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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
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Structural effects on persister control by brominated furanones.

Jiachuan Pan1, Dacheng Ren

  • 1Department of Biomedical and Chemical Engineering, Syracuse University, Syracuse, NY 13244, United States; Syracuse Biomaterials Institute, Syracuse University, Syracuse, NY 13244, United States.

Bioorganic & Medicinal Chemistry Letters
|November 26, 2013
PubMed
Summary

Certain brominated furanones inhibit bacterial quorum sensing (QS) and can reduce antibiotic tolerance in Pseudomonas aeruginosa persister cells. However, QS inhibition alone does not fully explain or control bacterial persistence.

Keywords:
Antibiotic toleranceBrominated furanonePersisterPseudomonas aeruginosaQuorum sensingStructural effect

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Area of Science:

  • Microbiology
  • Bacterial Physiology
  • Drug Discovery

Background:

  • Bacterial persister cells are dormant, antibiotic-tolerant subpopulations.
  • Quorum sensing (QS) regulates bacterial behavior and virulence.
  • Previous work identified (Z)-4-bromo-5-(bromomethylene)-3-methylfuran-2(5H)-one (BF8) as a QS inhibitor that reverts antibiotic tolerance in Pseudomonas aeruginosa persister cells.

Purpose of the Study:

  • To investigate the structure-activity relationship of synthetic brominated furanones (BFs) in controlling bacterial persister cells.
  • To determine if QS inhibition is the sole mechanism by which BFs affect persister cells.
  • To identify novel compounds with potential applications in combating antibiotic tolerance.

Main Methods:

  • Synthesis of several structurally related brominated furanones.
  • Assay of BFs for inhibition of acyl-homoserine lactone (AHL)-mediated QS in P. aeruginosa.
  • Evaluation of the ability of BFs to revert antibiotic tolerance in P. aeruginosa PAO1 persister cells at growth non-inhibitory concentrations.

Main Results:

  • Multiple synthetic BFs demonstrated inhibition of AHL-mediated QS.
  • Several BFs, including BF8, were effective in reverting antibiotic tolerance of P. aeruginosa persister cells.
  • Not all QS-inhibiting BFs could revert persister cell antibiotic tolerance at concentrations that did not inhibit bacterial growth.

Conclusions:

  • QS inhibition is a key factor but not the sole determinant for reverting antibiotic tolerance in bacterial persister cells.
  • The efficacy of BFs in persister control is complex and may involve additional mechanisms beyond QS inhibition.
  • Further research is needed to elucidate the precise mechanisms underlying BF-mediated persister cell modulation.