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Published on: May 15, 2019
Vinyl halogenated fatty acids display antibacterial activity against clinical isolates of methicillin-resistant
David J Sanabria-Rios1, Denisse Alequin-Torres2, Alenis De Jesus1
1Faculty of Science and Technology, Department of Natural Sciences, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, USA.
Abstract:
Methicillin-resistant Staphylococcus aureus is a pathogen responsible for skin and wound infections, pneumonia, and bloodstream infections. Serious attention is needed because Methicillin-resistant S. aureus is also resistant to many other commonly used antibiotics. This study explores the potential of vinyl halogenated fatty acids as antibacterial agents. Specifically, the total synthesis of vinyl halogenated fatty acids was performed to investigate their antibacterial activity against clinical isolates of methicillin-resistant S. aureus. The novel synthesis of the vinyl halogenated fatty acids was carried out by treating either 2-dodecynoic acid or 2-hexadecynoic acid with an allyl halide and 5 mol% of bis(benzonitrile)palladium (II) chloride as catalyst. Our results demonstrate that vinyl halogenated fatty acids displayed significant antibacterial activity against clinical isolates of methicillin-resistant S. aureus and low cytotoxicity against eukaryotic Vero Cells. Moreover, it was demonstrated that vinyl brominated fatty acids could disrupt the S. aureus plasma membrane and inhibit the expression of the norB gene.
Insights
Vinyl halogenated fatty acids show promise as antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA). These compounds exhibit significant MRSA activity with low cytotoxicity and disrupt bacterial membranes.
Area of Science:
- Organic Chemistry
- Microbiology
- Drug Discovery
Background:
- Methicillin-resistant Staphylococcus aureus (MRSA) is a significant pathogen causing severe infections.
- MRSA's resistance to multiple antibiotics necessitates novel therapeutic strategies.
- Vinyl halogenated fatty acids are explored for their potential antibacterial properties.
Purpose of the Study:
- To synthesize vinyl halogenated fatty acids.
- To evaluate their antibacterial activity against clinical MRSA isolates.
- To investigate their mechanism of action.
Main Methods:
- Total synthesis of vinyl halogenated fatty acids from 2-dodecynoic acid or 2-hexadecynoic acid.
- Palladium-catalyzed coupling reaction using bis(benzonitrile)palladium (II) chloride.
- Assessment of antibacterial activity against MRSA and cytotoxicity against Vero Cells.
Main Results:
- Vinyl halogenated fatty acids demonstrated significant antibacterial activity against MRSA.
- Low cytotoxicity was observed against eukaryotic Vero Cells.
- Vinyl brominated fatty acids disrupted the S. aureus plasma membrane and inhibited norB gene expression.
Conclusions:
- Vinyl halogenated fatty acids are effective antibacterial agents against MRSA.
- These compounds offer a potential new class of antibiotics with a specific mechanism of action.
- Further research into vinyl halogenated fatty acids is warranted for MRSA treatment.
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