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.
Highlights
The compound 2-amino-2-deoxy-D-glucopyranose (D-glucosamine, GA) is abundant among the natural polysaccharides and glycoconjugates [1,2] and is a carbohydrate component of many cellular glycoproteins, glycolipids and glycosaminoglycans; it plays an important role on cell surfaces [3,4,5]
The GA initiator and GA-PNIPAM were characterized by 1 HNMR, gel permeation chromatograph (GPC), FT-IR
Compared with the GA-PNIPAM (i) system, the conversion rate and molecular weight of the C-1 initiator of GA were low at the initial reaction; this may be caused by the stereospecific blockade of the phthalimide
Summary
The compound 2-amino-2-deoxy-D-glucopyranose (D-glucosamine, GA) is abundant among the natural polysaccharides and glycoconjugates [1,2] and is a carbohydrate component of many cellular glycoproteins, glycolipids and glycosaminoglycans; it plays an important role on cell surfaces [3,4,5]. The difference in reactivity between amino and hydroxyl groups in GA allows regioselectivity to synthesize derivatization with new features and functions [10,11,12]. GA derivatives have demonstrated potent biological activity and are used in medicinal research [13,14,15,16,17]. Amino oligosaccharides and glycoconjugates are important for developing new biologically active materials with anti-cancer activity.
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