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Multifunctional Glyconanomaterials: Applications in Biorecognition and Drug Delivery
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. (Ramström Group)
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 [en]
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: urn:nbn:se:kth:diva-171951ISBN: 978-91-7595-570-4 (print)OAI: oai:DiVA.org:kth-171951DiVA: diva2:844972
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
List of papers
1. Synthesis of Multifunctional Cellulose Nanocrystals for Lectin Recognition and Bacterial Imaging
Open this publication in new window or tab >>Synthesis of Multifunctional Cellulose Nanocrystals for Lectin Recognition and Bacterial Imaging
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2015 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 16, no 4, 1426-1432 p.Article in journal (Refereed) Published
Abstract [en]

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.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-165759 (URN)10.1021/acs.biomac.5b00227 (DOI)000353006000038 ()25738860 (PubMedID)2-s2.0-84927944680 (Scopus ID)
Funder
Swedish Research CouncilSwedish Research Council Formas
Note

QC 20150511

Available from: 2015-04-29 Created: 2015-04-29 Last updated: 2017-12-04Bibliographically approved
2. Glycan-Functionalized Fluorescent Chitin Nanocrystals for Biorecognition Applications
Open this publication in new window or tab >>Glycan-Functionalized Fluorescent Chitin Nanocrystals for Biorecognition Applications
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2014 (English)In: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 25, no 4, 640-643 p.Article in journal (Refereed) Published
Abstract [en]

A new platform based on chitin nanocrystals has been developed for biorecognition applications. TEMPO-oxidized chitin nanocrystals (TCNs) were labeled with a fluorescent imidazoisoquinolinone dye, and simultaneously conjugated with carbohydrate ligands, resulting in dually functionalized TCNs. The biorecognition properties of the nanocrystals were probed with lectins and bacteria, resulting in selective interactions with their corresponding cognate carbohydrate-binding proteins, as visualized by optical, fluorescence, STEM, and TEM imaging. This represents a new approach to multifunctional nanomaterials based on naturally occurring polymers, holding high potential for biomedical applications.

Keyword
Concanavalin-A, Soybean Agglutinin, Alpha-Chitin, Lectins, Binding, Nanoparticles, Recognition, Microarray, Proteins, Bacteria
National Category
Biochemistry and Molecular Biology Other Chemistry Topics
Identifiers
urn:nbn:se:kth:diva-145590 (URN)10.1021/bc500004c (DOI)000334657500002 ()2-s2.0-84899004041 (Scopus ID)
Funder
Formas, 2009-1687
Note

QC 20140611

Available from: 2014-06-11 Created: 2014-05-23 Last updated: 2017-12-05Bibliographically approved
3. 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
4. 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
5. 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
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(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
6. Lectin-gated, mesoporous, photofunctionalized glyconanoparticles for glutathione-responsive drug delivery
Open this publication in new window or tab >>Lectin-gated, mesoporous, photofunctionalized glyconanoparticles for glutathione-responsive drug delivery
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2015 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 51, no 48, 9833-9836 p.Article in journal (Refereed) Published
Abstract [en]

A stimuli-responsive drug delivery system based on fluorescent, lectin-gated, mesoporous glyconanoparticles has been developed and evaluated in normal- and cancer lung epithelial cells. The gating process proved efficient, exhibiting good sealing properties in the absence of the glutathione redox trigger, avoiding premature release in normal cells. In the presence of higher levels of glutathione in cancer cells, the lectin gate was rapidly opened and the anticancer drug released.

Keyword
Silica Nanoparticles, Controlled-Release, Concanavalin-A, Nanocontainers, Nanocarriers, Biocompatibility, Covalent, Glucose, System, Cancer
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-169982 (URN)10.1039/c5cc02907d (DOI)000355631700017 ()25989158 (PubMedID)2-s2.0-84930636671 (Scopus ID)
Note

QC 20150625

Available from: 2015-06-25 Created: 2015-06-25 Last updated: 2017-12-04Bibliographically approved

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