Self-assembly of nucleoamphiphiles: investigating nucleosides effect and the mechanism of micrometric helix formation.

A new family of self-assembling systems based on nucleoamphiphiles is described. Nano to micrometric left-handed helix formation in aqueous solution was induced simply by complexing a GMP or an AMP with a nonchiral monocationic amphiphile. The assembling behavior such as micellar formation, monolayer at air-water interface, as well as the aggregates in solution of these nucleoamphiphiles are strongly influenced by the presence of nucleosides in solution. The observed effects depend on the properties of complexed nucleotides and nucleosides with a complex mixture of pi stacking, hydrophobicity of the bases, and hydrogen bonding.