| 1. |
- Andrén, Oliver C. J., et al.
(författare)
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Therapeutic Nanocarriers via Cholesterol Directed Self-Assembly of Well-Defined Linear-Dendritic Polymeric Amphiphiles
- 2017
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Ingår i: Chemistry of Materials. - : American Chemical Society (ACS). - 0897-4756 .- 1520-5002. ; 29:9, s. 3891-3898
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Tidskriftsartikel (refereegranskat)abstract
- A novel platform of fluorescently labeled nanocarriers (NCs) is herein proposed based on amphiphilic linear-dendritic polymeric hybrids. These sophisticated polymers were synthesized with a high degree of structural control at a macro-molecular level, displayed hydrophobic cholesterol compartments as chain-terminus groups of the dendritic block and hydrophilic bifunctional linear poly(ethylene glycol) (PEG) block. Spherical supramolecular assemblies with therapeutically relevant properties were successfully achieved including (i) sizes in the region of 100 to 200 nm; (ii) narrow dispersity profile with values close to 0.12; and (iii) self-assembly down to nanomolar concentrations. The modular nature of the NCs permitted the encapsulation of single or dual anticancer drugs and in parallel provide intracellular fluorescent traceability. As polymer therapeutics, the NCs were proven to penetrate the cancerous cell membranes and deliver the cargo of drugs into the nuclei as well as the cytoplasm and mitochondria. The dual drug delivery of both doxorubicin (DOX) and triptolide substantially enhanced the therapeutic efficacy with a 63% significant increase against resistant breast cancer cells when compared to free DOX.
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| 2. |
- Antoni, Per, et al.
(författare)
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Pushing the Limits for Thiol-Ene and CuAAC Reactions : Synthesis of a 6th Generation Dendrimer in a Single Day
- 2010
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Ingår i: Macromolecules. - : American Chemical Society (ACS). - 0024-9297 .- 1520-5835. ; 43:16, s. 6625-6631
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Tidskriftsartikel (refereegranskat)abstract
- Dendrimer synthesis should not be tedious and time-consuming. By utilizing an AB(2)-CD2 approach and having orthogonal, "clickable" groups on each monomer, the time for dendrimer assembly can be drastically reduced. This was shown by preparation of a sixth generation dendrimer from starting monomer units in a single day.
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| 3. |
- Kang, Taegon, et al.
(författare)
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Facile access to internally functionalized dendrimers through efficient and orthogonal click reactions
- 2010
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Ingår i: Chemical Communications. - : Royal Society of Chemistry (RSC). - 1359-7345 .- 1364-548X. ; 46:9, s. 1556-1558
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Tidskriftsartikel (refereegranskat)abstract
- A simple synthetic strategy has been developed for accessing internally functionalized dendrimers. The key feature of this approach is the use of two orthogonal and efficient reactions` epoxy-amine' and 'thiol-ene' coupling-for rapid growth of the dendritic scaffold. This sequence of reactions allows for the introduction of reactive hydroxyl groups at each dendritic layer.
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| 4. |
- Lo Conte, Mauro, et al.
(författare)
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Exhaustive Glycosylation, PEGylation, and Glutathionylation of a [G4]-ene(48) Dendrimer via Photoinduced Thiol-ene Coupling
- 2011
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Ingår i: Journal of Polymer Science Part A. - : Wiley. - 0887-624X .- 1099-0518. ; 49:20, s. 4468-4475
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Tidskriftsartikel (refereegranskat)abstract
- The use of free-radical thiol-ene coupling (TEC) for the introduction of carbohydrate, poly(ethylene glycol), and peptide fragments at the periphery of an alkene functional dendrimer has been reported in this article. Four different sugar thiols including glucose, mannose, lactose, and sialic acid, two PEGylated thiols, and the natural tripeptide glutathione were reacted with a fourth generation alkene functional dendrimer [G4]-ene(48) on irradiation at lambda(max) 365 nm. In all cases, the (1)H NMR spectra of the crude reaction mixture revealed the complete disappearance of alkene proton signals indicating the quantitative conversion of all 48 alkene groups of the dendrimer. With one exception only, all dendrimer conjugates were isolated in high yields (70-94%), validating the high efficiency of multiple TEC reactions on a single substrate. All isolated and purified compounds were analyzed by matrix assisted laser desorption ionization-time of flight (MALDI-TOF) spectrometry and gave spectra consistent with the assigned structure.
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| 5. |
- Robb, Maxwell J., et al.
(författare)
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Thiol-ene approaches to dendrimer synthesis
- 2010
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Ingår i: Abstracts of Papers of the American Chemical Society. - : AMER CHEMICAL SOC. - 0065-7727. ; 240
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Tidskriftsartikel (övrigt vetenskapligt/konstnärligt)
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| 6. |
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| 7. |
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| 8. |
- Carlmark, Anna, et al.
(författare)
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New methodologies in the construction of dendritic materials
- 2009
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Ingår i: Chemical Society Reviews. - : Royal Society of Chemistry (RSC). - 0306-0012 .- 1460-4744. ; 38:2, s. 352-362
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Forskningsöversikt (refereegranskat)abstract
- Dendritic polymers are highly branched polymer structures, with complex, secondary architectures and well-defined spatial location of functional groups. Due to their unique physical and chemical features, applications in areas such as targeted drug-delivery, macromolecular carriers, catalysis, sensors, light harvesting, surface engineering and biomimetic materials have been proposed. However, only a few dendritic materials have been exploited commercially due to time consuming syntheses and the generation of significant waste/presence of unreacted starting materials. This tutorial review describes traditional synthesis of dendritic materials as well as recent advances in synthetic strategies, for example the use of Click chemistry, as a tool to efficiently obtain complex, functional dendritic structures.
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| 9. |
- Dukette, Tiffany E, et al.
(författare)
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Conformation of intramolecularly cross-linked polymer nanoparticles on solid substrates
- 2005
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Ingår i: Nano letters (Print). - : American Chemical Society (ACS). - 1530-6984 .- 1530-6992. ; 5:9, s. 1704-1709
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Tidskriftsartikel (refereegranskat)abstract
- The conformation of cross-linked, monomolecular, polystyrene nanoparticles on a solid substrate is considered as a function of cross-linking degree and substrate surface free energy. It is found that an extreme amount of cross-linking is necessary for the ca. 5-10 nm diameter nanoparticles to retain their original spherical shape, regardless of surface free energy. A lesser amount of cross-linking produces a nanoparticle that collapses to a pancake-like conformation on a high-energy substrate yet remains spherical on a low-energy surface. A simple model is developed to reveal the relationship between nanoparticle modulus and surface free energy to define the nanoparticle conformation.
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| 10. |
- Hagberg, Erik C., et al.
(författare)
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Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting
- 2007
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Ingår i: Nano letters (Print). - : American Chemical Society (ACS). - 1530-6984 .- 1530-6992. ; 7:2, s. 233-237
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Tidskriftsartikel (refereegranskat)abstract
- Thiol-ene photopolymers were studied as patternable resins for nanocontact molding imprint lithography. Photopolymerizable thiol and ene monomer mixtures were used, and after molding, patterned thiol-ene polymer features the size and shape of the original molds were replicated. Adhesion and release were examined and controlled by manipulating the surface chemistry of the substrate and mold. A direct correlation between cured thiol-ene polymer modulus and pattern fidelity was observed.
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| 11. |
- Khan, Anzar, et al.
(författare)
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Synthesis and characterization of hyperbranched polymers with increased chemical versatility for imprint lithographic resists
- 2008
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Ingår i: Journal of Polymer Science Part A. - : Wiley. - 0887-624X .- 1099-0518. ; 46:18, s. 6238-6254
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Tidskriftsartikel (refereegranskat)abstract
- Hyperbranched polymers were prepared from a variety of mono- and difunctional monomers and used in the development of novel UV-imprint lithography (UV-IL) resists. The unique physical and chemical properties of these hyperbranched materials significantly increase the range of molecular systems that could be imprinted. Traditional challenges, such as the use of monomers that have low boiling points or the use of insoluble/highly crystalline momomers, are overcome by the preparation of hyperbranched polymers that incorporate these repeat units. In addition, the low viscosity of the hyperbranched macromolecules and the large number of reactive chain ends overcome many difficulties that are traditionally associated with the use of polymeric materials as imprint resists. Hyperbranched polymers containing up to 12 mol % pendant vinyl groups, needed for secondary crosslinking during imprinting, were prepared with a wide range of repeat unit structures and successfully imprinted with features from tens of microns to similar to 100 nm.
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| 12. |
- Lundberg, Pontus, et al.
(författare)
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Click assisted one-pot multi-step reactions in polymer science : Accelerated synthetic Protocols
- 2008
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Ingår i: Macromolecular rapid communications. - : Wiley. - 1022-1336 .- 1521-3927. ; 29:12-13, s. 998-1015
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Forskningsöversikt (refereegranskat)abstract
- Presently, the majority of reports deal with combining chemical reactions, in a stepwise fashion, to obtain well-defined polymers. In the future, chemists need to address new challenges such as increase in the range of available efficient reactions, developing libraries of compatible one-pot reactions, and the application of obtained materials in key industries. Indeed, the rising importance of the click concept has now devised robust synthetic approaches in various fields of research. The unique selectivity of the click reaction is today a new found toolbox for scientists to investigate one-pot multi-step systems. Several accelerated protocols have elegantly been reported to obtain a library of advanced polymers.
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| 13. |
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| 14. |
- Lundberg, Pontus, et al.
(författare)
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pH-triggered self-assembly of biocompatible histamine-functionalized triblock copolymers
- 2013
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Ingår i: Soft Matter. - : Royal Society of Chemistry (RSC). - 1744-683X .- 1744-6848. ; 9:1, s. 82-89
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Tidskriftsartikel (refereegranskat)abstract
- Histamine functionalized poly(allyl glycidyl ether)-b-poly(ethylene glycol)-b-poly(allyl glycidyl ether) (PAGE-PEO-PAGE) triblock copolymers represent a new class of physically cross-linked, pH-responsive hydrogels with significant potential for biomedical applications. These telechelic triblock copolymers exhibited abrupt and reversible hydrogelation above pH 7.0 due to a hydrophilic/hydrophobic transition of the histamine units to form a network of hydrophobic domains bridged by a hydrophilic PEO matrix. These hydrophobic domains displayed improved ordering upon increasing pH and self-assembled into a body centered cubic lattice at pH 8.0, while at lower concentrations formed well-defined micelles. Significantly, all materials were found to be non-toxic when evaluated on three different cell lines and suggests a range of medical and biomedical applications.
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| 15. |
- Malkoch, Michael, et al.
(författare)
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Synthesis of well-defined hydrogel networks using Click chemistry
- 2006
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Ingår i: Chemical Communications. - 1359-7345 .- 1364-548X. ; :26, s. 2774-2776
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Tidskriftsartikel (refereegranskat)abstract
- New PEG-based hydrogel materials have been synthesized by Click chemistry and shown to result in well-defined networks having significantly improved mechanical properties; the selectivity of the azide/ acetylene coupling reaction also allows for the incorporation of various additives and functional groups leading to chemical tailoring of the hydrogels.
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| 16. |
- Montanez, Maria I., et al.
(författare)
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Accelerated Growth of Dendrimers via Thiol-Ene and Esterification Reactions
- 2010
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Ingår i: Macromolecules. - : American Chemical Society (ACS). - 0024-9297 .- 1520-5835. ; 43:14, s. 6004-6013
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Tidskriftsartikel (refereegranskat)abstract
- By taking advantage of the orthogonal nature of thiol-ene coupling and anhydride based esterification reactions, a facile and chemoselective strategy to dendritic macromolecules has been developed The ability to interchange growth steps based on thiol-ene and anhydride chemistry allows the synthesis of fifth-generation dendrimers in only five steps and under benign reaction conditions In addition, the presented coupling chemistries eliminate the traditional need for protection/deprotection steps and afford dendrimers in high yield and purity The modularity of this strategy coupled with the latent reactivity of the alkene/hydroxyl chain ends was demonstrated by using different cores (alkene and hydroxyl functional), various AB(2) and CD2 monomers and a range of chain end groups As a result, three dendritic libraries were prepared which exhibited tunability of both the chemical functionality and physical properties including the fabrication of PEG hydrogels.
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| 17. |
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| 18. |
- Vestberg, Robert, et al.
(författare)
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A General Strategy for Highly Efficient Nanoparticle Dispersing Agents Based on Hybrid Dendritic Linear Block Copolymers
- 2009
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Ingår i: Journal of Polymer Science Part A. - : Wiley. - 0887-624X .- 1099-0518. ; 47:5, s. 1237-1258
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Tidskriftsartikel (refereegranskat)abstract
- A modular approach to the synthesis of a library of hybrid dendriticlinear copolymers was developed based on RAFT polymerization from monodisperse dendritic macroRAFT agents. By accurately controlling the molecular weight of the linear block, generation number of the dendrimer and the nature of the dendritic chains ends, the performance of these hybrid block copolymers as dispersing agents was optimized for a range of nanoparticles. For titanium dioxide nanoparticles, dispersion in a poly(methyl methacrylate) matrix was maximized with a second generation dendrimer containing four carboxylic acid end groups, and the quality of dispersion was observed to be superior to commercial dispersing agents for TiO2. This approach also allowed novel hybrid dendritic-linear dispersing agents to be prepared for the dispersion of Au and CdSe nanoparticles based on disulphide and phosphine oxide end groups, respectively.
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| 19. |
- Vestberg, Robert, et al.
(författare)
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Role of architecture and molecular weight in the formation of tailor-made ultrathin multilayers using dendritic macromolecules and click chemistry
- 2007
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Ingår i: Journal of Polymer Science Part A. - : Wiley. - 0887-624X .- 1099-0518. ; 45:14, s. 2835-2846
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Tidskriftsartikel (refereegranskat)abstract
- The high efficiency and mild reaction conditions associated with the Cu(I) catalyzed cycloaddition of azides and alkynes were exploited for the covalent layer-by-layer synthesis of dendritic thin films on silicon wafers. The preparation of azide and alkyne-terminated dendrimers based on bisMPA was accomplished by a divergent strategy; combinations of these monodisperse building blocks from the 2nd to the 5th generation were used for construction of the thin films. The layer-by-layer self assembly process proceeds under ambient conditions and was monitored by ellipsometry, XPS, and ATR-IR, which showed extremely regular growth of the dendritic thin films. Film thickness could be accurately controlled by both the size/generation number of the dendrimers as well as the number of layers. In comparison with linear analogues, the growth of the dendritic films was significantly more controlled and defect-free with each layer being thinner than the corresponding films prepared from the isomeric linear polymers, demonstrating the well-defined, three-dimensional nature of the dendritic architecture.
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| 20. |
- Wu, Peng, et al.
(författare)
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Multivalent, bifunctional dendrimers prepared by click chemistry
- 2005
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Ingår i: Chemical Communications. - : Royal Society of Chemistry (RSC). - 1359-7345 .- 1364-548X. ; :46, s. 5775-5777
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Tidskriftsartikel (refereegranskat)abstract
- Unsymmetrical dendrimers, containing both mannose binding units and coumarin fluorescent units, have been prepared using click chemistry and shown to be highly efficient, dual-purpose recognition/detection agents for the inhibition of hemagglutination.
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| 21. |
- Zhang, Yuning, et al.
(författare)
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Histamine-functionalized copolymer micelles as a drug delivery system in 2D and 3D models of breast cancer
- 2015
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Ingår i: Journal of materials chemistry. B. - : Royal Society of Chemistry (RSC). - 2050-750X .- 2050-7518. ; 3:12, s. 2472-2486
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Tidskriftsartikel (refereegranskat)abstract
- Histamine functionalized block copolymers based on poly(allyl glycidyl ether)-b-poly(ethylene oxide) (PAGE-b-PEO) were prepared with different ratios of histamine and octyl or benzyl groups using UV-initiated thiol-ene click chemistry. At neutral pH, the histamine units are uncharged and hydrophobic, while in acidic environments, such as in the endosome, lysosomes, or extracellular sites of tumours, the histamine groups are positively charged and hydrophilic. pH responsible polymer drug delivery systems is a promising route to site specific delivery of drugs and offers the potential to avoid side effects of systemic treatment. Our detailed in vitro experiments of the efficacy of drug delivery and the intracellular localization characteristics of this library of NPs in 2D and 3D cultures of breast cancer revealed that the 50% histamine-modified polymer loaded with DOX exhibited rapid accumulation in the nucleus of free DOX within 2 h. Confocal studies showed enhanced mitochondrial localization and lysosomal escape when compared to controls. From these combined studies, it was shown that by accurately tuning the structure of the initial block copolymers, the resulting self-assembled NPs can be designed to exploit histamine as an endosomal escape trigger and the octyl/benzyl units give rise to a hydrophobic core resulting in highly efficacious drug delivery systems (DDS) with control over intracellular localization. Optimization and rational control of the intracellular localization of both DDS and the parent drug can give nanomedicines a substantial increase in efficacy and should be explored in future studies.
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