Synthetic Photoswitchable Neurotransmitters Based on Bridged Azobenzenes

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 pro...

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Bibliographic Details
Published in:Organic letters 2019-05, Vol.21 (10), p.3780-3784
Main Authors: Cabré, Gisela, Garrido-Charles, Aida, González-Lafont, Àngels, Moormann, Widukind, Langbehn, Daniel, Egea, David, Lluch, José M, Herges, Rainer, Alibés, Ramon, Busqué, Félix, Gorostiza, Pau, Hernando, Jordi
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01222