The power of the ring: A pH-responsive hydrophobic epoxide monomer for superior micelle stability

Jaeeun Song, L. Palanikumar, Yeongkyu Choi, Inhye Kim, Tae Young Heo, Eungjin Ahn, Soo Hyung Choi, Eunji Lee, Yuji Shibasaki, Ja Hyoung Ryu, Byeong Su Kim

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Abstract

Despite the growing interest in amphiphilic block copolymers for their application in micelles as ideal drug delivery carriers, there remain some challenges related to biocompatibility, stability, degradability, and loading efficiency of the micelles. Herein, we report a novel hydrophobic, pH-responsive epoxide monomer, tetrahydropyranyl glycidyl ether (TGE). Anionic ring-opening polymerization affords the controlled synthesis of a series of its homopolymers (PTGE) and amphiphilic polymers, poly(ethylene glycol)-block-poly(tetrahydropyranyl glycidyl ether) (PEG-b-PTGE). Interestingly, these block copolymers with cyclic TGE moieties showed superior stability in biological media, high loading capacity, tunable release, and controllable degradation compared to the block copolymers with its acyclic analogue, 1-ethoxyethyl glycidyl ether (EEGE), widely employed in polyether, which satisfy all the required design principles and address the challenges in drug delivery systems. The superior biocompatibility coupled with the high stability of the novel functional epoxide monomer is anticipated to lead to the development of a versatile platform for smart drug delivery systems.

Original languageEnglish
Pages (from-to)7119-7132
Number of pages14
JournalPolymer Chemistry
Volume8
Issue number46
DOIs
Publication statusPublished - 2017 Dec 14

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All Science Journal Classification (ASJC) codes

  • Bioengineering
  • Biochemistry
  • Polymers and Plastics
  • Organic Chemistry

Cite this

Song, J., Palanikumar, L., Choi, Y., Kim, I., Heo, T. Y., Ahn, E., Choi, S. H., Lee, E., Shibasaki, Y., Ryu, J. H., & Kim, B. S. (2017). The power of the ring: A pH-responsive hydrophobic epoxide monomer for superior micelle stability. Polymer Chemistry, 8(46), 7119-7132. https://doi.org/10.1039/c7py01613a