Communication

Water-Soluble, Donor–Acceptor Biphenyl Derivatives in the 2-(o-Nitrophenyl)propyl Series: Highly Efficient Two-Photon Uncaging of the Neurotransmitter γ-Aminobutyric Acid at λ=800 nm†

  1. Loïc Donato1,
  2. Dr. Alexandre Mourot2,‡,
  3. Dr. Christopher M. Davenport2,‡,
  4. Dr. Cyril Herbivo1,
  5. David Warther1,
  6. Dr. Jérémie Léonard3,
  7. Dr. Frédéric Bolze4,
  8. Prof. Dr. Jean-François Nicoud4,
  9. Prof. Dr. Richard H. Kramer2,
  10. Prof. Dr. Maurice Goeldner1,*,
  11. Dr. Alexandre Specht1,*

Article first published online: 11 JAN 2012

DOI: 10.1002/anie.201106559

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 8, pages 1840–1843, February 20, 2012

Additional Information

How to Cite

Donato, L., Mourot, A., Davenport, C. M., Herbivo, C., Warther, D., Léonard, J., Bolze, F., Nicoud, J.-F., Kramer, R. H., Goeldner, M. and Specht, A. (2012), Water-Soluble, Donor–Acceptor Biphenyl Derivatives in the 2-(o-Nitrophenyl)propyl Series: Highly Efficient Two-Photon Uncaging of the Neurotransmitter γ-Aminobutyric Acid at λ=800 nm. Angew. Chem. Int. Ed., 51: 1840–1843. doi: 10.1002/anie.201106559

Author Information

  1. 1

    Laboratoire de Conception et Application de Molécules Bioactives, UMR 7199, CNRS/UDS, Faculté de Pharmacie, 74 Route du Rhin, 67400 Illkirch (France)

  2. 2

    University of California Berkeley, Department of Molecular and Cell Biology, Berkeley, CA 94720-3200 (USA)

  3. 3

    Institut de Physique et Chimie des Matériaux de Strasbourg, UMR 7504, CNRS—Université de Strasbourg (France)

  4. 4

    Laboratoire de Biophotonique et Pharmacologie, UMR 7213, CNRS/UdS, Faculté de Pharmacie, 67400 Illkirch (France)

  1. ‡

    A.M. and C.M.D. contributed equally to the work.

*Laboratoire de Conception et Application de Molécules Bioactives, UMR 7199, CNRS/UDS, Faculté de Pharmacie, 74 Route du Rhin, 67400 Illkirch (France)

  1. †

    We thank Dr. M. Banghart for helpful discussions and critical comments on the manuscript. This work was supported by the Université de Strasbourg, the CNRS, the France-Berkeley Fund, and ANR (Contract No. 09-BLAN-0425-01 and PCV 07 1-0035).

Publication History

  1. Issue published online: 14 FEB 2012
  2. Article first published online: 11 JAN 2012
  3. Manuscript Received: 15 SEP 2011

Funded by

  • CNRS
  • France-Berkeley Fund
  • ANR. Grant Numbers: 09-BLAN-0425-01, 1-0035

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Keywords:

  • biaryls;
  • caged compounds;
  • neurotransmitters;
  • photolysis;
  • synthetic methods
Thumbnail image of graphical abstract

Rattling the cage: The two γ-aminobutyric acid (GABA) derivatives 1 and 2 exhibit efficient and rapid (<5×10−6 s) GABA photorelease upon one-photon excitation combined with two-photon uncaging cross-section at λ=800 nm. Compounds 1 and 2 were successfully used for two-photon GABA release in intact brain tissue, thus offering attractive perspectives in chemical neurosciences.

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