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Issue 3, 2020
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Sequential post-polymerization modification of a pentafluorophenyl ester-containing homopolymer: a convenient route to effective pH-responsive nanocarriers for anticancer drugs

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Abstract

Recently, pH-responsive polymeric micelles have gained significant attention as effective carriers for anti-cancer drug delivery. Herein, pH-responsive polymeric micelles were constructed by a simple post-polymerization modification of a single homopolymer, poly(pentafluorophenyl acrylate) (PPFPA). The PPFPA was first subjected to modification with 1-amino-2-propanol yielding the amphiphilic copolymer of poly(pentafluorophenyl acrylate)-ran-poly(N-(2-hydroxypropyl acrylamide)). A series of amphiphilic random copolymers of different compositions could self-assemble into spherical micelles with a unimodal size distribution in aqueous solution. Then, 1-(3-aminopropyl)imidazole (API), a reagent to introduce charge conversional entities, was reacted with the remaining PPFPA segment in the micellar core resulting in API-modified micelles which can encapsulate doxorubicin (DOX), a hydrophobic anti-cancer drug. As monitored by dynamic light scattering, the API-modified micelles underwent disintegration upon pH switching from 7.4 to 5.0, presumably due to imidazolyl group protonation. This pH-responsiveness of the API-modified micelles was responsible for the faster and greater in vitro DOX release in an acidic environment than neutral pH. Cellular uptake studies revealed that the developed carriers were internalized into MDA-MB-231 cells within 30 min via endocytosis and exhibited cytotoxicity in a dose-dependent manner.

Graphical abstract: Sequential post-polymerization modification of a pentafluorophenyl ester-containing homopolymer: a convenient route to effective pH-responsive nanocarriers for anticancer drugs

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Supplementary files

Article information


Submitted
23 Jul 2019
Accepted
28 Nov 2019
First published
02 Dec 2019

J. Mater. Chem. B, 2020,8, 454-464
Article type
Paper

Sequential post-polymerization modification of a pentafluorophenyl ester-containing homopolymer: a convenient route to effective pH-responsive nanocarriers for anticancer drugs

Y. Pinyakit, T. Palaga, S. Kiatkamjornwong and V. P. Hoven, J. Mater. Chem. B, 2020, 8, 454
DOI: 10.1039/C9TB01533G

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