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  • 1.
    Kong, Na
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Carbohydrate-Functionalized Nanomaterials: Synthesis, Characterization and Biorecognition Studies2015Doctoral 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.

  • 2.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Joen, Seaho
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Covalent Functionalization of Buckminsterfullerene with Perfluorophenyl Azide by Microwave Irradiation, Photochemical or Thermal ActivationManuscript (preprint) (Other academic)
  • 3.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Park, JaeHyeung
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Carbohydrate Functionalization of Few-Layer Graphene through Microwave-Assisted Reaction of Perfluorophenyl AzideManuscript (preprint) (Other academic)
  • 4.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Functionalization of carbon nanomaterials with perfluorophenyl azides and their application in biorecognition2014In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 247Article in journal (Other academic)
  • 5.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Shimpi, Manishkumar R.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Park, Jae Hyeung
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides2015In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 405, p. 33-38Article in journal (Refereed)
    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.

  • 6.
    Kong, Na
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Shimpi, Manishkumar R.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Park, Jaehyeung
    Univ Massachusetts, Dept Chem, Lowell, MA 01854 USA..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides (vol 405, pg 33, 2015)2015In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 412, p. 80-80Article in journal (Refereed)
  • 7.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Shimpi, Manishkumar
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Functionalization of carbohydrate-presenting single-walled carbon nanotubes using microwave-assisted phenylnitrene addition and their biorecognition applications2013In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 245Article in journal (Other academic)
  • 8.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Xie, Sheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Zhou, Juan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Menendez, Margarita
    Solis, Dolores
    Park, JaeHyeung
    Proietti, Giampiero
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Massachusetts Lowell, United States.
    Catalyst-Free Cycloaddition Reaction for the Synthesis of Glyconanoparticles2016In: ACS Applied Materials and Interfaces, ISSN 1944-8244, E-ISSN 1944-8252, Vol. 8, no 41, p. 28136-28142Article in journal (Refereed)
    Abstract [en]

    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.

  • 9.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zhou, Juan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Park, JaeHyeung
    University of Massachusetts, United States .
    Xie, Sheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Massachusetts, United States .
    Metal-Free Carbohydrate Immobilization on Nanoparticles Using Perfluorophenyl Azide-Based Azide-Aldehyde-Amine CycloadditionManuscript (preprint) (Other academic)
  • 10.
    Kong, Na
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zhou, Juan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Park, JaeHyeung
    University of Massachusetts, United States .
    Xie, Sheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Massachusetts, United States .
    Quantitative Fluorine NMR To Determine Carbohydrate Density on Glyconanomaterials Synthesized from Perfluorophenyl Azide-Functionalized Silica Nanoparticles by Click Reaction2015In: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 87, no 18, p. 9451-9458Article in journal (Refereed)
    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.

  • 11.
    Uppalapati, Suji
    et al.
    University of Massachusetts Lowell, United States.
    Kong, Na
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Norberg, Oscar
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Massachusetts Lowell, United States.
    Ionization of covalent immobilized poly(4-vinylphenol) monolayers measured by ellipsometry, QCM and SPR2015In: Applied Surface Science, ISSN 0169-4332, E-ISSN 1873-5584, Vol. 343, p. 166-171Article in journal (Refereed)
    Abstract [en]

    Covalently immobilized poly(4-vinylphenol) (PVP) monolayer films were fabricated by spin coating PVP on perfluorophenyl azide (PFPA)-functionalized surfaces followed by UV irradiation. The pH-responsive behavior of these PVP ultrathin films was evaluated by ellipsometry, quartz crystal microbalance (QCM) and surface plasmon resonance (SPR). By monitoring the responses of these films to pH in situ, the ionization constant of the monolayer thin films was obtained. The apparent plc, value of these covalently immobilized PVP monolayers, 13.4 by SPR, was 3 units higher than that of the free polymer in aqueous solution.

  • 12.
    Xie, Sheng
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Zhou, Juan
    Chen, Xuan
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA..
    Kong, Na
    Fan, Yanmiao
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Hammer, Gerry
    Univ Washington, Dept Bioengn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA.;Univ Washington, Dept Chem Engn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA..
    Castner, David G.
    Univ Washington, Dept Bioengn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA.;Univ Washington, Dept Chem Engn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    A versatile catalyst-free perfluoroaryl azide-aldehyde-amine conjugation reaction2019In: MATERIALS CHEMISTRY FRONTIERS, ISSN 2052-1537, Vol. 3, no 2, p. 251-256Article in journal (Refereed)
    Abstract [en]

    In a tri-component reaction, an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine react readily at room temperature without any catalysts in solvents including aqueous conditions to yield a stable amidine conjugate. The versatility of this reaction is demonstrated in the conjugation of an amino acid without prior protection of the carboxyl group, and in the synthesis of antibiotic-nanoparticle conjugates.

  • 13.
    Zhou, Juan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Jayawardana, Kalana
    University of Massachusetts, United States .
    Kong, Na
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ren, Yansong
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hao, Nanjing
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Massachusetts, United States .
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Trehalose-Conjugated Mesoporous Silica Nanoparticles for Efficient Delivery of Isoniazid into MycobacteriaManuscript (preprint) (Other academic)
  • 14.
    Zhou, Juan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Jayawardana, Kalana W.
    Kong, Na
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ren, Yansong
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hao, Nanjing
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. University of Massachusetts, United States.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Trehalose-Conjugated, Photofunctionalized Mesoporous Silica Nanoparticles for Efficient Delivery of Isoniazid into Mycobacteria2015In: ACS BIOMATERIALS-SCIENCE & ENGINEERING, ISSN 2373-9878, Vol. 1, no 12, p. 1250-1255Article in journal (Refereed)
    Abstract [en]

    Glyconanoparticle carriers have been synthesized and efficiently delivered into mycobacteria. Mesoporous silica nanoparticles were functionalized with a,a-trehalose through azide-mediated surface photoligation, and loaded with the antitubercular drug isoniazid. The glyconanoparticles showed high isoniazid loading capacity and higher antimicrobial activity than the free drug.

1 - 14 of 14
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