Rigid Oxazole Acinetobactin Analog Blocks Siderophore Cycling in Acinetobacter baumannii

ACS Infect Dis. 2017 Nov 10;3(11):802-806. doi: 10.1021/acsinfecdis.7b00146. Epub 2017 Oct 12.

Abstract

The emergence of multidrug resistant (MDR) Gram-negative bacterial pathogens has raised global concern. Nontraditional therapeutic strategies, including antivirulence approaches, are gaining traction as a means of applying less selective pressure for resistance in vivo. Here, we show that rigidifying the structure of the siderophore preacinetobactin from MDR Acinetobacter baumannii via oxidation of the phenolate-oxazoline moiety to a phenolate-oxazole results in a potent inhibitor of siderophore transport and imparts a bacteriostatic effect at low micromolar concentrations under infection-like conditions.

Keywords: antibiotic resistance; antivirulence agent; iron acquisition; metal chelation; metal homeostasis; metal transport; pathogenesis; siderophore; virulence.

MeSH terms

  • Acinetobacter baumannii / drug effects*
  • Acinetobacter baumannii / metabolism*
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Gene Expression Regulation, Bacterial / drug effects
  • Imidazoles / chemistry*
  • Iron / metabolism
  • Molecular Structure
  • Oxazoles / chemistry*
  • Siderophores / chemistry*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Imidazoles
  • Oxazoles
  • Siderophores
  • acinetobactin
  • Iron