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

Shinde, Sudhirkumar; El-Schich, Zahra; Malakpour, Atena LU ; Wan, Wei; Dizeyi, Nishtman LU ; Mohammadi, Reza; Rurack, Knut; Gjörloff Wingren, Anette LU and Sellergren, Börje (2015) In Journal of the American Chemical Society 137(43). p.13908-13912
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 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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the American Chemical Society
volume
137
issue
43
pages
13908 - 13912
publisher
The American Chemical Society
external identifiers
  • wos:000364355900034
  • scopus:84953439271
ISSN
1520-5126
DOI
10.1021/jacs.5b08482
language
English
LU publication?
yes
id
3f5528cf-f3d9-46b6-8bd6-848decb09b8c (old id 8380457)
date added to LUP
2016-01-04 07:04:59
date last changed
2017-11-19 03:58:10
@article{3f5528cf-f3d9-46b6-8bd6-848decb09b8c,
  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 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.},
  author       = {Shinde, Sudhirkumar and El-Schich, Zahra and Malakpour, Atena and Wan, Wei and Dizeyi, Nishtman and Mohammadi, Reza and Rurack, Knut and Gjörloff Wingren, Anette and Sellergren, Börje},
  issn         = {1520-5126},
  language     = {eng},
  month        = {09},
  number       = {43},
  pages        = {13908--13912},
  publisher    = {The American Chemical Society},
  series       = {Journal of the American Chemical Society},
  title        = {Sialic Acid-Imprinted Fluorescent Core-Shell Particles for Selective Labeling of Cell Surface Glycans},
  url          = {http://dx.doi.org/10.1021/jacs.5b08482},
  volume       = {137},
  year         = {2015},
}