Competitive hemiacetalization and acetalization: Cross‐linking of cellulose by glyoxal

Sangsari, Farid Hamedi; Chastrette, F.; Chastrette, M.; Blanc, A.; Mattioda, G.

doi:10.1002/recl.19901090705

Cited by 6 publications

(5 citation statements)

References 11 publications

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“…We further assume the hemi-acetals to from on C2 and C3 of the related glucose, mannose and glucuronic residues, as vicinal hydroxyl groups are more likely to hemi-acetylise. 17 Recollecting, we recorded a media-dependent varying elution pattern, with initial increased release rates at increase pH. This corroborates the pH-dependant release hypothesis.…”

Section: Hplcsupporting

confidence: 83%

“…We further assume the hemi-acetals to from on C2 and C3 of the related glucose, mannose and glucuronic residues, as vicinal hydroxyl groups are more likely to hemi-acetylise. 17…”

Section: Discussionmentioning

confidence: 99%

“…13,14 The similarity to cellulose, its widespread application, 15 and the possibility to cross-link Xanthan using dialdehydes 16 lead to the use of this biopolymer. Xanthan is cross-linked by glyoxal, 17 to obtain a pH-dependent antimicrobial effect. Glyoxal is listed as biocide according to the European Chemical Agency, 18 but is accepted in veterinary hygiene.…”

Section: Introductionmentioning

confidence: 99%

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Imperfect cross-linking of xanthan for pH-responsive bio-based composite moist wound dressings by stencil printing

Wurm,

Lenninger,

Mayr

et al. 2023

J Biomater Appl

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The work addresses the use of bio-based and –degradable materials for the production of a moist, adaptive and anti-microbial wound dressing. The dressing is targeted to exhibit a pH-dependent active agent release. Xanthan hydrogel structures are coated on cellulose fabrics via stencil printing and subsequently cross-linked using glyoxal. By alteration of the cross-linker content from 1 to 6% by mass, the hydrogel elasticity can be tuned within a range of 2–16 kPa storage modulus. Increasing initial glyoxal concentrations also result in higher amounts of glyoxal release. Glyoxal, an anti-microbial agent with approval in veterinary medicine, is mostly released upon wound application supporting infection management. As wound simulation, normal saline, as pH 5 and pH 8 buffer solutions, were used. The release profile and magnitude of approx. 65%–90% glyoxal is pH-dependent. Increased release rates of glyoxal are present in pH 8 fluids, which mostly base on faster hydrogel swelling. Higher total glyoxal release is present in pH 5 fluid and normal saline after 3 days. Accordingly, a pH-dependent release profile was encountered. As glyoxal attacks any cell unselectively, it is expected to be effective against antibiotic resistant bacteria. By stencil printing the dressing size can be adjusted to minimize healthy glyoxal tissue exposure.

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Section: Hplcsupporting

confidence: 83%

“…We further assume the hemi-acetals to from on C2 and C3 of the related glucose, mannose and glucuronic residues, as vicinal hydroxyl groups are more likely to hemi-acetylise. 17…”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Imperfect cross-linking of xanthan for pH-responsive bio-based composite moist wound dressings by stencil printing

Wurm,

Lenninger,

Mayr

et al. 2023

J Biomater Appl

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“…The main reactions behind the crosslinking process occur in relation with the hydroxyl and amino groups of the polymer or protein to be crosslinked [54]. Considering that methylglyoxal is an essential component in MH and that the mechanism of interaction between cellulose and glyoxal in acid environment has been established [55,56], showing the promotion of the crosslinking reaction through hemiacetalization and acetalization processes [57], the authors anticipated that a similar interaction would occur between MH and MC during the preparation of the present scaffolds.…”

Section: Crosslinking Of MC With Mhmentioning

confidence: 94%

Manuka honey and bioactive glass impart methylcellulose foams with antibacterial effects for wound-healing applications

et al. 2020

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Wound dressings able to deliver topically bioactive molecules represent a new generation of wound-regeneration therapies. In this article, foams based on methylcellulose cross-linked with Manuka honey were used as a platform to deliver borate bioactive glass particles doped additionally with copper. Borate bioactive glasses are of great interest in wound-healing applications due to a combination of favorable features, such as angiogenic and antibacterial properties. The multifunctional composite providing the dual effect of the bioactive glass and Manuka honey was produced by freeze-drying, and the resulting foams exhibit suitable morphology characterized by high porosity. Moreover, the performed tests showed improved wettability and mechanical performance with the addition of bioactive glass particles. Dissolution studies using simulated body fluid and cell biology tests using relevant skin cells further proved the excellent bioactivity and positive effects of the foams on cell proliferation and migration. Most interestingly, by the dual release of Manuka honey and ions from the copper-doped bioactive glass, an antibacterial effect against E. coli and S. aureus was achieved. Therefore, the multifunctional foams showed promising outcomes as potential wound dressings for the treatment of infected wounds.

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“…Acetalization can occur between vicinal diols stereochemically on the same side (cis) of the sugar units on the CMTG backbone, such as L-fucose, L-arabinose, D-galactose, D-xylose, and glutaraldehyde (Figure 1). Vicinal diols are much more reactive with aldehydes than alcohols isolated in an aqueous solution [59]. Hence, acetalization can be considered a competing reaction to hemiacetalization.…”

Section: E Effect Of the Amount Of Crosslinking Agent On The Water Absorbencymentioning

confidence: 99%

A Novel Superabsorbent Polymer from Crosslinked Carboxymethyl Tragacanth Gum with Glutaraldehyde: Synthesis, Characterization, and Swelling Properties

Bachra

Grouli

Damiri

et al. 2021

International Journal of Biomaterials

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Nowadays, current global environmental problems include measures to eliminate or reduce the negative impact of chemicals from petroleum sources and, therefore, the use of materials from natural resources is increasingly recommended. In this context, natural-based superabsorbent polymers derived from polypeptides and polysaccharides have undergone chemical and biochemical modifications to improve their ability to absorb and retain large amounts of liquids. In the present paper, a new process has been used to overcome the side effects of radical polymerization in the manufacture of conventional polyacrylate superabsorbents (SAPs). Tragacanth gum (TG) was selected to prepare a new superabsorbent material (CMTG-GA) based on carboxymethyl tragacanth (CMTG) crosslinked with glutaraldehyde (GA). The characterization of the polymer was carried out by FTIR, TGA, XRD, and SEM. The effect of the amount of crosslinking agent and the pH on the water absorption capacity was also examined. Subsequently, swelling studies were performed using free swelling capacity (FSC) and centrifuge retention capacity (CRC) techniques in distilled water, tap water, and saline solution. The results showed that the CRC of the new material is not less than 42.1 g/g, which was observed for a ratio of 20% by weight of GA to CMTG. Likewise, the maximum absorption results were 43.9 and 32.14 g/g, respectively, for FSC and CRC at pH 8.0. In addition, a comparison of the swelling capacities of the synthesized product with a commercial SAP extracted from a baby diaper, well known in the Moroccan market, showed that the performances were very similar.

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Competitive hemiacetalization and acetalization: Cross‐linking of cellulose by glyoxal

Cited by 6 publications

References 11 publications

Imperfect cross-linking of xanthan for pH-responsive bio-based composite moist wound dressings by stencil printing

Imperfect cross-linking of xanthan for pH-responsive bio-based composite moist wound dressings by stencil printing

Manuka honey and bioactive glass impart methylcellulose foams with antibacterial effects for wound-healing applications

A Novel Superabsorbent Polymer from Crosslinked Carboxymethyl Tragacanth Gum with Glutaraldehyde: Synthesis, Characterization, and Swelling Properties

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