Synthesis and Characterization of Periodate-Oxidized Polysaccharides: Dialdehyde Xylan (DAX)

Amer, Hassan; Nypelö, Tiina; Sulaeva, Irina; Bacher, Markus; Henniges, Ute; Potthast, Antje; Rosenau, Thomas

doi:10.1021/acs.biomac.6b00777

Cited by 97 publications

(59 citation statements)

References 61 publications

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“…According to the 2D 1 H‐ 13 C HSQC spectrum (Figure c) the new signals of CGO8 spectra around δ 4.8 to 5.2 ppm are correlated with signals on the 13 C peaks around δ 88.6–92 ppm. These signals were assigned by the authors, based on the literature data, to the hydrated form of aldehyde groups: H‐2, H‐3, or H‐4, (Figure a‐2), hemialdals (Figure a‐3), or hemiacetals intra‐residual (Figure a‐4). For CGO8 (Figure c), in the region δ 60–70 ppm three new signals of the methylene carbon diastereotopic (δ 58.75/3.66 and 4.02 ppm; δ 66.08/3.77 and 4.01 ppm; δ 68.24/3.87 and 3.97 ppm) were observed.…”

Section: Resultsmentioning

confidence: 99%

Oxidized Cashew Gum Scaffolds for Tissue Engineering

Maciel

Azevedo

Correia

et al. 2019

Macro Materials & Eng

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In the last few years, several strategies have been proposed to fabricate scaffolds for tissue engineering (TE) applications; however, they are based on harsh and time‐consuming techniques. The choice for natural polymers such as cashew gum (CG) allows to circumvent the demands of biocompatibility and degradability of TE systems. In this work, CG, a polysaccharide derived from Anacardium occidentale trees, is functionalized with aldehyde groups through periodate oxidation. The resultant oxidized cashew gum (CGO) is mixed with gelatin (GE) to yield a covalently crosslinked hydrogel. CGO/GE sponges are obtained by employing a freeze‐drying methodology to the previously obtained hydrogels. The mechanical properties, swelling ability, and porosity of the GE/CGO sponges are tuned by using CGO with different degrees of oxidation. The resultant sponges can maintain high levels of water absorption and recover their initial mechanical properties after cyclic compression. Moreover, these porous and mechanically robust devices can support the adhesion and proliferation of cells, which can envision their application for the regeneration of soft tissues.

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Section: Resultsmentioning

confidence: 99%

Oxidized Cashew Gum Scaffolds for Tissue Engineering

Maciel

Azevedo

Correia

et al. 2019

Macro Materials & Eng

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“…Accordingly, oxidized xylan showed only a slight reduction in molecular weight (from 7.7 to 6.6 kDa) after periodate‐mediated oxidation of the starting biopolymer. [ 56 ] This current work is focused in exploring the design of mechanochemical hydrogel networks with adaptable and patternable features, leveraging dynamic covalent chemistry principles. As such, evaluation of oxLAM molecular weight will be performed in a future study.…”

Section: Resultsmentioning

confidence: 99%

Mechanochemical Patternable ECM‐Mimetic Hydrogels for Programmed Cell Orientation

Lavrador

Gaspar

Mano

2020

Adv Healthcare Materials

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Native human tissues are supported by a viscoelastic extracellular matrix (ECM) that can adapt its intricate network to dynamic mechanical stimuli. To recapitulate the unique ECM biofunctionality, hydrogel design is shifting from typical covalent crosslinks toward covalently adaptable networks. To pursue such properties, herein hybrid polysaccharide-polypeptide networks are designed based on dynamic covalent assembly inspired by natural ECM crosslinking processes. This is achieved through the synthesis of an amine-reactive oxidized-laminarin biopolymer that can readily crosslink with gelatin (oxLAM-Gelatin) and simultaneously allow cell encapsulation. Interestingly, the rational design of oxLAM-Gelatin hydrogels with varying aldehyde-to-amine ratios enables a refined control over crosslinking kinetics, viscoelastic properties, and degradability profile. The mechanochemical features of these hydrogels post-crosslinking offer an alternative route for imprinting any intended nano-or microtopography in ECM-mimetic matrices bearing inherent cell-adhesive motifs. Different patterns are easily paved in oxLAM-Gelatin under physiological conditions and complex topographical configurations are retained along time. Human adipose-derived mesenchymal stem cells contacting mechanically sculpted oxLAM-Gelatin hydrogels sense the underlying surface nanotopography and align parallel to the anisotropic nanoridge/nanogroove intercalating array. These findings demonstrate that covalently adaptable features in ECM-mimetic networks can be leveraged to combine surface topography and cell-adhesive motifs as they appear in natural matrices.

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“…It has been determined that the concentration of free aldehyde groups in DAC or periodate-oxidized xylan is negligible because they are present in masked form as hemiacetals, (hemi)aldals, and aldehyde hydrates, which are subject to fast dynamic interconversion in aqueous solutions [13][14][15][16][17][18][19]. The periodate oxidation reaction can occur in any cis-vicinal diol structure in polysaccharides [20], so these masked aldehyde forms are also highly likely to be present in DAC. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…The present study was conducted to address these issues. Specifically, it explores (i) a general preparation method for DAC/PVA solutions, which are soluble in water at room temperature without the need for heating; (ii) a concept for avoiding any gelation of DAC/PVA aqueous solutions due to intermolecular hemiacetal formation [20]; (iii) a thorough material characterization of DAC/PVA ESNWs; and (iv) a post-spinning treatment for insolubilization of ESNWs with a diisocyanate [23], which can expand the scope of application for DAC thin fiber-based materials.…”

Section: Introductionmentioning

confidence: 99%

A General Protocol for Electrospun Non-Woven Fabrics of Dialdehyde Cellulose and Poly(Vinyl Alcohol)

et al. 2020

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In the past two decades, research on electrospinning has boomed due to its advantages of simple process, small fiber diameter, and special physical and chemical properties. The electrospun fibers are collected in a non-woven state in most cases (electrospun non-woven fabrics, ESNWs), which renders the electrospinning method an optimum approach for non-woven fabric manufacturing on the nano-scale. The present study establishes a convenient preparation procedure for converting water-soluble dialdehyde cellulose (DAC) into DAC-based electrospun non-woven fabrics (ESNWs) reinforced with poly(vinyl alcohol) (PVA). The aldehyde content, which was quantified by colorimetry using Schiff’s reagent, was 11.1 mmol per gram of DAC, which corresponds to a conversion yield of ca. 90%. DAC is fully water-soluble at room temperature between 10 and 30 wt%, and aqueous solutions turn into hydrogels within 24 h. To overcome gelation, NaHSO3, which forms bisulfite adducts with aldehyde functions, was added to the DAC and its concentration was optimized at 1 wt%. The electrospun (ES) dope containing 5 wt% DAC, 5 wt% PVA, and 1 wt% NaHSO3 in an aqueous solution was successfully transformed into ESNW, with an average fiber diameter of 345 ± 43 nm. Post-spinning treatment with excess hexamethylene diisocyanate was performed to insolubilize the ESNW materials. The occurrence of this chemical conversion was confirmed by energy-dispersive X-ray elemental analysis and vibrational spectra. The cross-linked DAC/PVA ESNW retained its thin fiber network upon soaking in distilled water, increasing the average fiber diameter to 424 ± 95 nm. This suggests that DAC/PVA-ESNWs will be applicable for incorporation or immobilization of biologically active substances.

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Synthesis and Characterization of Periodate-Oxidized Polysaccharides: Dialdehyde Xylan (DAX)

Cited by 97 publications

References 61 publications

Oxidized Cashew Gum Scaffolds for Tissue Engineering

Oxidized Cashew Gum Scaffolds for Tissue Engineering

Mechanochemical Patternable ECM‐Mimetic Hydrogels for Programmed Cell Orientation

A General Protocol for Electrospun Non-Woven Fabrics of Dialdehyde Cellulose and Poly(Vinyl Alcohol)

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