The effect of hydrazide linkers on hyaluronan hydrazone hydrogels

Šedová, Petra; Buffa, Radovan; Šilhár, Peter; Kovářová, Lenka; Vágnerová, Hana; Bednařík, Jiří; Basarabová, Ivana; Hejlová, Lenka; Ščigalková, Ivana; Šimek, Matěj; Velebný, Vladimı́r

doi:10.1016/j.carbpol.2019.04.011

Cited by 9 publications

(7 citation statements)

References 19 publications

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“…HA-modifying functional groups such as methacrylate, acrylate, and maleate are presented in the schematic. (C) Click chemistry involves mechanisms such as the Diels–Alder reaction, thiol–ene photocoupling, azide–alkyne Huisgen cycloaddition, and aldehyde–hydrazide coupling, forming covalent linkages in the HA hydrogels. For example, aldehyde–hydrazide coupling (HA-functionalized hydrazide and aldehyde groups are reacted to form a hydrazone bond) and thiol–ene photocoupling (HA-functionalized thiol and ene groups are activated to form a thioether under photoirradiation) are shown in the schematic.…”

Section: Cross-linking Mechanism Of Ha-based Bioinksmentioning

confidence: 99%

Hyaluronic Acid as Bioink and Hydrogel Scaffolds for Tissue Engineering Applications

Sekar

Suresh

Zennifer

et al. 2023

ACS Biomater. Sci. Eng.

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Bioprinting is an additive manufacturing technique that focuses on developing living tissue constructs using bioinks. Bioink is crucial in determining the stability of printed patterns, which remains a major challenge in bioprinting. Thus, the choices of bioink composition, modifications, and cross-linking methods are being continuously researched to augment the clinical translation of bioprinted constructs. Hyaluronic acid (HA) is a naturally occurring polysaccharide with the repeating unit of Nacetyl-glucosamine and D-glucuronic acid disaccharides. It is present in the extracellular matrix (ECM) of tissues (skin, cartilage, nerve, muscle, etc.) with a wide range of molecular weights. Due to the nature of its chemical structure, HA could be easily subjected to chemical modifications and cross-linking that would enable better printability and stability. These interesting properties have made HA an ideal choice of bioinks for developing tissue constructs for regenerative medicine applications. In this Review, the physicochemical properties, reaction chemistry involved in various cross-linking strategies, and biomedical applications of HA have been elaborately discussed. Further, the features of HA bioinks, emerging strategies in HA bioink preparations, and their applications in 3D bioprinting have been highlighted. Finally, the current challenges and future perspectives in the clinical translation of HA-based bioinks are outlined.

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Section: Cross-linking Mechanism Of Ha-based Bioinksmentioning

confidence: 99%

Hyaluronic Acid as Bioink and Hydrogel Scaffolds for Tissue Engineering Applications

Sekar

Suresh

Zennifer

et al. 2023

ACS Biomater. Sci. Eng.

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“…47 Collagen polymerizes more quickly at increased pH and temperatures, 16 whereas HA hydrazone bonds form more quickly at pH 6 than at pH 8. 48 Both hydrazone bonds 47 and collagen networks 49 form within minutes at physiological pH, and, as a result, the networks form around one another. Additionally, the reversibility of hydrazone bonds, which have been shown to equilibrate in less than an hour between pH 6 and 8, 47 suggests hydrazone bonds can break and reform as the collagen network develops.…”

Section: Retention Of Matrix Componentsmentioning

confidence: 99%

Interpenetrating Networks of Collagen and Hyaluronic Acid That Serve as In Vitro Tissue Models for Assessing Macromolecular Transport

Torres,

Meng,

Bhattacharya

et al. 2023

Biomacromolecules

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High-fidelity preclinical in vitro tissue models can reduce the failure rate of drugs entering clinical trials. Collagen and hyaluronic acid (HA) are major components of the extracellular matrix of many native tissues and affect therapeutic macromolecule diffusion and recovery through tissues. Although collagen and HA are commonly used in tissue engineering, the physical and mechanical properties of these materials are variable and depend highly on processing conditions. In this study, HA was chemically modified and crosslinked via hydrazone bonds to form interpenetrating networks of crosslinked HA (HAX) with collagen (Col). These networks enabled a wide range of mechanical properties, including stiffness and swellability, and microstructures, such as pore morphology and size, that can better recapitulate diverse tissues. We utilized these interpenetrating ColHAX hydrogels as in vitro tissue models to examine macromolecular transport and recovery for early-stage drug screening. Hydrogel formulations with varying collagen and HAX concentrations imparted different gel properties based on the ratio of collagen to HAX. These gels were stable and swelled up to 170% of their original mass, and the storage moduli of the ColHAX gels increased over an order of magnitude by increasing collagen and HA concentration. Interestingly, when HAX concentration was constant and collagen concentration increased, both the pore size and spatial colocalization of collagen and HA increased. HA in the system dominated the ζ-potentials of the gels. The hydrogel and macromolecule properties impacted the mass transport and recovery of lysozyme, β-lactoglobulin, and bovine serum albumin (BSA) from the ColHAX gels�large molecules were largely impacted by mesh size, whereas small molecules were influenced primarily by electrostatic forces. Overall, the tunable properties demonstrated by the ColHAX hydrogels can be used to mimic different tissues for early-stage assays to understand drug transport and its relationship to matrix properties.

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“…The severe inflammatory response of the PUS possibly originates from the functionalized hydrazide group. 40,41 When the hydrazide group of PUS was cross-linked with the aldehyde group of OHA to form a hydrazone bond in HA-PUS, the inflammatory response was significantly weakened. Even though HA was gradually degraded, there was no exposure of proinflammatory groups of the PUS particles; therefore, its inflammatory response did not aggravate in HA-PUS.…”

Section: Biocompatibility and Biodegradability Of The Ha-pus Hydrogel...mentioning

confidence: 99%

Scarless Healing of Injured Vocal Folds Using an Injectable Hyaluronic Acid-Waterborne Polyurethane Hybrid Hydrogel to Tune Inflammation and Collagen Deposition

Wang

Lei

et al. 2022

ACS Appl. Mater. Interfaces

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Vocal fold (VF) scarring results from injury to the unique layered structure and is one of the main reasons for long-lasting dysphonia. A minimally invasive procedure with injectable hydrogels is a promising method for therapy. However, current surgical techniques or standard injectable fillers do not yield satisfactory outcomes. In this work, an injectable hybrid hydrogel consisting of oxide hyaluronic acid and hydrazide-modified waterborne polyurethane emulsion was injected precisely into the injury site and cross-linked in situ by a dynamic hydrazone bond. The prepared hydrogel displays excellent injectability and self-healing ability, showing favorable biocompatibility and biodegradability to facilitate endogenous newborn cell migration and growth for tissue regeneration. With the aim of evaluating the antifibrosis and regeneration capacity of the hybrid hydrogel in the VF scarring model, the morphology and vibration characteristics of VFs, inflammatory response, and healing status were collected. The hybrid hydrogel can decrease the inflammation and increase the ratio of collagen III/collagen I to heal damaged scar-free tissue. Fascinatingly, the mucosal wave oscillations of healing VF by injecting the hybrid hydrogel were vibrated like the normal VF, achieving functional restoration. This work highlights the utility of hybrid hydrogels consisting of synthetic biodegradable waterborne polyurethane emulsions and natural hyaluronic acid as promising biomaterials for scarless healing of damaged VFs.

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The effect of hydrazide linkers on hyaluronan hydrazone hydrogels

Cited by 9 publications

References 19 publications

Hyaluronic Acid as Bioink and Hydrogel Scaffolds for Tissue Engineering Applications

Hyaluronic Acid as Bioink and Hydrogel Scaffolds for Tissue Engineering Applications

Interpenetrating Networks of Collagen and Hyaluronic Acid That Serve as In Vitro Tissue Models for Assessing Macromolecular Transport

Scarless Healing of Injured Vocal Folds Using an Injectable Hyaluronic Acid-Waterborne Polyurethane Hybrid Hydrogel to Tune Inflammation and Collagen Deposition

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