Chiral Gold Nanoparticles Decorated with Pseudopeptides

Peptide-functionalized gold nanoparticles are supramolecular systems that can mimic natural proteins or DNA. In this work, we describe the preparation, the analysis, and the biological evaluation of gold nanoparticles linked to pseudopeptide foldamers containing one to eight L-Ala-D-Oxd (Ala = alanine; Oxd = 4-carboxy-5-methyloxazolidin-2-one) residues. The nanoparticles become increasingly organized as the number of such moieties increases. Moreover, from the analysis of chiroptical signals we find that the chirality of the gold surface becomes more evident with decreasing foldamer length. Finally, these systems display no cytotoxicity towards HeLa cells and are good candidates to promote drug delivery once equipped with biologically active moieties.