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

doi:10.6023/cjoc202004007

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2949-2955.DOI: 10.6023/cjoc202004007 Previous Articles Next Articles

一种检测活细胞内铜离子的“关-开”型近红外荧光探针

房茹^a, 丁旭^a, 罗稳^a, 洪琛^b

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 发布日期:2020-06-28
通讯作者: 罗稳, 洪琛 E-mail:luowen83@163.com;hongchenbest@163.com
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.

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

Fang Ru^a, Ding Xu^a, Luo Wen^a, Hong Chen^b

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:2020-04-03 Revised:2020-05-27 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).

1. cjoc202004007辅助材料.pdf(589KB)

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

Cite this article

Fang Ru, Ding Xu, Luo Wen, Hong Chen. An “Off-On” Near-Infrared Fluorescent Probe for Cu²⁺ Detection in Living Cells[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2949-2955.

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一种检测活细胞内铜离子的“关-开”型近红外荧光探针

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

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