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Issue 5, 2011
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Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cells

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Abstract

Two reagents have been synthesized for selective labeling of cell surface azidoglycans, an unusually stable version of a dibenzo cyclooctyne (TMDIBO) and a third-generation difluorinated cyclooctyne (DIFO3). Both syntheses are efficient with minimal purification, and the dibenzo cyclooctyne is stable under basic and acidic conditions. Flow cytometric measurements with azidosugar labeled cancer cells, in which these reagents were linked to the fluorophore Alexa Fluor 647, gave a signal-to-background ratio of up to 35 with TMDIBO as compared to ≈10 for DIFO3 and ≈5 for a phosphine reagent. TMDIBO-based probes should have applications in molecular imaging of cell surface glycans in vivo.

Graphical abstract: Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cells

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Publication details

The article was received on 15 Dec 2010, accepted on 01 Feb 2011 and first published on 25 Feb 2011


Article type: Edge Article
DOI: 10.1039/C0SC00631A
Citation: Chem. Sci., 2011,2, 932-936
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    Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cells

    H. Stöckmann, A. A. Neves, S. Stairs, H. Ireland-Zecchini, K. M. Brindle and F. J. Leeper, Chem. Sci., 2011, 2, 932
    DOI: 10.1039/C0SC00631A

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