Journal
POLYMER CHEMISTRY
Volume 1, Issue 8, Pages 1205-1214Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0py00043d
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Funding
- National Natural Science Foundation of China [20704036]
- Major State Basic Research Project [2005CB623802]
- Committee of Science and Technology of Zhejiang Province
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Novel well-defined drug-grafted seven-arm amphiphilic star poly(epsilon-caprolactone-co-carbonate)-b-poly(ethylene glycol)s based on a beta-CD core [CDS-P(CL-co-DTC)-D-b-PEG] have been synthesized by the combination of controlled ring-opening polymerization (CROP), esterification coupling reactions and click reactions. First, 5,5-dibromomethyl-trimethylene carbonate (DBTC) bearing two bromide pendent groups was synthesized and used to copolymerize with CL to prepare seven-arm star random copolymers [CDS-P(CL-co-DBTC)] in the presence of per-2,3-acetyl-beta-cyclodextrin and Sn(Oct)(2). Second, esterification coupling reaction between CDS-P(CL-co-DBTC) and carboxyl-terminated mPEG led to amphiphilic seven-arm star copolymers [CDS-P(CL-co-DBTC)-b-PEG]. Subsequently, the bromide pendent groups on CDS-P(CL-co-DBTC)-b-PEG had been converted into azide groups by treating with NaN3. Finally, alkyne functionalized ibuprofen had been grafted onto the hydrophobic block of the star copolymers by copper(I)-catalyzed click reaction. H-1 NMR, FT-IR and SEC analyses confirmed the well-defined drug grafted star architecture. These copolymers could self-assemble into multi-morphological aggregates in water, which were characterized by dynamic light scattering (DLS) and transmission electron microscopy (TEM).
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