Crosslinking of hyaluronic acid with glutaraldehyde

Tomihata, Kenji; Ikada, Yoshito

doi:10.1002/(sici)1099-0518(19971130)35:16<3553::aid-pola22>3.0.co;2-d

Cited by 135 publications

(76 citation statements)

References 4 publications

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“…The explanation is that the aldehydes are converted to hemiacetals by reaction with neighboring alcohol groups on cellulose. Furthermore, the hemiacetals are difficult to detect in a carbohydrate such as cellulose (Tomihata and Ikada 1997). Nevertheless, the results in Fig.…”

Section: Discussionmentioning

confidence: 99%

The role of mild TEMPO–NaBr–NaClO oxidation on the wet adhesion of regenerated cellulose membranes with polyvinylamine

DiFlavio

Pelton

Leduc³

et al. 2006

Cellulose

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X-ray Photoelectron Spectroscopy (XPS) was used to characterize the functional groups present on regenerated cellulose films after mild oxidation with TEMPO-NaBr-NaClO and the results were correlated with the adhesion forces holding together two wet cellulose films laminated with a thin (i.e. less than 10 mg/m 2 ) layer of polyvinylamine (PVAm). There was no correlation between adhesion and carboxyl content, whereas wet adhesion was proportional to the total content of aldehyde and hemiacetal groups on the cellulose. It is proposed that aldehyde groups react with neighboring cellulose chains to form hemiacetals which serve as crosslinks strengthening the cellulose surface. The hemiacetals can also be attacked by primary amines to give imine and aminal covalent linkages to the PVAm adhesive layer.

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Section: Discussionmentioning

confidence: 99%

The role of mild TEMPO–NaBr–NaClO oxidation on the wet adhesion of regenerated cellulose membranes with polyvinylamine

DiFlavio

Pelton

Leduc³

et al. 2006

Cellulose

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“…For example, HA has been crosslinked by bisepoxide 65, 66 or divinyl sulfone derivatives 67 under alkaline conditions. HA can also be crosslinked by glutaraldehyde, 68 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) 68 , biscarbodiimide 69 and multifunctional hydrazides 70, 71 under acidic conditions. Compared to the native HA, the crosslinked hydrogels exhibit more robust mechanical properties and are less susceptible to enzymatic degradation.…”

Section: Ha Bulk Gelsmentioning

confidence: 99%

Hyaluronic acid-based hydrogels: from a natural polysaccharide to complex networks

et al. 2012

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Hyaluronic acid (HA) is one of nature's most versatile and fascinating macromolecules. Being an essential component of the natural extracellular matrix (ECM), HA plays an important role in a variety of biological processes. Inherently biocompatible, biodegradable and non-immunogenic, HA is an attractive starting material for the construction of hydrogels with desired morphology, stiffness and bioactivity. While the interconnected network extends to the macroscopic level in HA bulk gels, HA hydrogel particles (HGPs, microgels or nanogels) confine the network to microscopic dimensions. Taking advantage of various scaffold fabrication techniques, HA hydrogels with complex architecture, unique anisotropy, tunable viscoelasticity and desired biologic outcomes have been synthesized and characterized. Physical entrapment and covalent integration of hydrogel particles in a secondary HA network give rise to hybrid networks that are hierarchically structured and mechanically robust, capable of mediating cellular activities through the spatial and temporal presentation of biological cues. This review highlights recent efforts in converting a naturally occurring polysaccharide to drug releasing hydrogel particles, and finally, complex and instructive macroscopic networks. HA-based hydrogels are promising materials for tissue repair and regeneration.

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“…Since glutaraldehyde is toxic, a particular handling is required during the reaction and the purification of the final product [160,161].…”

Section: Modification Of Ha Hydroxyl Groupsmentioning

confidence: 99%

Hyaluronic Acid in the 3<sup>rd</sup> Millennium

Fallacara¹,

Baldini²,

Manfredini³

et al. 2018

Preprint

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Since its first isolation in 1934, hyaluronic acid (HA) has been studied across a variety of research areas. This unbranched glycosaminoglycan consisting of repeating disaccharide units of N-acetyl-D-glucosamine and D-glucuronic acid is almost ubiquitary in humans and in other vertebrates. HA is involved in many key processes -including cell signaling, wound reparation, tissue regeneration, morphogenesis, matrix organization and pathobiology-, and has unique physico-chemical properties -such as biocompatibility, biodegradability, mucoadhesivity, hygroscopicity and viscoelasticity. For these reasons, exogenous HA has been investigated as drug delivery system and treatment in cancer, ophthalmology, arthrology, pneumology, rhinology, urology, aesthetic medicine and cosmetic. To improve and customize its properties and applications, HA can be subjected to chemical modifications: conjugation and crosslinking. The present review gives an overview regarding HA, describing its history, physico-chemical, structural and hydrodynamic properties, and biology -occurrence, biosynthesis (by hyaluronan synthases), degradation (by hyaluronidases and oxidative stress), roles, mechanisms of action and receptors. Furthermore, both conventional and recently emerging methods developed for the industrial production of HA and its chemical derivatization are presented. Finally, the medical, pharmaceutical and cosmetic applications of HA and its derivatives are reviewed, reporting examples of HA-based products which currently are on the market or are undergoing further investigations.

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Crosslinking of hyaluronic acid with glutaraldehyde

Cited by 135 publications

References 4 publications

The role of mild TEMPO–NaBr–NaClO oxidation on the wet adhesion of regenerated cellulose membranes with polyvinylamine

The role of mild TEMPO–NaBr–NaClO oxidation on the wet adhesion of regenerated cellulose membranes with polyvinylamine

Hyaluronic acid-based hydrogels: from a natural polysaccharide to complex networks

Hyaluronic Acid in the 3<sup>rd</sup> Millennium

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