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Issue 3, 2012
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Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group

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Abstract

Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (λ < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group.

Graphical abstract: Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group

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Publication details

The article was received on 29 Sep 2011, accepted on 15 Nov 2011 and first published on 04 Jan 2012


Article type: Paper
DOI: 10.1039/C1PP05321C
Photochem. Photobiol. Sci., 2012,11, 522-532

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    Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group

    K. Kolmakov, C. Wurm, M. V. Sednev, M. L. Bossi, V. N. Belov and S. W. Hell, Photochem. Photobiol. Sci., 2012, 11, 522
    DOI: 10.1039/C1PP05321C

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