Facile synthesis of 5-(alkylidene)thiophen-2(5H)-ones. A new class of antimicrobial agents

Benneche, T.; Herstad, Gunnar; Rosenberg, Marianne Lenes; Assev, S.; Scheie, Anne Aamdal

doi:10.1039/c1ra00254f

Cited by 20 publications

(12 citation statements)

References 27 publications

(26 reference statements)

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“…A mixture of ( Z )‐5‐(bromomethylene)‐3‐(hydroxymethyl]thiophen‐2(5 H )‐one 1 (Benneche et al . ) (88 mg, 0·4 mmol) and triethoxy(3‐isocyanatopropyl)silane 2 (0·60 g, 2 mmol) in 2 ml toluene was heated at 80°C during 24 h. The volatiles were removed in vacuo , and the product mixture was purified by flash column chromatography on silica (0–40% ethyl acetate (EtOAc) in hexanes). Yield: 161 mg (86%) (clear, faintly yellow oil) R f : 0·10 (25% EtOAc in hexanes).…”

Section: Methodsmentioning

confidence: 99%

Staphylococcus epidermidis biofilm on implant material is reduced by a covalently linked thiophenone

et al. 2016

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Section: Methodsmentioning

confidence: 99%

Staphylococcus epidermidis biofilm on implant material is reduced by a covalently linked thiophenone

et al. 2016

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“…1 . The compounds were synhtesised as described before 17 23 . All the thiophenones were dissolved in pure ethanol at 5 mM and stored at −20 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Unfortunately, these brominated furanones are toxic to higher organisms 15 , which means that they will not be safe for practical applications. More recently, brominated thiophenones, sulphur analogues of the brominated furanones with the same mode of action, have been synthesized, and these compounds were found to be more active than the corresponding furanones 16 17 18 . One of these compounds, ( Z )-4-((5-(bromomethylene)-2-oxo-2,5-dihydrothiophen-3-yl)methoxy)-4-oxobutanoic acid (TF310, Fig.…”

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confidence: 99%

Specific quorum sensing-disrupting activity (AQSI) of thiophenones and their therapeutic potential

Yang

Scheie

Benneche

et al. 2015

Sci Rep

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Disease caused by antibiotic resistant pathogens is becoming a serious problem, both in human and veterinary medicine. The inhibition of quorum sensing, bacterial cell-to-cell communication, is a promising alternative strategy to control disease. In this study, we determined the quorum sensing-disrupting activity of 20 thiophenones towards the quorum sensing model bacterium V. harveyi. In order to exclude false positives, we propose a new parameter (AQSI) to describe specific quorum sensing activity. AQSI is defined as the ratio between inhibition of quorum sensing-regulated activity in a reporter strain and inhibition of the same activity when it is independent of quorum sensing. Calculation of AQSI allowed to exclude five false positives, whereas the six most active thiophenones (TF203, TF307, TF319, TF339, TF342 and TF403) inhibited quorum sensing at 0.25 μM, with AQSI higher than 10. Further, we determined the protective effect and toxicity of the thiophenones in a highly controlled gnotobiotic model system with brine shrimp larvae. There was a strong positive correlation between the specific quorum sensing-disrupting activity of the thiophenones and the protection of brine shrimp larvae against pathogenic V. harveyi. Four of the most active quorum sensing-disrupting thiophenones (TF 203, TF319, TF339 and TF342) were considered to be promising since they have a therapeutic potential of at least 10.

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“…Unfortunately, halogenated furanones are too toxic to higher organisms to be applied in practice, with toxic concentrations being only slightly higher than quorum sensing-disrupting concentrations. In the search for compounds with a higher therapeutic potential, the synthesis of brominated thiophenones, sulphur analogues of brominated furanones, has recently been reported (Benneche et al 2011). These compounds have the same effect on the quorum sensing system of vib- rios as brominated furanones, i.e.…”

Section: Quorum Sensing Disruptionmentioning

confidence: 99%

Virulence mechanisms of bacterial aquaculture pathogens and antivirulence therapy for aquaculture

Defoirdt

2013

Reviews in Aquaculture

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Although aquaculture continues to be the fastest-growing food-producing industry worldwide, the sector faces important challenges with respect to controlling infectious diseases. Indeed, the frequent use of antibiotics, which are traditionally the most important line of defence against bacterial disease, has raised problems related to the development and spread of resistance. As a result, we currently are in a race to develop novel therapeutics that should allow us to continue controlling bacterial disease in the future. In this respect, scientific progress of the past years has allowed us to start understanding the mechanisms by which bacterial pathogens are causing disease. This knowledge in its turn opens up novel possibilities to combat infections by interfering with these mechanisms, a strategy that has been termed antivirulence therapy. In this review, the current knowledge with respect to pathogenicity mechanisms of bacterial aquaculture pathogens is discussed, including adhesion mechanisms, production of extracellular polysaccharides and biofilm formation, production of lytic enzymes (e.g. haemolysins and proteases), mechanisms of iron acquisition, secretion systems and regulatory mechanisms such as quorum sensing and host-pathogen signalling with catecholamine stress hormones. Furthermore, an overview is given of the first steps towards antivirulence therapy for aquaculture, with a focus on quorum sensing disruption as a proof of concept

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Facile synthesis of 5-(alkylidene)thiophen-2(5H)-ones. A new class of antimicrobial agents

Cited by 20 publications

References 27 publications

Staphylococcus epidermidis biofilm on implant material is reduced by a covalently linked thiophenone

Staphylococcus epidermidis biofilm on implant material is reduced by a covalently linked thiophenone

Specific quorum sensing-disrupting activity (AQSI) of thiophenones and their therapeutic potential

Virulence mechanisms of bacterial aquaculture pathogens and antivirulence therapy for aquaculture

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