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Chiral Gold Nanoparticles Decorated with Pseudopeptides
Author(s) -
Fanelli Rossana,
Milli Lorenzo,
Cornia Andrea,
Moretto Alessandro,
Castellucci Nicola,
Zanicola,
Malachin Giulia,
Tavano Regina,
Tomasini Claudia
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500549
Subject(s) - chemistry , colloidal gold , hela , supramolecular chemistry , chirality (physics) , nanoparticle , combinatorial chemistry , foldamer , peptide , nanotechnology , stereochemistry , organic chemistry , in vitro , molecule , biochemistry , materials science , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
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.