Issue 5, 2011

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Dec 2010
Accepted
01 Feb 2011
First published
25 Feb 2011

Chem. Sci., 2011,2, 932-936

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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