Cross-Linked Hydrogels Formed through Diels–Alder Coupling of Furan- and Maleimide-Modified Poly(methyl vinyl ether-<i>alt</i>-maleic acid)

Stewart, S. Alison; Backholm, Matilda; Burke, Nicholas A. D.; Stöver, Harald D. H.

doi:10.1021/acs.langmuir.5b04450

Cited by 33 publications

(26 citation statements)

References 42 publications

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“…One solution to these challenges is the use of polymers bearing reactive functional groups for the assembly of gels. Polymers displaying reactive functionality can be easily assembled into gels by crosslinking with appropriately functionalized crosslinkers or by mixing with mutually reactive polymers . Reactive groups not used for crosslinking can subsequently be used to modify the gel .…”

Section: Introductionmentioning

confidence: 99%

“…Polymers displaying reactive functionality can be easily assembled into gels by crosslinking with appropriately functionalized crosslinkers or by mixing with mutually reactive polymers . Reactive groups not used for crosslinking can subsequently be used to modify the gel . When coupled with micropatterning techniques, such a reactive approach to hydrogel assembly would permit straightforward chemical modification of gels having a defined set of mechanical and/or topographical features.…”

Section: Introductionmentioning

confidence: 99%

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Fabrication, chemical modification, and topographical patterning of reactive gels assembled from azlactone‐functionalized polymers and a diamine

Wancura

Anex-Ries

Carroll

et al. 2017

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

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The work reported here demonstrates an approach to the fabrication of chemically reactive and topographically patterned hydrogels using the azlactone-functionalized polymer poly(2-vinyl-4,4'-dimethylazlactone) (PVDMA) and the hydrophilic diamine Jeffamine V R . Gels were initially assembled in DMSO but can be subsequently transferred into aqueous media to form hydrogels. Spectroscopic characterization of assembled gels demonstrated that variation in the stoichiometric ratio of azlactones to amines during gel synthesis permits control over the extent of crosslinking in the gels. Residual azlactones not consumed during crosslinking can be exploited to further functionalize these gels with hydrophobic, hydrophilic, and macromolecular amines that influence the physicochemical properties of these materials in aqueous solvents. The surface and bulk of these gels can be differentially functionalized (i.e., different functional groups on the gel surface relative to the bulk) by taking advantage of different rates of diffusion of macromolecular amines versus small molecule amines into assembled gels. Finally, these azlactone-functionalized gels can be topographically patterned with microwell arrays using a replica molding technique and chemically modified postfabrication with amine nucleophiles. This reactive approach to the fabrication of topographically patterned and chemically functionalized hydrogels offers a straightforward method for the rapid synthesis of micropatterned scaffolds of interest in a broad range of applications.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fabrication, chemical modification, and topographical patterning of reactive gels assembled from azlactone‐functionalized polymers and a diamine

Wancura

Anex-Ries

Carroll

et al. 2017

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

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“…The Diels‐Alder (DA) [4+2] cycloaddition reaction that occurs between an electron rich diene and an electron deficient dienophile was discovered by Otto Diels and Kurt Alder in 1928. Since its discovery, the reaction has been traditionally used in synthesis of complex natural products, and more recently has become a tool for synthesis of various functional materials and polymers . Interestingly, above a certain temperature, the DA cycloadduct readily undergoes the reverse fragmentation through the so‐called retro Diels‐Alder (rDA) reaction (Figure ).…”

Section: The Diels‐alder Reaction Based Protection‐deprotection Sequencementioning

confidence: 99%

The Taming of the Maleimide: Fabrication of Maleimide‐Containing ‘Clickable’ Polymeric Materials

Sanyal

2017

The Chemical Record

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Functional polymers are widely employed in various areas of biomedical sciences. In order to tailor them for desired applications, facile and efficient functionalization of these polymeric materials under mild and benign conditions is important. Polymers containing reactive maleimide groups can be employed for such applications since they provide an excellent handle for conjugation of thiol- and diene-containing molecules and biomolecules. Until recently, fabrication of maleimide containing polymeric materials has been challenging due to the interference from the highly reactive double bond. A Diels-Alder/retro Diels-Alder reaction sequence based strategy to transiently mask the maleimide group provides access to such polymeric materials. In this personal account, we summarize contributions from our group towards the fabrication and functionalization of maleimide-containing polymeric materials over the past decade.

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“…148, 149 The DA reaction has been exploited as an efficient strategy for hydrogel synthesis. 147, 150–157 For example, HA/PEG hydrogels with elastic moduli ranging from 275 to 680 Pa have been synthesized using furan-modified HA and PEG-bismaleimide. 152 EGF was photo-patterned into the hydrogels by two-photon technology employing a photolabile coumarin-HA-furan conjugate and iodoacetamide-functionalized EGF, thereby generating spatially defined growth factor gradients to direct cell function.…”

Section: Chemical Approaches To Hydrogel Synthesismentioning

confidence: 99%

Chemical synthesis of biomimetic hydrogels for tissue engineering

2017

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Owing to the high water content, porous structure, biocompatibility and tissue-like viscoelasticity, hydrogels have become attractive and promising biomaterials for use in drug delivery, 3D cell culture and tissue engineering applications. Various chemical approaches have been developed for hydrogel synthesis using monomers or polymers carrying reactive functional groups. For in vivo tissue repair and in vitro cell culture purposes, it is desirable that the crosslinking reactions occur under mild conditions, do not interfere with biological processes and proceed at high yield with exceptional selectivity. Additionally, the cross-linking reaction should allow straightforward incorporation of bioactive motifs or signaling molecules, at the same time, providing tunability of the hydrogel microstructure, mechanical properties, and degradation rates. In this review, we discuss various chemical approaches applied to the synthesis of complex hydrogel networks, highlighting recent developments from our group. The discovery of new chemistries and novel materials fabrication methods will lead to the development of the next generation biomimetic hydrogels with complex structures and diverse functionalities. These materials will likely facilitate the construction of engineered tissue models that may bridge the gap between 2D experiments and animal studies, providing preliminary insight prior to in vivo assessments.

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Cross-Linked Hydrogels Formed through Diels–Alder Coupling of Furan- and Maleimide-Modified Poly(methyl vinyl ether-alt-maleic acid)

Cited by 33 publications

References 42 publications

Fabrication, chemical modification, and topographical patterning of reactive gels assembled from azlactone‐functionalized polymers and a diamine

Fabrication, chemical modification, and topographical patterning of reactive gels assembled from azlactone‐functionalized polymers and a diamine

The Taming of the Maleimide: Fabrication of Maleimide‐Containing ‘Clickable’ Polymeric Materials

Chemical synthesis of biomimetic hydrogels for tissue engineering

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