New derivatives of dehydroabietic acid target planktonic and biofilm bacteria in Staphylococcus aureus and effectively disrupt bacterial membrane integrity

Eur J Med Chem. 2015 Sep 18:102:68-79. doi: 10.1016/j.ejmech.2015.07.038. Epub 2015 Jul 21.

Abstract

The combination of the dehydroabietic acid scaffold with different amino acids resulted in the discovery of a new class of hybrid compounds that targets both planktonic and biofilms bacteria in Staphylococcus aureus strains and are far more potent anti-biofilm agents than conventional antibiotics. Unlike dehydroabietic acid, these compounds can disrupt biofilms within a short time period and compromise the integrity of the bacterial membrane. Two of the compounds identified in our study are the most potent abietane-type anti-biofilm agents reported so far and display robust activity against pre-formed biofilms at concentrations only 3-6-fold higher than those required to inhibit biofilm formation. Their easy preparation based on proteolysis-resistant d- and unusual amino acids makes them useful chemical probes to gain a deeper understanding of bacterial biofilms and outstanding candidates for further development into new drugs to fight infections.

Keywords: Amino acids; Antimicrobial; Biofilms; Dehydroabietic acid; Diterpenoids; Natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemical synthesis
  • Abietanes / chemistry
  • Abietanes / pharmacology*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Biofilms / drug effects*
  • Cell Membrane / drug effects*
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Plankton / drug effects*
  • Staphylococcus aureus / cytology
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Abietanes
  • Anti-Bacterial Agents
  • dehydroabietic acid