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2020 , Vol. 40 >Issue 9: 2949 - 2955

DOI: https://doi.org/10.6023/cjoc202004007

研究简报

一种检测活细胞内铜离子的“关-开”型近红外荧光探针

  • 房茹 ,
  • 丁旭 ,
  • 罗稳 ,
  • 洪琛
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  • a 河南大学 河南省天然药物与免疫工程重点实验室 河南开封 475004;
    b 河南大学淮河医院 河南开封 475000

收稿日期: 2020-04-03

  修回日期: 2020-05-27

  网络出版日期: 2020-06-28

基金资助

国家自然科学基金（No.U1704176）、河南省科技计划（No.182102310504）、开封市科技局（No.1903004）和河南大学医学院青年人才（No.2019005）资助项目.

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An “Off-On” Near-Infrared Fluorescent Probe for Cu2+ Detection in Living Cells

  • Fang Ru ,
  • Ding Xu ,
  • Luo Wen ,
  • Hong Chen
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  • a Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004;
    b Huaihe Hospital, Henan University, Kaifeng, Henan 475000

Received date: 2020-04-03

  Revised date: 2020-05-27

  Online published: 2020-06-28

Supported by

Project supported by the National Natural Science Foundation of China (No. U1704176), the Science and Technology Planning Project of Henan Province (No. 182102310504), the Science and Technology Administration of Kaifeng City (No. 1903004) and the Young Talents Program of Medical School of Henan University (No. 2019005).

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摘要

以2-[6-（N，N-二甲胺基）萘基]-7-羟基-4H-色酮为荧光报告基团，2-吡啶甲酸酯为识别基团，设计合成了一种可识别铜离子的近红外荧光探针（6），并用1H NMR、13C NMR、MS和元素分析进行了结构鉴定.该探针能够快速地与Cu2+发生特异性反应，655 nm处荧光强度明显增加，同时肉眼可见溶液颜色发生改变.在0~2.0×10-5 mol/L内，荧光强度和Cu2+浓度呈现良好的线性关系，检测限为3.2×10-8 mol/L.机制研究表明，Cu2+可使探针的酯键发生特异性断裂，生成具有强荧光的2-[6-（N，N-二甲胺基）萘基]-7-羟基-4H-色酮（5）.此外，该探针可用于活细胞中铜离子荧光成像.

关键词： 黄酮; 铜离子; 近红外; 荧光探针

本文引用格式

房茹 , 丁旭 , 罗稳 , 洪琛 . 一种检测活细胞内铜离子的“关-开”型近红外荧光探针[J]. 有机化学, 2020 , 40(9) : 2949 -2955 . DOI: 10.6023/cjoc202004007

Abstract

A near-infrared fluorescent probe (6) was designed and synthesized by using 2-(6-(dimethylamino)naphthalen-2-yl)-7-hydroxy-4H-chromen-4-one as report group and 2-picolinate as recognition group. The probe was identified by 1H NMR, 13C NMR, MS and elemental analysis. The probe could react specifically with Cu2+ and its fluorescence intensity increased obviously at 655 nm, at the meantime, the color change of the solution can be seen by naked eyes. A linear relationship was obtained between the fluorescence intensity and concentration of Cu2+ in the range of 0~2.0×10-5 mol/L, and the detection limit was 3.2×10-8 mol/L. The mechanism study showed that Cu2+ catalyzed the cleavage of the ester bond and strongly fluorescent 2-[6-(N,N-dimethylamino)naphthyl]-7-hydroxy-4H-chromen-4-one (5) was generated. In addition, the probe 6 could be used for fluorescence imaging of Cu2+ in living cells.

Key words： flavone; copper ion; near-infrared; fluorescent probe

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