A new perylene bisimide bola amphiphile: synthesis, characterization, fluorescent properties and applications as a potential probe

Abstract

Fluorescently-tagged lipids are a powerful tool for investigating the dynamics of lipids in cell biological studies and in biophysical applications. Herein we report the synthesis and the characterization of a new bola amphiphile, PC12, based on a bisimidic perylene moiety: a central perylene unit is symmetrically linked to two aliphatic chains both ending with a quaternary ammonium group. Absorption and fluorescent properties of the newly synthesized compound were investigated in DMSO and in water as a function of concentration and temperature. Further, the entrapment efficiency, the fluorescence behavior in dimyristoyl-sn-glycero-phosphocholine (DMPC) liposomes, and cell uptake on human and murine glioblastoma cell lines were evaluated. When loaded in liposomes, PC12 follows the same destiny of liposomes themselves in the cell cultures: this is an interesting result because PC12 could be used both as an aspecific dye (free form) and as an organelle-specific lipid probe.