Repository logo
 

Metabolic Glycan Labeling of Cancer Cells Using Variably Acetylated Monosaccharides.

Published version
Peer-reviewed

Type

Article

Change log

Authors

Parle, Daniel R 
Bulat, Flaviu 
Fouad, Shahd 
Zecchini, Heather 

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 AcxManNCyoc, tri- and diacetylated derivatives generated significantly enhanced cell labeling compared to the tetra-acetylated monosaccharide. In contrast, for the more readily soluble azide-tagged sugars, a decrease in acetylation led to decreased glycan labeling. Ac3ManNCyoc gave better labeling than the azido-tagged Ac4ManNAz and has significant potential for in vitro and in vivo imaging of glycosylated cancer biomarkers.

Description

Funder: Engineering and Physical Sciences Research Council

Keywords

Acetylation, Monosaccharides, Neoplasms, Polysaccharides, Staining and Labeling

Journal Title

Bioconjug Chem

Conference Name

Journal ISSN

1043-1802
1520-4812

Volume Title

33

Publisher

American Chemical Society (ACS)
Sponsorship
Cancer Research Uk (None)
EPSRC (2112389)
CRUK grants C9545/A29580, C197/ A17242 and C197/A16465 Studentship from the EPSRC