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

Journal: Materials (Basel, Switzerland)
Published Date: Nov 10, 2016

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(-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--acetyl-2-deoxy-2-phthalimido--d-glucopyranose and 1,3,4,6-tetra--acetyl-2-amino-2-deoxy--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.

Authors

  • Guihua Cui
    Department of Chemistry, Jilin Medical College, Jilin 132013, China. cuiyuhan1981_0@sohu.com.
  • Zhengguo Gao
    Chemical and Engineering College, Yantai University, Yantai 264005, China. zggao_80@163.com.
  • Nannan Qiu
    NHC Key Laboratory of Food Safety Risk Assessment, China National Center for Food Safety Risk Assessment, Beijing 100021, PR China.
  • Toshifumi Satoh
    Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan. Satoh@polymer.ac.jp.
  • Toyoji Kakuchi
    Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan. Kakuchi@polymer.ac.jp.
  • Qian Duan
    Department of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022, China. duanqian88@hotmail.com.

Keywords

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