PEGylated calix[4]arene as a carrier for a Bodipy-based photosensitizer

Heavy atom substituted Bodipy compounds, unlike the parent chromophore, undergo rapid intersystem crossing to generate singlet oxygen, which is the primary cytotoxic agent exploited in PDT. In this work, we show that an organic soluble calix[4]arene can be functionalized by Knoevenagel reaction and then converted into an amphiphilic photosensitizer in a few steps. In addition to generating a potentially useful photosensitizer, the sequence of reactions is the first use of a Bodipy dye as a chromophoric/fluorogenic label without the typical reactive functional groups.