有机化学 ›› 2019, Vol. 39 ›› Issue (7): 2089-2093.DOI: 10.6023/cjoc201812047 上一篇    下一篇

研究简报

一种基于罗丹明类似物的Cys近红外荧光探针

田庆, 陈双虎, 陈景龙, 刘蕊, 汪雨诗, 杨晓朋, 叶勇   

  1. 郑州大学化学与分子工程学院 郑州 450001
  • 收稿日期:2018-12-26 修回日期:2019-02-25 出版日期:2019-07-25 发布日期:2019-03-08
  • 通讯作者: 叶勇 E-mail:yeyong03@tsinghua.org.cn
  • 基金资助:

    国家自然科学基金(No.21572209)、河南省高校科技创新人才计划(No.17IRTSTHN002)及郑州大学大学生创新创业训练计划(No.2018cxcy012)资助项目.

A Novel Rhodamine Analogues-Based Near-Infrared Fluorescent Probe for Cys

Tian Qing, Chen Shuanghu, Chen Jinglong, Liu Rui, Wang Yushi, Yang Xiaopeng, Ye Yong   

  1. College of Chemistry and Molecular Engineering of Zhengzhou University, Zhengzhou 450001
  • Received:2018-12-26 Revised:2019-02-25 Online:2019-07-25 Published:2019-03-08
  • Contact: 10.6023/cjoc201812047 E-mail:yeyong03@tsinghua.org.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21572209), the Program for Innovative Research Team (in Science and Technology) at University of Henan Province (No. 17IRTSTHN002) and Innovation and Entrepreneurship Training Plan for College Students of Zhengzhou University (No. 2018cxcy012).

基于罗丹明类似物作为荧光团合成了一例新型半胱氨酸(Cys)近红外荧光探针CS-Cys.该探针能特异性识别Cys,其他含巯基氨基酸不与探针响应,响应机理为:Cys与CS-Cys分子中的丙烯酸酯发生共轭加成-环化反应,进而羟基裸露并释放出荧光.通过对CS-Cys与Cys在不同pH环境中反应后的荧光变化进行研究,发现通过改变溶液pH值可调节给电子基的供电子能力和荧光团ICT过程,从而使荧光激发波长和发射波长达到近红外区域.

关键词: 荧光探针, 半胱氨酸, 近红外, 罗丹明类似物, ICT

A near-infrared fluorescence probe CS-Cys was synthesized using rhodamine analoguse as near-infrared fluorescent group. The probe can specifically response to Cys, not to other sulfhydryl amino acids. The response mechanism is that Cys reacts with the acrylic ester of CS-Cys and the conjugated addition-cyclization reaction occurs, then the hydroxyl groups are exposed and fluorescence is released. Through studying the fluorescence changes of CS-Cys and Cys in different pH environments, it was found that the donor ability of the electron-donor group and the process of the ICT could be monitored by changing the pH of probe solution, and the fluorescence excitation wavelength and the emission wavelength could be adjusted to the near infrared region.

Key words: fluorescent probe, cysteine, near-infrared, rhodamine analogues, ICT