An Optimized Glutamate Receptor Photoswitch with Sensitized Azobenzene Isomerization

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• 作者：Marta Gasc贸n-Moya ; Arnau Pejoan ; Merc猫 Izquierdo-Serra ; Silvia Pittolo ; Gisela Cabr茅 ; Jordi Hernando ; Ramon Alib茅s ; Pau Gorostiza ; F茅lix Busqu茅
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：October 16, 2015
• 年：2015
• 卷：80
• 期：20
• 页码：9915-9925
• 全文大小：526K
• ISSN：1520-6904

文摘

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鈥?i>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鈥損ull 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.