Sialic Acid-Imprinted Fluorescent Core-Shell Particles for Selective Labeling of Cell Surface Glycans

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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 nanopartides 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 X 10(5) M-1 in 2% water, 5.9 x 10(3) M-1 in 98% water, B-max, approximate to 10 mu mol g(-1)), whereas binding of the competitor glucuronic acid (GA) and other monosaccharides was considerably weaker (K (GA) = 1.8 X 10(3) 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.


  • Sudhirkumar Shinde
  • Zahra El-Schich
  • Atena Malakpour
  • Wei Wan
  • Nishtman Dizeyi
  • Reza Mohammadi
  • Knut Rurack
  • Anette Gjörloff Wingren
  • Börje Sellergren
Enheter & grupper
Externa organisationer
  • Malmö University
  • Federal Institute for Material Research and Testing (BAM) Germany

Ämnesklassifikation (UKÄ) – OBLIGATORISK

  • Medicinsk bioteknologi (med inriktning mot cellbiologi (inklusive stamcellsbiologi), molekylärbiologi, mikrobiologi, biokemi eller biofarmaci)
Sidor (från-till)13908-13912
TidskriftJournal of the American Chemical Society
Utgåva nummer43
StatusPublished - 2015 sep 28
Peer review utfördJa