Syntheses and photodynamic activity of some glucose-conjugated BODIPY dyes

The syntheses of three water-soluble glucose-conjugated BODIPY dyes with different wavelength emissions and studies of their photodynamic therapeutic (PDT) action on human lung cancer A549 cell line are disclosed. Amongst the chosen compounds, the BODIPY dye 4 possessing a glycosylated styryl moiety at the C-3 position showed best PDT property against the A549 cell line. In particular, it induced reactive oxygen species-mediated caspase-8/caspase-3-dependent apoptosis as revealed from the increased sub G1 cell population and changes in cell morphology. These results along with its localization in the endoplasmic reticulum, as revealed by confocal microscopy suggested that mitochondria may not be directly involved in the photo-cytotoxicity of 4. Compound 4 did not induce any dark toxicity to the A549 cells, and was non-toxic to normal lung cells. (C) 2016 Elsevier Masson SAS. All rights reserved.