Double-tailed long chain BODIPYs - Synthesis, characterization and preliminary studies on their use as lipid fluorescence probes

In this paper we report the synthesis of a series of double-tailed BODIPYs bearing twin alkoxy groups with long linear alkyl side chains (C10, C12, C14, C16) attached to the meso positioned phenyl unit. The compounds were fully characterized and exhibited the typical BODIPY strong absorbance in the visible region and emission maxima around 530 nm, with high fluorescence quantum yields (ca. 0.8) and small Stokes shifts. The goal was to improve the lipophilicity of the BODIPYs without disturbing their excellent fluorescent properties. All synthetized BODIPYs were tested in vivo as fluorescent sensors for lipids and one of them (BD-C12) showed great potential to act as a lipid fluorescent probe.