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

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-respon...

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Bibliographic Details
Published in:Polymer chemistry 2017-12, Vol.8 (46), p.7119-7132
Main Authors: Song, Jaeeun, Palanikumar, L., Choi, Yeongkyu, Kim, Inhye, Heo, Tae-young, Ahn, Eungjin, Choi, Soo-Hyung, Lee, Eunji, Shibasaki, Yuji, Ryu, Ja-Hyoung, Kim, Byeong-Su
Format: Article
Language:English
Subjects:
Biocompatibility
Block copolymers
Chemical synthesis
Control stability
Drug delivery systems
Micelles
Monomers
Polyethylene glycol
Polymer chemistry
Ring opening polymerization
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Summary: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.
ISSN:1759-9954
1759-9962
DOI:10.1039/C7PY01613A