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Carbohydrate-Functionalized Nanomaterials: Synthesis, Characterization and Biorecognition Studies
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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 [en]
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: urn:nbn:se:kth:diva-172990OAI: oai:DiVA.org:kth-172990DiVA: diva2:851444
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
List of papers
1. Metal-Free Carbohydrate Immobilization on Nanoparticles Using Perfluorophenyl Azide-Based Azide-Aldehyde-Amine Cycloaddition
Open this publication in new window or tab >>Metal-Free Carbohydrate Immobilization on Nanoparticles Using Perfluorophenyl Azide-Based Azide-Aldehyde-Amine Cycloaddition
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(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-172139 (URN)
Note

QS 2015

Available from: 2015-08-13 Created: 2015-08-13 Last updated: 2015-09-07Bibliographically approved
2. Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction
Open this publication in new window or tab >>Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction
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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.

National Category
Organic Chemistry Natural Sciences
Identifiers
urn:nbn:se:kth:diva-172137 (URN)10.1021/acs.analchem.5b02507 (DOI)000361416000049 ()2-s2.0-84941695598 (Scopus ID)
Note

QC 20151020

Available from: 2015-08-13 Created: 2015-08-13 Last updated: 2017-12-04Bibliographically approved
3. Trehalose-Conjugated Mesoporous Silica Nanoparticles for Efficient Delivery of Isoniazid into Mycobacteria
Open this publication in new window or tab >>Trehalose-Conjugated Mesoporous Silica Nanoparticles for Efficient Delivery of Isoniazid into Mycobacteria
Show others...
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-172141 (URN)
Note

QS 2015

Available from: 2015-08-13 Created: 2015-08-13 Last updated: 2015-09-07Bibliographically approved
4. Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides
Open this publication in new window or tab >>Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides
Show others...
2015 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 405, 33-38 p.Article in journal (Refereed) Published
Abstract [en]

Carbohydrate-functionalized single-walled carbon nanotubes (SWNTs) were synthesized using microwave-assisted reaction of perfluorophenyl azide with the nanotubes. The results showed that microwave radiation provides a rapid and effective means to covalently attach carbohydrates to SWNTs, producing carbohydrate-SWNT conjugates for biorecognition. The carbohydrate-functionalized SWNTs were furthermore shown to interact specifically with cognate carbohydrate-specific proteins (lectins), resulting in predicted recognition patterns. The carbohydrate-presenting SWNTs constitute a new platform for sensitive protein-or cell recognition, which pave the way for glycoconjugated carbon nanomaterials in biorecognition applications.

Keyword
Single-walled carbon nanotubes, Microwave, Perfluorophenyl azide, Covalent functionalization, Carbohydrate, Lectin
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-163964 (URN)10.1016/j.carres.2014.09.006 (DOI)000350748400005 ()25746392 (PubMedID)2-s2.0-84924200153 (Scopus ID)
Note

QC 20150505.

Correction in: Carbohydrate Research, Vol. 412, article number 6968, DOI: 10.1016/j.carres.2015.03.013, WOS: 000357542000012, Scopus: 2-s2.0-84934753187

Available from: 2015-05-05 Created: 2015-04-13 Last updated: 2017-12-04Bibliographically approved
5. Carbohydrate Functionalization of Few-Layer Graphene through Microwave-Assisted Reaction of Perfluorophenyl Azide
Open this publication in new window or tab >>Carbohydrate Functionalization of Few-Layer Graphene through Microwave-Assisted Reaction of Perfluorophenyl Azide
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-173003 (URN)
Note

QS 2015

Available from: 2015-09-07 Created: 2015-09-07 Last updated: 2015-09-07Bibliographically approved
6. Covalent Functionalization of Buckminsterfullerene with Perfluorophenyl Azide by Microwave Irradiation, Photochemical or Thermal Activation
Open this publication in new window or tab >>Covalent Functionalization of Buckminsterfullerene with Perfluorophenyl Azide by Microwave Irradiation, Photochemical or Thermal Activation
(English)Manuscript (preprint) (Other academic)
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-173004 (URN)
Note

QS 2015

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

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