Synthesis, Characterization, and Use of Asymmetric Pyrenyl-Gemini Surfactants as Emissive Components in DNA−Lipoplex Systems

Abstract

Gemini surfactants are potential candidates as synthetic vectors for the delivery of genes into cells to induce protein expression. With the ultimate objective of obtaining a better understanding of the mechanism of DNA transfection, two new asymmetric gemini surfactants (py-3-12 and py-6-12) have been synthesized as fluorescence probes. The physicochemical properties and morphologies of the self-assembled aggregates formed in aqueous solution have been studied using surface tension, specific conductance, dynamic light scattering (DLS), isothermal titration calorimetry (ITC), and fluorescence techniques. The interaction between pyrene-based gemini surfactants and DNA was investigated by using UV−vis and fluorescence spectroscopy. Binding constants for the DNA (salmon sperm)-gemini lipoplexes were measured. Fluorescence studies show that excimer emission occurs upon complexation with DNA.