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Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
University of Massachusetts, United States .
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2015 (English)In: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 87, no 18, 9451-9458 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2015. Vol. 87, no 18, 9451-9458 p.
National Category
Organic Chemistry Natural Sciences
Identifiers
URN: urn:nbn:se:kth:diva-172137DOI: 10.1021/acs.analchem.5b02507ISI: 000361416000049Scopus ID: 2-s2.0-84941695598OAI: oai:DiVA.org:kth-172137DiVA: diva2:845951
Note

QC 20151020

Available from: 2015-08-13 Created: 2015-08-13 Last updated: 2017-12-04Bibliographically approved
In thesis
1. Multifunctional Glyconanomaterials: Applications in Biorecognition and Drug Delivery
Open this publication in new window or tab >>Multifunctional Glyconanomaterials: Applications in Biorecognition and Drug Delivery
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis consists of three parts, which revolve around the fabrication of multifunctional glyconanomaterials (cellulose nanocrystals, chitin nanocrystals, mesoporous silica nanoparticles) and the development of their applications in biorecognition and nanomedicine.

Part one presents a detailed introduction to glyconanomaterials, focusing on cellulose nanocrystals, chitin nanocrystals and mesoporous silica nanoparticles, including their general preparations, properties and applications.

Part two demonstrates dually modified cellulose and chitin nanocrystals. They are prepared by TEMPO-mediated oxidation, followed by conjugation with a fluorescent dye and carbohydrate ligands. The two functional nanocrystals are applied in carbohydrate-lectin recognition and bacterial imaging as new types of glyconanomaterials.

Part three describes two types of drug delivery systems based on carbohydrate- conjugated mesoporous silica nanoparticles: the first type is a trehalose- functionalized nanoparticle which can selectively recognize mycobacteria, release antimicrobial drugs and kill them; the second type is a lectin-gated drug container, which can perform controlled delivery of drugs to cancer cells in response to glutathione.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 70 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:28
Keyword
glyconanomaterials, cellulose nanocrystals, chitin nanocrystals, mesoporous silica nanoparticles, lectin, biorecognition, drug delivery, bacteria, cytotoxicity, perfluorophenylazide, fluorescent dye, carbohydrate ligands.
National Category
Nano Technology
Identifiers
urn:nbn:se:kth:diva-171951 (URN)978-91-7595-570-4 (ISBN)
Public defence
2015-09-04, B2, Brinellvägen 23, KTH, Stockholm, 13:00 (English)
Opponent
Supervisors
Note

QC 20150813

Available from: 2015-08-13 Created: 2015-08-10 Last updated: 2015-08-13Bibliographically approved
2. Carbohydrate-Functionalized Nanomaterials: Synthesis, Characterization and Biorecognition Studies
Open this publication in new window or tab >>Carbohydrate-Functionalized Nanomaterials: Synthesis, Characterization and Biorecognition Studies
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis focuses on the development of carbohydrate coupling chemistry on nanomaterials and their biological activity studies. It is divided into two parts:

In part one, two carbohydrate immobilization approaches, based on perfluorophenyl azide (PFPA)-functionalized silica nanoparticles (SNPs), are presented, where the binding affinity of the glyconanoparticles was evaluated through carbohydrate-lectin interaction. In the first approach, PFPAfunctionalized SNPs were treated with propargylated glycosides and functionalized under copper-catalyzed azide-alkyne cycloaddition (CuAAC) conditions to give glyconanoparticles. For the second approach, a metal-free coupling chemistry based on perfluorophenyl azide-aldehyde-amine cycloaddition (AAAC) was developed for carbohydrate immobilization on PFPA-functionalized SNPs using glycosyl amine and phenylacetaldehyde. Subsequently, a quantitative fluorine nuclear magnetic resonance (19F qNMR) technique was developed to determine the carbohydrate density on the glyconanoparticles. The addition of an internal standard allowed the accurate determination of carbohydrate density, which was then used to calculate the apparent dissociation constant (Kd ) of the glyconanoparticles with lectin by a ligand competition assay. The developed approaches proved general and versatile, and the carbohydrate-presenting nanoplatforms showed high binding specificity in lectin binding.

In part two, microwave irradiation was used to functionalize carbon nanomaterials with PFPA followed by carbohydrate conjugation. The microwave-assisted method proved efficient for a number of carbon nanomaterials including carbon nanotubes (CNTs), graphene and fullerene. The carbohydrates on the glyconanomaterials retained their binding patterns towards cognate lectins.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 69 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:33
Keyword
carbohydrate, glyconanomaterials, perfluorophenyl azide (PFPA ), CuAAC, AAAC, coupling chemistry, 19 F q NMR, lectin, carbon nanomaterials, microwave irradiation
National Category
Chemical Sciences
Research subject
Chemistry; Biotechnology
Identifiers
urn:nbn:se:kth:diva-172990 (URN)
Public defence
2015-09-28, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20150907

Available from: 2015-09-07 Created: 2015-09-04 Last updated: 2015-12-31Bibliographically approved

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