Unsymmetrically substituted imidazolium salts: synthesis, characterization and antimicrobial activity

Çoban, Esin Poyrazoğlu; Fırıncı, Rukiye; Bıyık, Halil; Günay, M. Emın

doi:10.1590/s2175-97902017000115075

Cited by 8 publications

(6 citation statements)

References 26 publications

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“…Species of these genera cause significant economic losses to crop production worldwide (Dange et al ; Arriel et al ; Jones et al ; Singh and Miklas ; Kim et al ; Charkowski ; Ferraz et al ). Notably, the MIC for the imidazolium salts tested in this study were between 40 and 1000 µmol l −1 , a range similar to that observed in a previous study (20–800 µmol l −1 ) for growth inhibition of Micrococcus luteus , Staphylococcus aureus , Staphylococcus epidermis , Bacillus cereus , Bacillus subtilis , Bacillus thuringiensis and Listeria monocytogenes by structurally similar imidazolium salts (Çoban et al ). The identification of imidazolium salts that inhibit the growth of phytopathogenic bacteria could provide important alternatives for disease management.…”

Section: Discussionsupporting

confidence: 89%

“…Imidazolium salts have been shown to exhibit antibacterial activity against species belonging to diverse genera, including Micrococcus , Staphylococcus , Bacillus , Listeria , Escherichia , Salmonella , Enterococcus , Serratia , Proteus , Propionibacterium , and Pseudomonas (Demberelnyamba et al ; Postleb et al ; Zhang et al ; Çoban et al ; Uluçam and Tukyilmaz ). Those studies have shown that the strength of inhibition is highly dependent on the structure of the salt and the bacterial species.…”

Section: Discussionmentioning

confidence: 99%

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Imidazolium salts as alternative compounds to control diseases caused by plant pathogenic bacteria

Neves

Eloi

Freitas

et al. 2020

Journal of Applied Microbiology

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Aims: To evaluate the inhibitory effect of five structurally different imidazolium salts on the in vitro growth of plant pathogenic bacteria that belong to divergent taxonomic genera as well as their ability to reduce the severity of common bacterial blight of common bean caused by Xanthomonas axonopodis pv. phaseoli and bacterial speck of tomato caused by Pseudomonas syringae pv. tomato. Methods and Results: Growth inhibition of Xanthomonas, Pseudomonas, Erwinia, Pectobacterium and Dickeya strains by imidazolium salts was assessed in vitro by radial diffusion on agar medium and by ressazurin reduction in liquid medium. The reduction of common bacterial blight and bacterial speck symptoms and the area under de disease progress curves were determined by spraying two selected imidazolium salts on healthy plants 48 h prior to inoculation with virulent strains of the bacterial pathogens. All imidazolium salts inhibited the growth of all plant pathogenic bacteria when tested by radial diffusion on agar medium. The strength of inhibition differed among imidazolium salts when tested on the same bacterial strain and among bacterial strains when tested with the same imidazolium salt. In liquid medium, most imidazolium salts presented the same minimum inhibitory concentration (MIC) and minimum bactericidal concentration values (200 µmol l À1 ), the most notable exception of which was the MIC (at least 1000 µmol l À1 ) for the dicationic MImC 10 MImBr 2 . The imidazolium salts C 16 MImBr and C 16 MImCl caused significant reductions in the severity of common bacterial blight symptoms when compared with nontreated plants. Conclusion: Imidazolium salts inhibit the in vitro growth of plant pathogenic bacteria and reduce plant disease symptoms to levels comparable to an authorized commercial antibiotic product. Significance and Impact of the Study: New compounds exhibiting broadspectrum antibacterial activity with potential use in agriculture were identified.

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Section: Discussionsupporting

confidence: 89%

Section: Discussionmentioning

confidence: 99%

Imidazolium salts as alternative compounds to control diseases caused by plant pathogenic bacteria

Neves

Eloi

Freitas

et al. 2020

Journal of Applied Microbiology

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“…In sharp contrast, almost all imidazolium salts ( R 1 IR 2 ) exhibited a stronger antibacterial effect, including against ESBL-EC and MRSA ( p > 2.4). The antibacterial efficiency of R 1 IR 2 is quite similar to that of dehydroepiandrosterone-derived ( Hryniewicka et al, 2021 ), peptide-conjugated ( Reinhardt et al, 2014 ), ethoxyether-functionalized ( Huang et al, 2011 ), amino acid–derived ( Valls et al, 2020 ), polydiacetylene-conjugated ( Lee et al, 2016 ), and unsymmetrically substituted ( Çoban et al, 2017 ; Duman et al, 2019 ) imidazolium salts in previous reports. Furthermore, the antibacterial activity of imidazolium salts ( R 1 IR 2 ) increased following the substitution of methyl and bromobenzyl with dibromobenzyl groups and the change from one to two dibromobenzyl groups ( Table 3 ).…”

Section: Resultssupporting

confidence: 80%

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

et al. 2021

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The ability to detect hypochlorite (HOCl/ClO−) in vivo is of great importance to identify and visualize infection. Here, we report the use of imidazoline-2-thione (R1SR2) probes, which act to both sense ClO− and kill bacteria. The N2C=S moieties can recognize ClO− among various typical reactive oxygen species (ROS) and turn into imidazolium moieties (R1IR2) via desulfurization. This was observed through UV–vis absorption and fluorescence emission spectroscopy, with a high fluorescence emission quantum yield (ՓF = 43–99%) and large Stokes shift (∆v∼115 nm). Furthermore, the DIM probe, which was prepared by treating the DSM probe with ClO−, also displayed antibacterial efficacy toward not only Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) but also methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum ß-lactamase–producing Escherichia coli (ESBL-EC), that is, antibiotic-resistant bacteria. These results suggest that the DSM probe has great potential to carry out the dual roles of a fluorogenic probe and killer of bacteria.

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“…Both aryl imidazole derivatives (1 and 2) have been synthesized according to reported methods [25][26][27].…”

Section: Synthesis Of Precursors (1 and 2)mentioning

confidence: 99%

Synthesis and Characterization of Ag(I) Complexes Derived from New N-Heterocyclic Carbenes

2019

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Two new unsymmetrical imidazolium salts viz., [1-(4-ethylphenyl)-3-propyl-1H-imidazole-3-ium bromide] (3) and [1-(2,6-dimethylphenyl)-3-propyl-1H-imidazole-3-ium bromide] (4) have been synthesized via the reaction of propyl bromide with imidazole derivatives, [1-(4-ethylphenyl)-1Himidazole] (1) and [1-(2,6-dimethylphenyl)-1H-imidazole] (2) in absence of solvent. Then two new N-heterocyclic carbene silver complexes (5 and 6) were prepared through the reaction of imidazoluim salts (3 and 4) as a source of N-heterocyclic carbene with Ag2O by in situ method. These complexes can be used in the future as a transfer agent for preparing other transitional metal carbine complexes (NHCs) via transmetallation method. The formation of these compounds was confirmed by spectral analysis.

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Unsymmetrically substituted imidazolium salts: synthesis, characterization and antimicrobial activity

Cited by 8 publications

References 26 publications

Imidazolium salts as alternative compounds to control diseases caused by plant pathogenic bacteria

Imidazolium salts as alternative compounds to control diseases caused by plant pathogenic bacteria

Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

Synthesis and Characterization of Ag(I) Complexes Derived from New N-Heterocyclic Carbenes

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