Emulsion-templated porous polymers prepared by thiol-ene and thiol-yne photopolymerisation using multifunctional acrylate and non-acrylate monomers

Chen, Chaoyi; Eissa, Ahmed M.; Schiller, Tara L.; Cameron, Neil R.

doi:10.1016/j.polymer.2017.04.021

Cited by 43 publications

(33 citation statements)

References 34 publications

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“…Functionalization via this method allows for better control over the morphology and pore diameter of the polyHIPE. In the case of thiol-acrylate polyHIPEs, homopolymerization of acrylate monomers leads to materials bearing residual thiol groups, 36,37 since acrylate groups are consumed more rapidly (Fig. 1).…”

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confidence: 99%

Optimized peptide functionalization of thiol‐acrylate emulsion‐templated porous polymers leads to expansion of human pluripotent stem cells in 3D culture

Ratcliffe

Walker

Eissa

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Highly porous polymers produced by polymerization of the continuous phase of a high internal phase emulsion have been developed as scaffolds for 3D culture of human pluripotent stem cells. These emulsion‐templated polymerized high internal phase emulsion (polyHIPE) materials have an interconnected network of pores that provide support for the cells, while also allowing both cell ingress and nutrient diffusion. Thiol‐acrylate polyHIPE materials were prepared by photopolymerization, which, due to a competing acrylate homopolymerization process, leads to a material with residual surface thiols. These thiols were then used as a handle to allow postpolymerization functionalization with both maleimide and a maleimide‐derivatized cyclo‐RGDfK peptide, via Michael addition under benign conditions. Functionalization was evaluated using an Ellman's colorimetric assay, to monitor the residual thiol concentration, and X‐ray photoelectron spectroscopy. Maleimide was used as a model molecule to optimize conditions prior to peptide‐functionalization. The use of triethylamine as a catalyst and a mixed ethanol‐aqueous solvent system led to optimized reaction between surface‐bound thiols and maleimide. Peptide‐functionalized materials showed improved attachment and infiltration of human pluripotent stem cells over 7 days, demonstrating their promise as a scaffold for 3D stem cell culture and expansion. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1974–1981

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confidence: 99%

Optimized peptide functionalization of thiol‐acrylate emulsion‐templated porous polymers leads to expansion of human pluripotent stem cells in 3D culture

Ratcliffe

Walker

Eissa

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…The parent material that we have chosen to functionalize is a thiol‐acrylate polyHIPE that has been previously reported . TMPTMP and TMPTA were utilized to prepare a HIPE that was subsequently photopolymerized, producing polyHIPE materials of 80% porosity with a well‐defined morphology, determined by the aqueous internal phase.…”

Section: Resultsmentioning

confidence: 99%

“…The majority of polyHIPE materials are synthesized by free radical polymerization initiated either thermally or photochemically; however, other methods have been reported . PolyHIPE materials are versatile due to the ability to tune their chemical, physical, and mechanical properties by careful choice of monomers . These materials are attractive due to their high level of control over porosity and pore diameter, which are essential characteristics when developing scaffolds for tissue engineering.…”

Section: Introductionmentioning

confidence: 99%

Covalent Attachment of Fibronectin onto Emulsion‐Templated Porous Polymer Scaffolds Enhances Human Endometrial Stromal Cell Adhesion, Infiltration, and Function

RICHARDSON

Rawlings

Muter

et al. 2018

Macromolecular Bioscience

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A novel strategy for the surface functionalization of emulsion‐templated highly porous (polyHIPE) materials as well as its application to in vitro 3D cell culture is presented. A heterobifunctional linker that consists of an amine‐reactive N‐hydroxysuccinimide ester and a photoactivatable nitrophenyl azide, N‐sulfosuccinimidyl‐6‐(4′‐azido‐2′‐nitrophenylamino)hexanoate (sulfo‐SANPAH), is utilized to functionalize polyHIPE surfaces. The ability to conjugate a range of compounds (6‐aminofluorescein, heptafluorobutylamine, poly(ethylene glycol) bis‐amine, and fibronectin) to the polyHIPE surface is demonstrated using fluorescence imaging, FTIR spectroscopy, and X‐ray photoelectron spectroscopy. Compared to other existing surface functionalization methods for polyHIPE materials, this approach is facile, efficient, versatile, and benign. It can also be used to attach biomolecules to polyHIPE surfaces including cell adhesion‐promoting extracellular matrix proteins. Cell culture experiments demonstrated that the fibronectin‐conjugated polyHIPE scaffolds improve the adhesion and function of primary human endometrial stromal cells. It is believed that this approach can be employed to produce the next generation of polyHIPE scaffolds with tailored surface functionality, enhancing their application in 3D cell culture and tissue engineering whilst broadening the scope of applications to a wider range of cell types.

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“…With the increasing the amount of elastomeric monomers such as EHA, the glass transition temperature of the polymer decreases . The use of the reversible addition‐fragmentation chain transfer reaction results in residual catalysts, while residual thiol functionalities remains in thiol‐ene chemistry and both of these reactions are slow . Postpolymerization hypercrosslinking requires additional processing.…”

Section: Introductionmentioning

confidence: 99%

GMA‐based emulsion‐templated solid foams: Influence of co‐crosslinker on morphology and mechanical properties

Rezanavaz

Fee

Dimartino

2018

J of Applied Polymer Sci

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Highly open porous polymer foams formed from high internal phase emulsions (polyHIPEs) are attracting significant interest because of their potential applications in many areas of advanced materials science. In this work, the influence of the crosslinker or co-crosslinkers of different molecular weights on the morphology and mechanical properties of polyHIPEs containing glycidyl methacrylate (GMA) was studied. Several poly(ethylene glycol) dimethacrylate (PEGDMA) crosslinkers were considered. The results show that introducing higher molecular weight crosslinkers into polyHIPEs produces a more open structure, with significantly increased compression strength and deformation at breakage. This eliminated the undesirable brittleness and chalkiness commonly found in polyHIPE materials. The Young's modulus of GMA-based polyHIPEs containing 40% poly(ethylene glycol) dimethacrylate increased by 50% and the crush strength by 400% when compared with traditional GMA/ethylene glycol dimethylacrylate polyHIPEs. This improvement in mechanical properties is expected to improve the suitability of polyHIPEs for use in a wide range of applications.

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Emulsion-templated porous polymers prepared by thiol-ene and thiol-yne photopolymerisation using multifunctional acrylate and non-acrylate monomers

Abstract: Emulsiontemplated porous polymers prepared by thiol-ene and thiol-yne photopolymerisation using multifunctional acrylate and non-acrylate monomers. Polymer, 126. pp. 395-401.

Cited by 43 publications

References 34 publications

Optimized peptide functionalization of thiol‐acrylate emulsion‐templated porous polymers leads to expansion of human pluripotent stem cells in 3D culture

Optimized peptide functionalization of thiol‐acrylate emulsion‐templated porous polymers leads to expansion of human pluripotent stem cells in 3D culture

Covalent Attachment of Fibronectin onto Emulsion‐Templated Porous Polymer Scaffolds Enhances Human Endometrial Stromal Cell Adhesion, Infiltration, and Function

GMA‐based emulsion‐templated solid foams: Influence of co‐crosslinker on morphology and mechanical properties

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