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Injectable Click Chemistry-based Bioadhesives for Accelerated Wound Closure July 30,2020.

Tissue adhesives play a vital role in surgical processes as a substitute for sutures in wound closure. Tissue adhesives, have been widely used in dentistry , orthopedics , and cardiovascular wounds closure to partially replace the traditional suturing approaches that often induce tissue deformation, irregular blood flow, and wound dehiscence. However, many of the existing commercial tissue adhesives have flaws that become evident upon application. For example, cyanoacrylate (Super Glue), which is considered as the strongest tissue adhesive,  has been shown to possess strong cytotoxicity . Fibrin glueand polyethylene glycol adhesivesare widely used due to their fast closure and biodegradability .  However, both types of glue have limited applications due to their poor tissue-adhesive property and tensile strength.


This study present click chemistry enhanced, dual-crosslinked CS bioadhesive as a new strategy for wound closure with strong adhesive strength, injectability, and biocompatibility. In detail, CS-TCO and CS-Tz precursors were synthesized through carboxyl-to-amine crosslinking (Scheme 1). Upon administration, 4-arm PEG-PALD was mixed with one of the precursors and both of the precursors were injected and mixed within the wound (Scheme 1, 2). The crosslinking of the CS was through both, the rapid reaction between conjugated click chemistry pair TCO/Tz and the formation of Schiff bases between PEG-PALD and primary amines on CS. The mixture can form a solid hydrogel within 2 minutes. By optimizing the dosage of the co-crosslinker, adhesive strength, rheology, swelling ratio, and pore size of the hydrogel were characterized and compared, and the recipe that had the strongest adhesive strength was chosen for further animal study.



Scheme 1. Step-by-step synthesis of the precursors and crosslinking of CS bioadhesives.





Scheme 2. A depiction of the bonding structure between the CS bioadhesives and surrounding tissue.


In this study, click chemistry-based CS bioadhesives were fabricated and evaluated for their ability to accelerate wound closure and promote wound healing. By taking advantage of the rapid click chemistry reaction time, they are able to tune the gelation time of the CS bioadhesives to be around 60-70 seconds for various clinical applications. Through introducing Schiff bases formed within the CS bioadhesives and between the CS bioadhesives and the surrounding tissue, the adhesive strength of the CS bioadhesives was significantly elevated. With the optimized formulation, the adhesive strength of the CS bioadhesives was 2.3 folds higher than that of fibrin glue. The quantitative in vitro cytotoxicity evaluations of the CS bioadhesives supported the application of this material in the medical field. Finally, with the application of the CS bioadhesives for wound closure in mice, it showed that the material produced small tissue gap, accelerated wound closure, and led to a better healing outcome compared with traditional fibrin glue.


In conclusion, a copper-free click chemistry pair trans-cyclooctene/tetrazine, reacted through the inverse-demand Diels-Alder cycloaddition with high chemoselectivity and ultrafast kinetics, was introduced into CS polymers to form injectable bioadhesives. The new bioadhesives were injectable, with fast gelation time, minimal cytotoxicity, strong adhesion to tissue, and augmenting wound healing.



[1] Li S ,  Zhou J ,  Huang Y H , et al. Injectable Click Chemistry-Based Bioadhesives for Accelerated Wound Closure[J]. Social Science Electronic Publishing.


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