Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cells
Literature Information
Publication Date
2011-02-25
DOI
10.1039/C0SC00631A
Impact Factor
9.825
Authors
André A. Neves, Shaun Stairs, Heather Ireland-Zecchini, Kevin M. Brindle, Finian J. Leeper
View Original
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.
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Chemical Science
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