Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2835-2842.DOI: 10.6023/cjoc201904020 Previous Articles     Next Articles

Special Issue: 荧光探针-生物传感合辑 有机超分子化学合辑



程晓红a*(), 徐可a, 屈少华a, 阮志军b   

  1. a 湖北文理学院 低维光电材料与器件湖北省重点实验室 湖北襄阳 441053
    b 黄冈师范学院化学化工学院 湖北黄冈 438000
  • 收稿日期:2019-04-09 修回日期:2019-05-14 发布日期:2019-06-06
  • 通讯作者: 程晓红
  • 基金资助:

Ratiometric Fluorescent Probe for Homocysteine and CysteineBased on the Aldehyde Functionalized Coumarin and SuccessfulBioimaging Application

Cheng Xiaohonga*(), Xu Kea, Qu Shaohuaa, Ruan Zhijunb   

  1. a Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University ofArts and Science, Xiangyang 441053, Hubei
    b College of chemistry and Chemical Engineering, Huanggang Normal University,Huanggang 438000, Hubei
  • Received:2019-04-09 Revised:2019-05-14 Published:2019-06-06
  • Contact: Cheng Xiaohong
  • Supported by:
    Project supported by the National Natural Science Foundation of China(21704032);The Natural Science Foundation of Hubei Province(2018CFB454);The Hubei Superior and Distinctive Discipline Group of “Mechatronics and Automobiles”(XKQ2019038)

Novel reactive probes (C1 and C2) towards homocysteine/cysteine (Hcy/Cys) were designed and synthesized, based on the unique nucleophilic nature of bio-thiols. In the presence of Hcy/Cys, probe C1 displayed remarkable fluorescence enhancement. Meanwhile, ratiometric fluorescent probe C2 was designed through subtle structure adjustment. Differently, compound C2 displayed dramatic blue-shift in both fluorescence (100 nm) and absorption (95 nm) spectra upon the addition of Hcy/Cys. By virtue of the specific nucleophilic reaction, probe C2 had outstanding selectivity towards Hcy over Cys, GSH and other amino acids. The detection limit of probe C2 was calculated to be as low as 2.8×10 –7 mol/L. Moreover, C2 was successfully applied to microscopic imaging for the detection of Hcy in HeLa cells with ratiometric fluorescent methods.

Key words: chemosensor, bio-thiols, ratiometric fluorescence, intramolecular charge transfer, cell imaging