Here, we present the rational design of nanoscale degradable micelles containing a singlet oxygen (1O2)-cleavable group and their application for the delivery of the anticancer drug doxorubicin upon irradiation with light. Photodynamic therapy is a treatment that exploits a photosensitizer (S) to produce singlet oxygen (1O2) upon light irradiation to destroy cancer cells. The combination of photodynamic therapy with stimuli-responsive materials that release a trapped drug to tumor sites upon exposure to 1O2 would provide a more efficient approach for cancer treatment. The design of such functional 1O2-responsive materials requires a more complete understanding of degradation pathways, oxidation rates, and kinetics of singlet oxygen-cleavable linkers. In order to make these systems biocompatible, selected structural motifs have been synthesized and employed as building blocks for the preparation of water-soluble amphiphilic polymers. We designed two amphiphilic polymers, each containing a lipophilic stearyl chain (C18) and a hydrophilic PEG polymer connected by a singlet oxygen-cleavable linker. These amphiphilic polymers assemble into nanometric micelles in aqueous environment. The reaction of the cleavable linkers with UV light or singlet oxygen generated by photosensitization triggers the disassembly of the nanometric micelles. Our study paves the way for the development of materials that respond to 1O2 for applications in visible light-induced delivery of anticancer drugs, providing a practical and biocompatible method for enhanced photodynamic therapy.

Singlet oxygen degradable micelles for delivery of anticancer drugs

255th National Meeting (2018)

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