Synthetic Photoswitchable Neurotransmitters Based on Bridged Azobenzenes

Org Lett. 2019 May 17;21(10):3780-3784. doi: 10.1021/acs.orglett.9b01222. Epub 2019 May 9.

Abstract

Photoswitchable neurotransmitters of ionotropic kainate receptors were synthesized by tethering a glutamate moiety to disubstituted C2-bridged azobenzenes, which were prepared through a novel methodology that allows access to diazocines with higher yields and versatility. Because of the singular properties of these photochromes, photoisomerizable compounds were obtained with larger thermal stability for their inert cis isomer than for their biologically activity trans state. This enabled selective neuronal firing upon irradiation without background activity in the dark.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry*
  • Isomerism
  • Kainic Acid / chemistry*
  • Molecular Structure
  • Neurons
  • Neurotransmitter Agents / chemical synthesis*
  • Neurotransmitter Agents / chemistry
  • Photochemical Processes

Substances

  • Azo Compounds
  • Neurotransmitter Agents
  • azobenzene
  • Kainic Acid