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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.

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

Journal of materials chemistry. B (2019-12-14)
Yuwaporn Pinyakit, Tanapat Palaga, Suda Kiatkamjornwong, Voravee P Hoven
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-(3-Aminopropyl)imidazole, ≥97%
Sigma-Aldrich
Pentafluorophenyl acrylate, contains <200 ppm monomethyl ether hydroquinone as inhibitor, 98%