1,2,3‐Triazolium‐Based Cationic Amphipathic Peptoid Oligomers Mimicking Antimicrobial Helical Peptides |
| |
Authors: | Dr Radhe Shyam Nicolas Charbonnel Aurélie Job Christelle Blavignac Prof Dr Christiane Forestier Prof Dr Claude Taillefumier Dr Sophie Faure |
| |
Affiliation: | 1. Université Clermont Auvergne, CNRS, SIGMA Clermont, ICCF, Clermont-Ferrand, France;2. Université Clermont Auvergne, CNRS, LMGE, Clermont-Ferrand, France;3. Université Clermont Auvergne, Centre Imagerie Cellulaire Santé, Clermont-Ferrand, France |
| |
Abstract: | Amphipathic cationic peptoids (N‐substituted glycine oligomers) represent a promising class of antimicrobial peptide mimics. The aim of this study is to explore the potential of the triazolium group as a cationic moiety and helix inducer to develop potent antimicrobial helical peptoids. Herein we report the first solid‐phase synthesis of peptoid oligomers incorporating 1,2,3‐triazolium‐type side chains and their evaluation against Escherichia coli, Enterococcus faecalis, and Staphylococcus aureus. Several triazolium‐based oligomers, even of short length, selectively kill bacteria over mammalian cells. SEM visualization of S. aureus cells treated with a dodecamer and a hexamer reveals severe cell membrane damage and suggests that the longer oligomer acts by pore formation. |
| |
Keywords: | antimicrobial peptides foldamers peptidomimetics peptoids solid-phase synthesis |
|
|