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

• Published in: Polymer chemistry Vol. 11; no. 7; pp. 1321 - 1326
• Main Authors: Pan, Ruihao, Zeng, Yuan, Liu, Guoqiang, Wei, Yen, Xu, Yanshuang, Tao, Lei
• Format: Journal Article
• Language: English
• Published: Cambridge Royal Society of Chemistry 21.02.2020
• Subjects: Cancer; Conjugates; Copolymerization; Copolymers; Diketones; Monomers; Nanoparticles; Polymer chemistry; Polymers; Water chemistry
• ISSN: 1759-9954; 1759-9962
• DOI: 10.1039/c9py01596e

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. A phenylboronic acid (PBA)-containing copolymer was synthesized via the Hantzsch reaction and radical polymerization. Curcumin was dynamically included in this PBA-containing polymer to selectively kill cancer cells.