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Issue 28, 2016
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Azogabazine; a photochromic antagonist of the GABAA receptor

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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

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Publication details

The article was received on 19 May 2016, accepted on 10 Jun 2016 and first published on 21 Jun 2016


Article type: Communication
DOI: 10.1039/C6OB01101B
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Org. Biomol. Chem., 2016,14, 6676-6678
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    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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