有机化学 ›› 2023, Vol. 43 ›› Issue (1): 308-312.DOI: 10.6023/cjoc202207011 上一篇    下一篇

研究简报

一种点亮型硫化氢荧光探针的合成及其在红酒和细胞中的应用

杨雅馨,a, 陈琳,c, 胡晓玲a, 钟克利a,*(), 李世迪d, 燕小梅d, 张璟琳b,*(), 汤立军a   

  1. a 渤海大学化学与材料工程学院 辽宁锦州 121013
    b 北京工商大学 中国轻工业酿酒分子工程重点实验室 北京 100048
    c 辽宁省检验检测认证中心 沈阳 110000
    d 大连医科大学检验医学院 辽宁大连 116044
  • 收稿日期:2022-07-05 修回日期:2022-08-07 发布日期:2022-09-08
  • 通讯作者: 钟克利, 张璟琳
  • 作者简介:
    共同第一作者
  • 基金资助:
    北京工商大学中国轻工业酿酒分子工程重点实验室开放课题(BME-202202); 国家自然科学基金(22278038); 辽宁省自然科学基金指导计划(2020-MS-289); 辽宁省自然科学基金指导计划(20180551195)

Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells

Yaxin Yang,a, Lin Chen,c, Xiaoling Hua, Keli Zhonga(), Shidi Lid, Xiaomei Yand, Jinglin Zhangb(), Lijun Tanga   

  1. a College of Chemistry and Material Engineering, Bohai University, Jinzhou, Liaoning 121013
    b Key Laboratory of Brewing Molecular Engineering, China Light Industry, Beijing 100048
    c Liaoning Inspection, Examination & Certification Centre, Shenyang 121013
    d College of Laboratory Medicine, Dalian Medical University, Dalian, Liaoning 116044
  • Received:2022-07-05 Revised:2022-08-07 Published:2022-09-08
  • Contact: Keli Zhong, Jinglin Zhang
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    Open Project Program of the Key Laboratory of Brewing Molecular Engineering of China Light Industry(BME-202202); National Natural Science Foundation of China(22278038); Natural Science Foundation of Liaoning Province(2020-MS-289); Natural Science Foundation of Liaoning Province(20180551195)

合成了一种新颖的三苯胺衍生物Tdip, 利用硫化氢(H2S)触发Tdip发生串联反应, 释放出具有强荧光的前体化合物, 进而实现荧光点亮识别H2S. 该探针具有较好的选择性和抗干扰能力, 较大的斯托克斯位移(146 nm), 8~13的pH适用范围, 较低的检测限(2.24 μmol/L). 此外, Tdip能检测实际红酒样品中的H2S, 并可对活细胞中的H2S进行荧光成像.

关键词: 硫化氢, 点亮型, 荧光探针, 食品样品, 荧光成像

In this paper, a novel triphenylamine derivative (Tdip) was synthesized. Tdip can recognize hydrogen sulfide (H2S) with turn-on fluorescence response through tandem reaction triggered by HS to release precursor compound, which produces a strong fluorescent signal. Tdip displayed good selectivity and anti-interference ability toward H2S, a large Stokes shift (146 nm), a pH range of 8~13, and a low detection limit (2.24 μmol/L). In addition, Tdip can detect H2S in actual red wine samples and image H2S in living cells.

Key words: hydrogen sulfide, turn-on, fluorescent probe, food sample, fluorescence imaging