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1.
Environ Sci Pollut Res Int ; 31(24): 35553-35566, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38733444

RESUMO

Volatile organic compounds (VOCs) frequently pose a threat to the biosphere, impacting ecosystems, flora, fauna, and the surrounding environment. Industrial emissions of VOCs often include the presence of water vapor, which, in turn, diminishes the adsorption capacity and efficacy of adsorbents. This occurs due to the competitive adsorption of water vapor, which competes with target pollutants for adsorption sites on the adsorbent material. In this study, hydrophobic activated carbons (BMIMPF6-AC (L), BMIMPF6-AC (g), and BMIMPF6-AC-H) were successfully prepared using 1-butyl-3-methylimidazolium hexafluorophosphate (BMIMPF6) to adsorb toluene under humidity environment. The adsorption performance and mechanism of the resulting ionic liquid-modified activated carbon for toluene in a high-humidity environment were evaluated to explore the potential application of ionic liquids as hydrophobic modifiers. The results indicated that BMIMPF6-AC-H exhibited superior hydrophobicity. The toluene adsorption capacity of BMIMPF6-AC-H was 1.53 times higher than that of original activated carbon, while the adsorption capacity for water vapor was only 37.30% of it at 27 °C and 77% RH. The Y-N model well-fitted the dynamic adsorption experiments. To elucidate the microscopic mechanism of hydrophobic modification, the Independent Gradient Model (IGM) method was employed to characterize the intermolecular interactions between BMIMPF6 and toluene. Overall, this study introduces a new modifier for hydrophobic modification of activated carbon, which could enhance the efficiency of activated carbon in treating industrial VOCs.


Assuntos
Umidade , Líquidos Iônicos , Tolueno , Compostos Orgânicos Voláteis , Líquidos Iônicos/química , Adsorção , Tolueno/química , Compostos Orgânicos Voláteis/química , Carvão Vegetal/química , Poluentes Atmosféricos/química , Interações Hidrofóbicas e Hidrofílicas , Imidazóis/química
2.
Food Chem ; 451: 139521, 2024 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-38703735

RESUMO

This study explored the use of ionic liquid-ultrasound (ILU)-assisted extraction to enhance the extraction rate of Platycodon grandiflorum saponins (PGSs), and the content, extraction mechanism, antioxidant activity, whitening, and antiaging activity of PGSs prepared using ILU, ultrasound-water, thermal reflux-ethanol, and cellulase hydrolysis were compared. The ILU method particularly disrupted the cell wall, improved PGS extraction efficiency, and yielded a high total saponin content of 1.45 ± 0.02 mg/g. Five monomeric saponins were identified, with platycodin D being the most abundant at 1.357 mg/g. PGSs displayed excellent in vitro antioxidant activity and exhibited inhibitory effects on tyrosinase, elastase, and hyaluronidase. The results suggest that PGSs may have broad antioxidant, skin-whitening, and antiaging potential to a large extent. Overall, this study provided valuable insights into the extraction, identification, and bioactivities of PGSs, which could serve as a reference for future development and application of these compounds in the functional foods industry.


Assuntos
Antioxidantes , Líquidos Iônicos , Extratos Vegetais , Platycodon , Saponinas , Antioxidantes/química , Antioxidantes/farmacologia , Antioxidantes/isolamento & purificação , Saponinas/farmacologia , Saponinas/química , Saponinas/isolamento & purificação , Platycodon/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , Líquidos Iônicos/química , Envelhecimento da Pele/efeitos dos fármacos , Humanos , Ondas Ultrassônicas
3.
Chem Biol Interact ; 396: 111042, 2024 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-38735455

RESUMO

Ionic liquids (ILs) are a class of low melting point salts with physicochemical properties suitable for a range of industrial applications such as chemical processing and battery design. Major challenges to the wide-scale adoption of ILs in industry include their eco- and cytotoxic effects, however, this opens up the possibility of the use of ILs use as novel anticancer agents. Understanding the structural features that promote IL cytotoxicity is therefore important. Key structural features that can impact IL cytotoxicity include size and lipophilicity of the cationic head group. In this study, the cytotoxic effects of acridinium-based ILs containing relatively large tri- and tetracyclic cations were evaluated. It was found that 9-phenylacridinium-based ILs are potent cytotoxic agents that reduce the viability of human MDA-MB-231 breast cancer cells with IC50 concentrations in the nanomolar range. In mechanistic studies, it was found that unlike the pyridinium-based analogue, [C16Py][I], acridinium-based ILs did not inhibit oxidative phosphorylation or induce reactive oxygen species formation, and may instead target other mitochondrial processes or components such as mitochondrial DNA.


Assuntos
Acridinas , Líquidos Iônicos , Espécies Reativas de Oxigênio , Humanos , Líquidos Iônicos/química , Líquidos Iônicos/farmacologia , Acridinas/química , Acridinas/farmacologia , Relação Estrutura-Atividade , Linhagem Celular Tumoral , Espécies Reativas de Oxigênio/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Antineoplásicos/farmacologia , Antineoplásicos/química , Fosforilação Oxidativa/efeitos dos fármacos
4.
Mar Pollut Bull ; 202: 116311, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38574502

RESUMO

The synthesis of new surfactants helps to mitigate the environmental and financial effects of oil spills by providing efficient cleanup options. Herein, this study provides the development of a binary mixture of Span 80 and Choline myristate [Cho][Mys], a surface-active ionic liquid (SAIL) as green dispersant for oil spill remediation. The synergistic interaction at a 60:40 (w/w) ratio significantly lowered the critical micelle concentration (cmc) to 0.029 mM. Dispersion efficiency tests with Arab crude oil showed optimal performance at a 60:40 ratio of Span 80 and [Cho][Mys] (1:25 dispersant to oil ratio, v/v), achieving 81.16 % dispersion effectiveness in the baffled flask test. The binary mixture demonstrated superior emulsion stability (6 h) and the lowest interfacial tension (1.12 mN/m). Acute toxicity experiments revealed the dispersant's practical non-toxicity with an LC50 value of 600 mg/L. Overall, this environmentally benign surfactant combination shows promise as a safe and effective oil spill dispersant.


Assuntos
Recuperação e Remediação Ambiental , Líquidos Iônicos , Poluição por Petróleo , Petróleo , Tensoativos , Poluentes Químicos da Água , Líquidos Iônicos/química , Recuperação e Remediação Ambiental/métodos , Poluentes Químicos da Água/análise , Hexoses
5.
Food Chem ; 450: 139284, 2024 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-38640543

RESUMO

Polyprenols (PPs) are compounds with excellent biological activities and are applied in food, pharmaceutical, and cosmetic industries. However, its strong non-polar nature makes it difficult to separate with many saturated impurities (such as saturated fatty acids) extracted together. Complexation extraction is an effective method for separating saturated and polyunsaturated compounds. In this study, mesoporous silica MCM-41 was modified by imidazole-based ionic liquids (IL) followed by coating these MCM-41-supported IL compounds with silver salt to construct π-complexing adsorbent (AgBF4/IL•MCM-41) to enrich PPs from Ginkgo biloba leaves (GBL) extract. The mesoporous π-complexing sorbent was characterized by small-angle X-ray scattering (SAXS), FTIR, and nitrogen adsorption-desorption. The effect of the ratio of silver salt to IL•MCM-41 on the adsorption capacity of polyprenols from GBL was compared, and the dosage of AgBF4 was determined to be 1.5 mmol/g IL•MCM-41. Adsorption isotherms and kinetics indicate that the π-complexing adsorbent has excellent PPs adsorption performance (153 mg/g at 30 °C) and a fast adsorption rate (the time to reach adsorption equilibrium is 210 s). The PPs were separated using the fixed bed after treatment for only one cycle with AgBF4/IL•MCM-41, and the content of PPs in the product was increased from 38.54% to 70.2%, with a recovery rate of 86.6%. The π-complexing adsorbent showed excellent reusability for ≥3 adsorption-desorption cycles.


Assuntos
Ginkgo biloba , Imidazóis , Líquidos Iônicos , Folhas de Planta , Dióxido de Silício , Prata , Adsorção , Dióxido de Silício/química , Líquidos Iônicos/química , Prata/química , Folhas de Planta/química , Ginkgo biloba/química , Imidazóis/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Porosidade , Cinética
6.
Ultrason Sonochem ; 106: 106877, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38640683

RESUMO

Lycopene-rich guava (Psidium guajava L.) exhibits significant economic potential as a functional food ingredient, making it highly valuable for the pharmaceutical and agro-food industries. However, there is a need to enhance the extraction methods of lycopene to fully exploit its beneficial uses. In this study, we evaluated various ionic liquids to identify the most effective one for extracting lycopene from guava. Among thirteen ionic liquids with varying carbon chains or anions, 1-butyl-3-methylimidazolium chloride demonstrated the highest productivity. Subsequently, a single-factor experiment was employed to test the impact of several parameters on the efficiency of lycopene extraction using this selected ionic liquid. These parameters included extraction time, ultrasonic power, liquid-solid ratio, concentration of the ionic liquid, as well as material particle size. Moreover, models of artificial neural networks using genetic algorithms (ANN-GA) and response surface methodology (RSM) were employed to comprehensively assess the first four key parameters. The optimized conditions for ionic liquid ultrasound-assisted extraction (IL-UAE) were determined as follows: 33 min of extraction time, 225 W of ultrasonic power, 22 mL/g of liquid-solid ratio, 3.0 mol/L of IL concentration, and extraction cycles of three. Under these conditions, lycopene production reached an impressive yield of 9.35 ± 0.36 mg/g while offering advantages such as high efficiency, time savings, preservation benefits, and most importantly environmental friendliness.


Assuntos
Líquidos Iônicos , Licopeno , Redes Neurais de Computação , Psidium , Ondas Ultrassônicas , Licopeno/isolamento & purificação , Licopeno/química , Líquidos Iônicos/química , Psidium/química , Fracionamento Químico/métodos , Algoritmos , Carotenoides/isolamento & purificação , Carotenoides/química
7.
Mar Pollut Bull ; 201: 116280, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38518574

RESUMO

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.


Assuntos
Antracenos , Líquidos Iônicos , Poluição por Petróleo , Petróleo , Poluentes Químicos da Água , Animais , Líquidos Iônicos/toxicidade , Tensoativos/toxicidade , Poluição por Petróleo/análise , Poluentes Químicos da Água/toxicidade , Poluentes Químicos da Água/análise , Petróleo/toxicidade
8.
Int J Biol Macromol ; 265(Pt 1): 130758, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38462106

RESUMO

Diclofenac sodium (DCF) was reported as an important emerging environmental pollutant and its removal from wastewater is very urgent. In this study, different alkyl substituted ionic liquids (1-alkyl -3-vinyl- imidazolium bromide [CnVIm]Br, n = 4, 6, 8, 10, 12) functionalized tragacanth gum (TG-CnBr) are prepared by radiation induced grafting and crosslinking polymerization. The adsorption behaviors of ionic liquids functionalized tragacanth gum for diclofenac sodium from aqueous solutions are examined. The adsorption capacity of TG-CnBr for diclofenac sodium increases with the increasing of alkyl chain length of the imidazolium cation and the hydrophobicity of the hydrogels. The maximum adsorption capacity by TG-C12Br for diclofenac sodium at 30, 40 and 50 °C were 327.87, 310.56 and 283.29 mg/g, respectively. The adsorption of TG-C12Br towards diclofenac sodium was little decreased with NaCl increasing. The removal efficiency was still remained 94.55 % within 5 adsorption-desorption cycles by 1 M HCl. Also, the adsorption mechanism including electrostatic attraction, hydrophobic interaction, hydrogen bonding, and π - π interaction was proposed.


Assuntos
Líquidos Iônicos , Tragacanto , Poluentes Químicos da Água , Diclofenaco/química , Tragacanto/química , Hidrogéis/química , Água , Adsorção , Poluentes Químicos da Água/química
9.
Int J Mol Sci ; 25(5)2024 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-38473998

RESUMO

Interferon alpha-2b (IFN-α2b) is an essential cytokine widely used in the treatment of chronic hepatitis C and hairy cell leukemia, and serum albumin is the most abundant plasma protein with numerous physiological functions. Effective single-step aqueous biphasic system (ABS) extraction for the simultaneous purification of IFN-α2b and BSA (serum albumin protein) was developed in this work. Effects of the ionic liquid (IL)-based ABS functionalization, fluorinated ILs (FILs; [C​2C​1Im][C​4F​9SO​3] and [N​1112(OH)][C​4F​9SO​3]) vs. mere fluoro-containing IL ([C​4C​1Im][CF​3SO​3]), in combination with sucrose or [N​1112(OH)][H​2PO​4] (well-known globular protein stabilizers), or high-charge-density salt K​3PO​4 were investigated. The effects of phase pH, phase water content (%wt), phase composition (%wt), and phase volume ratio were investigated. The phase pH was found to have a significant effect on IFN-α2b and BSA partition. Experimental results show that simultaneous single-step purification was achieved with a high yield (extraction efficiency up to 100%) for both proteins and a purification factor of IFN-α2b high in the enriched IFN-α2b phase (up to 23.22) and low in the BSA-enriched phase (down to 0.00). SDS-PAGE analysis confirmed the purity of both recovered proteins. The stability and structure of IFN-α2b and BSA were preserved or even improved (FIL-rich phase) during the purification step, as evaluated by CD spectroscopy and DSC. Binding studies of IFN-α2b and BSA with the ABS phase-forming components were assessed by MST, showing the strong interaction between FILs aggregates and both proteins. In view of their biocompatibility, customizable properties, and selectivity, FIL-based ABSs are suggested as an improved purification step that could facilitate the development of biologics.


Assuntos
Líquidos Iônicos , Albumina Sérica , Humanos , Albumina Sérica/química , Líquidos Iônicos/química , Interferon-alfa/farmacologia , Água/química , Proteínas Recombinantes
10.
Biomater Sci ; 12(7): 1716-1725, 2024 Mar 26.
Artigo em Inglês | MEDLINE | ID: mdl-38344762

RESUMO

Emerging CRISPR-Cas9 systems can rebuild DNA sequences in the genome in a spatiotemporal manner, offering a magic tool for biological research, drug discovery, and gene therapy. However, low delivery efficiency remains a major roadblock hampering the wide application of CRISPR-Cas9 gene editing talent. Herein, ionic liquid-conjugated polymers (IL-CPs) are explored as efficient platforms for CRISPR-Cas9 plasmid delivery and in vivo genome editing-based tumor therapy. Via molecular screening of IL-CPs, IL-CPs integrated with fluorination monomers (PBF) can encapsulate plasmids into hybrid nanoparticles and achieve over 90% delivery efficiency in various cells regardless of serum interference. In vitro and in vivo experiments demonstrate that PBF can mediate Cas9/PLK1 plasmids for intracellular delivery and therapeutic genome editing in tumor, achieving efficient tumor suppression. This work provides a new tool for safe and efficient CRISPR-Cas9 delivery and therapeutic genome editing, thus opening a new avenue for the development of ionic liquid polymeric vectors for genome editing and therapy.


Assuntos
Edição de Genes , Líquidos Iônicos , Sistemas CRISPR-Cas/genética , Polímeros , Plasmídeos/genética
11.
Food Chem ; 445: 138706, 2024 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-38367557

RESUMO

The accurate detection of analytes in honey is affected by the complex substrates, making it crucial to employ an effective sample preparation technique. In this work, an imidazolium ionic liquid was functionalized to the silica surface by a click reaction for solid-phase extraction (SPE) column, and in situ anion-exchange process was performed with different organic anions (dodecyl sulfonate, dodecyl benzene sulfonate, and naphthalene sulfonate). These SPE columns were evaluated through extracting the estrogens. The naphthalene sulfonate-based SPE column displayed the best extraction ability among these, and it was combined with high-performance liquid chromatography-diode array detection to establish an online enrichment and analysis system. Under the optimal test conditions, an online analytical method was developed, with high enrichment factors (1872-4744), wide linear ranges (0.0033-1.50, 0.0165-1.50, and 0.0330-1.50 µg g-1), and low detection limits (0.001-0.010 µg g-1). The method successfully determined several estrogens in some honey samples, and achieved satisfactory recovery results.


Assuntos
Mel , Líquidos Iônicos , Dióxido de Silício , Estrogênios/análise , Mel/análise , Extração em Fase Sólida/métodos , Cromatografia Líquida de Alta Pressão , Ânions , Naftalenos
12.
J Chromatogr A ; 1719: 464751, 2024 Mar 29.
Artigo em Inglês | MEDLINE | ID: mdl-38387151

RESUMO

Two new extraction chromatographic resins (ECRs) were prepared by impregnating two exotic diglycolamide (DGA) ligands (having three or four DGA moieties tethered to aza-crown ether scaffolds) dissolved in an ionic liquid onto an inert solid support. A room temperature ionic liquid (RTIL) was used for enhancing the performance of the ECRs. The ECR containing triaza-9-crown-3 functionalized with three DGA moieties (TAM-3-DGA), and tetraaza-12-crown-4 tethered with four DGA arms (TAM-4-DGA) were evaluated for the separation of Am3+ and Pu4+from nitric acid solutions. The resin capacity for Eu3+ was 9.52 mg/g and 7.24 mg/g for TAM-3-DGA and TAM-4-DGA resins, respectively. Similarly, the resin capacity for Pu4+was 7.44 mg/g and 5.72 mg/g for TAM-3-DGA and TAM-4-DGA resins, respectively. These maximum loading values corresponded to the formation of a 1:1 metal/ligand complex for the Eu3+ ion and a 1:2 metal/ligand complex for the Pu4+ ion. The sorption of Eu3+and Pu4+on the resins followed a chemisorption phenomenon on both resins. The sorbed Eu3+and Pu4+ions from the resin phase could be efficiently desorbed with complexing ligands such as guanidine carbonate/HEDTA and oxalic acid, respectively.


Assuntos
Elementos da Série Actinoide , Complexos de Coordenação , Éteres de Coroa , Líquidos Iônicos , Líquidos Iônicos/química , Ligantes , Elementos da Série Actinoide/química , Cromatografia , Íons
13.
Food Chem ; 444: 138593, 2024 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-38310774

RESUMO

In this study, polymeric ionic liquids featuring different functional moieties were applied as sorbent coatings in direct-immersion solid-phase microextraction (DI-SPME) for the extraction of 2-methylimidazole (2-MI) and 4-methylimidazole (4-MI) from açaí-based food products followed by gas chromatography-mass spectrometry (GC-MS) analysis. The analytical method was optimized using a sequential experimental design. Variables used in GC-MS such as desorption time, as well as for SPME-DI, including extraction time, extraction temperature, incubation time of extraction, amount of NaCl in the extract, and stirring rate, were optimized. The fitness-for-purpose of the method was verified by the linearity of matrix-matched calibration curves (R2 ≥ 0.9921), adequate recoveries (81.7-89.7 %), and precision (relative standard deviations ≤11.2 %). The method was applied to twenty-five samples of açaí-based food products. 4-MI was found in four samples whereas 2-MI was not detected above the limit of detection. The method was found to be suitable for quality control analysis.


Assuntos
Imidazóis , Líquidos Iônicos , Microextração em Fase Sólida , Microextração em Fase Sólida/métodos , Líquidos Iônicos/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Polímeros/química , Limite de Detecção
14.
Biomacromolecules ; 25(3): 1527-1540, 2024 Mar 11.
Artigo em Inglês | MEDLINE | ID: mdl-38307005

RESUMO

Ionic liquids (ILs) showed a promising application prospect in the field of biomedicine due to their unique recyclability, modifiability, and structure adjustability. In this study, nanoporous microsphere of silk protein and blending with poly(d,l-lactic acid) as model drug delivery was fabricated, respectively, through an IL-induced self-assembly method. Their morphology, structure, and thermal properties were comparably investigated through scanning electron microscopy, transmission electron microscopy, Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, differential scanning calorimetry, X-ray diffraction, and thermogravimetric analyses, and the interaction mechanisms were also discussed to elucidate the effect of structure on drug delivery kinetics. The pure protein exhibited a bigger nanopore size in the microsphere compared to the composite one, facilitating more effective drug loading up to 88.7%. However, drug release was over 53.5% for the composite during initial 4 h, while pure protein was only about half of the composite. Both of them exhibited sustained slow release after 24 h and anticancer efficacy. Furthermore, the favorable compatibility between drug and microsphere vehicle was found and experienced improved thermal stability upon encapsulation, which could protect the drug molecules in high temperature at 200 °C. When the protein and its composite self-assembled to microspheres in ILs due to electrostatic and hydrophobic interaction, the drug could be infiltrated into the nanoporous matrix through biophysical action, and the protein structure displayed reversible transition during delivery. The sustained slow release from pure SF was attributed to the high ß-sheet block action and strong drug-protein interactions, whose strength could be tuned through blending poly(d,l-lactic acid) with protein. These findings indicated that the SF-based nanoporous microspheres formed from IL self-assembled system are an ideal and potential drug delivery vehicle which can be incorporated into various biomaterials in the future.


Assuntos
Líquidos Iônicos , Nanoporos , Seda/química , Microesferas , Sistemas de Liberação de Medicamentos , Ácido Láctico/química , Microscopia Eletrônica de Varredura , Espectroscopia de Infravermelho com Transformada de Fourier
15.
J Chromatogr A ; 1717: 464711, 2024 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-38320433

RESUMO

The solvation parameter model uses five system independent descriptors to characterize compound properties defined as excess molar refraction, E, dipolarity/polarizability, S, hydrogen-bond acidity, A, hydrogen-bond basicity, B, and the gas-liquid partition constant at 25 °C on n-hexadecane, L, to model transfer properties in gas-condensed phase biphasic systems. The E descriptor for compounds liquid at 20 °C is available by calculation using a refractive index value while E for solid compounds at 20 °C and the S, A, B, and L descriptors are determined by experiment. As a single-technique approach, it is shown that with up to 20 retention factor measurements on four columns comprising a poly(siloxane) containing methyloctyl or dimethyldiphenylsiloxane monomers (SPB-Octyl or HP-5), a poly(siloxane) containing methyltrifluoropropylsiloxane monomers (Rtx-OPP or DB-210), a poly(siloxane) containing bis(cyanopropylsiloxane) monomers (HP-88 or SGE BPX-90), and a poly(ethylene glycol) stationary phase (DB-WAXetr or HP-INNOWAX) are suitable for assigning the S, A, and L descriptors. Using the descriptors in the updated WSU compound descriptor database as target values the average absolute error in the descriptor assignments for 52 varied compounds in the temperature range 60-140 °C was 0.072 for E, 0.016 for S, 0.008 for A, and 0.022 for L corresponding to 30 %, 3.5 %, and 0.6 % as a relative average absolute error for E, S, and L, respectively. For the higher temperature range of 160-240 °C and 34 varied compounds that are liquid at 20 °C the average absolute error for the S, A and L descriptors was 0.026, 0.020, and 0.031, respectively, with the largest relative average absolute error for S of 3.2 % (< 1 % for the L descriptor). For 35 varied compounds that are solid at 20 °C the relative absolute error for the E, S, A, and L descriptors in the higher temperature range was 0.068, 0.035, 0.020, and 0.020, respectively, with a relative average absolute error for E (6.5 %), S (3.5 %) and L (0.88 %). The S, A, and L descriptor can be accurately assigned on the four-column system over a wide temperature range. The E descriptor for solid compounds at 20 °C exhibits greater variability than desirable. The B descriptor cannot be assigned by the four-column system, which lack hydrogen-bond acid functional groups, and is only poorly assigned on the weak hydrogen-bond acid ionic liquid column SLB-IL100.


Assuntos
Líquidos Iônicos , Siloxanas , Siloxanas/química , Polietilenoglicóis , Cromatografia Gasosa/métodos , Hidrogênio
16.
Anticancer Agents Med Chem ; 24(9): 691-708, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38321904

RESUMO

BACKGROUND: A number of research were conducted on the pyran and thiophene derivatives, which were attributed to have a wide range of biological activities, including anti-plasmodial, as well as acting as caspase, hepatitis C and cancer inhibitors. OBJECTIVE: The multicomponent reactions of the 5-acetyl-2-amino-4-(phenylamino)-thiophene-3-carbonitrile produced biologically active target molecules like pyran and their fused derivatives. Comparison between regular catalytic multi-component reactions and solvent-free ionic liquids immobilized multicomponent was studied. METHODS: The multicomponent reactions in this work were carried out not only under the reflux conditions using triethylamine as a catalyst but also in solvent-free ionic liquids immobilized magnetic nanoparticles (MNPs) catalysts. RESULTS: Through this work, thirty-one new compounds were synthesized and characterized and were evaluated toward the six cancer cell lines, namely A549, HT-29, MKN-45, U87MG, and SMMC-7721 and H460. The most active compounds were further screened toward seventeen cancer cell lines classified according to the disease. In addition, the effect of compound 11e on the A549 cell line was selected to make further morphological changes in the cell line. The Molecular docking studies of 11e and 11f were carried and promising results were obtained. CONCLUSION: The synthesis of heterocyclic compounds derived from thiophene derivatives has been receiving significant attention. After a detailed optimizing study, it has been found that the solvent-free ionic liquids immobilized multi-component syntheses afforded a high yield of compounds, opening a greener procedure for this synthetically relevant transformation. Many of the synthesized compounds can be considered anticancer agents, enhancing further studies.


Assuntos
Antineoplásicos , Proliferação de Células , Ensaios de Seleção de Medicamentos Antitumorais , Líquidos Iônicos , Simulação de Acoplamento Molecular , Tiofenos , Tiofenos/química , Tiofenos/farmacologia , Tiofenos/síntese química , Humanos , Líquidos Iônicos/química , Líquidos Iônicos/farmacologia , Líquidos Iônicos/síntese química , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/síntese química , Proliferação de Células/efeitos dos fármacos , Relação Estrutura-Atividade , Estrutura Molecular , Relação Dose-Resposta a Droga , Linhagem Celular Tumoral
17.
Mol Pharm ; 21(2): 535-549, 2024 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-38271213

RESUMO

We report an efficient sustainable two-step anion exchange synthetic procedure for the preparation of choline API ionic liquids (Cho-API-ILs) that contain active pharmaceutical ingredients (APIs) as anions combined with choline-based cations. We have evaluated the in vitro cytotoxicity for the synthesized compounds using three different cells lines, namely, HEK293 (normal kidney cell line), SW480, and HCT 116 (colon carcinoma cells). The solubility of APIs and Cho-API-ILs was evaluated in water/buffer solutions and was found higher for Cho-API-ILs. Further, we have investigated the antimicrobial potential of the pure APIs, ILs, and Cho-API-ILs against clinically relevant microorganisms, and the results demonstrated the promise of Cho-API-ILs as potent antimicrobial agents to treat bacterial infections. Moreover, the aggregation and adsorption properties of the Cho-API-ILs were observed by using a surface tension technique. The aggregation behavior of these Cho-API-ILs was further supported by conductivity and pyrene probe fluorescence. The thermodynamics of aggregation for Cho-API-ILs has been assessed from the temperature dependence of surface tension. The micellar size and their stability have been studied by dynamic light scattering, transmission electron microscopy, and zeta potential. Therefore, the duality in the nature of Cho-API-ILs has been explored with the upgradation of their physical, chemical, and biopharmaceutical properties, which enhance the opportunities for advances in pharmaceutical sciences.


Assuntos
Anti-Infecciosos , Líquidos Iônicos , Humanos , Solubilidade , Líquidos Iônicos/química , Células HEK293 , Micelas , Colina/química
18.
J Pharm Biomed Anal ; 240: 115941, 2024 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-38211517

RESUMO

A new method based on the immobilization of 2-(Aminomethyl) thiazole on the multi-walled carbon nanotubes (AMTZ@MWCNTs) was used to extract manganese (Mn) in the human blood, serum, and urine samples. First, 20 mg of AMTZ@MWCNTs, 0.2 mL of acetone, and 0.1 g of ionic liquid (IL) were completely mixed and injected into 2.0 mL human samples by a microscale syringe at pH 5.5. After shaking and centrifuging, the Mn ions were extracted and separated through the ultrasound-assisted- ionic liquid-dispersive micro solid-phase extraction (UAS-IL-D-µ-SPE) before being determined by the graphite furnace atomic absorption spectrometry (GF-AAS). According to the results, manganese in the blood of hepatic patients had higher concentrations than healthy people (Aged 25-60, 50 N). The Mn adsorption capacities for the AMTZ@MWCNTs and MWCNTs adsorbents were achieved at 192.5 mg/g and 26.3 mg/g, respectively. In the high enrichment factor (HEF), the limit of detection (LOD), linear range (LR), and mean relative standard division (RSD%) were calculated at 15 ng/L, 0.05-3.8 µg/L, and 2.34, respectively (n = 10). The methodology was validated using certified reference material (CRM) and spiking standard solutions to human samples.


Assuntos
Líquidos Iônicos , Nanotubos de Carbono , Humanos , Manganês , Líquidos Iônicos/química , Nanotubos de Carbono/química , Tiazóis , Extração em Fase Sólida/métodos , Íons , Limite de Detecção
19.
Int J Mol Sci ; 25(2)2024 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-38279291

RESUMO

Previously reported amphiphilic linear and graft copolymers, derived from the ionic liquid [2-(methacryloyloxy)ethyl]trimethylammonium chloride (TMAMA_Cl‾), along with their conjugates obtained through modification either before or after polymerization with p-aminosalicylate anions (TMAMA_PAS‾), were employed as matrices in drug delivery systems (DDSs). Based on the counterion type in TMAMA units, they were categorized into single drug systems, manifesting as ionic polymers with chloride counterions and loaded isoniazid (ISO), and dual drug systems, featuring ISO loaded in self-assembled PAS conjugates. The amphiphilic nature of these copolymers was substantiated through the determination of the critical micelle concentration (CMC), revealing an increase in values post-ion exchange (from 0.011-0.063 mg/mL to 0.027-0.181 mg/mL). The self-assembling properties were favorable for ISO encapsulation, with drug loading content (DLC) ranging between 15 and 85% in both single and dual systems. In vitro studies indicated ISO release percentages between 16 and 61% and PAS release percentages between 20 and 98%. Basic cytotoxicity assessments using the 2,5-diphenyl-2H-tetrazolium bromide (MTT) test affirmed the non-toxicity of the studied systems toward human non-tumorigenic lung epithelial cell line (BEAS-2B) cell lines, particularly in the case of dual systems bearing both ISO and PAS simultaneously. These results confirmed the effectiveness of polymeric carriers in drug delivery, demonstrating their potential for co-delivery in combination therapy.


Assuntos
Líquidos Iônicos , Polímeros , Humanos , Polímeros/química , Portadores de Fármacos/química , Cloretos , Sistemas de Liberação de Medicamentos , Micelas
20.
J Chromatogr A ; 1717: 464674, 2024 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-38290172

RESUMO

In this research, a sol-gel Carbowax 20M-zwitterionic ionic liquid composite sorbent-based capsule phase microextraction (CPME) device was developed in combination with liquid chromatography-post column derivatization for the first ever reported determination of a somatostatin analogue - lanreotide in human urine. The sol-gel Carbowax 20M-zwitterionic ionic liquid composite sorbent was encapsulated in the lumen of a polypropylene capillary tube and characterized by FT-IR spectroscopy and SEM with energy dispersive X-ray spectroscopy (EDS). The main steps of the CPME workflow were optimized to obtain high extraction efficiency for the target analyte. After the separation of the analyte on a C8 stationary phase, the peptide was derivatized online with o-phthalaldehyde before the fluorescence detection. The main experimental parameters of CPME and the post-column procedures were systematically investigated and optimized. The method was validated in terms of selectivity, linearity, accuracy, precision, limits of detection (LOD), and limits of quantification (LOQ). The relative bias ranged between 88.8 and 115.6 % for the peptide, while the RSD values for repeatability and intermediate precision were less than 14.3 %. The achieved limit of detection (LOD) was 0.2 µΜ while the limit of quantitation (LOQ) was established as 0.9 µΜ. Finally, the sol-gel Carbowax 20M-zwitterionic ionic liquid composite sorbent-based microextraction capsules were found to be reusable for at least 20 extractions. The developed method presented adequate overall performance, and it could be applied in the analysis of selected peptide in human urine samples.


Assuntos
Líquidos Iônicos , Microextração em Fase Líquida , Somatostatina/análogos & derivados , Humanos , Cromatografia Líquida de Alta Pressão/métodos , Polietilenoglicóis , Líquidos Iônicos/química , Espectroscopia de Infravermelho com Transformada de Fourier , Microextração em Fase Sólida/métodos , Peptídeos Cíclicos , Limite de Detecção
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