Photomediated oxime ligation as a bioorthogonal tool for spatiotemporally-controlled hydrogel formation and modification

“…Uncaging of reactive groups -PEG-based hydrogels [115] o-acylisourea. The active ester intermediate can then be attacked by primary amines on adjacent polymer chains, releasing urea as a by-product and yielding a hydrogel network stabilized by covalent amide crosslinks.…”

Section: Electromagnetic Radiationmentioning

confidence: 99%

Tailoring Gelation Mechanisms for Advanced Hydrogel Applications

Nele

Wojciechowski

Armstrong

et al. 2020

Adv Funct Materials

211

100

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Hydrogels are one of the most commonly explored classes of biomaterials. Their chemical and structural versatility has enabled their use across a wide range of applications, including tissue engineering, drug delivery, and cell culture. Hydrogels form upon a sol-gel transition, which can be elicited by different triggers designed to enable precise control over hydrogelation kinetics and hydrogel structure. The chosen hydrogelation trigger and chemistry can have a profound effect on the success of the targeted application. In this Progress Report, a critical overview of recent advances in hydrogel design is presented, with a focus on the available strategies used to trigger the formation of hydrogel networks (e.g., temperature, light, ultrasound). These triggers are presented within a new classification system, and their suitability for six key hydrogel-based applications is assessed. This Progress Report is intended to guide trigger selection for new hydrogel applications and inspire the rational design of new hydrogelation trigger mechanisms.

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“… 172 Recent reports on the increased decaging efficiency of methyl-coumarin capping groups, as a result of reduced chromophore isomerization upon irradiation, is likely to lead to a further increase in conjugation efficiency. 460 Although less commonly investigated, reports on the nitrobenzyl-capping of amines 461 for the “decaging” of Factor XIII substrates and hydroxylamines 235 , 462 for the spatially defined patterning of proteins via oxime ligation are also of note.…”

Section: Photocaging and Activation Of Reactive Functionalitiesmentioning

confidence: 99%

Achieving Controlled Biomolecule–Biomaterial Conjugation

2018

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The conjugation of biomolecules can impart materials with the bioactivity necessary to modulate specific cell behaviors. While the biological roles of particular polypeptide, oligonucleotide, and glycan structures have been extensively reviewed, along with the influence of attachment on material structure and function, the key role played by the conjugation strategy in determining activity is often overlooked. In this review, we focus on the chemistry of biomolecule conjugation and provide a comprehensive overview of the key strategies for achieving controlled biomaterial functionalization. No universal method exists to provide optimal attachment, and here we will discuss both the relative advantages and disadvantages of each technique. In doing so, we highlight the importance of carefully considering the impact and suitability of a particular technique during biomaterial design.

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Photomediated oxime ligation as a bioorthogonal tool for spatiotemporally-controlled hydrogel formation and modification

Abstract: Biocompatible, synthetic hydrogels were formed and modified by photomediated oxime ligation with full spatiotemporal control.

Cited by 61 publications

References 40 publications

Spatiotemporal hydrogel biomaterials for regenerative medicine

Spatiotemporal hydrogel biomaterials for regenerative medicine

Tailoring Gelation Mechanisms for Advanced Hydrogel Applications

Achieving Controlled Biomolecule–Biomaterial Conjugation

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