Structural effects of amino acid-based ionic liquids on thermophysical properties, and antibacterial and cytotoxic activity

Beck, Thaíssa S.; Mattos, Mara de; Jortieke, Carlos R.T.; Vieira, Jean C. B.; Verdi, Camila Marina; Santos, Roberto C.V.; Sagrillo, Michele Rorato; Rossato, Aline; Silveira, Larissa da Silva; Frizzo, Clarissa P.

doi:10.1016/j.molliq.2022.120054

Cited by 2 publications

(4 citation statements)

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“…The comparison of monocationic and dicationic ionic liquids in their studies proved that the toxicity of ILs is related mainly to the cation and not to the nature of the anion. DILs have been found to be a good alternative to monocationic ionic liquids and have a lower environmental impact and antimicrobial activity. , In contrast, ILs based on the [2-(methacryloyloxy)ethyl]dimethylheptylammonium cation and a series of anions synthesized by De Leo et al did not display any antibacterial activity toward the S. maltophilia strain even at concentrations up to 1.5% . In addition, research on the antimicrobial activity of dicationic imidazolium-based ionic liquids with dicarboxylate anions carried out by Kuhn et al showed that only DILs with spacers shorter than 10 carbons were active against bacteria (mainly S. aureus ) .…”

Section: Resultsmentioning

confidence: 99%

“…An outstanding example of dicationic ionic liquids (DILs) is salts with an amino acid anion. Studies on this class of compounds showed that monocationic ILs had better antimicrobial activity than DILs toward most strains tested . The lower microbial activity is an environmental advantage because when the DILs enter the environment, they will not degrade naturally existing microbes .…”

Section: Introductionmentioning

confidence: 99%

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Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Kaczmarek,

Pacholak,

Burlaga

et al. 2023

ACS Sustainable Chem. Eng.

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Due to the poor water solubility of indole-3-butyric acid (IBA), adding appropriate adjuvants to this compound during application is essential. The physicochemical properties of plant growth regulators can be easily modified by transforming them into ionic liquids. In this research, IBA was converted into an anion and conjugated with a bis-ammonium cation to form novel dicationic ionic liquids (DILs). The purpose of obtaining these new DILs was to improve the biological activity and determine the effects of the modifications on the stability and persistence of soil microorganisms. The synthesis method enabled the designed DILs to be obtained with yields above 85%. The surface tension and chemical stability results indicated that these properties could be optimized by selecting appropriate cations. A solubility study indicated that the transformation of IBA into DILs improved the solubility of the active ingredient in water. Analysis of the growth-stimulating activity of the DILs on corn showed that the application of DILs significantly increased the fresh and dry cobs' weight compared to control plants. An experiment evaluating the effects of DILs on soil microorganisms showed that high concentrations of IBA anion inhibited bacterial growth and could have distorted cell metabolism. The DILs presented in this research may be potential alternatives to commercially used formulations.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Kaczmarek,

Pacholak,

Burlaga

et al. 2023

ACS Sustainable Chem. Eng.

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“…21 As a result, DILs are relatively less toxic as compared to their monocationic counterparts carrying alkyl chains of comparable length. 28 The toxicity of MILs correlates with their ability to interact and perturb the cellular membrane. 10,12,29 Several computational and experimental studies have been employed to study the mechanism of the interaction of monocations with the model phospholipid membranes.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The presence of two charged moieties makes it difficult for the dications to exhibit a detergent-like activity as shown by monocations . As a result, DILs are relatively less toxic as compared to their monocationic counterparts carrying alkyl chains of comparable length . The toxicity of MILs correlates with their ability to interact and perturb the cellular membrane. ,, Several computational and experimental studies have been employed to study the mechanism of the interaction of monocations with the model phospholipid membranes. ,− However, the structural details of dication–membrane interaction and its correlation with ionic liquid toxicity are not well understood.…”

Section: Introductionmentioning

confidence: 99%

How 1,n-Bis(3-alkylimidazolium-1-yl) Alkane Interacts with the Phospholipid Membrane and Impacts the Toxicity of Dicationic Ionic Liquids

et al. 2022

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Ionic liquids based on doubly charged cations, often termed dicationic ionic liquids (DILs), offer robust physicochemical properties and low toxicity than conventional monocationic ionic liquids. In this design-based study, we used solid-state NMR spectroscopy to provide the interaction mechanism of two DILs,, with 1-palmitoyl-2-oleoyl-snglycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-snglycero-3-phospho-(1′-rac-glycerol) (POPG) phospholipid membranes, to explain the low toxicity of DILs toward HeLa, Escherichia coli, Bacillus subtilis, and Saccharomyces cerevisiae cell lines. Dications with a short linker and long terminal chains cause substantial perturbation to the bilayer structure, making them more membrane permeabilizing, as shown by fluorescence-based dye leakage assays. The structural perturbation is even higher than [C 12 (MIM)] + monocations, which carry a single 12-carbon long chain and exhibit a much higher membrane affinity, permeability, and cytotoxicity. These structural details are a crucial contribution to the design strategies aimed at harnessing the biological activity of ionic liquids.

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Structural effects of amino acid-based ionic liquids on thermophysical properties, and antibacterial and cytotoxic activity

Cited by 2 publications

References 44 publications

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

Dicationic Ionic Liquids with an Indole-3-butyrate Anion – Plant Growth Stimulation and Ecotoxicological Evaluations

How 1,n-Bis(3-alkylimidazolium-1-yl) Alkane Interacts with the Phospholipid Membrane and Impacts the Toxicity of Dicationic Ionic Liquids

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