Synthesis of new water-soluble ionic liquids and their antibacterial profile against gram-positive and gram-negative bacteria

Duman, Ali Niyazi; Öztürk, İsmail; Tunçel, Ayça; Ocakoğlu, Kasım; Çolak, Süleyman Gökhan; Hoşgör-Limoncu, Mine; Yurt, Fatma

doi:10.1016/j.heliyon.2019.e02607

Cited by 39 publications

(19 citation statements)

References 36 publications

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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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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 mechanism of IL antimicrobial activity is not known. Still, there is evidence that the long alkyl chain linear of the cation positively influences this activity, which may disrupt membrane proteins (Docherty and Kulpa., 2005;Duman et al, 2019;Florio et al, 2019). The optimized process is presented in Figure 2.…”

Section: Antimicrobial Activity Testmentioning

confidence: 99%

Red Propolis as a Source of Antimicrobial Phytochemicals: Extraction Using High-Performance Alternative Solvents

et al. 2021

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Propolis is a resinous material rich in flavonoids and involved in several biological activities such as antimicrobial, fungicide, and antiparasitic functions. Conventionally, ethanolic solutions are used to obtain propolis phytochemicals, which restrict their use in some cultures. Given this, we developed an alcohol-free high-performance extractive approach to recover antibacterial and antioxidants phytochemicals from red propolis. Thus, aqueous-solutions of ionic liquids (IL) and eutectic solvents were used and then tested for their total flavonoids, antioxidant, and antimicrobial activities. The surface-responsive technique was applied regarding some variables, namely, the time of extraction, the number of extractions, and cavitation power (W), to optimize the process (in terms of higher yields of flavonoids and better antioxidant activity). After that, four extractions with the same biomass (repetitions) using 1-hexyl-3-methylimidazolium chloride [C6mim]Cl, under the operational conditions fixed at 3.3 min and 300 W, were able to recover 394.39 ± 36.30 mg RuE. g−1 of total flavonoids, with total antioxidant capacity evaluated up to 7595.77 ± 5.48 μmol TE. g−1dried biomass, besides inhibiting the growth of Staphylococcus aureus and Salmonella enteritidis bacteria (inhibition halo of 23.0 ± 1.0 and 15.7 ± 2.1, respectively). Aiming at the development of new technologies, the antimicrobial effect also presented by [C6mim]Cl may be appealing, and future studies are required to understand possible synergistic actions with propolis phytochemicals. Thereby, we successfully applied a completely alcohol-free method to obtain antimicrobials phytochemicals and highly antioxidants from red propolis, representing an optimized process to replace the conventional extracts produced until now.

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“…added iodine‐131 on an IM bearing a 1,8‐naphthalene monoimide fragment (Figure 10) known for its fluorescence properties [50] . The latter IM derivative is also currently investigated for its excellent cytotoxic and antibacterial power [51,52] . In this article, the fragment's fluorescence has not been exploited for imaging purpose but could lead to a complementary study.…”

Section: Theranosticsmentioning

confidence: 99%

“…[50] The latter IM derivative is also currently investigated for its excellent cytotoxic and antibacterial power. [51,52] In this article, the fragment's fluorescence has not been exploited for imaging purpose but could lead to a complementary study. Instead, the intrinsic radioactivity of iodine-131 is measured to follow compounds uptake.…”

Section: Anticancer Imaging Agentsmentioning

confidence: 99%

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

2021

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Light and cognate phenomena, e. g., luminescence are powerful tools endowed with great sensitivity to explore the infinitely small. Molecular salts, especially those based on imidazolium units, are granted with original properties and structural versatility. Associated with fluorophores, they constitute highly bioavailable platforms. Their interactions with negatively charged species and biological membranes as well as their controllable cytotoxicity imparted their applications as anion receptors, but also a promising potential as antibacterial and anticancer agents whose mechanism of action can be observed using luminescence, opening the possibility of theranostics (therapy and diagnosis). One of the other assets of imidazolium salts is their flexible amphipathic character which promotes their self‐organizations into liquid‐crystal mesophases and their ability to mimic lipids. Combining luminescence to these amphipathic properties opens new prospects, e. g., following gene or drug delivery inside cells. These salts, all‐in‐one, should lead to new tools for biologists, as well as active theranostic molecules.

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Synthesis of new water-soluble ionic liquids and their antibacterial profile against gram-positive and gram-negative bacteria

Cited by 39 publications

References 36 publications

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

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

Red Propolis as a Source of Antimicrobial Phytochemicals: Extraction Using High-Performance Alternative Solvents

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

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