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Sialic Acid-Imprinted Fluorescent Core-Shell Particles for Selective Labeling of Cell Surface Glycans.
- Source :
-
Journal of the American Chemical Society . 11/4/2015, Vol. 137 Issue 43, p13908-13912. 5p. - Publication Year :
- 2015
-
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 ethylene glycol dimethacrylate (EGDMA) as cross-linker resulting in a shell thickness of ca. 10 nm. The particles displayed strong affinity for SA in methanol/water mixtures (K = 6.6 × 105 M-1 in 2% water, 5.9 × 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 × 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *SIALIC acids
*GLYCANS
*CELL membranes
*HYDROGEN bonding
*NANOPARTICLES
Subjects
Details
- Language :
- English
- ISSN :
- 00027863
- Volume :
- 137
- Issue :
- 43
- Database :
- Academic Search Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 111151485
- Full Text :
- https://doi.org/10.1021/jacs.5b08482