Synthesis of biodegradable amphiphilic Y-shaped block co-polymers via ring-opening polymerization for drug delivery.
A series of novel Y-shaped biodegradable block co-polymers of poly(ε-caprolactone) (PCL) and poly(ethyl ethylene phosphate) (PEEP) (PCL-(PEEP)2) were synthesized via ring-opening polymerization (ROP) of EEP with bis-hydroxy-functional ROP initiator (init-PCL-(OH)2). The init-PCL-(OH)2 was synthesized by ROP of CL using 4-hydroxybutyl acrylate (HBA) as initiator and L-tartaric acid as catalyst in bulk, and subsequently the resulting vinyl-terminated PCL was end-capped by acetyl chloride, followed by Michael addition using excess diethanolamine. The Y-shaped co-polymers and their intermediates were characterized by (1)H-, (13)C-, (31)P-NMR, FT-IR and gel-permeation chromatography. The results indicated that the molecular weight of the Y-shaped co-polymers increased with the increasing of the molar ratios of EEP to init-PCL-(OH)2 in the feed, while the PCL chain length was kept constant. The amphiphilic block co-polymers could self-assemble into micelles in aqueous solution, which was demonstrated by dynamic light scattering, (1)H-NMR and atomic force microscopy. A study of controlled release of indomethacin indicated that the amphiphilic block co-polymers could potentially provide novel vehicles for drug delivery.
Jia
Lin
L
a Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemical Physics, University of Science and Technology of China, Hefei 230026, P. R. China.
Yan
Lifeng
L
Li
Yang
Y
D000085:Acetates / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry; D000404:Ajmaline; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D016503:Drug Delivery Systems / Q000379:methods; D008823:Micelles; D015394:Molecular Structure; D008970:Molecular Weight; D011091:Polyesters / Q000138:chemical synthesis / Q000737:chemistry; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry; D013644:Tartrates / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000085:Acetates; D000179:Acrylates; D002712:Chlorides; D008823:Micelles; D011091:Polyesters; D011108:Polymers; D013501:Surface-Active Agents; D013644:Tartrates; D014867:Water; D000404:Ajmaline; C016240:polycaprolactone; C120172:4-hydroxybutyl acrylate; C081124:acetyl chloride; C029768:tartaric acid