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Issue 7, 2013
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Bio-inspired catechol conjugation converts water-insoluble chitosan into a highly water-soluble, adhesive chitosan derivative for hydrogels and LbL assembly

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Abstract

This report describes a simple method to prepare water-soluble chitosan derivative by conjugation of an enediol group, catechol. Chitosan functionalized with a catechol-containing compound, 3,4-dihydroxyhydrocinnamic acid, by a carbodiimide coupling method resulted in chitosancatechol conjugates. This one-step chemical modification of high-molecular-weight chitosan (approximately 100 kDa) dramatically increased the water solubility of the chitosan derivative to 60 mg mL−1 at pH 7.0. The degree of catechol conjugation was found critical in determining the solubility. The chitosancatechol conjugates are not only water-soluble but are adhesive, due to the intrinsic adhesive properties of catechol. Also, the water-soluble chitosan derivative allows one to directly form chitosan hydrogel in neutral buffer solutions. The utility of both the water solubility and the adhesive property of the chitosancatechol was demonstrated by the effective layer-by-layer assembly on substrates. The water-soluble chitosancatechol is expected to be useful in many areas of surface functionalization, drug delivery, tissue engineering, and tissue adhesives.

Graphical abstract: Bio-inspired catechol conjugation converts water-insoluble chitosan into a highly water-soluble, adhesive chitosan derivative for hydrogels and LbL assembly

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Article information


Submitted
03 Jan 2013
Accepted
04 Apr 2013
First published
02 May 2013

Biomater. Sci., 2013,1, 783-790
Article type
Paper

Bio-inspired catechol conjugation converts water-insoluble chitosan into a highly water-soluble, adhesive chitosan derivative for hydrogels and LbL assembly

K. Kim, J. H. Ryu, D. Y. Lee and H. Lee, Biomater. Sci., 2013, 1, 783
DOI: 10.1039/C3BM00004D

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