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通过原子转移自由基聚合反应，使用来自C-1和C-2位置的不同引发剂，以d-葡萄糖胺对聚（N-异丙基丙烯酰胺）进行端基官能化。

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

作者信息

Cui Guihua, Gao Zhengguo, Qiu Nannan, Satoh Toshifumi, Kakuchi Toyoji, Duan Qian

机构信息

Department of Chemistry, Jilin Medical College, Jilin 132013, China.

Department of Materials Science and Engineering, Changchun University of Science and Technology, Changchun 130022, China.

出版信息

Materials (Basel). 2016 Nov 10;9(11):913. doi: 10.3390/ma9110913.

DOI:10.3390/ma9110913
PMID:28774036
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5457247/
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.

摘要

首次研究了通过C-1和C-2位对d-葡萄糖胺（2-氨基-2-脱氧-d-吡喃葡萄糖，GA）进行区域选择性修饰，以通过原子转移自由基聚合（ATRP）合成热响应性D-葡萄糖胺-聚（-异丙基丙烯酰胺）（PNIPAM）。研究了使用3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚氨基-d-吡喃葡萄糖和1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-d-吡喃葡萄糖中间体合成具有明确结构的GA衍生物（GA-PNIPAM（i）和（ii））的两种不同方案。GA-PNIPAM（ii）在C-2位有一个氨基，而GA-PNIPAM（i）在该位置有一个羟基。所得的低聚物（i）和（ii）均具有较窄的分散度，并且在任何暴露时间下，在0.1μg/mL至1000μg/mL的浓度范围内，未在细胞系中观察到共聚物（i）和（ii）有明显的细胞毒性反应。此外，发现GA-PNIPAM（i）和（ii）随着浓度和时间的变化抑制人肝癌细胞HepG2的增殖，并且聚合物（ii）的抑制活性高于聚合物（i）。结果表明，GA-PNIPAM聚合物在体外表现出优异的生物相容性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/1869820ef647/materials-09-00913-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/e1e770f21202/materials-09-00913-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/fe77d6ddbaea/materials-09-00913-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/685fa92d8db2/materials-09-00913-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/46ce78c80986/materials-09-00913-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/94b30fe364c8/materials-09-00913-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/cb179424142f/materials-09-00913-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/1869820ef647/materials-09-00913-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/e1e770f21202/materials-09-00913-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/fe77d6ddbaea/materials-09-00913-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/685fa92d8db2/materials-09-00913-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/46ce78c80986/materials-09-00913-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/94b30fe364c8/materials-09-00913-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/cb179424142f/materials-09-00913-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2efe/5457247/1869820ef647/materials-09-00913-g006.jpg

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