Photochemically knocking out glutamate receptors in vivo

J Am Chem Soc. 2004 Nov 3;126(43):13886-7. doi: 10.1021/ja048331p.

Abstract

AMPA (alpha-amino-3-hydroxy-5-methyl-4-isooxazole) receptors, a major subtype of ionotropic glutamate receptors (iGluRs), mediate the majority of the fast communication between neurons, and the activity-dependent trafficking of AMPA receptors at synapses plays a role in mammalian learning and memory. Here we describe the design, synthesis, and evaluation of a photoreactive AMPA receptor antagonist that provides a means of "knocking out" AMPA receptors present on the surface of cells. The antagonist, 6-azido-7-nitro-1,4-dihydroquinoxaline-2,3-dione (ANQX), was designed by introducing a photoreactive azido group onto a quinoxalinedione inhibitor scaffold. Computational docking of ANQX to the AMPA receptor ligand-binding core predicted efficient binding to AMPA receptors. Glutamate-evoked currents were reversibly blocked at micromolar ANQX concentrations prior to photolysis and irreversibly blocked following photolysis. ANQX provides a means of directly evaluating the trafficking of native AMPA receptors with unparalleled spatiotemporal resolution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Excitatory Amino Acid Antagonists / chemistry
  • Excitatory Amino Acid Antagonists / pharmacology
  • Neurons / metabolism
  • Nitro Compounds / chemistry
  • Nitro Compounds / pharmacology
  • Photochemistry
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology
  • Receptors, AMPA / antagonists & inhibitors
  • Receptors, AMPA / chemistry
  • Receptors, AMPA / metabolism*
  • Receptors, AMPA / radiation effects*
  • Synapses / metabolism*
  • Ultraviolet Rays
  • Xenopus

Substances

  • 6-azido-7-nitro-1,4-dihydroquinoxaline-2,3-dione
  • Excitatory Amino Acid Antagonists
  • Nitro Compounds
  • Quinolines
  • Quinoxalines
  • Receptors, AMPA
  • FG 9041