Photoactive Fluoropolymer Surfaces that Release Sensitizer Drug Molecules

摘要

We describe a physical-organic study of two fluoropolymers bearing a photoreleasable PEGylated photosensitizer which generates ¹O2(¹Δg) [chlorin e6 methoxy tri(ethylene glycol) triester]. The surfaces are Teflon/polyvinylalcohol (PVA) nanocomposite and fluorinated silica. The relative efficiency of these surfaces to photorelease the PEGylated sensitizer [shown previously to be phototoxic to ovarian cancer cells (Kimani, S. et al J. Org. Chem >2012, 77, 10638)] was slightly higher for the nanocomposite. In the presence of red light and O2, ¹O2 is formed, which cleaves an ethene linkage to liberate the sensitizer in 68–92% yields. The fluoropolymers were designed to deal with multiple problems. Namely, their success relied not only high O2 solubility and drug repellency, but that the C−F bonds physically quench little ¹O2 for its productive use away from the surface. The results obtained here indicate that Teflon-like surfaces have potential uses of delivering sensitizer and singlet oxygen for applications in tissue repair and photodynamic therapy (PDT).