Issue 28, 2016

Azogabazine; a photochromic antagonist of the GABAA receptor

Abstract

The design and synthesis of azogabazine is described, which represents a highly potent (IC50 = 23 nM) photoswitchable antagonist of the GABAA receptor. An azologization strategy is adopted, in which a benzyl phenyl ether in a high affinity gabazine analogue is replaced by an azobenzene, with resultant retention of antagonist potency. We show that cycling from blue to UV light, switching between trans and cis isomeric forms, leads to photochemically controlled antagonism of the GABA ion channel.

Graphical abstract: Azogabazine; a photochromic antagonist of the GABAA receptor

Supplementary files

Article information

Article type
Communication
Submitted
19 May 2016
Accepted
10 Jun 2016
First published
21 Jun 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 6676-6678

Author version available

Azogabazine; a photochromic antagonist of the GABAA receptor

R. Huckvale, M. Mortensen, D. Pryde, T. G. Smart and J. R. Baker, Org. Biomol. Chem., 2016, 14, 6676 DOI: 10.1039/C6OB01101B

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