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Poly(ε-caprolactone) Dendrimer Cross-Linked via Metal-Free Click Chemistry: Injectable Hydrophobic Platform for Tissue Engineering.

ABSTRACT: The fabrication of injectable self-cross-linkable hyperbranched poly(ε-caprolactone) (hyPCL) formulation using metal-free click chemistry was reported. The cross-linking between hyPCL32-(1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethanol (hyPCL32-BCN) and hyPCL32-azide (hyPCL32-N₃) components was proceeded via strain-promoted alkyne-azide cycloaddition (SPAAC) click reaction. Cross-linking was tested to proceed effectively with the exclusion of any toxic cross-linking agents. Strong mechanical properties and excellent biocompatibility were demonstrated for the cross-linked substrates. These newly synthesized dendrimers may have broad applications in tissue engineering such as bone defect repair. In addition, the introduction of metal-free click chemistry to hydrophobic polymers provides an attractive new strategy for developing injectable stiff polymer formulations besides hydrogels for biomedical applications.

SUBMITTER: Liu X

PROVIDER: S-EPMC9271263 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Poly(ε-caprolactone) Dendrimer Cross-Linked via Metal-Free Click Chemistry: Injectable Hydrophobic Platform for Tissue Engineering.

Liu Xifeng X Miller A Lee AL Fundora Kevin A KA Yaszemski Michael J MJ Lu Lichun L

ACS macro letters 20161031 11

The fabrication of injectable self-cross-linkable hyperbranched poly(ε-caprolactone) (hyPCL) formulation using metal-free click chemistry was reported. The cross-linking between hyPCL32-(1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethanol (hyPCL32-BCN) and hyPCL32-azide (hyPCL32-N<sub>3</sub>) components was proceeded via strain-promoted alkyne-azide cycloaddition (SPAAC) click reaction. Cross-linking was tested to proceed effectively with the exclusion of any toxic cross-linking agents. Strong mechan ...[more]

PMID: 35614737

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Project description:3D-printed bone scaffolds hold great promise for the individualized treatment of critical-size bone defects. Among the resorbable polymers available for use as 3D-printable scaffold materials, poly(ε-caprolactone) (PCL) has many benefits. However, its relatively low stiffness and lack of bioactivity limit its use in load-bearing bone scaffolds. This study tests the hypothesis that surface-oxidized cellulose nanocrystals (SO-CNCs), decorated with carboxyl groups, can act as multi-functional scaffold additives that (1) improve the mechanical properties of PCL and (2) induce biomineral formation upon PCL resorption. To this end, an in vitro biomineralization study was performed to assess the ability of SO-CNCs to induce the formation of calcium phosphate minerals. In addition, PCL nanocomposites containing different amounts of SO-CNCs (1, 2, 3, 5, and 10 wt%) were prepared using melt compounding extrusion and characterized in terms of Young's modulus, ultimate tensile strength, crystallinity, thermal transitions, and water contact angle. Neither sulfuric acid-hydrolyzed CNCs (SH-CNCs) nor SO-CNCs were toxic to MC3T3 preosteoblasts during a 24 h exposure at concentrations ranging from 0.25 to 3.0 mg/mL. SO-CNCs were more effective at inducing mineral formation than SH-CNCs in simulated body fluid (1x). An SO-CNC content of 10 wt% in the PCL matrix caused a more than 2-fold increase in Young's modulus (stiffness) and a more than 60% increase in ultimate tensile strength. The matrix glass transition and melting temperatures were not affected by the SO-CNCs but the crystallization temperature increased by about 5.5°C upon addition of 10 wt% SO-CNCs, the matrix crystallinity decreased from about 43 to about 40%, and the water contact angle decreased from 87 to 82.6°. The abilities of SO-CNCs to induce calcium phosphate mineral formation and increase the Young's modulus of PCL render them attractive for applications as multi-functional nanoscale additives in PCL-based bone scaffolds.

Project description:Vascular endothelial growth factor (VEGF) is the major regulating factor for the formation of new blood vessels, also known as angiogenesis. VEGF is often incorporated in synthetic scaffolds to promote vascularization and to enhance the survival of cells that have been seeded in these devices. Such applications require sustained local delivery of VEGF of around 4 weeks for stable blood vessel formation. Most delivery systems for VEGF only provide short-term release for a couple of days, followed by a release phase with very low VEGF release. We now have developed VEGF-loaded polymeric microspheres that provide sustained release of bioactive VEGF for 4 weeks. Blends of two swellable poly(ε-caprolactone)-poly(ethylene glycol)-poly(ε-caprolactone)-b-poly(l-lactide) ([PCL-PEG-PCL]-b-[PLLA])-based multiblock copolymers with different PEG content and PEG molecular weight were used to prepare the microspheres. Loading of the microspheres was established by a solvent evaporation-based membrane emulsification method. The resulting VEGF-loaded microspheres had average sizes of 40-50 μm and a narrow size distribution. Optimized formulations of a 50:50 blend of the two multiblock copolymers had an average VEGF loading of 0.79 ± 0.09%, representing a high average VEGF loading efficiency of 78 ± 16%. These microspheres released VEGF continuously over 4 weeks in phosphate-buffered saline pH 7.4 at 37 °C. This release profile was preserved after repeated and long-term storage at -20 °C for up to 9 months, thereby demonstrating excellent storage stability. VEGF release was governed by diffusion through the water-filled polymer matrix, depending on PEG molecular weight and PEG content of the polymers. The bioactivity of the released VEGF was retained within the experimental error in the 4-week release window, as demonstrated using a human umbilical vein endothelial cells proliferation assay. Thus, the microspheres prepared in this study are suitable for embedment in polymeric scaffolds with the aim of promoting their functional vascularization.

Dataset Information

Poly(ε-caprolactone) Dendrimer Cross-Linked via Metal-Free Click Chemistry: Injectable Hydrophobic Platform for Tissue Engineering.

Publications

Poly(ε-caprolactone) Dendrimer Cross-Linked via Metal-Free Click Chemistry: Injectable Hydrophobic Platform for Tissue Engineering.

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