Ncm, a Photolabile Group for Preparation of Caged Molecules: Synthesis and Biological Application

PLoS One. 2016 Oct 3;11(10):e0163937. doi: 10.1371/journal.pone.0163937. eCollection 2016.


Ncm, 6-nitrocoumarin-7-ylmethyl, is a photolabile protective group useful for making "caged" molecules. Ncm marries the reliable photochemistry of 2-nitrobenzyl systems with the excellent stability and spectroscopic properties of the coumarin chromophore. From simple, commercially available starting materials, preparation of Ncm and its caged derivatives is both quick and easy. Photorelease of Ncm-caged molecules occurs on the microsecond time scale, with quantum efficiencies of 0.05-0.08. We report the synthesis and physical properties of Ncm and its caged derivatives. The utility of Ncm-caged glutamate for neuronal photostimulation is demonstrated in cultured hippocampal neurons and in brain slice preparations.

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / metabolism
  • Amino Acids / pharmacology
  • Animals
  • Auditory Cortex / drug effects
  • Auditory Cortex / physiology
  • Auditory Cortex / radiation effects
  • Cells, Cultured
  • Coumarins / chemical synthesis*
  • Coumarins / pharmacology*
  • Evoked Potentials / drug effects
  • Evoked Potentials / radiation effects
  • Glutamates / chemistry
  • Glutamates / metabolism
  • Glutamates / pharmacology
  • Hydrogen-Ion Concentration
  • Light
  • Mice
  • Photolysis
  • Pyramidal Cells / drug effects
  • Pyramidal Cells / metabolism
  • Pyramidal Cells / radiation effects


  • Amino Acids
  • Coumarins
  • Glutamates
  • coumarin