Supramolecular Assembly of TPE-Based Glycoclusters with Dicyanomethylene-4H-pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging

Chemistry. 2020 Nov 11;26(63):14445-14452. doi: 10.1002/chem.202002772. Epub 2020 Oct 6.

Abstract

Two red-emitting dicyanomethylene-4H-pyran (DM) based fluorescent probes were designed and used for peroxynitrite (ONOO- ) detection. Nevertheless, the aggregation-caused quenching effect diminished the fluorescence and restricted their further applications. To overcome this problem, tetraphenylethylene (TPE) based glycoclusters were used to self-assemble with these DM probes to obtain supramolecular water-soluble glyco-dots. This self-assembly strategy enhanced the fluorescence intensity, leading to an enhanced selectivity and activity of the resulting glyco-dot comparing to DM probes alone in PBS buffer. The glyco-dots also exhibited better results during fluorescence sensing of intracellular ONOO- than the probes alone, thereby offering scope for the development of other similar supramolecular glyco-systems for chemical biological studies.

Keywords: cell imaging; glycoclusters; peroxynitrite detection; self-assembly; tetraphenylethylene.

MeSH terms

  • Fluorescent Dyes* / chemistry
  • Fluorescent Dyes* / standards
  • Glycoconjugates / chemistry
  • Optical Imaging* / methods
  • Peroxynitrous Acid* / analysis
  • Pyrans* / chemistry
  • Stilbenes* / chemistry

Substances

  • Fluorescent Dyes
  • Glycoconjugates
  • Pyrans
  • Stilbenes
  • dicyanomethylene-4H-pyran
  • tetraphenylethylene
  • Peroxynitrous Acid