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Resorcinarene-centered amphiphilic star-block copolymers: Synthesis, micellization and controlled drug release

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Abstract

Eight-arm star-shaped poly(ɛ-caprolactone)-block-poly(ethylene glycol)s (SPCL-b-PEG) have been prepared by a combination of controlled ring-opening polymerization (CROP) and coupling reaction. First, eight-arm star-shaped poly(ɛ-caprolactone)s (SPCL) with a resorcinarene core were synthesized using octamethyl tetraundecylresorcinarene octaacetate as octa-initiator and yttrium tris(2,6-di-tert-butyl-4-methylphenolate) [Y(DBMP)3] as catalyst. Then the coupling reaction was carried out between SPCLs and carboxyl-terminated methoxy poly(ethylene glycol)s (mPEG-COOH) in the presence of N,N′-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP), resulting in eight-arm star-shaped SPCL-b-PEGs with controlled molecular weight and well-defined architecture. Furthermore, these amphiphilic eight-arm SPCL-b-PEGs could self-assemble into micelles with low critical micellar concentrations (CMC), which was characterized by fluorescent spectroscopy. Moreover, indomethacin loaded micelles with high drug loading content and high encapsulation efficiency can be prepared, which is probably due to the highly branched architecture. The morphologies of micelles were characterized by transmission electron microscopy (TEM), which exhibited diverse nanostructures as the drug loading contents varied. In vitro drug release of indomethacin from SPCL-b-PEG micelles was carried out in PBS, from which a sustained release behavior was observed. SPCL-b-PEG micelles did not show significant cytotoxicity at copolymer concentrations up to 1000 mg/L, making them very promising for drug delivery.

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Authors and Affiliations

  1. MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, China

    Chen Gao, Ying Wang, Wei-pu Zhu & Zhi-quan Shen  (沈之荃)

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  1. Chen Gao
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  2. Ying Wang
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  3. Wei-pu Zhu
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  4. Zhi-quan Shen  (沈之荃)
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Correspondence to Zhi-quan Shen  (沈之荃).

Additional information

This work was financially supported by the National Natural Science Foundation of China (Nos. 20704036 and 21274121) and the Major State Basic Research Project (No. 2011CB606001).

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Gao, C., Wang, Y., Zhu, Wp. et al. Resorcinarene-centered amphiphilic star-block copolymers: Synthesis, micellization and controlled drug release. Chin J Polym Sci 32, 1431–1441 (2014). https://doi.org/10.1007/s10118-014-1528-4

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  • DOI: https://doi.org/10.1007/s10118-014-1528-4

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