A soft tissue adhesive based on aldehyde-sodium alginate and amino-carboxymethyl chitosan preparation through the Schiff reaction

Wu, Yu; Liu, Yuan; Sheng, Nai An; Gu, Zi Qi; Feng, Wen Hao; Yin, Hai Yue; Morsi, Yos S.; Mo, Xiu

doi:10.1007/s11706-017-0392-x

Cited by 33 publications

(22 citation statements)

References 20 publications

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“…As the C=O stretching of amide I (1637 cm −1 ), as well as the C=N stretching vibration of imine (1623–1647 cm −1 ) are expected in the same region, the peak shift and broadening is most likely attributed to an overlay of peaks. The C=N stretching vibration, which indicates the successful formation of a Schiff base (imine) bond, has been shown to occur in the range of 1623–1647 cm −1 in various tissue engineering applications [ 10 , 37 , 38 , 39 , 40 ]. Specifically, Sarker et al published similar spectra before, suggesting the formation of Schiff base in their ADA-GEL hydrogels [ 10 ].…”

Section: Resultsmentioning

confidence: 99%

Differential Responses to Bioink-Induced Oxidative Stress in Endothelial Cells and Fibroblasts

Genç

Hazur

Karakaya

et al. 2021

IJMS

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A hydrogel system based on oxidized alginate covalently crosslinked with gelatin (ADA-GEL) has been utilized for different biofabrication approaches to design constructs, in which cell growth, proliferation and migration have been observed. However, cell–bioink interactions are not completely understood and the potential effects of free aldehyde groups on the living cells have not been investigated. In this study, alginate, ADA and ADA-GEL were characterized via FTIR and NMR, and their effect on cell viability was investigated. In the tested cell lines, there was a concentration-dependent effect of oxidation degree on cell viability, with the strongest cytotoxicity observed after 72 h of culture. Subsequently, primary human cells, namely fibroblasts and endothelial cells (ECs) were grown in ADA and ADA-GEL hydrogels to investigate the molecular effects of oxidized material. In ADA, an extremely strong ROS generation resulting in a rapid depletion of cellular thiols was observed in ECs, leading to rapid necrotic cell death. In contrast, less pronounced cytotoxic effects of ADA were noted on human fibroblasts. Human fibroblasts had higher cellular thiol content than primary ECs and entered apoptosis under strong oxidative stress. The presence of gelatin in the hydrogel improved the primary cell survival, likely by reducing the oxidative stress via binding to the CHO groups. Consequently, ADA-GEL was better tolerated than ADA alone. Fibroblasts were able to survive the oxidative stress in ADA-GEL and re-entered the proliferative phase. To the best of our knowledge, this is the first report that shows in detail the relationship between oxidative stress-induced intracellular processes and alginate di-aldehyde-based bioinks.

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Section: Resultsmentioning

confidence: 99%

Differential Responses to Bioink-Induced Oxidative Stress in Endothelial Cells and Fibroblasts

Genç

Hazur

Karakaya

et al. 2021

IJMS

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“…Some promising results also come from oxidized alginate covalently crosslinked with other free amino groups containing polymers (Wang, Wang, & Teng, 2016;Wu et al, 2017;Yuan et al, 2017). Wei et al (2015) developed self-healing hydrogels consisting of N-carboxyethyl chitosan-oxidized alginate-adipic acid dihydrazide linked by imine bonds obtained by Schiff base reaction between OA and CEC, as well as acylhydrazone bonds derived from reaction between OA and ADH.…”

Section: Covalently Crosslinked Injectable Hydrogelsmentioning

confidence: 99%

Alginate hydrogels for bone tissue engineering, from injectables to bioprinting: A review

Hernández-González

Téllez-Jurado

Rodríguez‐Lorenzo

2020

Carbohydrate Polymers

383

209

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This review focuses on recently developed alginate injectable hydrogels and alginate composites for applications in bone tissue regeneration, and it evaluates the alternatives to overcome the problems that avoid their utilization in the field. Section 2 covers the properties of alginates that have made them useful for medical applications, in particular their ionic gelling ability for preparing injectable compositions used as delivery drugs systems. The advantages and shortcomings of these preparations are revised together with the chemical modifications assayed. Section 3 describes how it has been taken advantage of alginates into the new field of biofabrication and the developments in bone engineering. The state of the art of this field is reviewed. Finally in Section 4, new developments and approaches that in opinion of the authors can lead to a breakthrough in bone tissue engineering using alginates are introduced.

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“…To enhance the separation and peak resolution in the 1500–1800 cm −1 region, the second derivative spectra were inspected ( Figure 1 B) and, due to the transmission mode, the local maximums within the deconvoluted spectra were inserted. A new vibration at 1646 cm −1 was observed, as well as a change in the Amide II region, both being related to Schiff-base formation [ 20 , 26 ]. Very similar FTIR data were obtained for all membranes (data not presented).…”

Section: Resultsmentioning

confidence: 99%

Microstructured and Degradable Bacterial Cellulose–Gelatin Composite Membranes: Mineralization Aspects and Biomedical Relevance

Gorgieva

Hribernik

2019

Nanomaterials

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Bacterial cellulose (BC)–gelatin (GEL) membranes were processed by successive periodate oxidation and a freeze-thawing/carbodiimide crosslinking procedure, first facilitating a Schiff-base reaction among respective aldehyde and hydroxyl groups, and later GEL stabilization and microstructuring. The formation of highly microporous structures within the GEL portion, with significant differences between bottom and top, was elucidated, and pores in the 27.6 ± 3 µm–108 ± 5 µm range were generated, exceeding the threshold value of ~10 µm sufficient for cell trafficking. During a relatively short (6 h) exhaustion procedure in supersaturated simulated body fluid solution, the membranes accommodated the combination of biologically relevant minerals, i.e., flake-like octacalcium phosphate (OCP) and (amorphous) apatite, onto their surface, forming a membrane with intensive swelling (650–1650%) and up to 90% weight loss in a 4-week period. The membranes´ 6-day eluates did not evoke any cytotoxic effects toward human fibroblast, MRC-5 cells. The same type of cells retained their morphology in direct contact with the membrane, attaching to the GEL porous site, while not attaching to the GEL thin-coated BC side, most probably due to combined, ablation effect of dominant β-sheet conformation and carbodiimide crosslinking. Together with arrested proliferation through the BC side, the membranes demonstrated beneficial properties for potential guided tissue regeneration (GTR) applications.

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A soft tissue adhesive based on aldehyde-sodium alginate and amino-carboxymethyl chitosan preparation through the Schiff reaction

Cited by 33 publications

References 20 publications

Differential Responses to Bioink-Induced Oxidative Stress in Endothelial Cells and Fibroblasts

Differential Responses to Bioink-Induced Oxidative Stress in Endothelial Cells and Fibroblasts

Alginate hydrogels for bone tissue engineering, from injectables to bioprinting: A review

Microstructured and Degradable Bacterial Cellulose–Gelatin Composite Membranes: Mineralization Aspects and Biomedical Relevance

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