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Micellar carrier based on methoxy poly(ethylene glycol)-block-poly(ε-caprolactone) block copolymers bearing ketone groups on the polyester block for doxorubicin delivery

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Abstract

Block copolymers of Methoxy poly(ethylene glycol)-block-poly(ε-caprolactone) bearing ketone groups (MPEG-b-P(CL-co-OPD)) are synthesized and evaluated for its potential to form micelles containing doxorubicin (DOX), a representative anticancer drug, by using an in vitro method based on membrane dialysis to emulate drug release in vivo. The 1H NMR spectra of the prepared block copolymers in D2O solution exhibit peaks due to the P(OPD-co-CL) in decreased intensity, indicates that the polymers form micelle particles containing the hydrophilic segments in their external parts. The CMC of the copolymer decrease with an increase in the content of ketone groups in the hydrophobic chain. Drug-free and drug-loaded solutions of structurally related copolymers indicate the polymeric aggregation into micellar-type constructs. The size of the drug-loaded micelles is found to be larger than corresponding drug-free micelles. The release rate of MPEG-b-PCL micelles is faster than MPEG-b-P(OPD-co-CL) micelles in pH 7.4 buffered solution and they have a similar release rate in pH 5.0 buffered solution. This study, therefore, confirms the potential of a novel functional block copolymers, Methoxy poly(ethylene glycol)-block-poly(ε-caprolactone) bearing ketone Groups, for the formation of polymeric micelles for drug delivery.

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Acknowledgment

This research was supported by the National Natural Science Foundation of China (20674019 and 20804015), “Shu Guang” Project of Shanghai Municipal Education Commission, Specialized Research Fund for the Doctoral Program of Higher Education (20060251015, 200802511021), the Natural Science Foundation of Shanghai, (08ZR1406000), Shanghai Key Laboratory Project (08DZ2230500) and Shanghai Leading Academic Discipline Project (B502).

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Authors and Affiliations

  1. Shanghai Key Laboratory of Advanced Polymeric Materials, Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, 130 Meilong Road, P.O. Box 391, Shanghai, 200237, People’s Republic of China

    He Yueying, Zhang Yan, Gu Chunhua, Dai Weifeng & Lang Meidong

  2. Key Laboratory of Molecular Engineering of Polymers, Fudan University, Ministry of Education, Shanghai, 200433, China

    Lang Meidong

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  1. He Yueying
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  2. Zhang Yan
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Correspondence to Lang Meidong.

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Yueying, H., Yan, Z., Chunhua, G. et al. Micellar carrier based on methoxy poly(ethylene glycol)-block-poly(ε-caprolactone) block copolymers bearing ketone groups on the polyester block for doxorubicin delivery. J Mater Sci: Mater Med 21, 567–574 (2010). https://doi.org/10.1007/s10856-009-3887-x

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