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Sialic acid imprinted fluorescent core-shell particles for selective labeling of cell surface glycans
Malmö högskola, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö högskola, Biofilms Research Center for Biointerfaces.
Malmö högskola, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö högskola, Biofilms Research Center for Biointerfaces.ORCID iD: 0000-0002-0841-5804
Malmö högskola, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö högskola, Biofilms Research Center for Biointerfaces.
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2015 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, no 43, p. 13908-13912Article in journal (Refereed)
Abstract [en]

The expression of cell surface glycans terminating with sialic acid (SA) residues has been found to correlate with various disease states there among cancer. We here report a novel strategy for specific fluorescence labeling of such motifs. This is based on sialic acid imprinted core-shell nanoparticles equipped with nitrobenzoxadiazole (NBD) fluorescent reporter groups allowing environmentally sensitive fluorescence detection at convenient excitation and emission wavelengths. Imprinting was achieved exploiting a hybrid approach combining reversible boronate ester formation between p-vinylphenylboronic acid and SA, the introduction of cationic amine functionalities and the use of an NBD-appended urea-monomer as a binary hydrogen bond donor targeting the SA carboxylic acid and OH functionalities. The monomers were grafted from 200 nm RAFT modified silica core particles using ethyleneglycol dimethacrylate (EGDMA) as crosslinker resulting in a shell thickness of ca 10 nm. The particles displayed strong affinity for SA in methanol/water mixtures (K = 6.6 x 105 M-1 in 2% water, 5.9 x 103 M-1 in 98% water, Bmax ≈ 10 μmol g–1) whereas binding of the competitor glucuronic acid (GA) and other monosaccharides was considerably weaker (K (GA) = 1.8 x 103 M-1 in 98% water). In cell imaging experiments the particles selectively stained different cell lines in correlation with the SA expression level. This was further verified by enzymatic cleavage of SA and by staining using a FITC labeled SA selective lectin.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2015. Vol. 137, no 43, p. 13908-13912
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Medical and Health Sciences
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URN: urn:nbn:se:mau:diva-15265DOI: 10.1021/jacs.5b08482ISI: 000364355900034PubMedID: 26414878Scopus ID: 2-s2.0-84953439271Local ID: 19815OAI: oai:DiVA.org:mau-15265DiVA, id: diva2:1418786
Available from: 2020-03-30 Created: 2020-03-30 Last updated: 2024-02-05Bibliographically approved

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El-Schich, ZahraGjörloff Wingren, AnetteSellergren, Börje

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