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Methoxy poly(ethylene glycol)-b-poly(ε-caprolactone) block-graft copolymers with pendant fluorescent groups: synthesis, characterization and cellular uptake

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Abstract

Block-graft methoxy poly(ethylene glycol)-b-poly(ε-caprolactone) copolymers with pendant fluorescent pyrene groups were synthesized by post-polymerization conjugation of 1-pyrenemethyl 4-pentynoate (PMP) onto azido-functionalized MPEG-b-PαN3CL using the “click” reaction. Copolymers were characterized by differential scanning calorimetry (DSC), 1H NMR, IR, and gel permeation chromatography. The block-graft copolymers formed micelles in the aqueous phase, with critical micelle concentrations (CMCs) in the range of 2.9–19.4 mg L−1. Transmission electron microscopy (TEM) was used to analyze micelle morphology, and it revealed a spherical structure. The mean hydrodynamic diameters of the micelles from dynamic light scattering were in the range of 38–96 nm. In vitro cell viability assay indicated that MPEG-b-(PαN3CL-g-PMP/alkyne) has low cytotoxicity. Doxorubicin hydrochloride (DOX)-loaded micelles facilitated human cervical cancer (HeLa) cell uptake of DOX; uptake was completed within 4 h, and DOX was able to reach intracellular compartments and enter nuclei by endocytosis.

DOX-loaded MPEG45-b-(PαNCL26-g-PMP7/Hexy19) micelles (13) provide greater uptake of DOX by HeLa cells compared to the non-encapsulated drug (A), and were able to enter nuclei by endocytosis (C).

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Acknowledgments

The research was supported by grants from National Science Council (NCS100-2221-E-182-016) and Chang Gung Memorial Hospital (CMRPD5B0011). The authors are grateful to Advanced Instrumentation Center, National Taiwan University for DSC measurements, and Prof. Shu-Er Chow for technical assistance in cellular uptake and valuable discussions.

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Authors and Affiliations

  1. Department of Natural Science, Center of General Education, Chang Gung University, 259 Wen-Hwa 1st Road, Kwei-Shan, Tao-Yuan, 333, Taiwan

    Kang-Yu Peng, Shiu-Wei Wang & Ren-Shen Lee

  2. Department of Chemical and Materials Engineering, Chang Gung University, Kwei-Shan, Tao-Yuan, Taiwan

    Mu-Yi Hua

Authors
  1. Kang-Yu Peng
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  2. Shiu-Wei Wang
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  3. Mu-Yi Hua
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  4. Ren-Shen Lee
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Correspondence to Ren-Shen Lee.

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Peng, KY., Wang, SW., Hua, MY. et al. Methoxy poly(ethylene glycol)-b-poly(ε-caprolactone) block-graft copolymers with pendant fluorescent groups: synthesis, characterization and cellular uptake. J Polym Res 20, 62 (2013). https://doi.org/10.1007/s10965-012-0062-8

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  • DOI: https://doi.org/10.1007/s10965-012-0062-8

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