title: Imaging cell surface glycosylation in vivo using "double click" chemistry.
abstract: Dynamic alterations in cell surface glycosylation occur in numerous biological processes that involve cell-cell communication and cell migration. We report here imaging of cell surface glycosylation in live mice using double click chemistry. Cell surface glycans were metabolically labeled using peracetylated azido-labeled N-acetylgalactosamine and then reacted, in the first click reaction, with either a cyclooctyne, in a Huisgen [3 + 2] cycloaddition, or with a Staudinger phosphine, via Staudinger ligation. The second click reaction was a [4 + 2] inverse electron demand Diels-Alder reaction between a trans-cyclooctene and a tetrazine, where the latter reagent had been fluorescently labeled with a far-red fluorophore. After administration of the fluorescent tetrazine, the bifunctional cyclooctyne-cyclooctene produced significant azido sugar-dependent fluorescence labeling of tumor, kidney, liver, spleen, and small intestine in vivo, where the kidney and tumor could be imaged noninvasively in the live mouse.
authors: Cancer Research U.K., Cambridge Institute, Li Ka Shing Centre, Robinson Way, Cambridge CB2 0RE, UK.
authors: André A
authors: AA
authors: Neves
authors: Henning
authors: H
authors: Stöckmann
authors: Yelena A
authors: YA
authors: Wainman
authors: Joe C-H
authors: JC
authors: Kuo
authors: Sarah
authors: S
authors: Fawcett
authors: Finian J
authors: FJ
authors: Leeper
authors: Kevin M
authors: KM
authors: Brindle
mesh_terms: D000116:Acetylgalactosamine / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D001386:Azides / Q000737:chemistry / Q000378:metabolism; D057930:Click Chemistry; D003500:Cyclization; D034242:Cyclooctanes / Q000737:chemistry / Q000378:metabolism; D005260:Female; D006031:Glycosylation; D006801:Humans; D051379:Mice; D008807:Mice, Inbred BALB C; D008819:Mice, Nude; D015394:Molecular Structure; D009369:Neoplasms / Q000175:diagnosis*; D011134:Polysaccharides / Q000737:chemistry / Q000378:metabolism; D014407:Tumor Cells, Cultured
chemical_list: D001386:Azides; D034242:Cyclooctanes; D011134:Polysaccharides; D000116:Acetylgalactosamine
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