Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 8, Issue 41, Pages 28136-28142Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.6b07471
Keywords
carbohydrates; glyconanomaterials; coupling chemistry; perfluoroaryl azides; F-19 qNMR
Funding
- National Institutes of Health [R21AI109896]
- National Science Foundation [CHE-1112436]
- KTH
- Marie Curie Initial Training Network DYNANO [PITN-GA-2011-289033]
- CIBER of Respiratory Diseases (CIBERES), an initiative from the Spanish Institute of Health Carlos III (ISCIII)
- Spanish Ministry of Economy and Competitiveness [BFU2012-36825, BFU2015-70052-R]
- China Scholarship Council
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A new conjugation method for the immobilization of carbohydrates on nanomaterials was demonstrated simply by mixing perfluorophenyl azide-functionalized silica nanoparticles (SNPs), an amine-derivatized carbohydrate, and phenylacetaldehyde under ambient conditions without any catalyst. The density of carbohydrates on the glyconanoparticles was determined using the quantitative F-19 NMR (F-19 qNMR) technique; for example, the density of D-mannose (Man) on Man-SNPs was 2.5 +/- 0.2 x 10(-16) nmol/nm(2). The glyconanoparticles retained their binding affinity and selectivity toward cognate lectins. The apparent dissociation constant of the glyconanoparticles was measured by a fluorescence competition assay, where the binding affinity of Man-SNPs was almost 4 orders of magnitude higher than that of Man with concanavalin A. Moreover, even with a ligand density of 2.6 times lower than Man-SNPs synthesized by the copper catalyzed azide-alkyne cycloaddition, the binding affinity of Man-SNPs prepared by the current method was more than 4 times higher.
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