Sialic acid imprinted fluorescent core-shell particles for selective labeling of cell surface glycans

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Sialic acid imprinted fluorescent core-shell particles for selective labeling of cell surface glycans

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Publication Article, peer reviewed scientific
Title Sialic acid imprinted fluorescent core-shell particles for selective labeling of cell surface glycans
Author(s) Shinde, Sudhirkumar ; El-Schich, Zahra ; Malakpour, Atena ; Wan, Wei ; Dizeyi, Nishtman ; Mohammadi, Reza ; Rurack, Knut ; Gjörloff Wingren, Anette ; Sellergren, Börje
Date 2015
English abstract
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.
DOI http://dx.doi.org/10.1021/jacs.5b08482 (link to publisher's fulltext)
Publisher ACS Publications
Host/Issue Journal of the American Chemical Society;43
Volume 137
ISSN 0002-7863
Pages 13908-13912
Language eng (iso)
Subject(s) Medicine
Research Subject Categories::MEDICINE
Handle http://hdl.handle.net/2043/19815 (link to this page)

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