In Vitro Study of the Effect of Inhibition of Quorum Sensing by Brominated Furanone on Peritoneal Dialysis-Associated Peritonitis Associated with Escherichia Coli Infection

Li, Jinqiu; Wei, Xiaofang; Song, Yashan; Li, Xiaohua; Wang, Chengyu

doi:10.1007/s00284-022-03040-y

Cited by 2 publications

(1 citation statement)

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“…Thus, many natural (isolated from the red algae Delisea pulchra ) and synthetic 2(5 H )-furanone derivatives have been reported to repress the formation of biofilms by various Gram-negative and Gram-positive bacteria, such as Staphylococcus aureus , Staphylococcus epidermidis , Bacillus subtilis , Bacillus cereus , Escherichia coli , and Pseudomonas aeruginosa , etc. [ 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 ]. However, the most important factor limiting the clinical use of halogenated furanones as antimicrobials is their toxicity to eukaryotic cells and low stability in aqueous solutions [ 36 , 47 , 50 ].…”

Section: Introductionmentioning

confidence: 99%

The Novel Chiral 2(5H)-Furanone Sulfones Possessing Terpene Moiety: Synthesis and Biological Activity

et al. 2023

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Over the past decades, 2(5H)-furanone derivatives have been extensively studied because of their promising ability to prevent the biofilm formation by various pathogenic bacteria. Here, we report the synthesis of a series of optically active sulfur-containing 2(5H)-furanone derivatives and characterize their biological activity. Novel thioethers were obtained by an interaction of stereochemically pure 5-(l)-menthyloxy- or 5-(l)-bornyloxy-2(5H)-furanones with aromatic thiols under basic conditions. Subsequent thioethers oxidation by an excess of hydrogen peroxide in acetic acid resulted in the formation of the corresponding chiral 2(5H)-furanone sulfones. The structure of synthesized compounds was confirmed by IR and NMR spectroscopy, HRMS, and single crystal X-ray diffraction. The leading compound, 26, possessing the sulfonyl group and l-borneol moiety, exhibited the prominent activity against Staphylococcus aureus and Bacillus subtilis with MICs of 8 μg/mL. Furthermore, at concentrations of 0.4–0.5 μg/mL, the sulfone 26 increased two-fold the efficacy of aminoglycosides gentamicin and amikacin against S. aureus. The treatment of the model-infected skin wound in the rat with a combination of gentamicin and sulfone 26 speeded up the bacterial decontamination and improved the healing of the wound. The presented results provide valuable new insights into the chemistry of 2(5H)-furanone derivatives and associated biological activities.

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