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Glycopolymer–peptide bioconjugates with antioxidant activity via RAFT polymerization
| Content Provider | Semantic Scholar |
|---|---|
| Author | Shi, Haiting Liu, Li da Wang, Xiao-Bei Li, Jingyi |
| Copyright Year | 2012 |
| Abstract | Well-defined protected glycopolymer poly(2-(2,3,4,6-tetra-O-acetyl-β-D-glucosyloxy)ethyl methacrylate) (PAcGlcEMA) is synthesized by reversible addition–fragmentation chain transfer (RAFT) radical polymerization. In the presence of ethanolamine and 2,2′-dithiodipyridine, PAcGlcEMA-PDS with end thiol-reactive pyridyldisulfide (PDS) group is generated by a one-pot approach. After deprotection of PAcGlcEMA, tripeptide reduced glutathione (GSH) is conjugated to PGlcEMA-PDS by thiol–disulfide exchange reaction under mild conditions. Fluorescent assay and TEM studies demonstrate that the pendant glucose residues on PGlcEMA have specific recognition with protein Concanavalin A (Con A). In comparison to PGlcEMA-PDS, the bioconjugation of GSH to PGlcEMA enhances the affinity of glycopolymer to Con A. The association constant (Ka) for the interaction of PGlcEMA-GSH bioconjugate and Con A is 6.1 × 103 M−1, displaying a high glycoside cluster effect. The disulfide-linked GSH bioconjugate PGlcEMA-GSH shows antioxidant activity. The radical scavenging activity is validated in vitro by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. It is found that the scavenging activity is dependent on reaction time and temperature. A sustained radical scavenging activity is observed at 37 °C, and about 50% DPPH radical is cleared after 24 h incubation. The recognition and the antioxidant activity make the peptide–glycopolymer bioconjugate PGlcEMA-GSH have potential for biodetection, biomimetics and targeted antioxidant delivery. |
| Starting Page | 1182 |
| Ending Page | 1188 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/C2PY20021J |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/py/c2/c2py20021j/c2py20021j.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/C2PY20021J |
| Volume Number | 3 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |