Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2442-2449.DOI: 10.6023/cjoc202004009 Previous Articles     Next Articles

一种基于苯并噻唑衍生物的高选择性比率型高半胱氨酸荧光探针及生物成像

申有名a, 谷标b, 刘歆a, 唐裕才a, 李海涛c   

  1. a 湖南文理学院 水处理功能材料湖南省重点实验室 湖南常德 415000;
    b 衡阳师范学院化学与材料工程学院 湖南衡阳 421008;
    c 湖南师范大学化学与化工学院 长沙 410081
  • 收稿日期:2020-04-06 修回日期:2020-05-07 出版日期:2020-08-25 发布日期:2020-05-28
  • 通讯作者: 申有名, 谷标 E-mail:ymshen79@163.com;biaogu@hynu.edu.cn
  • 基金资助:
    国家自然科学基金(No.21907026)、湖南省自然科学基金(No.2019JJ50009)、湖南省教育厅优秀青年基金(No.18B369)和衡阳师范学院环境监测与评价中心(No.KYJG1803)资助项目.

A Benzothiazole-Based Ratiometric Fluorescent Probe for Highly Selective Detection of Homocysteine and Its Bioimaging Application

Shen Youminga, Gu Biaob, Liu Xina, Tang Yucaia, Li Haitaoc   

  1. a Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Hunan University of Arts and Science, Changde, Hunan 415000;
    b College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008;
    c College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081
  • Received:2020-04-06 Revised:2020-05-07 Online:2020-08-25 Published:2020-05-28
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21907026), the Hunan Provincial Natural Science Foundation of China (No. 2019JJ50009), the Scientific Research Fund of Hunan Provincial Education Department (No. 18B369) and the Environmental Monitoring and Evaluation Center of Hengyang Normal University (No. KYJG1803).

Elevated homocysteine (Hcy) has been considered as a risk factor for vascular and renal diseases. Therefore, the development of Hcy-specific fluorescent probes, especially ratiometric fluorescent probes is of great importance. In the present study, a highly Hcy selective ratiometric fluorescent probe 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methyl-benzaldehyde (BA), based on an ortho-hydroxy aldehyde functionalized benzothiazole, is presented. The probe responded selectively to Hcy over other tested species including Cys and GSH with ratiometric fluorescence changes. The probe possessed itself green fluorescence (λem=544 nm). Addition of Hcy to the BA solution triggered remarkable blue fluorescence (λem=478 nm). The fluorescence intensity ratios (I478 nm/I544 nm) were linearly related to the amounts of Hcy from 0 to 1.0 mmol/L with a detection limit of 1.6 μmol/L. The probe BA possessed low cytotoxicity and desirable cell permeability, and could be employed for the ratiometric imaging of Hcy in living cells, suggesting its potential applications in biological systems. Moreover, the sensing mechanism of BA for Hcy was verified by NMR, HRMS and time-dependent density function theory calculations.

Key words: homocysteine, ratiometric, fluorescent probe, cell imaging