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Mater Sci Eng C Mater Biol Appl. 2016 Mar;60:489-502. doi: 10.1016/j.msec.2015.11.078. Epub 2015 Dec 2.

Synthesis and physicochemical characterization of chitin dihexanoate--A new biocompatible chitin derivative--In comparison to chitin dibutyrate.

Author information

1
Department of Research and Development, Celther Poland Sp. z o.o. ul. Ostrzykowizna 14A, 05-170 Zakroczym, Poland. Electronic address: karolina.skolucka@celther.com.
2
Department of Research and Development, Celther Poland Sp. z o.o. ul. Ostrzykowizna 14A, 05-170 Zakroczym, Poland.
3
Silesian University of Technology, Faculty of Chemistry, Department of Physical Chemistry and Technology of Polymers, ul. M. Strzody 9, 44-100 Gliwice, Poland.
4
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.

Abstract

Chitin dihexanoate (DHCH) is the novel biocompatible and technologically friendly highly substituted chitin diester. Here we described optimization of DHCH and chitin dibutyrate (dibutyryl chitin, DBC) synthesis conditions (temperature and reaction time) to obtain desired polymers with high reaction yield, high substitution degree (close to 2) and appropriately high molecular weights. A two-step procedure, employing acidic anhydrides (hexanoic or butyric anhydride) as the acylation agent and methanesulfonic acid both as the catalyst and the reaction medium, was applied. Chemical structures of DBC and DHCH were confirmed by NMR ((1)H and (13)C) and IR investigations. Mechanical properties, thermogravimetric analysis, differential scanning calorimetry and biocompatibility (Neutral red uptake assay, Skin Sensitization and Irritation Tests) were assessed. Both polymers proved highly biocompatible (non-cytotoxic in vitro, non-irritating and non-allergic to skin) and soluble in several organic solvents (dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, acetone, ethanol and others). It is worth emphasizing that DHCH and DBC can be easily processed by solvent casting method and the salt-leaching method, what gives the opportunity to prepare highly porous structures, which can be further successfully applied as the material for wound dressings and scaffolds for tissue engineering.

KEYWORDS:

Biomaterial; Biopolymers; Chitin; Esterification; Polysaccharides

PMID:
26706556
DOI:
10.1016/j.msec.2015.11.078
[Indexed for MEDLINE]

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