4.6 Article

Sensitive Near-Infrared Fluorescent Probes for Thiols Based on Se-N Bond Cleavage: Imaging in Living Cells and Tissues

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 36, Pages 11343-11349

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200671

Keywords

cleavage reactions; fluorescent probes; imaging agents; Se-N bonds; thiols

Funding

  1. National Natural Science Foundation of China [20975089, 81102415]
  2. Chinese Academy of Sciences [KZCX2-EW-206]
  3. 100 Talents Program of the Chinese Academy of Sciences

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Cy-NiSe and Cy-TfSe were designed and synthesized as sensitive near-infrared (NIR) fluorescent probes for detecting thiols on the basis of Se-N bond cleavage both in cells and in tissues. Since a donor-excited photoinduced electron transfer (d-PET) process occurs between the modulator and the fluorophore, Cy-NiSe and Cy-TfSe have weak fluorescence. On titration with glutathione, the free dye exhibits significant fluorescence enhancement. The two probes are sensitive and selective for thiols over other relevant biological species. They can function rapidly at pH 7.4, and their emission lies in the NIR region. Confocal imaging confirms that Cy-NiSe and Cy-TfSe can be used for detecting thiols in living cells and tissues.

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