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1.
SAR QSAR Environ Res ; 35(9): 757-770, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39345234

RESUMEN

Ionic liquids (ILs) have attracted considerable interest due to their unique properties and prospective uses in various industries. However, their potential toxicity, particularly regarding enzyme inhibition, has become a growing concern. In this study, a QSAR model was proposed to predict the enzyme inhibition toxicity of ILs. A dataset of diverse ILs with corresponding toxicity data against three enzymes was compiled. Molecular descriptors that capture the physicochemical, structural, and topological properties of the ILs were calculated. To optimize the selection of descriptors and develop a robust QSAR model, the chaotic spotted hyena optimization algorithm, a novel nature-inspired metaheuristic, was employed. The proposed algorithm efficiently searches for an optimal subset of descriptors and model parameters, enhancing the predictive performance and interpretability of the QSAR model. The developed model exhibits excellent predictive capability, with high classification accuracy and low computation time. Sensitivity analysis and molecular interpretation of the selected descriptors provide insights into the critical structural features influencing the toxicity of ILs. This study showcases the successful application of the chaotic spotted hyena optimization algorithm in QSAR modelling and contributes to a better understanding of the toxicity mechanisms of ILs, aiding in the design of safer alternatives for industrial applications.


Asunto(s)
Algoritmos , Líquidos Iónicos , Relación Estructura-Actividad Cuantitativa , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/toxicidad , Inhibidores Enzimáticos/farmacología , Animales
2.
Chemosphere ; 364: 143252, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39236918

RESUMEN

Ionic liquids (ILs) have found diverse applications in research and industry. Biocompatible ILs, a subset considered less toxic than traditional ILs, have expanded their applications into biomedical fields. However, there is limited understanding of the toxicity profiles, safe concentrations, and underlying factors driving their toxicity. In this study, we investigated the cytotoxicity of 13 choline-based ILs using four different cell lines: Human dermal fibroblasts (HDF), epidermoid carcinoma cells (A431), cervical cancer cells (HeLa), and gastric cancer cells (AGS). Additionally, we explored the haemolytic activity of these ILs. Our findings showed that the cytotoxic and haemolytic activities of ILs can be attributed to the hydrophobicity of the anions and the pH of the IL solutions. Furthermore, utilising quartz crystal microbalance with dissipation (QCM-D), we delved into the interaction of selected ILs, including choline acetate [Cho][Ac] and choline geranate [Cho][Ge], with model cell membranes composed of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC). The QCM-D data showed that ILs with higher toxicities exhibited more pronounced interactions with membranes. Increased variations in frequency and dissipation reflected substantial changes in membrane fluidity and mass following the addition of the more toxic ILs. Furthermore, total internal reflection fluorescence microscopy study revealed that [Cho][Ac] could cause lipid rearrangements and pore formation in the membrane, while [Cho][Ge] disrupted the bilayer packing. This study advances our understanding of the cellular toxicities associated with choline-based ILs and provides valuable insights into their mechanisms of action concerning IL-membrane interactions. These findings have significant implications for the safe and informed utilisation of biocompatible ILs in the realm of drug delivery and biotechnology.


Asunto(s)
Acetatos , Aminoácidos , Aniones , Membrana Celular , Colina , Líquidos Iónicos , Líquidos Iónicos/química , Líquidos Iónicos/toxicidad , Humanos , Colina/química , Aniones/química , Membrana Celular/efectos de los fármacos , Acetatos/química , Acetatos/toxicidad , Aminoácidos/química , Interacciones Hidrofóbicas e Hidrofílicas , Células HeLa , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos
3.
Chemosphere ; 364: 143271, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39241837

RESUMEN

Microplastics represent a novel category of environmental pollutants, and understanding their interactions with typical xenobiotics is crucial. In this study, we investigated the impact of ionic liquids (ILs) containing herbicidal anions, namely glyphosate [Glyph] and 2,4-dichlorophenoxyacetate [2,4-D], and the surfactant cation - dodecyltrimethylammonium [C12TMA] on acrylonitrile butadiene styrene (ABS) microplastics. The aim of the study was to assess the sorption capacity of microplastics that were present in both untreated and aged form using standard and modified Fenton methods. In addition, impact on toxicity and stress adaptation of the model soil bacterium Pseudomonas putida KT2440 was measured. Upon ageing, ABS microplastics underwent a fivefold increase in BET surface area and total pore volume (from 0.001 to 0.004 cm3/g) which lead to a dramatic increase in adsorption of the cations on ABS microplastics from 40 to 45% for virgin ABS to 75-80% for aged ABS. Toxicity was mainly attributed to hydrophobic cations in ILs (EC50 ∼ 60-65 mg/dm3), which was also mitigated by sorption on ABS. Furthermore, both cations and anions behaved similarly across different ILs, corresponding chlorides, and substrates used in the ILs synthesis. These findings highlight microplastics potential as hazardous sorbents, contributing to the accumulation of xenobiotics in the environment.


Asunto(s)
Ácido 2,4-Diclorofenoxiacético , Butadienos , Glicina , Glifosato , Herbicidas , Líquidos Iónicos , Microplásticos , Herbicidas/toxicidad , Herbicidas/química , Herbicidas/análisis , Microplásticos/toxicidad , Adsorción , Ácido 2,4-Diclorofenoxiacético/toxicidad , Ácido 2,4-Diclorofenoxiacético/química , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Glicina/análogos & derivados , Glicina/toxicidad , Glicina/química , Butadienos/toxicidad , Butadienos/química , Acrilonitrilo/toxicidad , Acrilonitrilo/química , Pseudomonas putida/efectos de los fármacos , Contaminantes del Suelo/toxicidad , Contaminantes del Suelo/análisis , Contaminantes del Suelo/química , Resinas Acrílicas , Poliestirenos
4.
Molecules ; 29(16)2024 Aug 14.
Artículo en Inglés | MEDLINE | ID: mdl-39202930

RESUMEN

Approximately half of the lubricants sold globally find their way into the environment. The need for Environmentally Acceptable Lubricants (EALs) is gaining increased recognition. A lubricant is composed of a base oil and multiple functional additives. The literature has been focused on EAL base oils, with much less attention given to eco-friendly additives. This study presents the tribological performance and aquatic toxicity of four short-chain phosphonium-phosphate and ammonium-phosphate ionic liquids (ILs) as candidate anti-wear and friction-reducing additives for EALs. The results are benchmarked against those of four commercial bio-derived additives. The four ILs, at a mere 0.5 wt% concentration in a synthetic ester, demonstrated a 30-40% friction reduction and >99% wear reduction, superior to the commercial baselines. More impressively, all four ILs showed significantly lower toxicity than the bio-derived products. In an EPA-standard chronic aquatic toxicity test, the sensitive model organism, Ceriodaphnia dubia, had 90-100% survival when exposed to the ILs but 0% survival in exposure to the bio-derived products at the same concentration. This study offers scientific insights for the future development of eco-friendly ILs as lubricant additives.


Asunto(s)
Líquidos Iónicos , Lubricantes , Líquidos Iónicos/química , Líquidos Iónicos/toxicidad , Lubricantes/química , Lubricantes/toxicidad , Animales , Contaminantes Químicos del Agua/toxicidad , Contaminantes Químicos del Agua/química , Fosfatos/química , Fosfatos/toxicidad
5.
Environ Int ; 191: 108968, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39213918

RESUMEN

Global sensitivity analysis combined with quantitative high-throughput screening (GSA-qHTS) uses random starting points of the trajectories in mixture design, which may lead to potential contingency and a lack of representativeness. Moreover, a scenario in which all factor levels were at stimulatory effects was not considered, thereby hindering a comprehensive understanding of GSA-qHTS. Accordingly, this study innovatively introduced an optimised experimental design, uniform design (UD), to generate non-random and representative sample points with smaller uniformity deviation as starting points of multiple trajectories. By combining UD with the previously optimised one-factor-at-a-time (OAT) method, a novel mixture design method was developed (UD-OAT). The single toxicity tests showed that three pyridinium and five imidazolium ionic liquids (ILs) exerted stimulatory effects on Vibrio qinghaiensis sp.-Q67; thus, four stimulatory effective concentrations of each IL were selected as factor levels. The UD-OAT generated 108 mixture samples with equal frequency and without repetition. High-throughput microplate toxicity analysis revealed that all 108 mixtures exhibited inhibitory effects. Among these, type B mixtures exhibited increasing toxicities that subsequently decreased, unlike type C mixtures, which consistently increased over time. GSA successfully identified three of the eight ILs as important factors influencing the toxicities of the mixtures. When individual ILs produced stimulatory effects, mixtures containing two to three ILs exhibited either stimulatory effects or none. In contrast, mixtures containing five to eight ILs exhibited inhibitory effects, while those containing four ILs showed a transition from stimulatory to inhibitory effects. This study provides a novel mixture design method for studying mixture toxicity and fills the application gap of GSA-qHTS. The phenomenon of individuals being beneficial while mixtures can be harmful challenges traditional mixture risk assessments.


Asunto(s)
Ensayos Analíticos de Alto Rendimiento , Líquidos Iónicos , Pruebas de Toxicidad , Vibrio , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Pruebas de Toxicidad/métodos , Ensayos Analíticos de Alto Rendimiento/métodos , Vibrio/efectos de los fármacos , Proyectos de Investigación , Imidazoles/toxicidad
6.
Ecotoxicol Environ Saf ; 283: 116845, 2024 Sep 15.
Artículo en Inglés | MEDLINE | ID: mdl-39116690

RESUMEN

Ionic liquids (ILs) have many beneficial properties that are extensively used in various fields. Despite their utility, the phytotoxic aspects of ILs are poorly known. This is especially true at the transcriptomic level and the role of nitric oxide (NO) in this process. Herein, we studied the mechanism by which endogenous NO reduces the toxicity of ILs in Arabidopsis. We examined the effects of two imidazolium-based ILs (IILs) on three Arabidopsis lines, each characterized by distinct endogenous NO levels, using a combination of physiological and transcriptomics methods. IILs impaired seed germination, seedling development, chlorophyll content, and redox homeostasis in Arabidopsis. Notably, 1,3-dibutyl imidazole bromide had greater toxicity than 1-butyl-3-methylimidazolium chloride. Nox1, a mutant with an elevated NO level, had enhanced resistance, while nia1nia2, a mutant with a diminished NO level, had increased susceptibility compared to the wild type. RNA sequencing results suggested that NO mitigates IILs-induced phytotoxicity by modulating the metabolism of chlorophyll and secondary metabolites, and by bolstering the antioxidant defense system. These findings illustrate the complex molecular networks that respond to IIL stress and reveal the potential of endogenous NO as a mitigating factor in plant stress physiology.


Asunto(s)
Arabidopsis , Germinación , Imidazoles , Líquidos Iónicos , Óxido Nítrico , Arabidopsis/efectos de los fármacos , Arabidopsis/genética , Arabidopsis/crecimiento & desarrollo , Óxido Nítrico/metabolismo , Imidazoles/toxicidad , Líquidos Iónicos/toxicidad , Germinación/efectos de los fármacos , Clorofila/metabolismo , Plantones/efectos de los fármacos , Plantones/crecimiento & desarrollo
7.
Biomolecules ; 14(8)2024 Aug 07.
Artículo en Inglés | MEDLINE | ID: mdl-39199346

RESUMEN

The adherence of pathogenic microorganisms to surfaces and their association to form antibiotic-resistant biofilms threatens public health and affects several industrial sectors with significant economic losses. For this reason, the medical, pharmaceutical and materials science communities are exploring more effective anti-fouling approaches. This review focuses on the anti-fouling properties, structure-activity relationships and environmental toxicity of quaternary ammonium salts (QAS) and, as a subclass, ionic liquid compounds. Greener alternatives such as QAS-based antimicrobial polymers with biocide release, non-fouling (i.e., PEG, zwitterions), fouling release (i.e., poly(dimethylsiloxanes), fluorocarbon) and contact killing properties are highlighted. We also report on dual-functional polymers and stimuli-responsive materials. Given the economic and environmental impacts of biofilms in submerged surfaces, we emphasize the importance of less explored QAS-based anti-fouling approaches in the marine industry and in developing efficient membranes for water treatment systems.


Asunto(s)
Biopelículas , Incrustaciones Biológicas , Compuestos de Amonio Cuaternario , Purificación del Agua , Compuestos de Amonio Cuaternario/química , Compuestos de Amonio Cuaternario/farmacología , Incrustaciones Biológicas/prevención & control , Biopelículas/efectos de los fármacos , Purificación del Agua/métodos , Polímeros/química , Polímeros/farmacología , Líquidos Iónicos/química , Líquidos Iónicos/toxicidad , Líquidos Iónicos/farmacología
8.
Neurotoxicology ; 104: 66-74, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39084264

RESUMEN

1-octyl-3-methylimidazolium bromide ([C8mim]Br), one of the ionic liquids (ILs), has been used in various fields as an alternative green solvent of conventional organic solvents. Increased application and stabilization of imidazole ring structure lead to its release into the aquatic environment and long-term retention. Structure-activity relationship consideration suggested that ILs may be acetylcholinesterase inhibitors; however, neurotoxicity in vivo, especially the underlying mechanisms is rarely studied. In this study, the zebrafish were exposed to 2.5-10 mg/L [C8mim]Br for 28 days to comprehensively evaluate the neurotoxicity of ILs on adult zebrafish from the behavioral profiles and neurotransmitter systems for the first time. The results indicate that zebrafish exhibit suppressed spatial working memory and anxious behaviors. To assess the potential neurotoxic mechanisms underlying the behavioral responses of zebrafish, we measured the levels of neurotransmitters and precursors, key enzyme activities, and expression levels of relevant genes. Nissl staining showed significant neural cell death in zebrafish after 28-day [C8mim]Br exposure, with corresponding decreases in the levels of neurotransmitters (acetylcholine, glutamate, 5-hydroxytryptophan, gamma-aminobutyric acid, dopamine, and norepinephrine). Furthermore, these results were associated with mRNA expression levels of the disrupted neurotransmitter key genes (th, tph2, mao, slc6a3, ache, gad67). Overall, our study determined that [C8mim]Br caused potential mental disorders like anxiety and memory deterioration in zebrafish by impairing neurotransmitter systems, providing recommendations for the industrial production and application of [C8mim]Br.


Asunto(s)
Ansiedad , Imidazoles , Líquidos Iónicos , Trastornos de la Memoria , Neurotransmisores , Pez Cebra , Animales , Neurotransmisores/metabolismo , Ansiedad/inducido químicamente , Ansiedad/psicología , Líquidos Iónicos/toxicidad , Imidazoles/toxicidad , Trastornos de la Memoria/inducido químicamente , Memoria a Corto Plazo/efectos de los fármacos , Masculino , Encéfalo/efectos de los fármacos , Encéfalo/metabolismo , Encéfalo/patología
9.
Chemosphere ; 364: 142964, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39074667

RESUMEN

Ionic liquids (ILs), earlier praised for their eco-friendliness, have emerged as key chemicals in advancing green chemistry, catalysis, solvent development, and more. However, the discovery of their notable toxicity has led to a controversial reputation of ILs and has shifted the research landscape towards understanding their biological impacts. The present study examines the mechanism of cytotoxicity of 32 ILs across six classes, highlighting their effects on the cell cycle of the Jurkat cell line. Focusing on five ILs with pronounced cytotoxicity, we uncover their genotoxic effects and their role in inducing apoptosis. Our findings suggest intricate interplay between the extrinsic and intrinsic apoptotic pathways at different time points after exposure to ILs. Moreover, the ILs studied displayed marked genotoxicity, likely stemming from the accumulation of double-strand DNA breaks in the Jurkat cells. This investigation offers a comprehensive view on interactions of ILs with eukaryotic cells, thereby providing new guidelines for developing safer pharmaceutical and industrial applications of these chemicals. The results not only broaden and enhance the previous perceptions but also open new avenues in research, emphasizing the dual potential of ILs in innovation and safety, and marking a significant step towards integrating chemical innovations with biological safety.


Asunto(s)
Apoptosis , Ciclo Celular , Líquidos Iónicos , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Apoptosis/efectos de los fármacos , Humanos , Células Jurkat , Ciclo Celular/efectos de los fármacos , Daño del ADN , Roturas del ADN de Doble Cadena/efectos de los fármacos
10.
Chemosphere ; 363: 142827, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39019179

RESUMEN

A class of chemical with a potentially important perceived future contribution to the net zero carbon goal (as "green" solvents) is the methylimidazolium ionic liquids (MILs). These solvents are used in industrial processes such as biofuel production yet little is known about their environmental stability or toxicity in man although one MIL - 1-octyl-3-methylimidazolium (M8OI) - has been shown to activate the human estrogen receptor alpha (ERα). The stabilities of the chloride unsubstituted methylimidazolium (MI) and MILs possessing increasing alkyl chain lengths (2C, 1-ethyl-3-methylimidazolium (EMI); 4C, 1-butyl-3-methylimidazolium (BMI); 6C; 1-hexyl-3-methylimidazolium (HMI), 8C, M8OI; 10C, 1-decyl-3-methylimidazolium (DMI)) were examined in river water and a human liver model system. The MILs were also screened for their abilities to activate the human ERα in vitro and induce uterine growth in pre-pubertal rats in vivo. Short chain MILs (EMI, BMI and HMI) underwent negligible metabolism and mineralisation in river water; were not metabolised in a model of human liver metabolism; activated the human ERα in vitro and were estrogenic in vivo in rats. A structure-based computational approach predicted short chain MIL binding to both the estrogen binding site and an additional site on the human estrogen receptor alpha. Longer chain MILs (M8OI and DMI) were metabolised in river water and partially mineralised. Based on structure-activity considerations, some of these environmentally-derived metabolites may however, remain a hazard to the population. MILs therefore have the potential to become forever chemicals with adverse effects to both man, other animals and the environment in general.


Asunto(s)
Disruptores Endocrinos , Receptor alfa de Estrógeno , Imidazoles , Líquidos Iónicos , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Imidazoles/toxicidad , Imidazoles/química , Disruptores Endocrinos/toxicidad , Disruptores Endocrinos/química , Humanos , Receptor alfa de Estrógeno/metabolismo , Animales , Ratas , Femenino
11.
J Hazard Mater ; 474: 134793, 2024 Aug 05.
Artículo en Inglés | MEDLINE | ID: mdl-38850954

RESUMEN

Progress in the development of biodegradable or biobased ionic liquids (ILs) has led to the design of green compounds for several applications. Herein, four biocompatible dicationic ionic liquids (DILs) with ammonium-phosphonium cations and amino acid anions were synthesized and investigated their environmental impact. The structures of the DILs were confirmed by spectral analyses (1H, 13C and 31P NMR). Furthermore, physicochemical properties such as density, viscosity and refractive index were determined. Water content, bromide content and solubility were thereafter determined as the parameters needed for further studies. Subsequently, their antifeedant activity towards economically important pests of grain in storage warehouses: the granary weevil, the confused flour beetle, and the khapra beetle was examined, showing the dependence on structure. Moreover, selected DILs were investigated for toxicity towards white mustard, Daphnia magna, and Artemia franciscana to specify the environmental impact. These studies were complemented by understand the biodegradation of DILs by bacterial communities derived from soil at the agricultural land. The result was DILs with limited environmental footprints that have great potential for further application studies.


Asunto(s)
Aminoácidos , Artemia , Daphnia , Líquidos Iónicos , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Animales , Aminoácidos/química , Aminoácidos/análisis , Daphnia/efectos de los fármacos , Artemia/efectos de los fármacos , Compuestos de Amonio/química , Compuestos Organofosforados/química , Cationes , Aniones/química , Ambiente , Biodegradación Ambiental , Escarabajos/efectos de los fármacos
12.
Food Res Int ; 188: 114498, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38823878

RESUMEN

The emulsifying potential of a biocompatible ionic liquid (IL) to produce lipid-based nanosystems developed to enhance the bioaccessibility of cannabidiol (CBD) was investigated. The IL (cholinium oleate) was evaluated at concentrations of 1 % and 2 % to produce nanoemulsions (NE-IL) and nanostructured lipid carriers (NLC-IL) loaded with CBD. The IL concentration of 1 % demonstrated to be sufficient to produce both NE-IL and NLC-IL with excellent stability properties, entrapment efficiency superior to 99 %, and CBD retention rate of 100 % during the storage period evaluated (i.e. 28 days at 25 °C). The in vitro digestion evaluation demonstrated that the NLC-IL provided a higher stability to the CBD, while the NE-IL improved the CBD bioaccessibility, which was mainly related to the composition of the lipid matrices used to obtain each nanosystem. Finally, it was observed that the CBD cytotoxicity was reduced when the compound was entrapped into both nanosystems.


Asunto(s)
Cannabidiol , Emulsionantes , Líquidos Iónicos , Cannabidiol/química , Líquidos Iónicos/química , Líquidos Iónicos/toxicidad , Emulsionantes/química , Humanos , Emulsiones , Digestión , Nanoestructuras/química , Supervivencia Celular/efectos de los fármacos , Disponibilidad Biológica , Nanopartículas/química , Portadores de Fármacos/química , Células CACO-2 , Tamaño de la Partícula
13.
Sci Total Environ ; 945: 173738, 2024 Oct 01.
Artículo en Inglés | MEDLINE | ID: mdl-38844219

RESUMEN

Ionic liquids (ILs) become emerging environmental pollutants. Especially, alkyl imidazolium ILs commonly showed stimulation in toxicological studies and mechanisms remained to be explored. In the present study, alkyl imidazolium tetrafluoroborate ([amim]BF4), with ethyl ([emim]), hexyl ([hmim]) and octyl ([omim]) as side-chains, were chosen as target ILs. Their toxicities on the reproduction and lifespan of Caenorhabditis elegans were explored with two types (A and B) exposure arrangements to mimic realistic intermittent multi-generational exposure scenarios. In type A scenario, there was an exposure every 4 generations with 12 generations in total, and in type B one, there was an exposure every two generations with 12 generations in total. Result showed that [emim]BF4 caused inhibition on the reproduction in 8 generations in type A exposure but 6 ones in type B exposure. Meanwhile, [hmim]BF4 showed inhibition in one generation and stimulation in 3 generations in type A exposure, but stimulation in 6 generations in type B exposure. Also, [omim]BF4 showed stimulation in one generation in type B exposure. Collectively, the results demonstrated less frequencies of inhibition, or more frequencies of stimulation, in the exposure scenario with more frequent exposures. Further mechanism exploration was performed to measure the lipid storage and metabolism in the aspect of energy supply. Results showed that [emim]BF4, [hmim]BF4 and [omim]BF4 commonly stimulated the triglyceride (TG) levels across generations. They also disturbed the activities of glycerol-3-phosphate acyltransferase (GPAT) and acetyl CoA carboxylase (ACC) in lipogenesis, those of adipose triglyceride lipase (ATGL) and carnitine acyl transferase (CPT) in lipolysis, and also the contents of acetyl-CoA (ACA). Further data analysis indicated the energy allocation among life traits including reproduction, antioxidant responses and hormone regulations.


Asunto(s)
Caenorhabditis elegans , Imidazoles , Líquidos Iónicos , Metabolismo de los Lípidos , Reproducción , Animales , Caenorhabditis elegans/efectos de los fármacos , Caenorhabditis elegans/fisiología , Metabolismo de los Lípidos/efectos de los fármacos , Imidazoles/toxicidad , Reproducción/efectos de los fármacos , Líquidos Iónicos/toxicidad , Contaminantes Ambientales/toxicidad , Boratos/toxicidad
14.
Biochemistry (Mosc) ; 89(3): 451-461, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38648765

RESUMEN

Ionic liquids (ILs) are organic salts with a low melting point. This is due to the fact that their alkyl side chains, which are covalently connected to the ion, hinder the crystallization of ILs. The low melting point of ILs has led to their widespread use as relatively harmless solvents. However, ILs do have toxic properties, the mechanism of which is largely unknown, so identifying the cellular targets of ILs is of practical importance. In our work, we showed that imidazolium ILs are not able to penetrate model membranes without damaging them. We also found that inactivation of multidrug resistance (MDR) pumps in yeast cells does not increase their sensitivity to imidazolium ILs. The latter indicates that the target of toxicity of imidazolium ILs is not in the cytoplasm. Thus, it can be assumed that the disruption of the barrier properties of the plasma membrane is the main reason for the toxicity of low concentrations of imidazolium ILs. We also showed that supplementation with imidazolium ILs restores the growth of cells with kinetically blocked glycolysis. Apparently, a slight disruption of the plasma membrane caused by ILs can, in some cases, be beneficial for the cell.


Asunto(s)
Membrana Celular , Imidazoles , Líquidos Iónicos , Saccharomyces cerevisiae , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Imidazoles/toxicidad , Imidazoles/química , Imidazoles/farmacología , Membrana Celular/efectos de los fármacos , Membrana Celular/metabolismo , Saccharomyces cerevisiae/efectos de los fármacos , Saccharomyces cerevisiae/metabolismo
15.
Environ Toxicol ; 39(7): 3846-3855, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38546349

RESUMEN

Ionic liquid tetrafluoroborated-1-tetradecyl-3-methylimidazole salt ([C14mim]BF4) immunotoxicity was investigated in rats using three exposure groups (12.5, 25, and 50 mg kg-1), one recovery group (50 mg kg-1), and a control group without any treatment. The findings demonstrated that, at low doses, [C14mim]BF4 could raise WBC, NEU, and MID and lysozyme levels as well as spleen T-lymphocyte stimulation index in rats, however at high doses, the aforementioned indices were dramatically lowered. As the dose was raised, the proportion of RBC and PLT in the blood as well as CD4+ and CD8+ in the spleen increased, but the quantity of immunoglobulin IgG, IgA, and IgM in the serum as well as the number of NK cells in the spleen considerably dropped. Even though there were varying degrees of improvement 30 days after ceasing exposure, all these changes were unable to return to normal, and the number of NK cells was further decreased. The study demonstrates that [C14mim]BF4 can damage the specific immunity and non-specific immunity of rats, and cause immune dysfunction.


Asunto(s)
Imidazoles , Líquidos Iónicos , Bazo , Animales , Bazo/efectos de los fármacos , Bazo/inmunología , Líquidos Iónicos/toxicidad , Masculino , Ratas , Imidazoles/toxicidad , Células Asesinas Naturales/efectos de los fármacos , Células Asesinas Naturales/inmunología , Ratas Sprague-Dawley , Muramidasa , Linfocitos T/efectos de los fármacos , Linfocitos T/inmunología
16.
Mar Pollut Bull ; 201: 116280, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38518574

RESUMEN

The utilization of chemical dispersants as a way of mitigating of oil spills in marine eco-system has been extensively documented worldwide. Hence, in this research we have successfully synthesized two amphiphilic asymmetric Dicaionic Ionic Liquids (DILs). The efficacy of these synthesized DILs as dispersants was assessed using the baffled flask test (BFT). The results indicated a dispersant effectiveness ranging from 47.98 % to 79.76 % for the dispersion of heavy crude oil across various temperature ranges (10-30 °C). These dispersant-to-oil ratios (DOR) were maintained at 3: 100 (V%), showcasing promising dispersant capabilities for mitigating heavy crude oil spills. Additionally, acute toxicity tests conducted on Nile tilapia and Oreochromis niloticus have demonstrated the relatively low toxicity of the IL-dispersants, with Lethal Concentration 50 (LC50) values exceeding 100 ppm after 96 h. This suggests a practically slight toxic effect on the tested fish. In summary, the newly developed IL-dispersants are considered to be conducive to environmentally benign oil spill remediation.


Asunto(s)
Antracenos , Líquidos Iónicos , Contaminación por Petróleo , Petróleo , Contaminantes Químicos del Agua , Animales , Líquidos Iónicos/toxicidad , Tensoactivos/toxicidad , Contaminación por Petróleo/análisis , Contaminantes Químicos del Agua/toxicidad , Contaminantes Químicos del Agua/análisis , Petróleo/toxicidad
17.
J Phys Chem B ; 128(10): 2504-2515, 2024 Mar 14.
Artículo en Inglés | MEDLINE | ID: mdl-38416751

RESUMEN

Ionic liquids (ILs) are a diverse class of solvents which can be selected for task-specific properties, making them attractive alternatives to traditional solvents. To tailor ILs for specific biological applications, it is necessary to understand the structure-property relationships of ILs and their interactions with cells. Here, a selection of carboxylate anion-based ILs were investigated as cryoprotectants, which are compounds added to cells before freezing to mitigate lethal freezing damage. The cytotoxicity, cell permeability, thermal behavior, and cryoprotective efficacy of the ILs were assessed with two model mammalian cell lines. We found that the biophysical interactions, including permeability of the ILs, were influenced by considering the IL pair together, rather than as single species acting independently. All of the ILs tested had high cytotoxicity, but ethylammonium acetate demonstrated good cryoprotective efficacy for both cell types tested. These results demonstrate that despite toxicity, ILs may be suitable for certain biological applications. It also demonstrates that more research is required to understand the contribution of ion pairs to structure-property relationships and that knowing the behavior of a single ionic species will not necessarily predict its behavior as part of an IL.


Asunto(s)
Líquidos Iónicos , Animales , Líquidos Iónicos/toxicidad , Solventes , Aniones , Iones , Criopreservación , Mamíferos
18.
Sci Total Environ ; 922: 171062, 2024 Apr 20.
Artículo en Inglés | MEDLINE | ID: mdl-38401717

RESUMEN

The following research provides novel and relevant insights into potential environmental consequences of combination of various organic cations with commercial systemic herbicide (dicamba), in accordance with a 'herbicidal ionic liquids' (HILs) strategy. Toxicity assays of five dicamba-based HILs comprising different hydrophobic and hydrophilic cations, namely choline [CHOL][DIC], ethyl betainate [BETC2][DIC], decyl betainate [BETC10][DIC], hexadecyl betainate [BETC16][DIC] and didecyldimethylammonium [DDA][DIC]), have been tested towards bacteria (Pseudomonas putida, Escherichia coli, Bacillus subtilis), algae (Chlorella vulgaris), fresh and marine water crustaceans (Daphnia magna, Artemia franciscana). The structure of respective substituents in the cation emerged as a decisive determinant of toxicity in the case of tested species. In consequence, small ions of natural origin ([CHOL] and [BETC2]) demonstrated toxicity numerous orders of magnitude lower compared to fully synthetic [DDA]. These results emphasize the role of cations' hydrophobicity, as well as origin, in the observed acute toxic effect. Time-dependent toxicity assays also indicated that betaine-type cations comprising an ester bond can rapidly transform into less harmful substances, which can generally result in a reduction in toxicity by even several orders of magnitude. Nonetheless, these findings challenge the concept of ionic liquids with herbicidal activity and give apparent parallels to adjuvant-dependent toxicity issues recently noted in typical herbicidal formulations.


Asunto(s)
Chlorella vulgaris , Herbicidas , Líquidos Iónicos , Pseudomonas putida , Herbicidas/toxicidad , Herbicidas/química , Dicamba/química , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Cationes/química
19.
Food Chem Toxicol ; 183: 114202, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-38007213

RESUMEN

Ionic liquids (ILs) are a class of low melting point salts with physicochemical properties that make them suitable for a range of industrial applications. Accumulating evidence suggests that certain ILs are cytotoxic and potential environmental pollutants, thus understanding the structural features that promote IL cytotoxicity is important. Amphiphilic ionic liquids (AmILs), a class of ILs with lipophilic N-alkyl chains, containing aromatic head groups are generally more cytotoxic than their aliphatic counterparts, however the impact of other head group properties are less clear. This study therefore sought to provide new structure activity relationship (SAR) insights regarding the role of the cationic head group on AmIL cytotoxicity. A series of AmILs bearing a range of structurally diverse aromatic cations varying in size, charge, and lipophilicity was synthesised and screened against human MDA-MB-231 breast cancer cells. It was found that larger and more lipophilic head groups increased cytotoxicity, although the magnitude of the changes were modest. The mitochondrial effects of representative ILs were assessed. The AmILs induced mitochondrial dysfunction in MDA-MB-231 cells at cytotoxic concentrations, suggesting that they target mitochondria. The new SAR information from this study may assist in the design of AmILs with controlled cytotoxicity.


Asunto(s)
Líquidos Iónicos , Humanos , Líquidos Iónicos/toxicidad , Líquidos Iónicos/química , Estructura de Grupo , Relación Estructura-Actividad , Cationes/química
20.
ACS Biomater Sci Eng ; 10(1): 178-190, 2024 01 08.
Artículo en Inglés | MEDLINE | ID: mdl-38141007

RESUMEN

Cryopreservation of cells, tissues, and organs is widely used in the biomedical and research world. There are different cryopreservatives that are used for this process; however, many of them, such as DMSO, are used despite the problems they present, mainly due to the toxicity it presents to certain types of samples. The aim of this Review is to highlight the different types of substances used in the cryopreservation process. It has been shown that some of these substances are well-known, as in the case of the families of alcohols, sugars, sulfoxides, etc. However, in recent years, other compounds have appeared, such as ionic liquids, deep eutectic solvents, or certain polymers, which open the door to new cryopreservation methods and are also less toxic to frozen samples.


Asunto(s)
Crioprotectores , Líquidos Iónicos , Criopreservación , Línea Celular , Líquidos Iónicos/toxicidad , Sulfóxidos
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