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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Zhao Xiaolong , Li Na , Liu Fayu , Gao Chao , Feng Jiubiao , Liu Leping , Guan Xiaolin , Yan Na . Synthesis and Application of Water-Soluble Reaction-Based Boron-Dipyrromethene (BODIPY) Probes for Fluorescent Detection of Peroxynitrite with High Selectivity[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4339 -4343 . DOI: 10.6023/cjoc202007022

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