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An antenna-sensitised 1-acyl-7-nitroindoline that has good solubility properties in the presence of calcium ions and is suitable for use as a caged l-glutamate in neuroscience

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Abstract

A new version of a benzophenone antenna-sensitised photolabile derivative of l-glutamate, which has a dicarboxylic acid substituent on the benzophenone to promote water solubility, has been synthesised. It does not show problems of precipitation in the presence of calcium ions that were encountered with related compounds in which one or two phosphate groups were present as water-solubilising substituents but retains the enhanced photolytic efficiency that results from the benzophenone antenna. Photolysis of the compound proceeds with stoichiometric release of l-glutamate and pharmacological evaluations have shown that the compound itself has no evidence of agonist or antagonist activity in its unphotolysed form.

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Authors and Affiliations

  1. MRC National Institute for Medical Research, The Ridgeway, Mill Hill, London, NW7 1AA, UK

    George Papageorgiou & John E. T. Corrie

  2. Laboratoire Physiologie Cerebrale, Université Paris 5, 75006, France

    David Ogden

Authors
  1. George Papageorgiou
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  2. David Ogden
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  3. John E. T. Corrie
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Correspondence to John E. T. Corrie.

Additional information

Electronic supplementary information (ESI) available: Details of the synthesis of compounds 5, 6, 17–21, 24, 25 and 27, (plus compounds A–E that are described only in the ESI), photolysis spectrum for 27 (Fig. S1) and the kinetic plot for reaction of dithiothreitol ( DTT) with the nitroso compound formed on photolysis of 27. See DOI:10.1039/b800683k

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Papageorgiou, G., Ogden, D. & Corrie, J.E.T. An antenna-sensitised 1-acyl-7-nitroindoline that has good solubility properties in the presence of calcium ions and is suitable for use as a caged l-glutamate in neuroscience. Photochem Photobiol Sci 7, 423–432 (2008). https://doi.org/10.1039/b800683k

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  • DOI: https://doi.org/10.1039/b800683k

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