Vinyl halogenated fatty acids display antibacterial activity against clinical isolates of methicillin-resistant Staphylococcus aureus

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.

Synthesis of the Novel N-(2-Hexadecynoyl)-l-Homoserine Lactone and Evaluation of Its Antiquorum Sensing Activity in Chromobacterium violaceum

“…42 This work is the first report providing evidence that previously synthesized 2-alkynoic antibacterial fatty acids can be used as starting materials for the synthesis of novel analogs of C6-HSL (Figure 1) with the potential to inhibit QS-mediated mechanisms. 28,29,31,32 In this study, we synthesized three HSLs using synthetic strategies described in Schemes 1−3. Once these compounds were synthesized, the effect of HSL on bacterial cell growth and violacein production was investigated (Figure 2).…”

Halogenated Antimicrobial Agents to Combat Drug-Resistant Pathogens

“…aureus (Fig. 15D) (Sanabria-Rios et al, 2022), and brominated derivatives of vinyl FAs were antileishmanial and inhibited topoisomerase IB enzyme of Leishmania sp. due to halogen bond formation (Carballeira et al, 2019).…”

“…17). During this review, we observed that the majority of new and existing compounds functionalized with halogens had a greater affinity for Gram-positive bacteria and fungi than Gram-negative bacteria (Doyle et al, 2019;Sanabria-Rios et al, 2022). In addition, despite exhibiting excellent druglike properties, including blood-brain penetration and high GI absorption, Br-and Clsubstituted cyclohexanol benzo[b]thiophene derivatives lacked activity against Gramnegative bacteria at high doses (Masih et al, 2021).…”

A Critical Review on Triboelectric Nanogenerators (TENGs) with Flame Retardant, Antibacterial, Self-Cleaning, or Water Repellent Properties

“…Bactericidal surfaces are generally obtained by use of quaternary ammonium compounds, , other cationic compounds , like PEI, bromides, chlorine containing compounds like triclosan − and N-halamines, , silver and nanoparticles, other metal nanoparticles, carbon based materials like carbon nanotubes (CNT) and graphene and so on, each having their own method of action. Other than that, natural antibacterial polymers like chitosan and bioderived compounds like lignin, coumarin, and others can also be used.…”