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Molecular Engineering of Photoremovable Protecting Groups for Two-Photon Uncaging

Authors

  • Sylvestre Gug,

    1. Institut Gilbert Laustriat, Pharmacologie et Physicochimie, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch (France), Fax: (+33) 3-90-24-43-13
    2. Institut Gilbert Laustriat, Chimie Bio-organique, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch (France)
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  • Frédéric Bolze Dr.,

    1. Institut Gilbert Laustriat, Pharmacologie et Physicochimie, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch (France), Fax: (+33) 3-90-24-43-13
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  • Alexandre Specht Dr.,

    1. Institut Gilbert Laustriat, Chimie Bio-organique, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch (France)
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  • Cyril Bourgogne Dr.,

    1. Institut de Physique et Chimie des Matériaux de Strasbourg, 23 rue du Loess, 67034 Strasbourg cedex 2 (France)
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  • Maurice Goeldner Prof. Dr.,

    1. Institut Gilbert Laustriat, Chimie Bio-organique, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch (France)
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  • Jean-François Nicoud Prof. Dr.

    1. Institut Gilbert Laustriat, Pharmacologie et Physicochimie, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch (France), Fax: (+33) 3-90-24-43-13
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  • We wish to acknowledge Prof. Dr. Y. Mély, Dr. Y. Arntz, and Dr. P. Didier for two-photon irradiations, and Dr. C. Andraud for calculations. This work was financially supported by the ANR and MNERT.

Abstract

original image

Open the cage: Symmetrical photoremovable bis-glutamate cages have been designed, synthesized, and characterized that can release a neurotransmitter with unprecedented two-photon efficiencies (see picture), up to 5 GM for BNSF–Glu (BNSF=2,7-bis-{4-nitro-8-[3-(2-propyl)-styryl]}-9,9-bis-[1-(3,6-dioxaheptyl)]-fluorene) at 800 nm, the optimal window both for tissue transparency and classically available laser sources.

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