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

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

研究论文

基于萘酰亚胺的次氯酸荧光探针的合成及细胞成像性能研究

  • 王欣宇 ,
  • 戚少龙 ,
  • 杜建时 ,
  • 李强 ,
  • 祝录宝 ,

  • 薛龙启     ,
  • 赵晴 ,
  • 杨清彪 ,
  • 李耀先 ,
  • 丛宪玲
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  • a 吉林大学中日联谊医院 长春 130033
    b 吉林大学化学学院 长春 130061
    c 吉林大学中日联谊医院 吉林省淋巴外科重点实验室 吉林省淋巴外科工程实验室 长春 130033
    d 吉林大学中日联谊医院 吉林省记忆与认知障碍疾病工程实验室 长春 130031
* Corresponding authors. E-mail: ;
† 共同第一作者(These authors contributed equally to this work).

收稿日期: 2020-08-06

  修回日期: 2020-09-01

  网络出版日期: 2020-09-22

基金资助

吉林省重点实验室建设项目(20190901002JC); 吉林省自然科学基金(20200201169JC); 吉林省创新能力建设(2019C007)

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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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摘要

以萘酰亚胺结构为荧光发色团, 设计开发了一种含C=C双键的、具有分子内电荷转移(ICT)效应的新型水溶性优化的次氯酸荧光探针3-(2-氰基丙烯酸乙酯基)-4-羟基-N-正丙基-1,8-萘酰亚胺(NAEC). 添加次氯酸后, 探针分子NAEC中的C=C双键被氧化, 生成醛基, 探针NAEC原有的ICT效应被破坏, 产生荧光信号. 经核磁、质谱、荧光发射光谱和UV-Vis吸收光谱对其结构和检测性能进行了研究. 结果表明, 在pH=7.4的N,N-二甲基甲酰胺(DMF)/磷酸缓冲盐溶液(PBS) (V∶V=1∶19)缓冲体系中, 探针NAEC可在10 s内完成对次氯酸的检测, 荧光分析检测限为2.4 nmol/L, 斯托克斯位移为100 nm; 探针NAEC显示出较强的抗干扰性, 能在其他活性氧、小分子生物硫醇及常见阴离子等22种干扰物存在下完成次氯酸的专一检测. 同时, 该探针分子的膜透性与生物相容性良好, 具备较好的活体内源性ClO–荧光成像能力, 在生物检测及环境监控等领域具有良好的应用前景.

关键词： 萘酰亚胺; 次氯酸; 荧光探针; 细胞成像

本文引用格式

王欣宇 , 戚少龙 , 杜建时 , 李强 , 祝录宝 ,
薛龙启 , 赵晴 , 杨清彪 , 李耀先 , 丛宪玲 . 基于萘酰亚胺的次氯酸荧光探针的合成及细胞成像性能研究[J]. 有机化学, 2021 , 41(2) : 719 -725 . DOI: 10.6023/cjoc202008005

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

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