Synthesis,self‐assembly and drug‐loading capacity of well‐defined drug‐conjugated amphiphilic A2B2 type miktoarm star copolymers based on poly(ε‐caprolactone) and poly(ethylene glycol) |
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Authors: | Peng‐Fei Gou Wei‐Pu Zhu Ning Xu Zhi‐Quan Shen |
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Institution: | Key Laboratory of Macromolecule Synthesis and Functionalization of Ministry of Education, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, People's Republic of China |
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Abstract: | Well‐defined drug‐conjugated amphiphilic A2B2 miktoarm star copolymers (PCL)2‐(PEG)2‐D] were prepared by the combination of controlled ring‐opening polymerization (CROP) and “click” reaction strategy. First, bromide functionalized poly(ε‐caprolactone) (PCL‐Br) with double hydroxyl end groups was synthesized by the CROP of ε‐caprolactone using 2,2‐bis(bromomethyl)propane‐1,3‐diol as a difunctional initiator in the presence of Sn(Oct)2 at 110 °C. Next, the bromide groups of PCL‐Br were quantitatively converted to azide form by NaN3 to give PCL‐N3. Subsequently, the end hydroxyl groups of PCL‐N3 were capped with ibuprofen as a model drug at room temperature. Finally, copper(I)‐catalyzed cycloaddition reaction between ibuprofen‐conjugated PCL‐N3 and slightly excess alkyne‐terminated poly(ethylene glycol) (A‐PEG) led to ibuprofen‐conjugated A2B2 miktoarm star copolymer (PCL)2‐(PEG)2‐D]. The excess A‐PEG was removed by dialysis. 1H NMR, FTIR and SEC analyzes confirmed the expected miktoarm star architecture. These amphiphilic miktoarm star copolymers could self‐assemble into multimorphological aggregates in aqueous solution, which were characterized by dynamic light scattering (DLS) and transmission electron microscopy (TEM). In addition, the drug‐loading capacity of these drug‐conjugated miktoarm star copolymers as well as their nondrug‐conjugated analogs were also investigated in detail. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2009 |
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Keywords: | amphiphiles “ click” chemistry controlled ring‐opening polymerization (CROP) drug‐conjugation drug delivery miktoarm star copolymer polyesters poly(ethylene glycol) poly(ε ‐caprolactone) self‐assembly |
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