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Molecules 2017, 22(1), 156; doi:10.3390/molecules22010156

Novel Amino-Pyridine Functionalized Chitosan Quaternary Ammonium Derivatives: Design, Synthesis, and Antioxidant Activity

1
Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, Shangdong, China
2
College of Chemistry, Chemical Engineering and Materials science, Shandong Normal University, Jinan 250014, Shandong, China
3
University of Chinese Academy of Sciences, Beijing 100039, China
4
Alliance Pharma, Inc., 17 Lee Boulevard, Malvern, PA 19355, USA
*
Author to whom correspondence should be addressed.
Academic Editors: Luciano Saso, László Dux, Grzegorz Wegrzyn and Tamás Csont
Received: 9 December 2016 / Revised: 11 January 2017 / Accepted: 12 January 2017 / Published: 18 January 2017
(This article belongs to the Special Issue Chemistry and Pharmacology of Modulators of Oxidative Stress)
View Full-Text   |   Download PDF [1255 KB, uploaded 18 January 2017]   |  

Abstract

Chemical modification of chitosan is increasingly studied for its potential of providing new applications of chitosan. Here, a group of novel chitosan quaternary ammonium derivatives containing pyridine or amino-pyridine were designed and successfully synthesized through chemical modification of chitosan. Pyridine and amino-pyridine were used as functional groups to improve the antifungal activity of chitosan derivatives. The chitosan derivatives’ antioxidant activity against hydroxyl-radical and 1,1-Diphenyl-2-picrylhydrazyl (DPPH)-radical was tested in vitro. The results showed that chitosan derivatives had better water solubility and stronger antioxidant activity compared with chitosan in all assays. Especially, compounds 3C and 3E (with 3-amino pyridine and 2,3-diamino pyridine as substitute respectively) exhibited stronger hydroxyl-radical and DPPH-radical scavenging ability than other synthesized compounds. These data demonstrated that the synergistic effect of the amino group and pyridine would improve the antioxidant activity of chitosan derivatives, and the position of the amino group on pyridine could influence the antioxidant property of chitosan derivatives. View Full-Text
Keywords: antioxidant activity; chemical modification; chitosan derivatives; amino-pyridine antioxidant activity; chemical modification; chitosan derivatives; amino-pyridine
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Li, Q.; Zhang, C.; Tan, W.; Gu, G.; Guo, Z. Novel Amino-Pyridine Functionalized Chitosan Quaternary Ammonium Derivatives: Design, Synthesis, and Antioxidant Activity. Molecules 2017, 22, 156.

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