Terpene-functionalized macrocyclic amphiphiles on pillar[5]arene platform as a bioimaging system: Synthesis, membranotropic activity and complexation with azo dye

Abstract

For the first time, terpene-functionalized pillar[5]arenes containing geranyl, perillyl or farnesyl fragments were synthesized. The obtained compounds did not have a pronounced cytotoxic effect on A549 cells in the studied concentration range (0.025–1 mg/mL). The ability of the obtained compounds to self-assemble in aqueous solutions was evaluated by DLS method. It was shown that the synthesized compounds are formed monodisperse nanosized aggregates with a diameter of 87–180 nm (PDI 0.18–0.33). The morphology of the formed aggregates was studied by transmission electron microscopy. The incorporation of the obtained amphiphilic macrocycles into the lipid bilayer of model lipid biomembranes was definitely confirmed by turbidimetry. Synthesized pillar [5]arenes form a complex with the aza dye methyl orange in a 1:2 ratio (logK11 = 2.12, logK12 = 8.63) This complex retains stability both in neutral (pH 7.4) and in an acidic environment (pH 2.7).