Carbene formation as a mechanism for efficient intracellular uptake of cationic antimicrobial carbon acid polymers

Nat Commun. 2025 Jul 12;16(1):6460. doi: 10.1038/s41467-025-61724-y.

Abstract

Cationic polymers have emerged as promising next-generation antimicrobial agents, albeit with inherent limitations such as low potency and limited biocompatibility. Classical cationic polymers kill bacteria via physical membrane disruption. We propose a non-classical mechanism of crossing the bacterial plasma membrane barrier, a step required for subsequent inhibition of intracellular targets, by cationic polymers which are carbon acids. Oligoimidazolium (OIM) carbon acids, instead of lysing bacteria, transiently deprotonate in water to form hydrophobic N-heterocyclic carbenes (NHCs) and exhibit efficient plasma membrane translocation. Only OIMs that are carbon acids have potent antibacterial activities against even colistin- and multidrug-resistant bacteria. OIM amide derivatives exhibit excellent antibacterial efficacy in murine sepsis and thigh infection models, while a polymeric version acts as a prophylactic agent against bovine mastitis, which is a global agricultural problem. This study unveils a promising path for the development of an alternative class of potent antimicrobial agents.

MeSH terms

  • Animals
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Anti-Infective Agents* / chemistry
  • Anti-Infective Agents* / pharmacology
  • Cations / chemistry
  • Cattle
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Female
  • Methane* / analogs & derivatives
  • Methane* / chemistry
  • Methane* / metabolism
  • Mice
  • Microbial Sensitivity Tests
  • Polymers* / chemistry
  • Polymers* / pharmacology

Substances

  • Methane
  • carbene
  • Anti-Bacterial Agents
  • Polymers
  • Cations
  • Anti-Infective Agents