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Reversible Off–On Fluorescence Probe for Hypoxia and Imaging of Hypoxia–Normoxia Cycles in Live Cells

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‡ †Faculty of Pharmaceutical Sciences and ‡Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
§ Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama-shi, Kanagawa 226-8501, Japan
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Cite this: J. Am. Chem. Soc. 2012, 134, 48, 19588–19591
Publication Date (Web):November 16, 2012
https://doi.org/10.1021/ja310049d
Copyright © 2012 American Chemical Society
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    Abstract

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    We report a fully reversible off–on fluorescence probe for hypoxia. The design employs QSY-21 as a Förster resonance energy transfer (FRET) acceptor and cyanine dye Cy5 as a FRET donor, based on our finding that QSY-21 undergoes one-electron bioreduction to the radical under hypoxia, with an absorbance decrease at 660 nm. At that point, FRET can no longer occur, and the dye becomes strongly fluorescent. Upon recovery of normoxia, the radical is immediately reoxidized to QSY-21, with loss of fluorescence due to restoration of FRET. We show that this probe, RHyCy5, can monitor repeated hypoxia–normoxia cycles in live cells.

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    Full experimental procedures, characterization data for all compounds, spectral properties of cyanine dyes and QSY-21 derivatives, compounds as candidates for a hypoxia-sensing moiety other than QSY-21, ESR spectra, HPLC analyses, and fluorescence imaging under normoxia. This material is available free of charge via the Internet at http://pubs.acs.org.

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