Reversible and Selective Fluorescence Detection of Histidine Using a Naphthalimide-Based Chemosensing Ensemble

Chem Asian J. 2015 Nov;10(11):2411-8. doi: 10.1002/asia.201500690. Epub 2015 Aug 20.

Abstract

We described a new ensemble-approach-based chemosensor, NCH-Cu(2+), for highly selective and reversible detection of histidine (His) in aqueous solution and live cells. The ligand NCH exhibited specific binding with Cu(2+) ions over other metal ions, accompanied with a 92.2% fluorescence quenching. The decomplexation of NCH-Cu(2+) ensemble by His led to the liberation of the fluorophore, NCH, and thus the fluorescence was recovered. The specific fluorescence enhancement of NCH-Cu(2+) towards His showed a good linearity with a detection of limit at 70 nm. Quantification of intracellular His at the single cell level was achieved by microscopy and flow cytometry. Besides the UV/Vis and emission titration, reversibility of the NCH-Cu(2+) towards His was further confirmed by imaging and cytometry analysis. In addition, microscopy studies revealed that NCH-Cu(2+) was distributed in the lysosome of live cells, where it could be employed as a fluorescent biosensor for imaging of His at subcellular level.

Keywords: chemosensor; fluorescence imaging; histidine; lysosome; quantification.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biosensing Techniques
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Copper / chemistry
  • Fluorescent Dyes / chemistry
  • Histidine / analysis*
  • Humans
  • Ions / chemistry
  • Microscopy, Confocal
  • Naphthalimides / chemistry*
  • Naphthalimides / toxicity
  • Spectrometry, Fluorescence*

Substances

  • Fluorescent Dyes
  • Ions
  • Naphthalimides
  • Histidine
  • Copper