A thiazolo[4,5-b]pyridine-based fluorescent probe for detection of zinc ions and application for in vitro and in vivo bioimaging

Talanta. 2018 Aug 1:185:396-404. doi: 10.1016/j.talanta.2018.03.061. Epub 2018 Mar 31.

Abstract

2-HPTP, a novel thiazolo [4, 5-b] pyridine-based Zn2+ selective fluorescent probe has been synthesized and investigated. This probe exhibited a high selectivity towards Zn2+ over other biologically essential cations such as Na+, K+, Ca2+, or Mg2+. 2-HPTP formed a 1:1 complex with Zn2+ and showed a fluorescent enhancement with a long emission wavelength red-shift (85 nm) upon complex formation with Zn2+. The detection limit and association constant were calculated as 3.48 × 10-7 M and 2.40 × 106 M-1 by a fluorescence titration experiment. Furthermore, the live cell imaging experiment showed that 2-HPTP was membrane permeable and photostable, and hence, could be used to monitor the concentration changes of intracellular Zn2+. The co-staining experiments in the cells demonstrated that 2-HPTP possessed high lysosomal selectivity in living cells. Finally, using the nematode C. elegans as an experimental model, we established that 2-HPTP could be successful in imaging Zn2+ concentration changes in living tissues. Therefore, this molecule should be useful for studies on the biological functions of Zn2+.

Keywords: Fluorescent probe; Lysosomal selectivity; Membrane permeable; Thiazolo[4,5-b]pyridine; Zinc ions.

MeSH terms

  • Animals
  • Biosensing Techniques*
  • Caenorhabditis elegans / chemistry*
  • Caenorhabditis elegans / growth & development
  • Cell Proliferation / drug effects
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Humans
  • Ions / analysis
  • Molecular Structure
  • Optical Imaging
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Tumor Cells, Cultured
  • Zinc / analysis*

Substances

  • Fluorescent Dyes
  • Ions
  • Pyridines
  • Triazoles
  • Zinc