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Advanced polymeric scaffolds for functional materials in biomedical applications
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Advancements in the biomedical field are driven by the design of novel materials with controlled physical and bio-interactive properties. To develop such materials, researchers rely on the use of highly efficient reactions for the assembly of advanced polymeric scaffolds that meet the demands of a functional biomaterial. In this thesis two main strategies for such materials have been explored; these include the use of off-stoichiometric thiol-ene networks and dendritic polymer scaffolds. In the first case, the highly efficient UV-induced thiol-ene coupling (TEC) reaction was used to create crosslinked polymeric networks with a predetermined and tunable excess of thiol or ene functionality. These materials rely on the use of readily available commercial monomers. By adopting standard molding techniques and simple TEC surface modifications, patterned surfaces with tunable hydrophobicity could be obtained. Moreover, these materials are shown to have great potential for rapid prototyping of microfluidic devices. In the second case, dendritic polymer scaffolds were evaluated for their ability to increase surface interactions and produce functional 3D networks. More specifically, a self-assembled dendritic monolayer approach was explored for producing highly functional dendronized surfaces with specific interactions towards pathogenic E. coli bacteria. Furthermore, a library of heterofunctional dendritic scaffolds, with a controllable and exact number of dual-purpose azide and ene functional groups, has been synthesized. These scaffolds were explored for the production of cell interactive hydrogels and primers for bone adhesive implants. Dendritic hydrogels decorated with a selection of bio-relevant moieties and with Young’s moduli in the same range as several body tissues could be produced by facile UV-induced TEC crosslinking. These gels showed low cytotoxic response and relatively rapid rates of degradation when cultured with normal human dermal fibroblast cells. When used as primers for bone adhesive patches, heterofunctional dendrimers with high azide-group content led to a significant increase in the adhesion between a UV-cured hydrophobic matrix and the wet bone surface (compared to patches without primers).

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2014. , 72 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:1
Keyword [en]
Dendrimer, hydrogel, PEG, dendritic monolayers, thiol-ene networks, off-stochiometric
National Category
Polymer Technologies Medical Materials Materials Chemistry Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-139944ISBN: 978-91-7501-978-9 (print)OAI: oai:DiVA.org:kth-139944DiVA: diva2:687856
Public defence
2014-01-31, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20140116

Available from: 2014-01-16 Created: 2014-01-15 Last updated: 2014-01-16Bibliographically approved
List of papers
1. UV initiated thiol-ene chemistry: a facile and modular synthetic methodology for the construction of functional 3D networks with tunable properties
Open this publication in new window or tab >>UV initiated thiol-ene chemistry: a facile and modular synthetic methodology for the construction of functional 3D networks with tunable properties
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2013 (English)In: Journal of Materials Chemistry A, ISSN 2050-7488, Vol. 1, no 44, 13732-13737 p.Article in journal (Refereed) Published
Abstract [en]

A facile methodology for the fabrication of functional crosslinked three dimensional (3D) networks has herein been explored via the benign and UV initiated thiol-ene coupling (TEC) chemistry. The careful selection of monomers or polymers and their feed ratio resulted in straightforward design of organic, inorganic and hydrogel networks with readily available alkenes or thiol functional groups. All crosslinked networks were fabricated within 1 second of UV exposure at wavelengths of 320-390 nm and generally exhibited excellent gel fractions around 90%. By introducing off-stoichiometric thiol and ene (OSTE) monomer feed ratios the window of mechanical properties could be manipulated. For the organic triazine system, the Young's modulus was altered from 780 MPa at an equimolar monomer ratio to soft 106 kPa for 2.5 equiv. with excess of thiol compared to enes. Postfunctionalizations with hydrophilic polyethylene glycols or acrylic acid and hydrophobic heneicosa-fluorododecyl acrylate were explored for the manipulation of functional networks. In this case, the rigid networks with excess of thiols were used as model substrates of which the initial contact angle (CA) of 60 degrees was decreased to 43 degrees by the introduction of acrylic acid and increased to 140 degrees by successful attachment of fluorinated molecules. Finally, amalgamating micropatterning strategy with simple postfunctionalizations of hydrophobic groups resulted in superhydrophobic rigid surfaces with a CA of 173 degrees.

Keyword
Microfluidic Devices, Poly(Dimethylsiloxane), Strategies
National Category
Materials Chemistry
Identifiers
urn:nbn:se:kth:diva-136533 (URN)10.1039/c3ta12963b (DOI)000326463400005 ()2-s2.0-84886447725 (Scopus ID)
Funder
Swedish Research Council, 2010-453
Note

QC 20131209

Available from: 2013-12-09 Created: 2013-12-05 Last updated: 2017-05-30Bibliographically approved
2. BEYOND PDMS:: OFF-STOCHIOMETRY THIOL-ENE BASED SOFT LITHOGRAPHY FOR RAPID PROTOTYPING OF MICROFLUIDIC DEVICES
Open this publication in new window or tab >>BEYOND PDMS:: OFF-STOCHIOMETRY THIOL-ENE BASED SOFT LITHOGRAPHY FOR RAPID PROTOTYPING OF MICROFLUIDIC DEVICES
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2010 (English)In: 14th International Conference on Miniaturized Systems for Chemistry and Life Sciences (micro TAS 2010), 2010, 70-72 p.Conference paper, Published paper (Refereed)
Abstract [en]

We present an easy to use, rapid fabrication platform for microfluidic systems, based on micro-molding of novel thiolene based polymer formulations. The novel fabrication platform addresses major drawbacks of PDMS by allowing large freedom in material and surface properties, including: (photo)patterning of stable surface modifications, bonding without plasma treatment, rapid UV or thermal curing, variable E-modulus, minimized leaching of uncured components [1] and suppressed non-specific binding of biomolecules [2]. This process is potentially suited for both rapid prototyping in the laboratory and medium-scale commercial production, bridging the “development gap”.

Keyword
Click chemistry, Soft lithography, Thiol-ene
National Category
Other Electrical Engineering, Electronic Engineering, Information Engineering Polymer Technologies Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-49437 (URN)2-s2.0-84883815123 (Scopus ID)978-161839062-2 (ISBN)
Conference
14th International Conference on Miniaturized Systems for Chemistry and Life Sciences (micro TAS 2010), Groningen, Netherlands, 3-7 Oct, 2010
Projects
Intopsens
Note

QC 20140819

Available from: 2011-11-27 Created: 2011-11-27 Last updated: 2015-06-18Bibliographically approved
3. Templating Gold Surfaces with Function: A Self-Assembled Dendritic Monolayer Methodology Based on Monodisperse Polyester Scaffolds
Open this publication in new window or tab >>Templating Gold Surfaces with Function: A Self-Assembled Dendritic Monolayer Methodology Based on Monodisperse Polyester Scaffolds
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2013 (English)In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 29, no 1, 456-465 p.Article in journal (Refereed) Published
Abstract [en]

The antibiotic resistance developed among several pathogenic bacterial strains has spurred interest in understanding bacterial adhesion down to a molecular level. Consequently, analytical methods that rely on bioactive and multivalent sensor surfaces are sought to detect and suppress infections. To deliver functional sensor surfaces with an optimized degree of molecular packaging, we explore a library of compact and monodisperse dendritic scaffolds based on the nontoxic 2,2-bis(methylol)propionic acid (bis-MPA). A self-assembled dendritic monolayer (SADM) methodology to gold surfaces capitalizes on the design of aqueous soluble dendritic structures that bear sulfur-containing core functionalities. The nature of sulfur (either disulfide or thiol), the size of the dendritic framework (generation 1-3), the distance between the sulfur and the dendritic wedge (4 or 14 angstrom), and the type of functional end group (hydroxyl or mannose) were key structural elements that were identified to affect the packaging densities assembled on the surfaces. Both surface plasmon resonance (SPR) and resonance-enhanced surface impedance (RESI) experiments revealed rapid formation of homogenously covered SADMs on gold surfaces. The array of dendritic structures enabled the fabrication of functional gold surfaces displaying molecular covering densities of 0.33-2.2 molecules.nm(-2) and functional availability of 0.95-5.5 groups.nm(-2). The cell scavenging ability of these sensor surfaces for Escherichia coli MS7fim+ bacteria revealed 2.5 times enhanced recognition for G3-mannosylated surfaces when compared to G3-hydroxylated SADM surfaces. This promising methodology delivers functional gold sensor surfaces and represents a facile route for probing surface interactions between multivalently presented motifs and cells in a controlled surface setting.

Keyword
Escherichia-Coli, Click Chemistry, Bifunctional Dendrimers, Patterned Surface, Type-1 Fimbriae, Cell-Adhesion, Dendron-Thiol, Fimh, Multivalent, Disulfides
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-118006 (URN)10.1021/la3041314 (DOI)000313305900055 ()2-s2.0-84872111151 (Scopus ID)
Funder
VinnovaSwedish Research Council, 2011-5358 2010-453
Note

QC 20130211

Available from: 2013-02-11 Created: 2013-02-08 Last updated: 2017-12-06Bibliographically approved
4. Dual-purpose PEG scaffolds for the preparation of soft and biofunctional hydrogels: the convergence between CuAAC and thiol-ene reactions
Open this publication in new window or tab >>Dual-purpose PEG scaffolds for the preparation of soft and biofunctional hydrogels: the convergence between CuAAC and thiol-ene reactions
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2013 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, no 62, 6938-6940 p.Article in journal (Refereed) Published
Abstract [en]

Orthogonally functionalized PEGs displaying alkenes and azides have been prepared and their dual-purpose scaffolding potential was exploited via click chemistry for controlled insertion of bio-relevant moieties as well as facile fabrication of soft, non-toxic and degradable hydrogels.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-125778 (URN)10.1039/c3cc42084a (DOI)000321576000002 ()2-s2.0-84882247505 (Scopus ID)
Funder
VinnovaSwedish Research Council, 2011-5358 2010-453
Note

QC 20130814

Available from: 2013-08-14 Created: 2013-08-13 Last updated: 2017-12-06Bibliographically approved
5. Multipurpose heterofunctional dendritic scaffolds as crosslinkers towards functional soft hydrogels and implant adhesives in bone fracture applications
Open this publication in new window or tab >>Multipurpose heterofunctional dendritic scaffolds as crosslinkers towards functional soft hydrogels and implant adhesives in bone fracture applications
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2013 (English)In: Journal of Materials Chemistry B, ISSN 2050-7518, Vol. 1, no 44, 6015-6019 p.Article in journal (Refereed) Published
Abstract [en]

Two sets of heterofunctional dendritic frameworks displaying an inversed and exact number of ene and azide groups have successfully been synthesized and post-functionalized with biorelevant molecules. Their facile scaffolding ability enabled the fabrication of soft and azide functional dendritic hydrogels with modulus close to muscle tissue. The dendritic scaffolds are furthermore shown to be promising primers for the development of novel bone fracture stabilization adhesives with shear strengths succeeding commercial Histroacryl (R).

Keyword
Azide group, Bone fracture, Cross-linkers, Muscle tissues
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-127460 (URN)10.1039/c3tb21061h (DOI)000326244900001 ()2-s2.0-84886628793 (Scopus ID)
Funder
Knut and Alice Wallenberg Foundation, 2012-0196Swedish Research Council, 2011-5358 2010-453
Note

QC 20131128. Updated from manuscript to article in journal.

Available from: 2013-08-30 Created: 2013-08-30 Last updated: 2014-01-16Bibliographically approved

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