Biodegradable amphiphilic triblock copolymer bearing pendant glucose residues: preparation and specific interaction with Concanavalin A molecules.
A novel biodegradable amphiphilic block copolymer PLGG-PEG-PLGG bearing pendant glucose residues is successfully prepared by the coupling reaction of 3-(2-aminoethylthio)propyl-alpha-D-glucopyranoside with the pendant carboxyl groups of PLGG-PEG-PLGG in the presence of N,N'-carbonyldiimidazole. The polymer PLGG-PEG-PLGG, i.e., poly{(lactic acid)-co-[(glycolic acid)-alt-(L-glutamic acid)]}-block-poly(ethylene glycol)-block- poly{(lactic acid)-co-[(glycolic acid)-alt-(L-glutamic acid)]}, is prepared by ring-opening copolymerization of L-lactide (LLA) with (3s)-benzoxylcarbonylethylmorpholine-2,5-dione (BEMD) in the presence of dihydroxyl PEG with molecular weight of 2000 as macroinitiator and Sn(Oct)2 as catalyst, and then by catalytic hydrogenation. The glucose-grafted copolymer shows a lower degree of cytotoxicity to ECV-304 cells and improved specific recognition and binding with Concanavalin A (Con A). Therefore, this kind of glucose-grafted copolymer may find biomedical applications.
Lu
Changhai
C
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China.
Chen
Xuesi
X
Xie
Zhigang
Z
Lu
Tiancheng
T
Wang
Xin
X
Ma
Jia
J
Jing
Xiabin
X
D001673:Biodegradation, Environmental; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003208:Concanavalin A / Q000737:chemistry*; D003543:Cysteamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D042783:Endothelial Cells / Q000187:drug effects; D005947:Glucose / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011092:Polyethylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011485:Protein Binding
C512880:3-(2-aminoethylthio)propyl glucopyranoside; D005960:Glucosides; D011091:Polyesters; C512879:poly(lactic acid-co-((glycolic acid)-alt-(L-glutamic acid))glucose)-poly(ethylene glycol)-poly(lactic acid-co-((glycolic acid)-alt-(L-glutamic acid))glucose); D003208:Concanavalin A; D011092:Polyethylene Glycols; D003543:Cysteamine; D005947:Glucose