<i>In Situ</i> Supramolecular Assembly and Modular Modification of Hyaluronic Acid Hydrogels for 3D Cellular Engineering

Park, Kyeng Min; Yang, Jeong-A; Jung, Hyuntae; Yeom, Junseok; Park, Ji Sun; Park, Keun-Hong; Hoffman, Allan S.; Hahn, Sei Kwang; Kim, Kimoon

doi:10.1021/nn204123p

Cited by 226 publications

(192 citation statements)

References 34 publications

(127 reference statements)

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“…Furthermore, subcutaneous injection CB [6]-hyaluronic acid and polyamine-grafted hyaluronic acid led to in situ hydrogel formation in mice and finally 11 days lasting fluorescence. [50] Reversibility was not shown here, but pH sensitivity is conceivable by protonation and deprotonation of the polyamine linker.…”

Section: Host-guest Chemistry Of Cucurbit[n]urilsmentioning

confidence: 71%

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Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Wiemann

Jonkheijm

2017

Israel Journal of Chemistry

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Supramolecular functional surfaces are at the heart of many materials and medical applications. Increasing interest can be seen for devising new supramolecular functionalization strategies of surfaces. In this review we place particular emphasis on the use of cucurbit[n]urilmediated host-guest complexation as surface functionalization strategy. The state of the art of cucurbit[n]uril-mediated host-guest complexes on surfaces is reviewed. Cucurbit [n] urils (CB[n]) are able to form strong host-guest complexes with affinities that span several orders of magnitudes up to the regime of the biotin-streptavidin pair and that can be modulated by applying remote stimuli provided suitably sensitive guests were selected. Strategies to fabricate stimuliresponsive surfaces creates versatile supramolecular systems and several applications of these types of surfaces are outlined.

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Section: Host-guest Chemistry Of Cucurbit[n]urilsmentioning

confidence: 71%

“…Recently, CB[n]-based hydrogels ( Figure 3 and Figure 4a), [50,51] polymer networks [51] and nanoparticles [52,53] , with potential use in biomedical science have been made. For example, Kim and coworkers designed a CB [6]-based hydrogel containing hyaluronic acid.…”

Section: Host-guest Chemistry Of Cucurbit[n]urilsmentioning

confidence: 99%

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Wiemann

Jonkheijm

2017

Israel Journal of Chemistry

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“…Indeed, many have exploited self-assembling peptide domains found widely in nature as crosslinking points between polymers or proteins for hydrogel formation (4)(5)(6)(7)(8)(9)(10)(11). Moreover, systems have been reported leveraging synthetic host-guest motifs based on the macrocyclic oligomers cyclodextrin and cucurbit [n]uril that form inclusion complexes with a wide variety of guest molecules (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24), or natural receptor-ligand pairs, such as (strep)avidin with biotin (25,26). In each of these examples, self-assembly of functional materials via noncovalent, intermolecular interactions with dynamic and reversible macroscopic behavior allows for shear-responsive moldability of the formed materials; however, their applicability in many industrial applications is severely limited by challenging, costly, and poorly scalable synthesis of the macromolecular components, requiring resource-intensive protein engineering or complex, multistep functionalization chemistries.…”

mentioning

confidence: 99%

Scalable manufacturing of biomimetic moldable hydrogels for industrial applications

Chen

Chan

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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Hydrogels are a class of soft material that is exploited in many, often completely disparate, industrial applications, on account of their unique and tunable properties. Advances in soft material design are yielding next-generation moldable hydrogels that address engineering criteria in several industrial settings such as complex viscosity modifiers, hydraulic or injection fluids, and sprayable carriers. Industrial implementation of these viscoelastic materials requires extreme volumes of material, upwards of several hundred million gallons per year. Here, we demonstrate a paradigm for the scalable fabrication of self-assembled moldable hydrogels using rationally engineered, biomimetic polymer-nanoparticle interactions. Cellulose derivatives are linked together by selective adsorption to silica nanoparticles via dynamic and multivalent interactions. We show that the self-assembly process for gel formation is easily scaled in a linear fashion from 0.5 mL to over 15 L without alteration of the mechanical properties of the resultant materials. The facile and scalable preparation of these materials leveraging self-assembly of inexpensive, renewable, and environmentally benign starting materials, coupled with the tunability of their properties, make them amenable to a range of industrial applications. In particular, we demonstrate their utility as injectable materials for pipeline maintenance and product recovery in industrial food manufacturing as well as their use as sprayable carriers for robust application of fire retardants in preventing wildland fires.hydrogels | manufacturing | nanotechnology | industrial applications | supramolecular I ndustrial settings present many unique and complicated engineering challenges. Inefficiencies arise in manufacturing because large volumes of material need to be pumped from one location to another and vast lengths of pipe of varying diameters must be cleaned frequently (1). Applications as diverse as hydraulic fracturing and cosmetics rely on processable fluids with complex viscoelastic properties. Moreover, many products and coatings are applied through spraying, which often requires uniform application and tunable retention of solvent and/or product. The advent of macromolecular chemistry has provided myriad polymeric materials that are used in diverse applications, including as food/cosmetic additives and viscosity modifiers. Several aqueous-based applications have exploited covalently cross-linked hydrogels, which comprise a class of soft materials that bind and retain large amounts of water and exhibit broadly tunable mechanical properties. However, the irreversibility of their cross-links is severely limiting and many applications would benefit enormously from new technologies allowing for stimuliresponsive aqueous viscosity modification and/or the ability to rearrange their shape in response to applied stress (2).Recent advances in supramolecular chemistry and materials science are enabling unique solutions to many critical industrial challenges via the production of mo...

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“…[10] The stable CB [6]-based host-guest interactions were exploited as as upramolecular crosslinkert of orm ar obusts elf-assembling hydrogel by as imple mixingo fC B [6]conjugated hyaluronic acid with DAH-conjugated hyaluronic acid. [11] Since this simple in situ-formed hydrogel showed robust physical properties and good biocompatibility,i tc ould be used to entrap live cells. The CB [6]-DAH-based hydrogels have been extensively utilized for various biological applications including 3D cell culture, [11] cell delivery, [12] and 3D cell printing.…”

mentioning

confidence: 99%

“…[11] Since this simple in situ-formed hydrogel showed robust physical properties and good biocompatibility,i tc ould be used to entrap live cells. The CB [6]-DAH-based hydrogels have been extensively utilized for various biological applications including 3D cell culture, [11] cell delivery, [12] and 3D cell printing. [13] However,t hese CB [6]-and CB[8]-based hydrogels were formed with at least two different hydrophilic polymers each with differentf unctionalities, which were synthesized by laboriousmultistep processes.…”

mentioning

confidence: 99%

Self‐Healable Supramolecular Hydrogel Formed by Nor‐Seco‐Cucurbit[10]uril as a Supramolecular Crosslinker

Park

Roh

Sung

et al. 2017

Chemistry An Asian Journal

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As upramolecularh ydrogel was formed by as imple mixingo fs olutions of nor-seco-cucurbit [10]uril ) and adamantylamine-terminated 4-armed polyethylene glycol (AdA-4-arm-PEG). In the formation of the hydrogel, NS-CB[10] acted as anoncovalent crosslinker to form at ernary complex with two AdA moieties. The dynamic and selectiven ature of the host-guest interaction between NS-CB [10] and AdA enabled the supramolecular hydrogel to rapidly recover its physicalp roperties after it was damaged. In addition, the recovered hydrogel retained its physicalp roperties with negligible differences from those of the pristine material, even after multiple self-healingc ycles.T he NS-CB[10]-based hydrogel with the self-healingp roperty may be useful for variousb iological applicationss uch as drug delivery,c ell therapy and tissue engineering.Hydrogels are soft materials containing al arge amount of water in three-dimensional networks of crosslinkedh ydrophilic polymers. Since the hydrogels provide an aqueous 3D environment similar to tissues containing various cells and biomolecules, they have been exploited for various biological applications such as woundh ealing materials, tissue engineering scaffolds, cell or drugd elivery materials and 3D cell printing inks. [1] For practical applications, maintaining the physicalp roperties duringt he period of use is crucial.O ne way to address this is to prepares elf-healing materials whicha re able to recover their original properties after sustaining damage. [2] Supramolecular hydrogels, [3] that is, hydrogels formed by supramolecular interactions such as hydrogen bonding, proteinligand interactions,h ost-guest interactions and hydrophobic interactions for noncovalentc rosslinking have been investigated as self-healing soft materials by harnessing the reversible natureo ft he noncovalent interactions for efficient recovery of their physicalp roperties. [4] However,m ost of these noncovalent interactions are too weak to hold the shape of ah ydrogel in af ree-standing form without externalr igidifying scaffolds. A recentr emarkable example demonstrated the formation of ar obust supramolecular hydrogel using multiple hydrogen bondsb etween clay disks and dendrons. [5] However, the recovery of the physical properties of the hydrogel was suppressed over time due to rapid passivation of the exposed ionic surfaces of the hydrogel with otherc ounter ions in an onspecific manner.M aterials crosslinked with specific high-affinity interactions would possess greatlyi mproved self-healing andd urability properties. [6] Cucurbit[n]urils (CB[n], n = 6-8, 10, 14), af amily of pumpkinshaped macrocycle hostm olecules, have specific and strong bindinga ffinities to various guest molecules. [7, 8] CB [8] accommodates two aromatic moieties (such as methylviologen (MV) and naphthyl( Np) units) in its cavity to form at ernary complex, which hasb een utilized as as upramolecular crosslinker to link MV-a nd Np-conjugated hydrophilic polymers together to form ah ydrogel. [9] Another approacht ...

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In Situ Supramolecular Assembly and Modular Modification of Hyaluronic Acid Hydrogels for 3D Cellular Engineering

Cited by 226 publications

References 34 publications

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Stimuli‐Responsive Cucurbit[n]uril‐Mediated Host‐Guest Complexes on Surfaces

Scalable manufacturing of biomimetic moldable hydrogels for industrial applications

Self‐Healable Supramolecular Hydrogel Formed by Nor‐Seco‐Cucurbit[10]uril as a Supramolecular Crosslinker

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