Elsevier

Tetrahedron Letters

Volume 45, Issue 47, 15 November 2004, Pages 8721-8724
Tetrahedron Letters

An indicator displacement system for fluorescent detection of phosphate oxyanions under physiological conditions

https://doi.org/10.1016/j.tetlet.2004.09.133Get rights and content

Abstract

A fluorogenic chemosensing system is described and shown to selectively detect pyrophosphate under physiological conditions. In the best case, pyrophosphate and hydrogen phosphate are capable of displacing a fluorescent coumarin-derived indicator from a bis Zn2+-dipicolylamine coordination compound with association constants of 107 and 105 M−1, respectively.

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Acknowledgements

The National Science Foundation and the University of Notre Dame are acknowledged for financial support.

References and notes (16)

  • L. Fabbrizzi et al.

    Angew. Chem., Int. Ed.

    (2001)
  • A.P. de Silva et al.

    Chem. Rev.

    (1997)
    T.S. Snowden et al.

    Curr. Opin. Chem. Biol.

    (1999)
    P.D. Beer

    Acc. Chem. Res.

    (1998)
    L. Fabbrizzi et al.

    Dalton Trans.

    (2003)
    S.L. Wiskur et al.

    Acc. Chem. Res.

    (2001)
    R. Martinez-Manez et al.

    Chem. Rev.

    (2003)
  • L.L. Zhou et al.

    Org. Lett.

    (2004)
  • K. Niikura et al.

    J. Chem. Soc., Perkin Trans. 2

    (1999)
  • M.S. Han et al.

    Angew. Chem., Int. Ed.

    (2002)
  • L. Fabbrizzi et al.

    Angew. Chem., Int. Ed.

    (2002)
  • P.A. Gale et al.

    Chem. Commun.

    (1999)
  • J.J. Lavigne et al.

    Angew. Chem., Int. Ed.

    (1999)
    A.M. Piatek et al.

    J. Am. Chem. Soc.

    (2004)
There are more references available in the full text version of this article.

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