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Curcumin–polymer conjugates with dynamic boronic acid ester linkages for selective killing of cancer cells

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Abstract

The poor water-solubility of curcumin limits the broad applications of this promising traditional herb. In this study, we developed a strategy to prepare curcumin–polymer conjugates with a dynamic covalent linkage. A phenylboronic acid (PBA)-containing monomer was synthesized via the Hantzsch reaction. This monomer was then copolymerized with a water-soluble monomer through radical polymerization to obtain a water-soluble copolymer. Curcumin was included in this copolymer via covalent linkage between the PBA group in the polymer and 1,3-diketone group in curcumin. The resulting curcumin–polymer conjugate formed stable nanoparticles at pH ∼ 7.4 that quickly decomposed at pH ∼ 5.5. Further, it was found that the curcumin–polymer conjugates could selectively kill different cancer cells, which illustrates the potential of this curcumin–polymer conjugate for cancer therapy. This report is the first to describe a synthetic strategy for curcumin–polymer conjugates involving a dynamic linkage between PBA and curcumin. Thus, the applicability of PBA-containing polymers has been expanded to deliver curcumin for therapeutic applications.

Graphical abstract: Curcumin–polymer conjugates with dynamic boronic acid ester linkages for selective killing of cancer cells

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Supplementary files

Article information


Submitted
23 Oct 2019
Accepted
30 Dec 2019
First published
03 Jan 2020

Polym. Chem., 2020, Advance Article
Article type
Paper

Curcumin–polymer conjugates with dynamic boronic acid ester linkages for selective killing of cancer cells

R. Pan, Y. Zeng, G. Liu, Y. Wei, Y. Xu and L. Tao, Polym. Chem., 2020, Advance Article , DOI: 10.1039/C9PY01596E

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