Preserving DNA hybridization in organic solvents could someday serve as a means of significantly extending the applicability of DNA-based technologies. It has been shown that cationic surfactants that fall within a very narrow window of water solubility are capable of screening the highly concentrated negative charge on the DNA backbone and shuttling double-stranded DNA into the organic phase. Here, we present a ligand exchange method that largely expands the variety of surfactants that can be used to complex DNA in organic solvents. The method is based on first precipitating a DNA molecule from the aqueous environment with an anilinium derivative and subsequently exchanging this moiety with an amine-containing surfactant in an organic solvent. The substitution is driven by a proton exchange between the weakly basic anilinium and the nucleophilic amine group on the substituting surfactant. We demonstrate that this method yields complete exchange of the surfactant and allows for the modification of DNA with highly hydrophobic primary, secondary and tertiary alkylamines as well as ordered functional p-systems. 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 utility of DNA-based nano- and biotechnologies.

High density functionalization of DNA by electrostatic interactions

248th National Meeting (2014)

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