Antibacterial Diamines Targeting Bacterial Membranes

J Med Chem. 2016 Apr 14;59(7):3140-51. doi: 10.1021/acs.jmedchem.5b01912. Epub 2016 Mar 28.

Abstract

Antibiotic resistance is a growing threat to human health exacerbated by a lack of new antibiotics. We now describe a series of substituted diamines that produce rapid bactericidal activity against both Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus and stationary-phase bacteria. These compounds reduce biofilm formation and promote biofilm dispersal in Pseudomonas aeruginosa. The most potent analogue, 3 (1,13-bis{[(2,2-diphenyl)-1-ethyl]thioureido}-4,10-diazatridecane), primarily acts by depolarization of the cytoplasmic membrane and permeabilization of the bacterial outer membrane. Transmission electron microscopy confirmed that 3 disrupts membrane integrity rapidly. Compound 3 is also synergistic with kanamycin, demonstrated by the checkerboard method and by time-kill kinetic experiments. In human cell toxicity assays, 3 showed limited adverse effects against the HEK293T human kidney embryonic cells and A549 human adenocarcinoma cells. In addition, 3 produced no adverse effects on Caenorhabditis elegans development, survival, and reproduction. Collectively, diamines related to 3 represent a new class of broad-spectrum antibacterials against drug-resistant pathogens.

Publication types

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

MeSH terms

  • Animals
  • Anti-Bacterial Agents / adverse effects
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Biofilms / drug effects
  • Caenorhabditis elegans / drug effects
  • Caenorhabditis elegans / growth & development
  • Cell Membrane / drug effects*
  • Cell Membrane Permeability / drug effects
  • Chemistry Techniques, Synthetic
  • Diamines / chemistry*
  • Diamines / pharmacology
  • Drug Evaluation, Preclinical / methods
  • Drug Interactions
  • Escherichia coli / drug effects
  • HEK293 Cells / drug effects
  • Humans
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Diamines