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

  • Sudhirkumar Shinde
  • Zahra El-Schich
  • Atena Malakpour
  • Wei Wan
  • Nishtman Dizeyi
  • Reza Mohammadi
  • Knut Rurack
  • Anette Gjörloff Wingren
  • Börje Sellergren
Publishing year: 2015-09-28
Language: English
Pages: 13908-13912
Publication/Series: Journal of the American Chemical Society
Volume: 137
Issue: 43
Document type: Journal article
Publisher: The American Chemical Society

Abstract english

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.


  • Medical Biotechnology


  • ISSN: 1520-5126
Atena Malakpour
E-mail: atena [dot] malakpour_permlid [at] biol [dot] lu [dot] se

Doctoral student

Functional zoology

+46 76 82 05 37


Sölvegatan 35, Lund, Lund


Doctoral student



Doctoral Researcher

Research group

Animal Physiology


Main supervisor

Stina Oredsson

Assistant supervisor

Per Fredrik Johansson