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Novel Fluoroquinolones With Pinane Moiety: Synthesis and Antimicrobial Activity.
Ilmir R Gilfanov1,2, Alyona I Kolesnikova1, Roman S Pavelyev3
1Institute of Fundamental Medicine and Biology, Kazan Federal University, Kazan, Russia.
Chemistry & Biodiversity
|January 5, 2025
Summary
Researchers created novel fluoroquinolone antimicrobials by fusing monoterpenes. These dual-acting compounds show enhanced activity against Staphylococcus aureus biofilms, offering new strategies for infection treatment.
Area of Science:
- Medicinal Chemistry
- Microbiology
- Drug Discovery
Background:
- Fluoroquinolones are broad-spectrum antibiotics.
- Antibiotic resistance and biofilm formation pose significant challenges.
- Monoterpenes are natural compounds with potential biological activities.
Purpose of the Study:
- To synthesize and evaluate novel fluoroquinolone-monoterpene hybrids.
- To assess the antimicrobial activity against Staphylococcus aureus, including methicillin-resistant strains (MRSA).
- To investigate the compounds' efficacy against bacterial biofilms and their mechanism of action.
Main Methods:
- Synthesis of fluoroquinolone derivatives fused with monoterpene moieties (trans-3-hydroxy-cis-myrtanylamine and (-)-nopylamine).
- Determination of minimal inhibitory concentrations (MICs) against Staphylococcus aureus isolates.
- Assessment of anti-biofilm activity and membrane potential changes.
- In silico analysis of binding energies with DNA gyrase.
Main Results:
- Fluoroquinolone-myrtanylamine hybrid 18 showed lower MICs against MSSA but higher MICs against MRSA compared to moxifloxacin.
- Fluoroquinolone-nopylamine hybrid 16 had reduced activity against MSSA but similar activity against MRSA compared to moxifloxacin.
- Both hybrids 16 and 18 demonstrated fourfold greater activity against biofilms than moxifloxacin and ciprofloxacin.
- Compounds 16 and 18 induced membrane potential drop and exhibited strong binding to DNA gyrase, suggesting a dual mechanism.
Conclusions:
- Monoterpene fusion to fluoroquinolones creates dual-acting bipharmacophores.
- These novel compounds show promising activity against Staphylococcus aureus, particularly in biofilm infections.
- The findings highlight the potential of combining antibiotic scaffolds with natural products for enhanced antimicrobial therapies.
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