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- Kong, Na, et al.
(författare)
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Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles
- 2016
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Ingår i: ACS Applied Materials and Interfaces. - : American Chemical Society (ACS). - 1944-8244 .- 1944-8252. ; 8:41, s. 28136-28142
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Tidskriftsartikel (refereegranskat)abstract
- 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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- Kong, Na, et al.
(författare)
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Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction
- 2015
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Ingår i: Analytical Chemistry. - : American Chemical Society (ACS). - 0003-2700 .- 1520-6882. ; 87:18, s. 9451-9458
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Tidskriftsartikel (refereegranskat)abstract
- A quantitative fluorine NMR (F-19 qNMR) method was developed to determine the carbohydrate density on glyconanomaterials. Mannose (Man)- and galactose (Gal)-conjugated silica nanoparticles (SNPs) were synthesized from perfluorophenyl azide (PFPA)-functionalized SNPs and propargylated Man or Gal by copper-catalyzed azide-alkyne cycloaddition (click reaction). After treating PFPA-SNPs or Man-SNPs with hydrofluoric acid followed by lyophilization, the remaining residues were directly subjected to F-19 NMR analysis. The density of PFPA on PFPA-SNP was determined to be 7.7 +/- 0.2 x 10(-16) nmol/nm(2) and Man on Man-SNP to be 6.4 +/- 0.2 x 10(-16) nmol/nm(2) giving a yield of similar to 83% for the click coupling reaction. The apparent dissociation constant (K-d) of Man-SNPs with fluorescein isothiocyanate(FITC)-concanavalin A (Con A) was determined using a fluorescence competition assay to be 0.289 +/- 0.003 mu M, which represents more than 3 orders of magnitude affinity increase compared to free Man with Con A.
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- Park, Jaehyeung, et al.
(författare)
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Three-Dimensional Graphene-TiO2 Nanocomposite Photocatalyst Synthesized by Covalent Attachment
- 2016
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Ingår i: ACS Omega. - : American Chemical Society (ACS). - 2470-1343. ; 1:3, s. 351-356
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Tidskriftsartikel (refereegranskat)abstract
- We report the synthesis of a three-dimensional graphene (3DG)-TiO2 nanocomposite by covalently attaching P25 TiO2 nanoparticles onto pristine 3DG through a perfluorophenyl azide-mediated coupling reaction. The TiO2 nanoparticles were robustly attached on the 3DG surface, with minimal particle agglomeration. In photocatalytic CO2 reduction, the 3DG-TiO2 nanocomposite demonstrated excellent activity, about 11 times higher than that of the P25 TiO2 nanoparticles. The enhanced activity can be partially attributed to the highly dispersed state of the P25 TiO2 nanoparticles on the 3DG substrate. This 3DG-based system offers a new platform for fabricating photocatalytic materials with enhanced activities.
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- Sundhoro, Madanodaya, et al.
(författare)
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Perfluoroaryl Azide Staudinger Reaction : A Fast and Bioorthogonal Reaction
- 2017
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Ingår i: Angewandte Chemie International Edition. - : WILEY-V C H VERLAG GMBH. - 1433-7851 .- 1521-3773. ; 56:40, s. 12117-12121
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Tidskriftsartikel (refereegranskat)abstract
- We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18m(-1)s(-1) was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.
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- Sundhoro, Madanodaya, et al.
(författare)
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Poly(HEMA-co-HEMA-PFPA) : Synthesis and preparation of stable micelles encapsulating imaging nanoparticles
- 2017
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Ingår i: Journal of Colloid and Interface Science. - : ACADEMIC PRESS INC ELSEVIER SCIENCE. - 0021-9797 .- 1095-7103. ; 500, s. 1-8
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Tidskriftsartikel (refereegranskat)abstract
- We report the preparation of stable micelles from random copolymers of 2-hydroxyethyl methacrylate (HEMA) and perfluorophenyl azide (PFPA)-derivatized HEMA (HEMA-PFPA). The copolymers were synthesized by RAFT polymerization at room temperature under mild conditions without affecting the azide functionality. Upon addition of water to the copolymer solution in DMSO, the random copolymers self assembled into micelles even at the percentage of HEMA-PFPA as low as 4.5%. The size of the micelles can be controlled by the molecular weight and the concentration of the copolymer, and the percentage of HEMA-PFPA in the copolymer. In addition, iron oxide nanoparticles and quantum dots were successfully encapsulated into the micelles with high encapsulation efficiency (similar to 80%). These nanoparticles, which were hydrophobic and formed agglomerates in water, became fully dispersed after encapsulating into the micelles. The micelles were stable and the size remained unchanged for at least 6 months.
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- Zhou, Juan, et al.
(författare)
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Synthesis of Multifunctional Cellulose Nanocrystals for Lectin Recognition and Bacterial Imaging
- 2015
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Ingår i: Biomacromolecules. - : American Chemical Society (ACS). - 1525-7797 .- 1526-4602. ; 16:4, s. 1426-1432
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Tidskriftsartikel (refereegranskat)abstract
- Multifunctional cellulose nanocrystals have been synthesized and applied as a new type of glyconanomaterial in lectin binding and bacterial imaging. The cellulose nanocrystals were prepared by TEMPO-mediated oxidation and acidic hydrolysis, followed by functionalization with a quinolone fluorophore and carbohydrate ligands. The cellulose nanocrystals were subsequently applied in interaction studies with carbohydrate-binding proteins and in bacterial imaging. The results show that the functional cellulose nanocrystals could selectively recognize the corresponding cognate lectins. In addition, mannosylated nanocrystals were shown to selectively interact with FimH-presenting E. coli, as detected by TEM and confocal fluorescence microscopy. These glyconanomaterials provide a new application of cellulose nanocrystals in biorecognition and imaging.
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