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Structure-Function Insights into Quinuclidine-3-One BisQACs: Synthesis, Modulation of Bacterial Resistance,

Antonio Sabljić1,2, Doris Čarija1, Alma Ramić3

  • 1Department of Chemistry, Faculty of Science, University of Split, R. Bošković 33, 21000 Split, Croatia.

Pharmaceuticals (Basel, Switzerland)
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Summary

Novel quinuclidine-based bisquaternary ammonium compounds (bisQACs) show potent antimicrobial activity against resistant bacteria. These new agents disrupt bacterial membranes and reduce biofilm formation, offering a promising path for next-generation antibiotics with lower resistance potential.

Keywords:
antimicrobial resistancebiofilm inhibitionbisquaternary ammonium compounds (bisQACs)cytotoxicitymembrane permeabilizationmolecular docking

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Area of Science:

  • Medicinal Chemistry
  • Microbiology
  • Drug Discovery

Background:

  • Rising antibiotic resistance necessitates novel antimicrobial agents targeting bacterial membranes.
  • Bisquaternary ammonium compounds (bisQACs) show enhanced membrane disruption compared to monoquaternary analogs.
  • Limited research exists on bisQACs derived from natural scaffolds like quinuclidine.

Purpose of the Study:

  • To synthesize and evaluate novel quinuclidine-based bisQACs for antimicrobial activity.
  • To investigate the structure-activity relationships by varying alkyl chain and linker lengths.
  • To assess the potential for reduced resistance development.

Main Methods:

  • Synthesis of twelve novel quinuclidine-based bisQACs.
  • Systematic variation of alkyl chain and linker lengths.
  • Antimicrobial activity testing against key bacterial pathogens (S. aureus, MRSA, L. monocytogenes, E. coli).
  • Cytotoxicity assessment on human cell lines (RPE1, HEK293).
  • Biofilm inhibition assays and molecular docking studies with QacR efflux regulator.

Main Results:

  • Several synthesized bisQACs demonstrated potent activity against Gram-positive and Gram-negative bacteria.
  • Compound 2(QC16)6 exhibited the highest potency (MICs 5-38 µM).
  • Compounds showed favorable selectivity indices and inhibited biofilm formation.
  • Molecular docking indicated modulated binding to QacR, suggesting reduced efflux-mediated resistance.

Conclusions:

  • Quinuclidine-based bisQACs are effective membrane-disrupting agents against resistant bacteria.
  • These compounds offer a promising therapeutic window and reduced potential for resistance.
  • This class of compounds represents promising leads for next-generation antimicrobial therapies.