Corannulene Amino Acid-Derived Water-Soluble Amphiphilic Buckybowls as Broad-Spectrum Membrane Targeting Antibacterial Agents

J Med Chem. 2024 Sep 12;67(17):15041-15060. doi: 10.1021/acs.jmedchem.4c00666. Epub 2024 Aug 30.

Abstract

To date, the use of corannulene has been restricted in the area of material science, but its application in biomedical research has yet to be established due to its nonsolubility in an aqueous environment and synthetic infeasibility. Herein, we detail the development of a new family of highly curved π-conjugated corannulene-containing unnatural α-amino acid (CAA) derivatives to overcome this challenge. These CAAs have been extended as novel constituents for the synthesis of corannulene-containing water-soluble cationic peptides (CCPs), which display inhibitory activity against broad-spectrum pathogenic bacteria along with drug-resistant bacteria via a membrane-damaging mechanism. Importantly, several of the synthesized peptides were found to be appreciably nonhemolytic against hRBCs and noncytotoxic against mammalian 3T3 cells. In vivo efficacy studies of the potent and least cytotoxic peptide 6a demonstrated clearance of bacteria from the spleen, liver, lung, and blood of mice infected with S. aureus ATCC 25923.

MeSH terms

  • Amino Acids* / chemistry
  • Amino Acids* / pharmacology
  • Animals
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Antimicrobial Cationic Peptides / chemical synthesis
  • Antimicrobial Cationic Peptides / chemistry
  • Antimicrobial Cationic Peptides / pharmacology
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Humans
  • Mice
  • Microbial Sensitivity Tests*
  • Polycyclic Aromatic Hydrocarbons / chemical synthesis
  • Polycyclic Aromatic Hydrocarbons / chemistry
  • Polycyclic Aromatic Hydrocarbons / pharmacology
  • Solubility*
  • Staphylococcal Infections / drug therapy
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Water* / chemistry

Substances

  • Anti-Bacterial Agents
  • Amino Acids
  • Water
  • corannulene
  • Polycyclic Aromatic Hydrocarbons
  • Antimicrobial Cationic Peptides