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

Abstract

Sodium alginate and carboxymethyl chitosan have been extensively applied in tissue engineering and other relative fields due to their low price and excellent biocompatibility. In this paper, we oxidized sodium alginate with sodium periodate to convert 1,2-hydroxyl groups into aldehyde groups to get aldehyde-sodium alginate (A-SA). Carboxymethyl chitosan was modified with ethylenediamine (ED) in the presence of water-soluble N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) to introduce additional amino groups to get amino-carboxymethyl chitosan (A-CS). Upon mixing the A-SA and A-CS aqueous solutions together, a gel rapidly formed based on the Schiff’s base reaction between aldehyde groups in A-SA and amino groups in A-CS. FTIR analysis confirmed the characteristic peak of Schiff’s base group in the hydrogel. It was confirmed that the gelation time be dependent on the aldehyde group content in A-SA and amino group content in A-CS. The fasted hydrogel formation takes place within 10 min. The data of bonding strength and cytotoxicity measurement also showed that the hydrogel had good adhesion and biocompatibility. All these results support that this gel has the potential as soft tissue adhesive.

Keywords

oxidized sodium alginate / amino-carboxymethyl chitosan / tissue adhesive / Schiff’s base

References

[1] Lloyd J D, Marque  M J 3rd, Kacprowicz  R F. Closure techniques. Emergency Medicine Clinics of North America, 2007, 25(1): 73–81

[2] Yang T L. Chitin-based materials in tissue engineering: applications in soft tissue and epithelial organ. International Journal of Molecular Sciences, 2011, 12(3): 1936–1963

[3] Ladewig K. Drug delivery in soft tissue engineering. Expert Opinion on Drug Delivery, 2011, 8(9): 1175–1188

[4] Tay C Y, Irvine  S A, Boey  F Y, . Micro-/nano-engineered cellular responses for soft tissue engineering and biomedical applications. Small, 2011, 7(10): 1361–1378

[5] Zhang F, He  C, Cao L , . Fabrication of gelatin-hyaluronic acid hybrid scaffolds with tunable porous structures for soft tissue engineering. International Journal of Biological Macromolecules, 2011, 48(3): 474–481

[6] Ryu J H, Lee  Y, Kong W H , . Catechol-functionalized chitosan/pluronic hydrogels for tissue adhesives and hemostatic materials. Biomacromolecules, 2011, 12(7): 2653–2659

[7] Lee Y, Chung  H J, Yeo  S, . Thermo-sensitive, injectable, and tissue adhesive sol–gel transition hyaluronic acid/pluronic composite hydrogels prepared from bio-inspired catechol-thiol reaction. Soft Matter, 2010, 6(5): 977–983

[8] Quinn J, Wells  G, Sutcliffe T , . Tissue adhesive versus suture wound repair at 1 year: randomized clinical trial correlating early, 3-month, and 1-year cosmetic outcome. Annals of Emergency Medicine, 1998, 32(6): 645–649

[9] Chung H, Grubbs  R H. Rapidly cross-linkable DOPA containing terpolymer adhesives and PEG-based cross-linkers for biomedical applications. Macromolecules, 2012, 45(24): 9666–9673

[10] Balakrishnan B, Banerjee  R. Biopolymer-based hydrogels for cartilage tissue engineering. Chemical Reviews, 2011, 111(8): 4453–4474

[11] Smith T J, Kennedy  J E, Higginbotham  C L. Rheological and thermal characteristics of a two phase hydrogel system for potential wound healing applications. Journal of Materials Science, 2010, 45(11): 2884–2891

[12] Balakrishnan B, Jayakrishnan  A. Self-cross-linking biopolymers as injectable in situ forming biodegradable scaffolds. Biomaterials, 2005, 26(18): 3941–3951

[13] Mo X, Iwata  H, Matsuda S , . Soft tissue adhesive composed of modified gelatin and polysaccharides. Journal of Biomaterials Science Polymer Edition, 2000, 11(4): 341–351

[14] Yuan L, Wu  Y, Fang J , . Modified alginate and gelatin cross-linked hydrogels for soft tissue adhesive. Artificial Cells, Nanomedicine, and Biotechnology, 2017, 45(1): 76–83

[15] Gomez C, Rinaudo  M, Villar M . Oxidation of sodium alginate and characterization of the oxidized derivatives. Carbohydrate Polymers, 2007, 67(3): 296–304

[16] Balakrishnan B, Mohanty  M, Umashankar P R , . Evaluation of an in situ forming hydrogel wound dressing based on oxidized alginate and gelatin. Biomaterials, 2005, 26(32): 6335–6342

[17] Geng X, Mo  X, Fan L , . Hierarchically designed injectable hydrogel from oxidized dextran, amino gelatin and 4-arm poly(ethylene glycol)-acrylate for tissue engineering application. Journal of Materials Chemistry, 2012, 22(48): 25130–25139

[18] Mo X, Iwata  H, Ikada Y . A tissue adhesives evaluated in vitro and in vivo analysis. Journal of Biomedical Materials Research Part A, 2010, 94(1): 326–332

[19] Hoare D G, Olson  A, Koshland D E  Jr. The reaction of hydroxamic acids with water-soluble carbodiimides. A Lossen rearrangement. Journal of the American Chemical Society, 1968, 90(6): 1638–1643

[20] Geng X H, Yuan  L, Mo X M . Oxidized dextran/amino gelatin/hyaluronic acid semi-interpenetrating network hydrogels for tissue engineering application. Advanced Materials Research, 2013, 627: 745–750

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