A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells

Org Biomol Chem. 2014 Mar 7;12(9):1412-8. doi: 10.1039/c3ob42267d.

Abstract

A general probe designed to induce a cascading sequence of reactions on a target protein was efficiently synthesized. The cascading reaction sequence involved (i) ligand-directed azaelectrocyclization with lysine and (ii) the autooxidation-induced release of a fluorescence quencher from the labeled protein. The probe was linked to a cyclic RGDyK peptide to enable the selective visualization of integrin αVβ3 on the surfaces of live cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aza Compounds / chemical synthesis
  • Aza Compounds / chemistry*
  • Cell Line
  • Cell Survival
  • Cyclization
  • Fluorescence*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Humans
  • Ligands
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Peptides, Cyclic / chemistry
  • Proteins / chemistry*
  • Surface Properties

Substances

  • Aza Compounds
  • Fluorescent Dyes
  • Ligands
  • Peptides, Cyclic
  • Proteins