Nanostructured assemblies from nucleotide-based amphiphiles

A synthetic route to 3′-O-alkyl nucleotides is described that provides easy access to a series of nucleotide-based amphiphiles. Physicochemical experiments demonstrate that these nucleotide amphiphiles possess different aggregating properties compared to both their non-nucleotide analogues and simple nucleotides. The data collected from TEM, SEM, FT-IR and WAXS studies indicate that the aqueous dispersion of these nucleotide amphiphiles provides nanostructured assemblies such as ribbon-like structures for the thymidine derivatives and small aggregates for adenine. These results indicate that the nature of the base has an impact on aggregate morphology. A molecular model illustrating the 3D supramolecular arrangements of a thymidine nucleoamphiphile forming ribbons is proposed.