Helical Antimicrobial Sulfono-γ-AApeptides

J Med Chem. 2015 Jun 11;58(11):4802-11. doi: 10.1021/acs.jmedchem.5b00537. Epub 2015 May 28.

Abstract

Host-defense peptides (HDPs) such as magainin 2 have emerged as potential therapeutic agents combating antibiotic resistance. Inspired by their structures and mechanism of action, herein we report the first example of antimicrobial helical sulfono-γ-AApeptide foldamers. The lead molecule displays broad-spectrum and potent antimicrobial activity against multi-drug-resistant Gram-positive and Gram-negative bacterial pathogens. Time-kill studies and fluorescence microscopy suggest that sulfono-γ-AApeptides eradicate bacteria by taking a mode of action analogous to that of HDPs. Clear structure-function relationships exist in the studied sequences. Longer sequences, presumably adopting more-defined helical structures, are more potent than shorter ones. Interestingly, the sequence with less helical propensity in solution could be more selective than the stronger helix-forming sequences. Moreover, this class of antimicrobial agents are resistant to proteolytic degradation. These results may lead to the development of a new class of antimicrobial foldamers combating emerging antibiotic-resistant pathogens.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acids, Sulfur / chemistry*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antimicrobial Cationic Peptides / chemistry
  • Antimicrobial Cationic Peptides / pharmacology*
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Erythrocytes / drug effects
  • Gram-Negative Bacteria / drug effects*
  • Hemolysis / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Microscopy, Fluorescence
  • Models, Molecular
  • Molecular Structure
  • Peptide Fragments / chemistry
  • Peptide Fragments / pharmacology*
  • Peptidomimetics / chemistry
  • Peptidomimetics / pharmacology*
  • Scattering, Small Angle
  • Structure-Activity Relationship

Substances

  • Amino Acids, Sulfur
  • Anti-Bacterial Agents
  • Antimicrobial Cationic Peptides
  • Peptide Fragments
  • Peptidomimetics