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dc.contributor.authorParle, Daniel R
dc.contributor.authorBulat, Flaviu
dc.contributor.authorFouad, Shahd
dc.contributor.authorZecchini, Heather
dc.contributor.authorBrindle, Kevin M
dc.contributor.authorNeves, André A
dc.contributor.authorLeeper, Finian J
dc.date.accessioned2022-07-07T23:30:12Z
dc.date.available2022-07-07T23:30:12Z
dc.date.issued2022-07-25
dc.identifier.issn1043-1802
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/338890
dc.description.abstractMethylcyclopropene (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.
dc.description.sponsorshipCRUK grants C9545/A29580, C197/ A17242 and C197/A16465 Studentship from the EPSRC
dc.publisherAmerican Chemical Society (ACS)
dc.rightsAll Rights Reserved
dc.rights.urihttp://www.rioxx.net/licenses/all-rights-reserved
dc.titleMetabolic Glycan Labeling of Cancer Cells Using Variably Acetylated Monosaccharides.
dc.typeArticle
dc.publisher.departmentDepartment of Chemistry
dc.date.updated2022-07-07T09:05:41Z
prism.publicationNameBioconjug Chem
dc.identifier.doi10.17863/CAM.86297
dcterms.dateAccepted2022-07-07
rioxxterms.versionofrecord10.1021/acs.bioconjchem.2c00169
rioxxterms.versionAM
dc.contributor.orcidBrindle, Kevin M [0000-0003-3883-6287]
dc.contributor.orcidNeves, André A [0000-0003-2740-5166]
dc.contributor.orcidLeeper, Finian J [0000-0003-3408-5199]
dc.identifier.eissn1520-4812
rioxxterms.typeJournal Article/Review
pubs.funder-project-idCancer Research Uk (None)
pubs.funder-project-idEPSRC (2112389)
cam.issuedOnline2022-07-25
cam.orpheus.successWed Aug 03 09:46:03 BST 2022 - Embargo updated
cam.orpheus.counter1
cam.depositDate2022-07-07
pubs.licence-identifierapollo-deposit-licence-2-1
pubs.licence-display-nameApollo Repository Deposit Licence Agreement
rioxxterms.freetoread.startdate2023-07-25


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