Sialic Acid-Imprinted Fluorescent Core-Shell Particles for Selective Labeling of Cell Surface Glycans
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/8380457
- author
- Shinde, Sudhirkumar ; El-Schich, Zahra ; Malakpour, Atena LU ; Wan, Wei ; Dizeyi, Nishtman LU ; Mohammadi, Reza ; Rurack, Knut ; Gjörloff Wingren, Anette LU and Sellergren, Börje
- organization
- publishing date
- 2015-09-28
- 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 (ACS)
- external identifiers
-
- wos:000364355900034
- scopus:84953439271
- pmid:26414878
- ISSN
- 1520-5126
- DOI
- 10.1021/jacs.5b08482
- language
- English
- LU publication?
- yes
- additional info
- Copyright © 2015 American Chemical Society
- id
- 3f5528cf-f3d9-46b6-8bd6-848decb09b8c (old id 8380457)
- date added to LUP
- 2016-04-01 14:37:26
- date last changed
- 2022-04-14 18:44:53
@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 (ACS)}}, 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}}, doi = {{10.1021/jacs.5b08482}}, volume = {{137}}, year = {{2015}}, }