title: An Optimized Glutamate Receptor Photoswitch with Sensitized Azobenzene Isomerization.
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.
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Gascón-Moya
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Arnau
authors.initials: A
authors.lastname: Pejoan
authors.affiliation: Institut de Bioenginyeria de Catalunya (IBEC) , Barcelona, Spain.
authors.forename: Mercè
authors.initials: M
authors.lastname: Izquierdo-Serra
authors.affiliation: Institut de Bioenginyeria de Catalunya (IBEC) , Barcelona, Spain.
authors.forename: Silvia
authors.initials: S
authors.lastname: Pittolo
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Gisela
authors.initials: G
authors.lastname: Cabré
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Jordi
authors.initials: J
authors.lastname: Hernando
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Ramon
authors.initials: R
authors.lastname: Alibés
authors.affiliation: Institut de Bioenginyeria de Catalunya (IBEC) , Barcelona, Spain.|Centro de Investigación Biomédica en Red en Bioingeniería, Biomateriales y Nanomedicina (CIBER-BBN), Zaragoza, Spain.|Institució Catalana de Recerca i Estudis Avançats (ICREA), Barcelona, Spain.
authors.forename: Pau
authors.initials: P
authors.lastname: Gorostiza
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Félix
authors.initials: F
authors.lastname: Busqué
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009474:Neurons / Q000737:chemistry; D055668:Photochemical Processes; D058468:Receptors, Ionotropic Glutamate / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001391:Azo Compounds; D008024:Ligands; D058468:Receptors, Ionotropic Glutamate; C009850:azobenzene