TY - JOUR A1 - Shinde, S. A1 - El-Schich, Z. A1 - Malakpour, A. A1 - Wan, Wei A1 - Dizeyi, N. A1 - Mohammadi, R. A1 - Rurack, Knut A1 - Gjörloff Wingren, A. A1 - Sellergren, B. T1 - Sialic acid-imprinted fluorescent core-shell particles for selective labeling of cell surface glycans T2 - Journal of the American Chemical Society : JACS N2 - 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. PB - American Chemical Society CY - Washington, DC, USA KW - Glycoproteine KW - Biomarker KW - Fluoreszenz KW - Polymere KW - Krebsdiagnostik PY - 2015 UR - https://opus4.kobv.de/opus4-bam/frontdoor/index/index/docId/35227 AN - OPUS4-35227 SN - 0002-7863 SN - 1520-5126 VL - 137 IS - 43 SP - 13908 EP - 13912 AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany