Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 9915-9925Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01402
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Funding
- Ministerio de Economia y Competitividad (MINECO) [CTQ2012-30853, CTQ2013-41161-12]
- Universitat Autonoma de Barcelona
- RecerCaixa foundation [2010ACUP00378]
- Marato de TV3 Foundation [111531]
- European Union [270483, 210355, 335011]
- Catalan government [2012FI_B 01122, 2014SGR-1251]
- Spanish Government [CTQ2013-43892R]
- Ramon Areces foundation
- ERANET SynBio program
- ICREA Funding Source: Custom
- European Research Council (ERC) [210355, 335011] Funding Source: European Research Council (ERC)
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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.
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