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Multifunctional Dendritic Scaffolds: Synthesis, Characterization and Potential applications
KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknik, Ytbehandlingsteknik.
2013 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

The development of materials for advanced applications requires innovative macromolecules with well-defined structures and the inherent ability to be tailored in a straightforward manner. Dendrimers, being a subgroup of the dendritic polymer family, possess properties which fulfill such demands. They have a highly branched architecture with a high number of functional groups and are one of the most well-defined types of macromolecules ever synthesized. However, despite their well-defined nature and high functional density, traditional dendrimers commonly lack diverse chemical functionalities. Therefore, this thesis focuses on the synthesis of more complex dendritic materials to extend their tailoring capacity by introduction of dualfunctionalities for multipurpose actions. It covers the synthesis of dualfunctional dendrimers, dendritic modification of linear poly(ethylene glycol) polymers and cellulose surfaces, and the synthesis of linear dendritic hybrids. The building blocks enabling this synthesis, AB2C monomers, were also developed during this work. The orthogonal nature between click groups (azide, alkyne and alkene) and hydroxyl groups have efficiently been utilized for postfunctionalization by robust click chemistry and traditional esterification reactions. Furthermore, linear dendritic hybrids were synthesized, merging the properties of linear and dendritic macromolecules. The dendritic frameworks were tailored towards the production of bone fracture adhesives, novel biofunctional dendritic hydrogels, biosensors and micellar drug delivery vehicles.

Abstract [sv]

Utveckling av material för avancerade applikationer kräver innovativa makromolekyler med väldefinierade strukturer och som kan skräddarsys på ett enkelt sätt. Dendrimerer är en undergrupp av dendritiska polymerer vars egenskaper uppfyller dessa krav. De har en mycket förgrenad arkitektur med många funktionella grupper och är en av de mest väldefinierade befintliga syntetiska makromolekylerna. Trots dess väldefinierade karaktär och höga funktionalitet saknar ofta traditionella dendrimerer multipla kemiska funktionaliteter. Denna avhandling fokuserar därför på syntesen av mer komplexa dendritiska material för att förbättra deras kapacitet att skräddarsys, detta görs genom att introducera fler funktionaliteter som kan utnyttjas för multipla ändamål . Avhandlingen redogör för syntesen av difunktionella dendrimerer, dendritiska modifikationer av polyetylenglykol och cellulosaytor samt syntes av traditionella dendritiska hybrider. Byggstenarna som möjliggör syntesen, AB2C monomerer, framställdes också under detta arbete. Den ortogonala karaktären mellan klick grupper (azid, alkyn och alkene) och hydroxylgrupper har utnyttjats effektivt för funktionaliseringar genom användande av robust ”Click”-kemi och traditionella esterifikationsreaktioner. Vidare tillverkades de linjära dendritiska hybrider för att kombinera egenskaperna hos både linjära och traditionella dendritiska polymerer i en och samma makromolekyl. Samtliga dendritiska strukturer skräddarsyddes för applikationer så som benlimmer, biofunktionella dendritiska hydrogeler, biosensorer och läkemedels-bärande miceller.

sted, utgiver, år, opplag, sider
Stockholm: KTH Royal Institute of Technology, 2013. , s. 87
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2013:32
Emneord [en]
Dendrimer, AB2C monomer, Click chemistry, CuAAC, thiol-ene coupling chemistry, TEC, linear dendritic hybrids, micelle, hydrogel, bone adhesive
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-127429ISBN: 978-91-7501-817-1 (tryckt)OAI: oai:DiVA.org:kth-127429DiVA, id: diva2:644266
Disputas
2013-09-20, Sal F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad

QC 20130830

Tilgjengelig fra: 2013-08-30 Laget: 2013-08-29 Sist oppdatert: 2013-08-30bibliografisk kontrollert
Delarbeid
1. Bifunctional Dendrimers: From Robust Synthesis and Accelerated One-Pot Postfunctionalization Strategy to Potential Applications
Åpne denne publikasjonen i ny fane eller vindu >>Bifunctional Dendrimers: From Robust Synthesis and Accelerated One-Pot Postfunctionalization Strategy to Potential Applications
Vise andre…
2009 (engelsk)Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, nr 12, s. 2126-2130Artikkel i tidsskrift (Fagfellevurdert) Published
Emneord
click chemistry, dendrimers, gels, nanoparticles, synthetic methods, phosphorus-containing dendrimers, dendritic macromolecules, click, chemistry, rapid synthesis, terminal alkynes, polymers, architectures, molecules, growth, azides
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-18270 (URN)10.1002/anie.200804987 (DOI)000264411800015 ()19117006 (PubMedID)2-s2.0-61949478182 (Scopus ID)
Merknad

QC 20100525

Tilgjengelig fra: 2010-08-05 Laget: 2010-08-05 Sist oppdatert: 2020-03-09bibliografisk kontrollert
2. Bifunctional Dendronized Cellulose Surfaces as Biosensors
Åpne denne publikasjonen i ny fane eller vindu >>Bifunctional Dendronized Cellulose Surfaces as Biosensors
Vise andre…
2011 (engelsk)Inngår i: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 12, nr 6, s. 2114-2125Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Well-defined dendronized cellulose substrates displaying multiple representations of dual-functionality were constructed by taking advantage of the efficiency of the click reaction combined with traditional anhydride chemistry. First, activated cellulose surfaces were decorated with several generations of dendrons, and their peripheral reactive groups were subsequently reacted with a trifunctional orthogonal monomer. The generated substrate tool box was successfully explored by accurately tuning the surface function using a versatile orthogonal dual postfunctionalization approach. In general, the reactions were monitored by using a click-dye reagent or a quartz crystal microbalance (QCM) technique, and the resulting surfaces were well-characterized using XPS, and contact angle measurements. Utilizing this approach two different surfaces have been obtained; that is, triethylenglycol oligomers and amoxicillin molecules were efficiently introduced to the dendritic surface. As a second example, mannose-decorated hydroxyl functional surfaces illustrated their potential as biosensors by multivalent detection of lectin protein at concentration as low as 5 nM.

Emneord
CLICK-CHEMISTRY, EFFICIENT SYNTHESIS, FUTURE-DIRECTIONS, DENDRIMERS, AZIDE, FILMS
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-35633 (URN)10.1021/bm200201y (DOI)000291499900019 ()21524091 (PubMedID)2-s2.0-79958779836 (Scopus ID)
Forskningsfinansiär
Swedish Research Council, 2006-3617Swedish Research Council, 2009-3259
Merknad
QC 20110704Tilgjengelig fra: 2011-07-04 Laget: 2011-07-04 Sist oppdatert: 2020-03-09bibliografisk kontrollert
3. Dual-purpose PEG scaffolds for the preparation of soft and biofunctional hydrogels: the convergence between CuAAC and thiol-ene reactions
Åpne denne publikasjonen i ny fane eller vindu >>Dual-purpose PEG scaffolds for the preparation of soft and biofunctional hydrogels: the convergence between CuAAC and thiol-ene reactions
Vise andre…
2013 (engelsk)Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, nr 62, s. 6938-6940Artikkel i tidsskrift (Fagfellevurdert) 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.

HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-125778 (URN)10.1039/c3cc42084a (DOI)000321576000002 ()23629453 (PubMedID)2-s2.0-84882247505 (Scopus ID)
Forskningsfinansiär
VinnovaSwedish Research Council, 2011-5358 2010-453
Merknad

QC 20130814

Tilgjengelig fra: 2013-08-14 Laget: 2013-08-13 Sist oppdatert: 2020-03-09bibliografisk kontrollert
4. Multipurpose heterofunctional dendritic scaffolds as crosslinkers towards functional soft hydrogels and implant adhesives in bone fracture applications
Åpne denne publikasjonen i ny fane eller vindu >>Multipurpose heterofunctional dendritic scaffolds as crosslinkers towards functional soft hydrogels and implant adhesives in bone fracture applications
Vise andre…
2013 (engelsk)Inngår i: Journal of Materials Chemistry B, ISSN 2050-7518, Vol. 1, nr 44, s. 6015-6019Artikkel i tidsskrift (Fagfellevurdert) 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).

Emneord
Azide group, Bone fracture, Cross-linkers, Muscle tissues
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-127460 (URN)10.1039/c3tb21061h (DOI)000326244900001 ()2-s2.0-84886628793 (Scopus ID)
Forskningsfinansiär
Knut and Alice Wallenberg Foundation, 2012-0196Swedish Research Council, 2011-5358 2010-453
Merknad

QC 20131128. Updated from manuscript to article in journal.

Tilgjengelig fra: 2013-08-30 Laget: 2013-08-30 Sist oppdatert: 2014-01-16bibliografisk kontrollert
5. Side-by-side comparison of dendritic-linear hybrids and their hyperbranched analogs as micellar carriers of chemotherapeutics
Åpne denne publikasjonen i ny fane eller vindu >>Side-by-side comparison of dendritic-linear hybrids and their hyperbranched analogs as micellar carriers of chemotherapeutics
Vise andre…
2013 (engelsk)Inngår i: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 51, nr 19, s. 3992-3996Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Amphiphilic block copolymers are successfully synthesized possessing a hydrophobic dendritic component based on the bis-MPA monomer and a hydrophilic linear polyethylene glycol (PEG) component. The hybrids were either conjured in small scale using robust click reactions between perfect dendrons and linear PEG or multigram polycondensation of hyperbranched blocks from PEG. In all cases, the amphiphiles were assembled to micelles, were found nontoxic and successfully loaded with the chemotherapeutic doxorubicin.

Emneord
amphiphilic, biocompatibility, 2, 2-bis(hydroxymethyl)propionic acid, bis-MPA, block copolymers, click chemistry, dendritic-linear hybrids, drug delivery, micelles, synthesis
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-127462 (URN)10.1002/pola.26825 (DOI)000323654300002 ()2-s2.0-84883208788 (Scopus ID)
Forskningsfinansiär
VinnovaSwedish Research Council, 2011-3720 2010-453 2009-3259
Merknad

QC 20131004

Tilgjengelig fra: 2013-08-30 Laget: 2013-08-30 Sist oppdatert: 2017-12-06bibliografisk kontrollert

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