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Keywords:

  • glutamate cage;
  • neurotransmitters;
  • photolabile protecting groups;
  • photolysis;
  • two-photon uncaging

Abstract

A π-extended [2-(2-nitrophenyl)propoxy]carbonyl (NPPOC) derivative has been prepared as an efficient UV and near-IR photolabile protecting group for glutamate. This glutamate cage compound exhibits efficient photorelease upon one-photon excitation (εΦ=990 M−1cm−1 at 315 nm). In addition, it also shows efficient photorelease in activation of glutamate receptors in electrophysiological recordings. Combined with a high two-photon uncaging cross-section (δΦ=0.45 GM at 800 nm), its overall properties make this new cage—3-(2-propyl)-4′-methoxy-4-nitrobiphenyl (PMNB)—for glutamate a very promising tool for two-photon neuronal studies.