Abstract

128
Henning Stöckmann, Andre A. Neves, Shaun Stairs, Heather Ireland-Zecchini, Kevin M. Brindle and Finian J. Leeper, “Efficient synthesis of cyclooctynes for cell surface glycan labeling in cancer models” Chem. Sci., 2011, 2, 932-936. Full Text.

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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