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2020 , Vol. 40 >Issue 12: 4339 - 4343

DOI: https://doi.org/10.6023/cjoc202007022

研究简报

高选择性检测ONOO－的水溶性反应型氟硼二吡咯(BODIPY)荧光探针的合成与应用

  • 赵小龙 ,
  • 李娜 ,
  • 刘发玉 ,
  • 高超 ,
  • 丰久彪 ,
  • 刘乐平 ,
  • 关晓琳 ,
  • 燕娜
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  • a 西北师范大学化学化工学院 教育部生态环境相关高分子重点实验室 兰州 730070;
    b 兰州大学药学院 兰州 730000

收稿日期: 2020-07-07

  修回日期: 2020-07-29

  网络出版日期: 2020-08-11

基金资助

国家自然科学基金（Nos.21462039，21761032）资助项目.

收起

Synthesis and Application of Water-Soluble Reaction-Based Boron-Dipyrromethene (BODIPY) Probes for Fluorescent Detection of Peroxynitrite with High Selectivity

  • Zhao Xiaolong ,
  • Li Na ,
  • Liu Fayu ,
  • Gao Chao ,
  • Feng Jiubiao ,
  • Liu Leping ,
  • Guan Xiaolin ,
  • Yan Na
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  • a Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
    b School of Pharmacy, Lanzhou University, Lanzhou 730000

Received date: 2020-07-07

  Revised date: 2020-07-29

  Online published: 2020-08-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21462039, 21761032).

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摘要

开发了两种水溶性的反应型氟硼二吡咯（BODIPY）荧光探针Ac-Phe-BODIPY和Ac-BODIPY，并将其用于活性氧物种（ROS）和活性氮物种（RNS）中过氧亚硝酸盐（ONOO-）的检测，发现其具有灵敏度高、检测限低和对ONOO-的选择性好等优点.Ac-Phe-BODIPY的水解产物通过柱层析法分离得到，并用1H NMR和ESI-MS表征水解产物为BODIPY-1，证明了光致电子转移（PET）机理与密度泛函理论（DFT）的计算结果相符合.

关键词： 氟硼二吡咯(BODIPY)荧光探针; 过氧化亚硝酸盐; 水溶性; 荧光检测

本文引用格式

赵小龙 , 李娜 , 刘发玉 , 高超 , 丰久彪 , 刘乐平 , 关晓琳 , 燕娜 . 高选择性检测ONOO－的水溶性反应型氟硼二吡咯(BODIPY)荧光探针的合成与应用[J]. 有机化学, 2020 , 40(12) : 4339 -4343 . DOI: 10.6023/cjoc202007022

Abstract

Two reaction-based water-soluble boron-dipyrromethene (BODIPY) fluorescent probes, Ac-Phe-BODIPY and Ac-BODIPY, were developed for peroxynitrite (ONOO-) measurement. High sensitivity, low detection limit and excellent selectivity toward ONOO- were obtained for determining reactive oxygen species (ROS) and reactive nitrogen species (RNS). The reaction-based probe Ac-Phe-BODIPY was hydrolyzed into BODIPY-1 which was isolated by column chromatography and proved by 1H NMR and ESI-MS. The characterization results revealed the photoinduced electron transfer (PET) mechanism which was simultaneously in agreement with density functional theory (DFT) calculation.

Key words： boron-dipyrromethene (BODIPY) fluorescent probe; peroxynitrite; water-soluble; fluorescent detection

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