An optimized glutamate receptor photoswitch with sensitized azobenzene isomerization
Gascón Moya, Marta (Universitat Autònoma de Barcelona. Departament de Química)
Pejoan, Arnau (Universitat Autònoma de Barcelona. Departament de Química)
Izquierdo-Serra, Mercè (Institut de Bioenginyeria de Catalunya)
Pittolo, Silvia (Institut de Bioenginyeria de Catalunya)
Cabré Segura, Gisela (Universitat Autònoma de Barcelona. Departament de Química)
Hernando Campos, Jordi (Universitat Autònoma de Barcelona. Departament de Química)
Alibes, Ramón (Universitat Autònoma de Barcelona. Departament de Química)
Gorostiza, Pau (Institut de Bioenginyeria de Catalunya)
Busqué Sánchez, Félix (Universitat Autònoma de Barcelona. Departament de Química)

Date:	2015
Abstract:	A new azobenzene-based photoswitch, 2, has been designed to enable optical control of ionotropic glutamate receptors in neurons via sensitized two-photon excitation with NIR light. In order to develop an efficient and versatile synthetic route for this molecule, a modular strategy is described which relies on the use of a new linear fully protected glutamate derivative stable in basic media. The resulting compound undergoes one-photon trans-cis photoisomerization via two different mechanisms: direct excitation of its azoaromatic unit and irradiation of the pyrene sensitizer, a well-known two-photon sensitive chromophore. Moreover, 2 presents large thermal stability of its cis isomer, in contrast to other two-photon responsive switches relying on the intrinsic nonlinear optical properties of push-pull substituted azobenzenes. As a result, the molecular system developed herein is a very promising candidate for evoking large photoinduced biological responses during the multiphoton operation of neuronal glutamate receptors with NIR light, which require accumulation of the protein-bound cis state of the switch upon repeated illumination.
Rights:	Tots els drets reservats.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Subject:	Aromatic compounds ; Hydrocarbons ; Mixtures ; Monomers ; Peptides and proteins
Published in:	Journal of organic chemistry, Vol. 80, issue 20 (Oct. 2015) , p. 9915-9925, ISSN 1520-6904

DOI: 10.1021/acs.joc.5b01402

Postprint 34 p, 1.2 MB

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Synthesis of Bioactive Organic Compounds and Functional Materials (SynOrgFUN)
Articles > Research articles
Articles > Published articles