An Optimized Glutamate Receptor Photoswitch with Sensitized Azobenzene Isomerization

Marta Gascón-Moya, Arnau Pejoan, Mercè Izquierdo-Serra, Silvia Pittolo, Gisela Cabré, Jordi Hernando, Ramon Alibés, Pau Gorostiza, Félix Busqué

Research output: Contribution to journalArticleResearchpeer-review

12 Citations (Scopus)

Abstract

© 2015 American Chemical Society. 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.
Original languageEnglish
Pages (from-to)9915-9925
JournalJournal of Organic Chemistry
Volume80
Issue number20
DOIs
Publication statusPublished - 16 Oct 2015

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