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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 2: 719 - 725

DOI: https://doi.org/10.6023/cjoc202008005

Article

A Naphthalimide-Based Hypochlorous Acid-Selective Fluorescent Probe and Its Application in Cell Imaging

  • Xinyu Wang ,
  • Shaolong Qi ,
  • Jianshi Du ,
  • Qiang Li ,
  • Lubao Zhu ,
  • Longqi Xue ,
  • Qing Zhao ,
  • Qingbiao Yang ,
  • Yaoxian Li ,
  • Xianling Cong
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  • a China-Japan Union Hospital of Jilin University, Changchun 130061
    b College of Chemistry, Jilin University, Changchun 130061
    c Key Laboratory of Lymphatic Surgery Jilin Province, Engineering Laboratory of Lymphatic Surgery Jilin Province, China-Japan Union Hospital of Jilin University, Changchun 130031
    d Engineering Laboratory of Memory and Cognitive Impairment Disease Jilin Province, China-Japan Union Hospital of Jilin University, Changchun 130031

Received date: 2020-08-06

  Revised date: 2020-09-01

  Online published: 2020-09-22

Supported by

the Key Laboratory Construction Project of Jilin Province(20190901002JC); the Natural Science Foundation of Jilin Province(20200201169JC); the Innovation Building Projects of Jilin Province(2019C007)

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Abstract

A novel naphthalimide-based fluorescence probe ethyl (E)-3-(2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo- [de]isoquinolin-5-yl)-2-cyanoacrylate (NAEC) containing C=C double bond group with intramolecular charge transfer (ICT) effect for hypochloric acid detection was synthesized, which could selectively and sensitively respond to hypochloric acid within 10 s in phosphate buffer saline (PBS) buffer solution [N,N-dimethylformamide (DMF)/PBS (V∶V=1∶19), pH=7.4]. The mechanism is that the C=C double bond in the probe can be oxidized and turned to aldehyde group, then the original ICT effect of probe is destroyed, and the fluorescence of naphthalimide restores. The spectroscopic properties of the probe NAEC towards ClO– were studied through UV-vis absorption and ?uorescence emission spectroscopies. The results showed that the probe NAEC possessed a large pseudo Stokes shift (100 nm) and the limit of detection (LOD) for NAEC has been estimated to be 2.4 nmol/L. In addition, the probe exhibited good response and anti-interference performance for hypochloric acid in the presence of 22 kinds of interferences, such as other reactive oxygen, small molecule biosulphol and common anions. And probe NAEC exhibited good cell permeability and was successfully applied in living cells by fluorescence imaging. The method is expected to be extended to the diagnosis of diseases and the detection in environmental samples, etc.

Key words： naphthalimide; hypochlorous acid; fluorescence probe; cellular imaging

Cite this article

Xinyu Wang , Shaolong Qi , Jianshi Du , Qiang Li , Lubao Zhu , Longqi Xue , Qing Zhao , Qingbiao Yang , Yaoxian Li , Xianling Cong . A Naphthalimide-Based Hypochlorous Acid-Selective Fluorescent Probe and Its Application in Cell Imaging[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 719 -725 . DOI: 10.6023/cjoc202008005

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