Here, we present the synthesis of biocompatible amphiphilic polymers containing hydrophilic poly(ethylene glycol) and lipophilic stearyl chains connected through a cleavable alkoxyanthracene linker. The self-assembly of these amphiphilic polymers in water gives rise to degradable micelles with diameters of ~20 nm. Irradiation with UV light causes the photo-oxidation of the alkoxyanthracene linker to anthraquinone and triggers the degradation of the micelles. When the micelles were loaded with the chemotherapeutic agent doxorubicin, a combination of drug release and photodynamic mechanisms killed cancer cells <i>in vitro </i>upon irradiation at 365 nm. The degradation products and the kinetics of the photo-oxidation reaction were characterized by NMR and UV-vis spectroscopy. We demonstrated that singlet oxygen is involved in the photo-oxidation reaction, making these micelles suitable platform for enhanced photodynamic therapy – the combination of photodynamic therapy with singlet oxygen-responsive materials that can release a trapped drug to tumor sites.

Photoregulated delivery of anticancer drugs with cleavable polymer amphiphiles

2019 Fall National Meeting

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