有机化学 ›› 2020, Vol. 40 ›› Issue (8): 2502-2507.DOI: 10.6023/cjoc202003007 上一篇    下一篇

研究论文

一种新型比率型荧光探针用于细胞内半胱氨酸的检测

周小琴a, 崔梦园b, 贾程利a, 杨敏a, 吉民a, 王鹏b   

  1. a 东南大学生物科学与医学工程学院 南京 210009;
    b 中国药科大学生物医学工程学院 南京 211198
  • 收稿日期:2020-03-03 修回日期:2020-05-04 发布日期:2020-05-20
  • 通讯作者: 吉民, 王鹏 E-mail:101010516@seu.edu.cn;wangpeng159seu@hotmail.com
  • 基金资助:
    国家自然科学基金(No.81671745)资助项目.

Novel Ratio-Based Fluorescent Probe for Intracellular Cys Detection

Zhou Xiaoqina, Cui Mengyuanb, Jia Chenglia, Yang Mina, Ji Mina, Wang Pengb   

  1. a School of Biological Sciences and Medical Engineering, Southeast University, Nanjing 210009;
    b School of Biomedical Engineering, China Pharmaceutical University, Nanjing 211198
  • Received:2020-03-03 Revised:2020-05-04 Published:2020-05-20
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 81671745).

半胱氨酸是人体重要生物成分,一种新型的吲哚菁类比率型荧光探针的水平与多种疾病相关,对半胱氨酸浓度进行快速、准确的响应,就显得尤其重要.本研究基于经典的半胱氨酸响应机理,半胱氨酸的巯基与丙烯酸酯发生迈克尔加成,再进一步发生分子内环化,可特异性识别半胱氨酸.设计合成了一种新型比率型荧光探针,结果发现,该探针能特异性识别半胱氨酸,检出限可达到75 nmol·L-1,在30 min内能完全响应,稳定性好,能稳定存在于细胞内,对细胞毒副作用小.因此,该探针在解决了水溶性差这一问题的基础上,能快速地对细胞内半胱氨酸的浓度进行精确分析,为多种疾病的研究提供了新手段,为化学材料的发展提供了新的思路.

关键词: 半胱氨酸, 比率型, 荧光探针, 迈克尔加成, 吲哚菁类

Cysteine is an important biological component of the human body, its levels are related to many diseases. It is especially important to respond quickly and accurately to cysteine concentrations. This study is based on the classical cysteine response mechanism. The thiol group of cysteine undergoes Michael addition to acrylate, and then undergoes intramolecular cyclization to specifically recognize cysteine. A novel ratio-based fluorescent probe was designed and synthesized in this study. The research results found that the probe can specifically recognize cysteine, the detection limit can reach 75 nmol·L-1, can fully respond within 30 min, and has good stability. It exists in cells and has little cytotoxic effects. Therefore, on the basis of solving the problem of poor water solubility, the probe can quickly and accurately analyze the concentration of cysteine in cells, which provides a new means for the study of various diseases and new ideas for the development of chemical materials.

Key words: cysteine, ratio-based, fluorescent probe, michael addition, indocyanines