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Materials 2016, 9(11), 913; doi:10.3390/ma9110913

End-Functionalized Poly(N-isopropylacrylamide) with d-Glucosamine through Different Initiator from C-1 and C-2 Positions via Atom Transfer Radical Polymerization

1
Department of Chemistry, Jilin Medical College, Jilin 132013, China
2
Department of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022, China
3
Chemical and Engineering College, Yantai University, Yantai 264005, China
4
Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Jie Zheng
Received: 13 September 2016 / Revised: 17 October 2016 / Accepted: 20 October 2016 / Published: 10 November 2016
(This article belongs to the Special Issue Smart Biomaterials and Biointerfaces)
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Abstract

Regioselective modification of d-glucosamine (2-amino-2-deoxy-d-glucopyranose, GA) through C-1 and C-2 positions to synthesized thermo-responsive D-Glucosamine-poly(N-iso-propylacrylamide) (PNIPAM) via atom transfer radical polymerization (ATRP) was investigated for the first time. Two different schemes of the synthesis for GA derivatives (GA-PNIPAM (i) and (ii)) with well-defined structures using 3,4,6-tri-o-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranose and 1,3,4,6-tetra-o-acetyl-2-amino-2-deoxy-β-d-glucopyranose intermediates were examined. The GA-PNIPAM (ii) had an amino at C-2 position, while there was a hydroxyl in GA-PNIPAM (i) at this position. Both the resulting oligomers (i) and (ii) had a narrow dispersity, and no significant cytotoxic response of copolymers (i) and (ii) was observed in the cell line over the concentration range from 0.1 μg/mL to 1000 μg/mL at any of the exposure times. In addition, it was discovered that GA-PNIPAM (i) and (ii) inhibited the proliferation of Human Hepatocellular Carcinoma Cells HepG2 as the concentration and the time changed, and the inhibitory activity of polymer (ii) was higher than that of he (i). The results suggest that the GA-PNIPAM polymers show excellent biocompatibility in vitro. View Full-Text
Keywords: poly(N-isopropylacrylamide) (PNIPAM); d-glucosamine (GA); atom transfer radical polymerization (ATRP); lower critical solution temperature (LCST) poly(N-isopropylacrylamide) (PNIPAM); d-glucosamine (GA); atom transfer radical polymerization (ATRP); lower critical solution temperature (LCST)
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MDPI and ACS Style

Cui, G.; Gao, Z.; Qiu, N.; Satoh, T.; Kakuchi, T.; Duan, Q. End-Functionalized Poly(N-isopropylacrylamide) with d-Glucosamine through Different Initiator from C-1 and C-2 Positions via Atom Transfer Radical Polymerization. Materials 2016, 9, 913.

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