影像科学与光化学 ›› 2018, Vol. 36 ›› Issue (3): 236-244.DOI: 10.7517/j.issn.1674-0475.2018.03.004

• 论文 • 上一篇    下一篇

基于菁染料高选择性检测半胱氨酸的近红外荧光探针

马亚光, 张玉涛, 马一宇, 郭志前, 朱为宏   

  1. 华东理工大学 精细化工研究所, 上海 200237
  • 收稿日期:2017-08-03 修回日期:2017-08-29 出版日期:2018-05-15 发布日期:2018-05-15
  • 通讯作者: 郭志前
  • 基金资助:
    国家自然科学基金项目(21622602)资助

Near-infrared Cyanine-based Fluorescent Probe for Cysteine with High Selectivity

MA Yaguang, ZHANG Yutao, MA Yiyu, GUO Zhiqian, ZHU Weihong   

  1. Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, P. R. China
  • Received:2017-08-03 Revised:2017-08-29 Online:2018-05-15 Published:2018-05-15

摘要: 本文设计合成了以菁染料为荧光团,以4-(三氟甲基)苯硫基为半胱氨酸响应识别基团的近红外荧光探针(Cy-CF3)。利用探针分子Cy-CF3与半胱氨酸和谷胱甘肽反应发生的机理不同,实现了对半胱氨酸特异性识别。探针分子Cy-CF3与半胱氨酸发生芳香亲核取代反应生成巯基取代产物,进一步通过分子内重排反应生成氨基取代产物Cy-Cys。光谱研究结果表明,探针分子Cy-CF3与半胱氨酸作用后发生明显的吸收波长蓝移(160 nm),并且可观察到明显的颜色变化;荧光光谱中,随着半胱氨酸的加入,探针分子Cy-CF3在780 nm处的近红外荧光显著增强。Cy-CF3能高选择性检测半胱氨酸,并且不受其它氨基酸尤其是结构类似的谷胱甘肽干扰。探针分子Cy-CF3被成功地应用于活体细胞中检测半胱氨酸。

关键词: 近红外, 半胱氨酸, 荧光探针, 菁染料

Abstract: We developed a turn-on cyanine-based near-infrared (NIR) probe which can selectively detect cysteine. In this probe Cy-CF3, 4-(trifluoromethyl)thiophenol moiety is employed as both the recognition unit and fluorescence quenching group. With the titration of cysteine, a large blue shift (160 nm) is observed in the absorption spectra of Cy-CF3, accompanying with significant color changes. The probe Cy-CF3 shows obviously fluorescent enhancement at 780 nm in emission spectra. Over all, the probe Cy-CF3 exhibits high selectivity for cysteine over glutathione and other potential interferences. The reaction mechanism of Cy-CF3 with cysteine is verified by mass spectra, 1HNMR spectra and absorption spectra, indicating that 4-(trifluoromethyl)thiophenol in the probe Cy-CF3 could be replaced by cysteine, and then the PET process from 4-(trifluoromethyl)thiophenol to cyanine is blocked. The cell experiments also demonstrate that this probe could be successfully applied for the detection of cysteine in living cells.

Key words: near-infrared, cysteine, fluorescent probe, cyanine