Metabolic Glycan Labeling of Cancer Cells Using Variably Acetylated Monosaccharides.

ABSTRACT: Methylcyclopropene (Cyoc)-tagged tetra-acetylated monosaccharides, and in particular mannosamine derivatives, are promising tools for medical imaging of cancer using metabolic oligosaccharide engineering and the extremely fast inverse electron-demand Diels-Alder bioorthogonal reaction. However, the in vivo potential of these monosaccharide derivatives has yet to be fully explored due to their low aqueous solubility. To address this issue, we sought to vary the extent of acetylation of Cyoc-tagged monosaccharides and probe its effect on the extent of glycan labeling in various cancer cell lines. We demonstrate that, in the case of Ac_xManNCyoc, tri- and diacetylated derivatives generated significantly enhanced cell labeling compared to the tetra-acetylated monosaccha

SUBMITTER: Parle DR 

PROVIDER: S-EPMC9389531 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature