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Biomater Res. 2018 Sep 26;22:30. doi: 10.1186/s40824-018-0137-7. eCollection 2018.

Synthesis and characterization of thiolated hexanoyl glycol chitosan as a mucoadhesive thermogelling polymer.

Author information

1
1Department of Organic Materials Engineering, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon, 34134 Republic of Korea.
2
2Predictive Model Research Center, Korea Institute of Toxicology, 141, Gajeong-ro, Yuseong-gu, Daejeon, 34114 Republic of Korea.
3
ezlab, 120, Heungdeokjungang-ro, Giheung-gu, Yongin-si, Gyeonggi-do 16950 Republic of Korea.
4
4Human and Environmental Toxicology Program, University of Science and Technology, 217, Gajeong-ro, Yuseong-gu, Daejeon, 34113 Republic of Korea.
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Contributed equally

Abstract

Background:

Mucoadhesive polymers, which may increase the contact time between the polymer and the tissue, have been widely investigated for pharmaceutical formulations. In this study, we developed a new polysaccharide-based mucoadhesive polymer with thermogelling properties.

Methods:

Hexanoyl glycol chitosan (HGC), a new thermogelling polymer, was synthesized by the chemical modification of glycol chitosan using hexanoic anhydride. The HGC was further modified to include thiol groups to improve the mucoadhesive property of thermogelling HGC. The degree of thiolation of the thiolated HGCs (SH-HGCs) was controlled in the range of 5-10% by adjusting the feed molar ratio. The structure of the chemically modified polymers was characterized by 1H NMR and ATR-FTIR. The sol-gel transition, mucoadhesiveness, and biocompatibility of the polymers were determined by a tube inverting method, rheological measurements, and in vitro cytotoxicity tests, respectively.

Results:

The aqueous solution (4 wt%) of HGC with approximately 33% substitution showed a sol-gel transition temperature of approximately 41 °C. SH-HGCs demonstrated lower sol-gel transition temperatures (34 ± 1 and 31 ± 1 °С) compared to that of HGC due to the introduction of thiol groups. Rheological studies of aqueous mixture solutions of SH-HGCs and mucin showed that SH-HGCs had stronger mucoadhesiveness than HGC due to the interaction between the thiol groups of SH-HGCs and mucin. Additionally, we confirmed that the thermogelling properties might improve the mucoadhesive force of polymers. Several in vitro cytotoxicity tests showed that SH-HGCs showed little toxicity at concentrations of 0.1-1.0 wt%, indicating good biocompatibility of the polymers.

Conclusions:

The resultant thiolated hexanoyl glycol chitosans may play a crucial role in mucoadhesive applications in biomedical areas.

KEYWORDS:

Chemical modification; Hexanoyl glycol chitosan; Mucoadhesive polymer; Rheological measurements; Thermogelling property; Thiolation

Conflict of interest statement

Not applicable.All authors have consented to the submission of this manuscript for publication.The authors declare that they have no competing interests.Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

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