Novel dicationic pyrimidine-based nucleolipid bearing piperidine head groups: Synthesis, aggregation behavior, solubilization capacity and interaction with DNA decamer

Abstract Novel dicationic nucleolipid bearing piperidine head groups has been synthesized. Using various physico-chemical methods (tensiometry, conductometry, pH-metry, fluorescence spectroscopy, spectrophotometry) its aggregation behavior in aqueous solutions has been examined. It has been revealed, that replacement of ammonium head group by piperidine results in a decrease in aggregation thresholds (critical micellar concentration equals 1.1 mM), as well as affects morphological behavior dramatically. In particular, existence of aggregates with both hydrodynamic diameters of 2 nm and ∼100 nm depending on the amphiphile concentration has been demonstrated. Spectrophotometric analysis has revealed, that fabricated aggregates of nucleolipid exhibit high capability to increase the solubility of lipophilic azodye Orange OT in water. Using dynamic and electrophoretic light scattering techniques interaction of this nucleolipid with double-stranded DNA decamer has been performed. It has been shown, that nucleolipid binds with DNA decamer electrostatically (isoelectric point was found at Camphiphile / Coligonuceotide ∼ 0.5) and forms lipoplexes with hydrodynamic diameter in the range of 300−400 nm.