Diels−Alder Click Cross-Linked Hyaluronic Acid Hydrogels for Tissue Engineering

Nimmo, Chelsea M.; Owen, Shawn C.; Shoichet, Molly S.

doi:10.1021/bm101446k

Cited by 377 publications

(337 citation statements)

References 100 publications

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“…In this case, users may consider using non-photoinitiated materials systems, such as azide-alkyne, 12 FXIII, 31 or Diels Alder-based hydrogel formation chemistries. 33 Facile techniques to detect and quantify patterning of biochemical cues within gels also are presented (3.1 and 3.2). Ellman's assay is of particular interest because the reagents are commercially available and no extra synthetic processing steps or more expensive reagents (e.g., fluorescently-labeled peptide) are required.…”

Section: Discussionmentioning

confidence: 99%

Light-mediated Formation and Patterning of Hydrogels for Cell Culture Applications

Sawicki

Kloxin

2016

JoVE

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Click chemistries have been investigated for use in numerous biomaterials applications, including drug delivery, tissue engineering, and cell culture. In particular, light-mediated click reactions, such as photoinitiated thiol−ene and thiol−yne reactions, afford spatiotemporal control over material properties and allow the design of systems with a high degree of user-directed property control. Fabrication and modification of hydrogel-based biomaterials using the precision afforded by light and the versatility offered by these thiol−X photoclick chemistries are of growing interest, particularly for the culture of cells within well-defined, biomimetic microenvironments. Here, we describe methods for the photoencapsulation of cells and subsequent photopatterning of biochemical cues within hydrogel matrices using versatile and modular building blocks polymerized by a thiol−ene photoclick reaction. Specifically, an approach is presented for constructing hydrogels from allyloxycarbonyl (Alloc)-functionalized peptide crosslinks and pendant peptide moieties and thiol-functionalized poly(ethylene glycol) (PEG) that rapidly polymerize in the presence of lithium acylphosphinate photoinitiator and cytocompatible doses of long wavelength ultraviolet (UV) light. Facile techniques to visualize photopatterning and quantify the concentration of peptides added are described. Additionally, methods are established for encapsulating cells, specifically human mesenchymal stem cells, and determining their viability and activity. While the formation and initial patterning of thiol-alloc hydrogels are shown here, these techniques broadly may be applied to a number of other light and radical-initiated material systems (e.g., thiol-norbornene, thiol-acrylate) to generate patterned substrates.

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Section: Discussionmentioning

confidence: 99%

Light-mediated Formation and Patterning of Hydrogels for Cell Culture Applications

Sawicki

Kloxin

2016

JoVE

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“…Commonly used conditions to trigger in situ crosslinking include: (1) exposure to a specific wavelength of light [Piantino et al, 2006;Khaing et al, 2011], temperature [Gupta et al, 2006;Bearat et al, 2012], or pH [Prang et al, 2006;Pawar et al, 2015b], and (2) combining two separate components that spontaneously react upon mixing [Johnson et al, 2010a;Nimmo et al, 2011;Liang et al, 2013;Führmann et al, 2015;Kim et al, 2016]. In situ crosslinking of hydrogels in response to various triggers has been achieved by covalent chemistries (e.g.…”

Section: Fabrication Strategies For Injectable Hydrogelsmentioning

confidence: 99%

“…Nonphoto-induced 'click' reactions (e.g. Diels-Alder type) also proceed by stepgrowth polymerization, enabling more controlled network formation [Hiemstra et al, 2007;Nimmo et al, 2011;Shih and Lin, 2012;Azagarsamy and Anseth, 2013 Führmann et al [2015] used HA-based hydrogels produced using a nonphoto-induced click chemistry. The authors reported that these hydrogels swelled to 40-60% of their original mass and did not cause any damage to the spinal cord after intrathecal injection and in situ formation.…”

Section: Fabrication Strategies For Injectable Hydrogelsmentioning

confidence: 99%

Injectable Hydrogels for Spinal Cord Repair: A Focus on Swelling and Intraspinal Pressure

Khaing

Ehsanipour

Hofstetter

et al. 2016

Cells Tissues Organs

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Spinal cord injury (SCI) is a devastating condition that leaves patients with limited motor and sensory function at and below the injury site, with little to no hope of a meaningful recovery. Because of their ability to mimic multiple features of central nervous system (CNS) tissues, injectable hydrogels are being developed that can participate as therapeutic agents in reducing secondary injury and in the regeneration of spinal cord tissue. Injectable biomaterials can provide a supportive substrate for tissue regeneration, deliver therapeutic factors, and regulate local tissue physiology. Recent reports of increasing intraspinal pressure after SCI suggest that this physiological change can contribute to injury expansion, also known as secondary injury. Hydrogels contain high water content similar to native tissue, and many hydrogels absorb water and swell after formation. In the case of injectable hydrogels for the spinal cord, this process often occurs in or around the spinal cord tissue, and thus may affect intraspinal pressure. In the future, predictable swelling properties of hydrogels may be leveraged to control intraspinal pressure after injury. Here, we review the physiology of SCI, with special attention to the current clinical and experimental literature, underscoring the importance of controlling intraspinal pressure after SCI. We then discuss how hydrogel fabrication, injection, and swelling can impact intraspinal pressure in the context of developing injectable biomaterials for SCI treatment.

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“…[25] In a recent study, Shoichet and co-workers reported the synthesis of hyaluronic acid (HA) based hydrogels by the Diels-Alder reaction. [26] Furan appended HA derivatives were crosslinked with bis-maleimide PEG polymers in aqueous media (Figure 14). The hydrogels showed excellent cytocompatibility with cell survivals > 98 % after 14 days in culture.…”

Section: Hydrogels Through Diels-alder Click Reactionmentioning

confidence: 99%

Fabrication and Functionalization of Hydrogels through “Click” Chemistry

Yiğit

Sanyal

2011

Chemistry An Asian Journal

121

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On the occasion of the 10th anniversary of click chemistry FOCUS REVIEWSAbstract: Hydrogels are crosslinked polymeric materials that play a vital role in many biomedical areas such as drug delivery, sensor technology, and tissue engineering. Increasing demand of these materials for such advanced applications has necessitated the development of hydrogels with complex chemical compositions such as incorporating small molecules and biomolecules that provide the functional attributes. This Focus Review highlights the tremendous impact of click chemistry on the design, synthesis, and functionalization of hydrogels. The high efficiency and fidelity of the click reactions have enabled rapid and modular synthesis of hydrogels with near-ideal network structures. Efficient incorporation of biomolecular building blocks, such as peptide sequences either during or after the fabrication of hydrogels, have been achieved through various click reactions. Utilization of these efficient reactions has led to the fabrication of many stimuli-responsive or 'smart' hydrogels in recent years.

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Diels−Alder Click Cross-Linked Hyaluronic Acid Hydrogels for Tissue Engineering

Cited by 377 publications

References 100 publications

Light-mediated Formation and Patterning of Hydrogels for Cell Culture Applications

Light-mediated Formation and Patterning of Hydrogels for Cell Culture Applications

Injectable Hydrogels for Spinal Cord Repair: A Focus on Swelling and Intraspinal Pressure

Fabrication and Functionalization of Hydrogels through “Click” Chemistry

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