Design of Triazolium-Grafted Peptidomimetic Macrocycles with Facial Amphipathicity to Target Pathogenic Bacteria

Org Lett. 2024 May 17;26(19):4088-4092. doi: 10.1021/acs.orglett.4c01149. Epub 2024 May 6.

Abstract

Access to 1,2,3-triazolium-grafted peptoid macrocycles was developed by macrocyclization and multivalent postmodification of linear peptoid oligomers carrying an alternance of benzylic and propargyl groups as side chains. X-ray analysis and NMR studies revealed a conformational preference for constrained hairpin-shaped structures leading to the facial amphipathic character of these macrocycles. A preliminary evaluation showed the antimicrobial activities of these new cationic amphipathic architectures.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bacteria / drug effects
  • Crystallography, X-Ray
  • Macrocyclic Compounds* / chemical synthesis
  • Macrocyclic Compounds* / chemistry
  • Macrocyclic Compounds* / pharmacology
  • Microbial Sensitivity Tests*
  • Molecular Structure
  • Peptidomimetics* / chemical synthesis
  • Peptidomimetics* / chemistry
  • Peptidomimetics* / pharmacology
  • Peptoids / chemical synthesis
  • Peptoids / chemistry
  • Peptoids / pharmacology
  • Triazoles* / chemistry
  • Triazoles* / pharmacology