A series of BODIPY-based probes for the detection of cysteine and homocysteine in living cells

Talanta. 2019 Apr 1:195:281-289. doi: 10.1016/j.talanta.2018.11.066. Epub 2018 Nov 22.

Abstract

Biothiols, such as glutathione (GSH), homocysteine (Hcy) and cysteine (Cys), are important biomarkers and play crucial roles in many physiological processes. Thus, the detection of biothiols is highly important for early diagnosis of diseases and evaluation of disease progression. Herein, new types of BODIPY-based fluorescent probes (probe 1, probe 2 and probe 3) capable of cysteine (Cys)/homocysteine (Hcy) sensing with high selectivity over other amino acids were developed. In addition, we further studied the influence of different electronegativity substituents on these probes to sensing Cys/Hcy. Ultimately, we concluded that the electron withdrawing group on probe 1 can accelerate the probe response to Cys/Hcy, and probe 1 was successfully applied for selective imaging Cys/Hcy in living cells.

Keywords: BODIPY; Cysteine; Fluorescent probe; Homocysteine.

MeSH terms

  • Boron Compounds / chemistry*
  • Cysteine / analysis*
  • Cysteine / chemistry
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Homocysteine / analysis*
  • Homocysteine / chemistry
  • Humans
  • Spectrometry, Fluorescence

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Homocysteine
  • Cysteine