Synthesis and photodynamic activity of novel asymmetrically substituted fluorinated phthalocyanines.
A series of asymmetrically substituted dodecafluorinated phthalocyanines has been synthesized via the Kobayashi ring expansion reaction of the corresponding dodecafluorinated boron subphthalocyanine with differently substituted 1,3-diiminoisoindolines. The mild reaction conditions employed during this ring expansion reaction gave rise exclusively to 3:1 asymmetrically substituted dodecafluorinated phthalocyanines. Metal insertion into the metal-free phthalocyanines was accomplished by heating at 40 degrees C in N,N-dimethylformamide in the presence of zinc bromide. The resulting zinc dodecafluorophthalocyanines were formulated as Cremophor EL oil-water emulsions and evaluated as photosensitizers in vitro against EMT-6 mouse mammary tumor cells. As compared to the previously studied zinc hexadecafluorophthalocyanine, these new asymmetrical zinc dodecafluorophthalocyanines exhibited improved photodynamic activity.
Sharman
Wesley M
WM
Department of Nuclear Medicine and Radiobiology, Faculty of Medicine, Université de Sherbrooke, Sherbrooke, Québec, Canada J1H 5N4.
van Lier
Johan E
JE
D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects / Q000528:radiation effects; D005461:Fluorine / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D054833:Isoindoles; D051379:Mice; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010778:Photochemotherapy; D013057:Spectrum Analysis; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry
D007211:Indoles; D054833:Isoindoles; D005461:Fluorine; D014364:Tryptophan; D006861:Hydrogen Peroxide; C013647:phthalocyanine