High-Density Noncovalent Functionalization of DNA by Electrostatic Interactions

Abstract

Preserving DNA hybridization in organic solvents could someday serve to significantly extend the applicability of DNA-based technologies. Here, we present a method that can be used to solubilize double-stranded DNA at high concentrations in organic media. This method requires first precipitating a DNA molecule from the aqueous environment with an anilinium derivative and subsequently exchanging this moiety with an amine-containing surfactant in organic solvent. We demonstrate that this method yields complete exchange of the surfactant and allows for the modification of DNA with hydrophobic primary, secondary, and tertiary alkylamines and ordered functional π-systems. Using this approach, we fabricate a multichromophoric light harvesting system that would be unattainable by traditional methods. Additionally, this method makes it possible to use small, hydrophilic molecules to solubilize DNA in organic solvents, which reduces the shielding around the DNA and makes the macromolecule more accessible for further chemical modification. We believe that this approach will prove tremendously beneficial in expanding the scope of DNA-based nano- and biotechnologies.