Surface-Modified Hydrogels for Chemoselective Bioconjugation

Plunkett, Kyle N.; Chatterjee, Aveek; Aluru, N. R.; Moore, Jeffrey S.

doi:10.1021/ma035166+

Cited by 7 publications

(5 citation statements)

References 34 publications

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“…Moreover, they exploited this feature to promote a superficial modification of the HGs. 40 In our case, the kinetic dependence of DAT-cleavage upon periodate diffusion was reflected in the obtained results (see S.I 1). The rate of change of SR with the reaction time showed a clear dependency with the amount of DAT in the HGs.…”

Section: Resultssupporting

confidence: 68%

Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links

Wolfel

Igarzabal

Romero

2020

European Polymer Journal

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The development of new materials with smart properties is currently expanding the development of new technologies. Therefore, the design of materials with novel sensitivities and smart behavior is important for the development of smart systems with automated responsivity. We have recently reported the synthesis of hydrogels, crosslinked by N,N'-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating changes in the hydrogel properties, as well as generating valuable α-oxo-aldehyde functional groups useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from 2-aminoethyl methacrylate hydrochloride (AEMA), coexisting with DAT into the same network. Herein, α-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds.In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a timewindow in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.

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Section: Resultssupporting

confidence: 68%

Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links

Wolfel

Igarzabal

Romero

2020

European Polymer Journal

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“…Hydrazide, (thio)semicarbazide, and aminooxy functional units have been utilized in reactions with aldehyde and ketone moieties selectively, for bioconjugation strategies, [25][26][27][28] profragrance construction, 29 and the design of drug-delivery systems. 30,31 Such chemoselective reactions are currently being applied to polyester functionalization.…”

Section: General Strategy For Functionalization and Cross-linkingmentioning

confidence: 99%

Cross-linked and functionalized polyester materials constructed using ketoxime ether linkages

Horn¹,

Wooley²

2007

Soft Matter

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A modular and simple approach to the graft functionalization and cross-linking of ketonecontaining poly(e-caprolactone)s has been investigated for the preparation of novel gel and nanoparticulate materials. Poly(e-caprolactone-co-2-oxepane-1,5-dione) (P(CL-co-OPD)), was grafted by reaction with 1-aminooxydodecane and cross-linked by reaction with 1,6-bis(aminooxy)hexane, each at room temperature in tetrahydrofuran at 1 and 10 wt% polymer in the absence of an acid catalyst, and at 1, 5 and 10 wt% polymer in the presence of p-toluenesulfonic acid. The grafting process served as a model system for the cross-linking reactions, affording products that were fully characterizable and retained the physical properties of (P(CL-co-OPD)), with a slight increase in measured molecular weight and characteristic spectroscopic signatures for the dodecyl chains and the newly introduced ketoxime functionalities. Early stages of the intermolecular cross-linking were followed by gel permeation chromatography and atomic force microscopy. Ultimately, insoluble, but tetrahydrofuran-swollen gelled products were obtained, which were characterized by infrared spectroscopy, differential scanning calorimetry and thermogravimetric analysis. These materials exhibited interesting melting transition profiles, undergoing melting at lower temperatures and broader temperature ranges than observed for their polymer precursors. This study represents an advance in the development of rapid and efficient chemistry for the preparation of functional and robust hydrolyticallydegradable polymer materials with degradable linkages.

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“…However, inefficient presentation of the cell adhesive signal from the hydrogels and change in the mechanical properties have been regarded as technical problems [21]. Surface modification of hydrogels has been accomplished via plasma treatment, hydrolysis, and gamma ray irradiation [36]. Conjugation of cell adhesive molecules such as gelatin, FN, and RGD peptide have sequentially been conducted on functionalized hydrogels [37,38].…”

Section: Surface Modification Of the Hydrogels And Cell Adhesionmentioning

confidence: 99%

One-step delivery of a functional multi-layered cell sheet using a thermally expandable hydrogel with controlled presentation of cell adhesive proteins

Lee

Byun

et al. 2018

Biofabrication

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In this study, we developed a new system enabling rapid delivery of a multi-layered cell sheet by combining layer-by-layer (LBL) coating of a cell membrane and surface engineered thermally expandable hydrogel. Human dermal fibroblasts were LBL-coated with fibronectin (FN) and gelatin to form a multi-layered cell sheet in a single seeding step via spontaneous 3D cell-cell interactions. FN was covalently immobilized onto the surface of a Tetronic-based hydrogel at two different concentrations (1 and 5 μg ml) for stable adhesion of the multi-layered cell sheet, followed by polydopamine coating. In both conditions, a multi-layered cell sheet was stably formed. Then, the cell sheet on the hydrogel modified with 1 μg ml FN rapidly detached (>90% efficiency) in response to the expansion of the hydrogel when temperature changed from 37 °C to 4 °C, while the other group had a reduced detachment due to excessive cell-hydrogel interaction. The multi-layered cell sheet was evident in cell-extracellular matrix and cell-cell junction formation, and bFGF was continuously secreted over 7 days of in vitro culture. The multi-layered transplanted to the mouse subcutaneous tissue also exhibited evidence of vascular ingrowth, which collectively suggest that the delivery system maintaining cellular functions is applicable for regenerative medicine.

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Surface-Modified Hydrogels for Chemoselective Bioconjugation

Cited by 7 publications

References 34 publications

Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links

Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links

Cross-linked and functionalized polyester materials constructed using ketoxime ether linkages

One-step delivery of a functional multi-layered cell sheet using a thermally expandable hydrogel with controlled presentation of cell adhesive proteins

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