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Photolabile Glutamate Protecting Group with High One- and Two-Photon Uncaging Efficiencies

Authors

  • Sylvestre Gug,

    1. Institut Gilbert Laustriat, Pharmacologie et Physicochimie, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch, France, Fax: (+33) 390-24-43-13
    2. Institut Gilbert Laustriat, Chimie Bio-organique, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch, France
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  • Sébastien Charon,

    1. Institut Gilbert Laustriat, Pharmacologie et Physicochimie, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch, France, Fax: (+33) 390-24-43-13
    2. Institut Gilbert Laustriat, Chimie Bio-organique, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch, France
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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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  • Karine Alarcon Dr.,

    1. Institut Gilbert Laustriat, Chimie Bio-organique, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch, France
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  • David Ogden Dr.,

    1. Laboratoire de Physiologie Cérébrale, Université René Descartes, Paris 75006, France
    2. Present Address: National Institute for Medical Research, The Ridgeway, Mill Hill NW7 1AA, UK
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  • Burkhard Zietz Dr.,

    1. Institut de Physique et Chimie des Matériaux de Strasbourg, Groupe d'Optique Non-Linéaire et d'Optoélectronique, 23 rue du Loess, 67034 Strasbourg Cedex 2, France
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  • Jérémie Léonard Dr.,

    1. Institut de Physique et Chimie des Matériaux de Strasbourg, Groupe d'Optique Non-Linéaire et d'Optoélectronique, 23 rue du Loess, 67034 Strasbourg Cedex 2, France
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  • Stefan Haacke Prof. Dr.,

    1. Institut de Physique et Chimie des Matériaux de Strasbourg, Groupe d'Optique Non-Linéaire et d'Optoélectronique, 23 rue du Loess, 67034 Strasbourg Cedex 2, 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) 390-24-43-13
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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) 390-24-43-13
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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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Abstract

A π-extended [2-(2-nitrophenyl)propoxy]carbonyl (NPPOC) derivative has been prepared as an efficient UV and near-IR photolabile protecting group for glutamate. This glutamate cage compound exhibits efficient photorelease upon one-photon excitation (εΦ=990 M−1cm−1 at 315 nm). In addition, it also shows efficient photorelease in activation of glutamate receptors in electrophysiological recordings. Combined with a high two-photon uncaging cross-section (δΦ=0.45 GM at 800 nm), its overall properties make this new cage—3-(2-propyl)-4′-methoxy-4-nitrobiphenyl (PMNB)—for glutamate a very promising tool for two-photon neuronal studies.

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