A caged metabolic precursor for DT-diaphorase-responsive cell labeling

Chem Commun (Camb). 2018 May 8;54(38):4878-4881. doi: 10.1039/c8cc01715h.

Abstract

In this study, we report incorporation of a covalent linker at the anomeric position of N-azidoacetylmannosamine (ManNAz) for caging its metabolic process. We synthesized a DT-diaphorase-responsive metabolic precursor, HQ-NN-AAM, using an optimized linker. The caged metabolite showed responsiveness to DT-diaphorase in vitro, resulting in metabolic incorporation of an azido sugar into the cell surface in multiple cell lines.

MeSH terms

  • Azides / chemical synthesis
  • Azides / chemistry
  • Azides / metabolism*
  • Cell Line, Tumor
  • Cell Tracking / methods*
  • Click Chemistry
  • Ethylenediamines / chemistry
  • Glycosylation
  • Hexosamines / chemical synthesis
  • Hexosamines / chemistry
  • Hexosamines / metabolism*
  • Humans
  • NAD(P)H Dehydrogenase (Quinone) / metabolism*
  • Polysaccharides / biosynthesis*
  • Quinones / chemical synthesis
  • Quinones / chemistry
  • Quinones / metabolism*

Substances

  • Azides
  • Ethylenediamines
  • Hexosamines
  • N-azidoacetylmannosamine
  • Polysaccharides
  • Quinones
  • dimethylethylenediamine
  • NAD(P)H Dehydrogenase (Quinone)