 Revised:2017-06-05 Online:2017-07-15 Published:2017-07-15

摘要:

本文通过在BODIPY母体中引入丙二腈,设计合成了一个新型不对称BODIPY荧光染料CN-B-Cl。由于丙二腈强吸电作用,荧光染料CN-B-Cl具有优异的化学活性,能够与含巯基的化合物在buffer体系中迅速发生芳香亲核取代反应;与GSH反应生成硫取代BODIPY,而与Cys/Hcy反应生成氮取代BODIPY。根据不同取代基BODIPY化合物发光性能的不同,该荧光探针可选择性区分GSH与Cys/Hcy。

关键词: BODIPY, 芳香亲核取代, 荧光探针, GSH

Abstract:

Here, a BODIPY-based dye was constructed by appending malononitrile, an electron acceptor, to the BODIPY core via a vinylene bridge. The designed BODIPY proceeded aromatic nucleophilic substitution (SNAr) toward sulfhydryl-containing nucleophiles in buffer systems. Experimental data demonstrated that the reactions between CN-B-Cl and thiol-containing amino acids (GSH, Cys/Hcy) produced different BODIPYs with distinct fluorescent signals, thus allowing CN-B-Cl for discriminating GSH from Cys/Hcy.

Key words: BODIPY, aromatic nucleophilic substitution, fluorescent probe, GSH