title: Photoactive fluoropolymer surfaces that release sensitizer drug molecules.
abstract: We describe a physical-organic study of two fluoropolymers bearing a photoreleasable PEGylated photosensitizer that generates (1)O2((1)Δg) [chlorin e6 methoxy tri(ethylene glycol) triester]. The surfaces are Teflon/poly(vinyl alcohol) (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, (1)O2 is formed, which cleaves an ethene linkage to liberate the sensitizer in 68-92% yield. The fluoropolymers were designed to deal with multiple problems. Namely, their success relied not only on high O2 solubility and drug repellency but also on the C-F bonds, which physically quench little (1)O2, for singlet oxygen's productive use away from the surface. The results obtained here indicate that Teflon-like surfaces have potential uses in delivering sensitizer and singlet oxygen for applications in tissue repair and photodynamic therapy (PDT).
authors: Department of Chemistry and Graduate Center, Brooklyn College, City University of New York , Brooklyn, New York 11210, United States.
authors: Goutam
authors: G
authors: Ghosh
authors: Mihaela
authors: M
authors: Minnis
authors: Ashwini A
authors: AA
authors: Ghogare
authors: Inna
authors: I
authors: Abramova
authors: Keith A
authors: KA
authors: Cengel
authors: Theresa M
authors: TM
authors: Busch
authors: Alexander
authors: A
authors: Greer
mesh_terms: D002735:Chlorophyllides; D054879:Halogenation; D053761:Nanocomposites / Q000737:chemistry; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry; D011138:Polytetrafluoroethylene / Q000737:chemistry; D011142:Polyvinyl Alcohol / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry
chemical_list: D002735:Chlorophyllides; D017319:Photosensitizing Agents; D011166:Porphyrins; D026082:Singlet Oxygen; D011092:Polyethylene Glycols; C062985:phytochlorin; D012822:Silicon Dioxide; D011138:Polytetrafluoroethylene; D011142:Polyvinyl Alcohol