Self-crosslinking smart hydrogels through direct complexation between benzoxaborole derivatives and diols from hyaluronic acid

Figueiredo, Tamiris Vilas Boas; Ogawa, Yu; Jing, Jing; Stortz, Carlos A.; Jeacomine, Isabelle; Olsson, Johan; Gerfaud, Thibaud; Boiteau, Jean‐Guy; Harris, Craig S.; Auzély‐Velty, Rachel

doi:10.1039/d0py00308e

Cited by 20 publications

(27 citation statements)

References 52 publications

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“…This study showed that the resulting partially fluorinated material had a higher dynamic modulus and a faster relaxation time than the non-fluorinated analog. 236 Figure 16. Synthesis of a network based on boronic esters a. polyethylene glycol (PEG) monomers functionalized by boronic acids (blue) and diols (red) and their equilibrium with the boronic ester form b. schematic representation of the network.…”

Section: -228mentioning

confidence: 99%

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

et al. 2021

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Vitrimers constitute a fascinating class of polymer materials which make the link between the historically opposed 3D networks (thermosets) and linear polymers (thermoplastics). Their chemical resistance, reshaping ability and unique rheological behavior upon heating make them promising for future applications in industry. However many vitrimers require the use of high catalyst loadings, which raises concerns for their durability, and limits their potential applications. To cope with this issue, internal catalysis and neighboring group participation (NGP) can be used to enhance the reshaping ability of such materials. A few studies report the effect of activating groups on the exchange reactions in vitrimers. Nevertheless, knowledge on this topic remains scarce, although research on vitrimers would greatly benefit from NGP already known in organic chemistry. The present perspective article presents the different types of exchangeable bonds implemented in vitrimers and discusses chemical groups known to have or potentially capable of an enhancing effect on exchange reactions. This analysis is underpinned by a thorough mechanistic discussion of the various exchangeable bonds presented.

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Section: -228mentioning

confidence: 99%

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

et al. 2021

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“…Hyaluronan itself contains diols, which may form additional complexes with boronic acids to stabilize the gel, as suggested by the complexation of benzoxaborole derivatives and hyaluronic acid diols at physiological pH. [ 20 ] However, the slower gelation precludes cell encapsulation in aqueous environments. In contrast, a fast gelling hydrogel of HA modified with phenylboronic acid (PBA) and poly(vinyl alcohol) (PVA) enabled 3D culture of neural progenitor cells.…”

Section: Case Studies Of 3d Cell Culture In DCC Hydrogelsmentioning

confidence: 99%

“…Dynamic covalent bonds are reversible chemical bonds which can break and reform on time scales relevant for cell‐based matrix remodeling, an important feature for 3D culture. [ 17 ] Specific examples of DCC which have been tailored to be compatible with 3D cell culture include boronate ester, [ 18–23 ] hydrazone, [ 24–30 ] Diels‐Alder, [ 31–37 ] oxime, [ 38–43 ] thiol–disulfide exchange, [ 44–46 ] and imine crosslinking. [ 17,47,48 ] These crosslinking methods can be performed at physiological pH and temperature, are fast reacting, and their reaction kinetics can be tailored to achieve a wide range of viscoelastic properties.…”

Section: Introductionmentioning

confidence: 99%

Designing Hydrogels for 3D Cell Culture Using Dynamic Covalent Crosslinking

Rizwan

Baker

Shoichet

2021

Adv Healthcare Materials

109

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Designing simple biomaterials to replicate the biochemical and mechanical properties of tissues is an ongoing challenge in tissue engineering. For several decades, new biomaterials have been engineered using cytocompatible chemical reactions and spontaneous ligations via click chemistries to generate scaffolds and water swollen polymer networks, known as hydrogels, with tunable properties. However, most of these materials are static in nature, providing only macroscopic tunability of the scaffold mechanics, and do not reflect the dynamic environment of natural extracellular microenvironment. For more complex applications such as organoids or co‐culture systems, there remain opportunities to investigate cells that locally remodel and change the physicochemical properties within the matrices. In this review, advanced biomaterials where dynamic covalent chemistry is used to produce stable 3D cell culture models and high‐resolution constructs for both in vitro and in vivo applications, are discussed. The implications of dynamic covalent chemistry on viscoelastic properties of in vitro models are summarized, case studies in 3D cell culture are critically analyzed, and opportunities to further improve the performance of biomaterials for 3D tissue engineering are discussed.

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“…Some key factors for the formation of the boronic ester bonds include the binding affinity of the boronic acid derivate towards the diol (Ka), their pKa, and the pH of the medium. The optimal pH for the formation of the ester bond can be found between the pKa values of boronic acid and the diol [37][38][39][40]. The estimation was proposed by "the charge rule": "sum of the charges of the free esterifying species is equal to the charge of the ester" [41].…”

Section: Boronic-ester Formationmentioning

confidence: 99%

Hyaluronic Acid Hydrogels Crosslinked in Physiological Conditions: Synthesis and Biomedical Applications

et al. 2021

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Hyaluronic acid (HA) hydrogels display a wide variety of biomedical applications ranging from tissue engineering to drug vehiculization and controlled release. To date, most of the commercially available hyaluronic acid hydrogel formulations are produced under conditions that are not compatible with physiological ones. This review compiles the currently used approaches for the development of hyaluronic acid hydrogels under physiological/mild conditions. These methods include dynamic covalent processes such as boronic ester and Schiff-base formation and click chemistry mediated reactions such as thiol chemistry processes, azide-alkyne, or Diels Alder cycloaddition. Thermoreversible gelation of HA hydrogels at physiological temperature is also discussed. Finally, the most outstanding biomedical applications are indicated for each of the HA hydrogel generation approaches.

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Self-crosslinking smart hydrogels through direct complexation between benzoxaborole derivatives and diols from hyaluronic acid

Abstract: By tailoring the structure of benzoxaborole (BOR), self-crosslinking hydrogels based on hyaluronic acid (HA) modified with BOR derivatives are obtained for the first time through the direct BOR-HA diol complexation at physiological pH.

Cited by 20 publications

References 52 publications

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

Neighboring Group Participation and Internal Catalysis Effects on Exchangeable Covalent Bonds: Application to the Thriving Field of Vitrimer Chemistry

Designing Hydrogels for 3D Cell Culture Using Dynamic Covalent Crosslinking

Hyaluronic Acid Hydrogels Crosslinked in Physiological Conditions: Synthesis and Biomedical Applications

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