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Insulin Transdermal Delivery System for Diabetes Treatment Using a Biocompatible Ionic Liquid-Based Microemulsion

Islam MR, Uddin S, Chowdhury MR, Wakabayashi R, Moniruzzaman M, Goto M

ACS Appl Mater Interfaces, 2021 Sep 15;13(36):42461-42472.
PMID: 34460218 DOI: 10.1021/acsami.1c11533

Since injection administration for diabetes is invasive, it is important to develop an effective transdermal method for insulin. However, transdermal delivery remains challenging owing to the strong barrier function of the stratum corneum (SC) of the skin. Here, we developed ionic liquid (IL)-in-oil microemulsion formulations (MEFs) for transdermal insulin delivery using choline-fatty acids ([Chl][FAs])-comprising three different FAs (C18:0, C18:1, and C18:2)-as biocompatible surface-active ILs (SAILs). The MEFs were successfully developed using [Chl][FAs] as surfactants, sorbitan monolaurate (Span-20) as a cosurfactant, choline propionate IL as an internal polar phase, and isopropyl myristate as a continuous oil phase. Ternary phase behavior, dynamic light scattering, and transmission electron microscopy studies revealed that MEFs were thermodynamically stable with nanoparticle size. The MEFs significantly enhanced the transdermal permeation of insulin via the intercellular route by compromising the tight lamellar structure of SC lipids through a fluidity-enhancing mechanism. In vivo transdermal administration of low insulin doses (50 IU/kg) to diabetic mice showed that MEFs reduced blood glucose levels (BGLs) significantly compared with a commercial surfactant-based formulation by increasing the bioavailability of insulin in the systemic circulation and sustained the insulin level for a much longer period (half-life > 24 h) than subcutaneous injection (half-life 1.32 h). When [Chl][C18:2] SAIL-based MEF was transdermally administered, it reduced the BGL by 56% of its initial value. The MEFs were biocompatible and nontoxic (cell viability > 90%). They remained stable at room temperature for 3 months and their biological activity was retained for 4 months at 4 °C. We believe SAIL-based MEFs will alter current approaches to insulin therapy and may be a potential transdermal nanocarrier for protein and peptide delivery.

Matched MeSH terms: Ionic Liquids/chemistry*
Favipiravir-Based Ionic Liquids as Potent Antiviral Drugs for Oral Delivery: Synthesis, Solubility, and Pharmacokinetic Evaluation

Moshikur RM, Ali MK, Wakabayashi R, Moniruzzaman M, Goto M

Mol Pharm, 2021 08 02;18(8):3108-3115.
PMID: 34250805 DOI: 10.1021/acs.molpharmaceut.1c00324

Coronavirus disease 2019 (COVID-19) has spread across the world, and no specific antiviral drugs have yet been approved to combat this disease. Favipiravir (FAV) is an antiviral drug that is currently in clinical trials for use against COVID-19. However, the delivery of FAV is challenging because of its limited solubility, and its formulation is difficult with common organic solvents and water. To address these issues, four FAV ionic liquids (FAV-ILs) were synthesized as potent antiviral prodrugs and were fully characterized by nuclear magnetic resonance (NMR) spectroscopy, Fourier-transform infrared (FT-IR) spectrometry, powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA), derivative thermogravimetry (DTG), and differential scanning calorimetry (DSC). The aqueous solubility and in vivo pharmacokinetic properties of the FAV-ILs were also evaluated. The FAV-ILs exhibited improved aqueous solubility by 78 to 125 orders of magnitude when compared with that of free FAV. Upon oral dosing in mice, the absolute bioavailability of the β-alanine ethyl ester FAV formulation was increased 1.9-fold compared with that of the control FAV formulation. The peak blood concentration, elimination half-life, and mean absorption time of FAV were also increased by 1.5-, 2.0-, and 1.5-fold, respectively, compared with the control. Furthermore, the FAV in the FAV-ILs exhibited significantly different biodistribution compared with the control FAV formulation. Interestingly, drug accumulation in the lungs and liver was improved 1.5-fold and 1.3-fold, respectively, compared with the control FAV formulation. These results indicate that the use of ILs exhibits potential as a simple, scalable strategy to improve the solubility and oral absorption of hydrophobic drugs, such as FAV.

Matched MeSH terms: Ionic Liquids/chemistry*
Biocompatible Ionic Liquid-Mediated Micelles for Enhanced Transdermal Delivery of Paclitaxel

Ali MK, Moshikur RM, Wakabayashi R, Moniruzzaman M, Goto M

ACS Appl Mater Interfaces, 2021 May 05;13(17):19745-19755.
PMID: 33891816 DOI: 10.1021/acsami.1c03111

Chemotherapeutic cytotoxic agents such as paclitaxel (PTX) are considered essential for the treatment of various cancers. However, PTX injection is associated with severe systemic side effects and high rates of patient noncompliance. Micelle formulations (MFs) are nano-drug delivery systems that offer a solution to these problems. Herein, we report an advantageous carrier for the transdermal delivery of PTX comprising a new MF that consists of two biocompatible surfactants: cholinium oleate ([Cho][Ole]), which is a surface-active ionic liquid (SAIL), and sorbitan monolaurate (Span-20). A solubility assessment confirmed that PTX was readily solubilized in the SAIL-based micelles via multipoint hydrogen bonding and cation-π and π-π interactions between PTX and SAIL[Cho][Ole]. Dynamic light scattering (DLS) and transmission electron microscopy revealed that in the presence of PTX, the MF formed spherical PTX-loaded micelles that were well-distributed in the range 8.7-25.3 nm. According to DLS, the sizes and size distributions of the micelle droplets did not change significantly over the entire storage period, attesting to their physical stability. In vitro transdermal assessments using a Franz diffusion cell revealed that the MF absorbed PTX 4 times more effectively than a Tween 80-based formulation and 6 times more effectively than an ethanol-based formulation. In vitro and in vivo skin irritation tests revealed that the new carrier had a negligible toxicity profile compared with a conventional ionic liquid-based carrier. Based on these findings, we believe that the SAIL[Cho][Ole]-based MF has potential as a biocompatible nanocarrier for the effective transdermal delivery of poorly soluble chemotherapeutics such as PTX.

Matched MeSH terms: Ionic Liquids/chemistry*
Fulltext A review on microalgae cultivation and harvesting, and their biomass extraction processing using ionic liquids

Tan JS, Lee SY, Chew KW, Lam MK, Lim JW, Ho SH, et al.

Bioengineered, 2020 12;11(1):116-129.
PMID: 31909681 DOI: 10.1080/21655979.2020.1711626

The richness of high-value bio-compounds derived from microalgae has made microalgae a promising and sustainable source of useful product. The present work starts with a review on the usage of open pond and photobioreactor in culturing various microalgae strains, followed by an in-depth evaluation on the common harvesting techniques used to collect microalgae from culture medium. The harvesting methods discussed include filtration, centrifugation, flocculation, and flotation. Additionally, the advanced extraction technologies using ionic liquids as extractive solvents applied to extract high-value bio-compounds such as lipids, carbohydrates, proteins, and other bioactive compounds from microalgae biomass are summarized and discussed. However, more work needs to be done to fully utilize the potential of microalgae biomass for the application in large-scale production of biofuels, food additives, and nutritive supplements.

Matched MeSH terms: Ionic Liquids/chemistry
Fulltext Performance of p-Toluenesulfonic Acid-Based Deep Eutectic Solvent in Denitrogenation: Computational Screening and Experimental Validation

Kamarudin AF, Hizaddin HF, El-Blidi L, Ali E, Hashim MA, Hadj-Kali MK

Molecules, 2020 Nov 03;25(21).
PMID: 33152997 DOI: 10.3390/molecules25215093

Deep eutectic solvents (DESs) are green solvents developed as an alternative to conventional organic solvents and ionic liquids to extract nitrogen compounds from fuel oil. DESs based on p-toluenesulfonic acid (PTSA) are a new solvent class still under investigation for extraction/separation. This study investigated a new DES formed from a combination of tetrabutylphosphonium bromide (TBPBr) and PTSA at a 1:1 molar ratio. Two sets of ternary liquid-liquid equilibrium experiments were performed with different feed concentrations of nitrogen compounds ranging up to 20 mol% in gasoline and diesel model fuel oils. More than 99% of quinoline was extracted from heptane and pentadecane using the DES, leaving the minutest amount of the contaminant. Selectivity was up to 11,000 for the heptane system and up to 24,000 for the pentadecane system at room temperature. The raffinate phase's proton nuclear magnetic resonance (1H-NMR) spectroscopy and GC analysis identified a significantly small amount of quinoline. The selectivity toward quinoline was significantly high at low solute concentrations. The root-mean-square deviation between experimental data and the non-random two-liquid (NRTL) model was 1.12% and 0.31% with heptane and pentadecane, respectively. The results showed that the TBPBr/PTSADES is considerably efficient in eliminating nitrogen compounds from fuel oil.

Matched MeSH terms: Ionic Liquids/chemistry
Fulltext Optimization for Liquid-Liquid Extraction of Cd(II) over Cu(II) Ions from Aqueous Solutions Using Ionic Liquid Aliquat 336 with Tributyl Phosphate

Lee LY, Morad N, Ismail N, Talebi A, Rafatullah M

Int J Mol Sci, 2020 Sep 18;21(18).
PMID: 32962106 DOI: 10.3390/ijms21186860

This study investigates the separation of two heavy metals, Cd(II) and Cu(II), from the mixed synthetic feed using a liquid-liquid extraction. The current study uses tri-octyl methylammonium chloride (Aliquat 336) as the extractant (with tributyl phosphate (TBP) as a phase modifier), diluted in toluene, in order to investigate the selective extraction of Cd(II) over Cu(II) ions. We investigate the use of ethylenediaminetetraacetic acid (EDTA) as a masking agent for Cu(II), when added in aqueous feed, for the selective extraction of Cd(II). Five factors that influence the selective extraction of Cd(II) over Cu(II) (the equilibrium pH (pHeq), Aliquat 336 concentration (Aliquat 336), TBP concentration (TBP), EDTA concentration (EDTA), and organic to aqueous ratio (O:A)) were analyzed. Results from a 25-1 fractional factorial design show that Aliquat 336 significantly influenced Cd(II) extraction, whereas EDTA was statistically significant for the antagonistic effect on the E% of Cu(II) in the same system. Moreover, results from optimization experiment showed that the optimum conditions are Aliquat 336 concentration of 99.64 mM and EDTA concentration of 48.86 mM-where 95.89% of Cd(II) was extracted with the least extracted Cu(II) of 0.59%. A second-order model was fitted for optimization of Cd(II) extraction with a R2 value of 0.998, and ANOVA results revealed that the model adequately fitted the data at a 5% significance level. Interaction between Aliquat 336 and Cd(II) has been proven via FTIR qualitative analysis, whereas the addition of TBP does not affect the extraction mechanism.

Matched MeSH terms: Ionic Liquids/chemistry
Primary purification of intracellular Halomonas salina ectoine using ionic liquids-based aqueous biphasic system

Ng HS, Wan PK, Ng TC, Lan JC

J Biosci Bioeng, 2020 Aug;130(2):200-204.
PMID: 32389469 DOI: 10.1016/j.jbiosc.2020.04.003

Ectoine is a zwitterionic amino acid derivative that can be naturally sourced from halophilic microorganisms. The increasing demands of ectoine in various industries have urged the researches on the cost-effective approaches on production of ectoine. Ionic liquids-based aqueous biphasic system (ILABS) was applied to recover Halomonas salina ectoine from cells hydrolysate. The 1-butyl-3-methylimidazolium tetrafluoroborate (Bmim)BF4 was used in the ILABS and the recovery efficiency of ILABS to recover ectoine from H. salina cells lysate was evaluated by determining the effects of phase composition; pHs; crude loading and additional neutral salt (NaCl). The hydrophilic ectoine was targeted to partition to the hydrophilic salt-rich phase. A total yield (YB) of 96.32% ± 1.08 of ectoine was obtained with ILABS of phase composition of 20% (w/w) (Bmim)BF4 and 30% (w/w) sulfate salts; system pH of 5.5 when the 20% (w/w) of crude feedstock was applied to the ILABS. There was no significant enhancement on the ectoine recovery efficiency using the ILABS when NaCl was added, therefore the ILABS composition without the additional neutral salt was recommended for the primary purification of ectoine. Partition coefficient (KE) of 30.80 ± 0.42, purity (PE) of 95.82% and enrichment factor (Ef) of 1.92 were recorded with the optimum (Bmim)BF4/sulfate ILABS. These findings have provided an insight on the feasibility of recovery of intracellular biomolecules using the green solvent-based aqueous system in one single-step operation.

Matched MeSH terms: Ionic Liquids/chemistry*
Efficiency of Ionic Liquids-Based Aqueous Two-phase Electrophoresis for Partition of Cytochrome c

Kee PE, Lan JC, Yim HS, Tan JS, Chow YH, Ng HS

Appl Biochem Biotechnol, 2020 May;191(1):376-386.
PMID: 31907777 DOI: 10.1007/s12010-019-03202-y

Cytochrome c is a small water-soluble protein that is abundantly found in the mitochondrial intermembrane space of microorganism, plants and mammalians. Ionic liquids (ILs)-based aqueous two-phase electrophoresis system (ATPES) was introduced in this study to investigate the partition efficiency of cytochrome c to facilitate subsequent development of two-phase electrophoresis for the separation of cytochrome c from microbial fermentation. The 1-Hexyl-3-methylimidazolium bromide, (C6mim)Br and potassium citrate salt were selected as the phase-forming components. Effects of phase composition; position of electrodes; pH and addition of neutral salt on the partition efficiency of cytochrome c in the ATPES were evaluated. Highest partition coefficient (K = 179.12 ± 0.82) and yield of cytochrome c in top phase (YT = 99.63% ± 0.00) were recorded with IL/salt ATPES composed of 30% (w/w) (C6mim)Br and 20% (w/w) potassium citrate salt of pH 7 and 3.0% (w/w) NaCl addition with anode at the bottom phase and cathode at the top phase. The SDS-PAGE profile revealed that cytochrome c with a molecular weight of 12 kDa was preferably partitioned to the IL-rich top phase. Present findings suggested that the single-step ATPES is a potential separation approach for the recovery of cytochrome c from microbial fermentation. Graphical Abstract.

Matched MeSH terms: Ionic Liquids/chemistry*
Synergistic effect of probe sonication and ionic liquid for extraction of phenolic acids from oak galls

Sukor NF, Jusoh R, Kamarudin NS, Abdul Halim NA, Sulaiman AZ, Abdullah SB

Ultrason Sonochem, 2020 Apr;62:104876.
PMID: 31796331 DOI: 10.1016/j.ultsonch.2019.104876

Phenolic acids of oak gall were extracted using ultrasonic-probe assisted extraction (UPAE) method in the presence of ionic liquid. It was compared with classical ultrasonic-bath assisted extraction (CUBAE) and conventional aqueous extraction (CAE) method, with and without the presence of ionic liquid. Remarkably, the UPAE method yielded two-fold higher extraction yield with the presence of ionic liquid, resulting 481.04 mg/g for gallic acids (GA) and 2287.90 mg/g for tannic acids (TA), while a decreased value of 130.36 mg/g for GA and 1556.26 mg/g for TA were resulted with the absence of ionic liquid. Intensification process resulted the highest yield of 497.34 mg/g and 2430.48 mg/g for GA and TA, respectively, extracted at temperature 50 °C with sonication intensity of 8.66 W/cm2 and 10% duty cycle, diluted in ionic liquid, 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [Bmim][Tf2N] at concentration of 0.10 M with sample-to-solvent ratio 1:10 for 8 h. Peleg's model successfully predicted the UPAE process confirming that extraction capacity is the controlling factor in extracting phenolic acids. Hence, it can be concluded that UPAE method and ionic liquid have synergistic effect as it effectively enhanced the extraction efficiency to increase the bioactive constituents yield.

Matched MeSH terms: Ionic Liquids/chemistry*
An Overview on the Toxicological Properties of Ionic Liquids toward Microorganisms

Sivapragasam M, Moniruzzaman M, Goto M

Biotechnol J, 2020 Apr;15(4):e1900073.
PMID: 31864234 DOI: 10.1002/biot.201900073

Ionic liquids (ILs), a class of materials with unique physicochemical properties, have been used extensively in the fields of chemical engineering, biotechnology, material sciences, pharmaceutics, and many others. Because ILs are very polar by nature, they can migrate into the environment with the possibility of inclusion in the food chain and bioaccumulation in living organisms. However, the chemical natures of ILs are not quintessentially biocompatible. Therefore, the practical uses of ILs must be preceded by suitable toxicological assessments. Among different methods, the use of microorganisms to evaluate IL toxicity provides many advantages including short generation time, rapid growth, and environmental and industrial relevance. This article reviews the recent research progress on the toxicological properties of ILs toward microorganisms and highlights the computational prediction of various toxicity models.

Matched MeSH terms: Ionic Liquids/chemistry*
Fulltext COSMO-RS Based Prediction for Alpha-Linolenic Acid (ALA) Extraction from Microalgae Biomass Using Room Temperature Ionic Liquids (RTILs)

Rezaei Motlagh S, Harun R, Awang Biak DR, Hussain SA, Omar R, Elgharbawy AA

Mar Drugs, 2020 Feb 12;18(2).
PMID: 32059424 DOI: 10.3390/md18020108

One of the essential fatty acids with therapeutic impacts on human health is known to be omega-3 polyunsaturated fatty acids (PUFA). More lately, ionic liquids (ILs) have received significant attention among scientists in overcoming the disadvantages of traditional solvents in biomass lipid extraction. However, the large pool of cations and anions possibly accessible will lead to a growing number of innovatively synthesized ILs. Nevertheless, the exhaustive measurement of all these systems is economically impractical. The conductive screening model for real solvents (COSMO-RS) is considered a precious approach with the availability of a few models to predict the characteristics of ILs. This work introduces the estimate of capacity values at infinite dilution for a range of ILs using COSMO-RS software as part of solid-liquid extraction. This favorable outcome presented that the capacity values of the IL molecules are extremely dependent on both anions and cations. Among the 352 combinations of cation/anion tested, short alkyl chain cations coupled with inorganic anions were found to be most efficient and therefore superior in the extraction method. Sulphate-, chloride-, and bromide-based ILs were found to have higher extraction capacities in contrast with the remainders, while propanoate revealed an extraordinary capacity when combined with ethyl-based cations. Eventually, the predicted results from COSMO-RS were validated through the experimentally calculated extraction yield of alpha-linolenic acid (ALA) compound from Nannochloropsis sp. microalgae. Three selected ILs namely [EMIM][Cl], [TMAm][Cl], and [EMPyrro][Br] were selected from COSMO-RS for empirical extraction purpose and the validation results pinpointed the good prediction capability of COSMO-RS.

Matched MeSH terms: Ionic Liquids/chemistry*
Synthesis and characterization of choline-fatty-acid-based ionic liquids: A new biocompatible surfactant

Ali MK, Moshikur RM, Wakabayashi R, Tahara Y, Moniruzzaman M, Kamiya N, et al.

J Colloid Interface Sci, 2019 Sep 01;551:72-80.
PMID: 31075635 DOI: 10.1016/j.jcis.2019.04.095

Ionic liquid (IL) surfactants have attracted great interest as promising substitutes for conventional surfactants owing to their exceptional and favorable physico-chemical properties. However, most IL surfactants are not eco-friendly and form unstable micelles, even when using a high concentration of the surfactant. In this study, we prepared a series of halogen-free and biocompatible choline-fatty-acid-based ILs with different chain lengths and degrees of saturation, and we then investigated their micellar properties in aqueous solutions. Characterization of the synthesized surface-active ILs (SAILs) was performed by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, differential scanning calorimetry, and elemental analysis. The surface-active properties of the SAILs were investigated by tensiometry, conductometry, and dynamic light scattering measurements. The critical micelle concentration of the SAILs was found to be 2-4 times lower than those of conventional surfactants. The thermodynamic properties of micellization (ΔG0m, ΔH0m, and ΔS0m) indicate that the micellization process of the SAILs is spontaneous, stable, and entropy-driven at room temperature. The cytotoxicity of the SAILs was evaluated using mammalian cell line NIH 3T3. Importantly, [Cho][Ole] shows lower toxicity than the analogous ILs with conventional surfactants. These results clearly suggest that these environmentally friendly SAILs can be used as a potential alternative to conventional ILs for various purposes, including biological applications.

Matched MeSH terms: Ionic Liquids/chemistry*
Antiproliferative activity of ionic liquid-graviola fruit extract against human breast cancer (MCF-7) cell lines using flow cytometry techniques

Daddiouaissa D, Amid A, Kabbashi NA, Fuad FAA, Elnour AM, Epandy MAKMS

J Ethnopharmacol, 2019 May 23;236:466-473.
PMID: 30853648 DOI: 10.1016/j.jep.2019.03.003

ETHNOPHARMACOLOGICAL RELEVANCE: Medicinal plants have been used for ages by indigenous communities around the world to help humankind sustain its health. Graviola (Annona muricata), also called soursop, is a member of the Annonaceae family and is an evergreen plant that is generally distributed in tropical and subtropical areas of the world. Graviola tree has a long history of traditional use due to its therapeutic potential including anti-inflammatory, antimicrobial, antioxidant, insecticide and cytotoxic to tumor cells.
AIM OF THE STUDY: This study aimed to investigate the in vitro antiproliferative effects and apoptotic events of the ionic liquid extract of Graviola fruit (IL-GFE) on MCF-7 breast cancer cells and their cytokinetics behaviour to observe their potential as a therapeutic alternative in cancer treatment.
MATERIALS AND METHODS: The cell viability assay of the extract was measured using tetrazolium bromide (MTT assay) to observe the effects of Graviola fruit extract. Then the cytokinetics behaviour of MCF-7 cells treated with IL-GFE is observed by plotting the growth curve of the cells. Additionally, the cell cycle distribution and apoptosis mechanism of IL-GFE action on MCF-7 cancer cells were observed by flow cytometry.
RESULTS: IL-GFE exhibited anti-proliferative activity on MCF-7 with the IC50 value of 4.75 μg/mL, compared to Taxol with an IC50 value of 0.99 μg/mL. IL- GFE also reduced the number of cell generations from 3.71 to 1.67 generations compared to 2.18 generations when treated with Taxol. Furthermore, the anti-proliferative activities were verified when the growth rate was decreased dynamically from 0.0077 h to 1 to 0.0035 h-1. Observation of the IL-GFE-treated MCF-7 under microscope demonstrated detachment of cells and loss of density. The growth inhibition of the cells by extracts was associated with cell cycle arrest at the G0/G1 phase, and phosphatidylserine externalisation confirms the anti-proliferation through apoptosis.
CONCLUSIONS: ionic liquid Graviola fruit extract affect the cytokinetics behaviour of MCF-7 cells by reducing cell viability, induce apoptosis and cell cycle arrest at the G0/G1 phase.

Matched MeSH terms: Ionic Liquids/chemistry
Magnetic poly(β-cyclodextrin-ionic liquid) nanocomposites for micro-solid phase extraction of selected polycyclic aromatic hydrocarbons in rice samples prior to GC-FID analysis

Boon YH, Mohamad Zain NN, Mohamad S, Osman H, Raoov M

Food Chem, 2019 Apr 25;278:322-332.
PMID: 30583379 DOI: 10.1016/j.foodchem.2018.10.145

Poly(β-cyclodextrin functionalized ionic liquid) immobilized magnetic nanoparticles (Fe3O4@βCD-Vinyl-TDI) as sorbent in magnetic µ-SPE was developed for the determination of selected polycyclic aromatic hydrocarbons (PAHs) in rice samples coupled with gas chromatographic-flame ionization detector (GC-FID). The nanocomposite was characterized by various tools and significant parameters that affected the extraction efficiency of PAHs were investigated. The calibration curves were linear for the concentration ranging between 0.1 and 500 μg kg-1 with correlation determinations (R2) from 0.9970 to 0.9982 for all analytes. Detection limits ranged at 0.01-0.18 μg kg-1 in real matrix. The RSD values ranged at 2.95%-5.34% (intra-day) and 4.37%-7.05% (inter-day) precision for six varied days. The sorbents showed satisfactory reproducibility in 2.9% to 9.9% range and acceptable recovery values at 80.4%-112.4% were obtained for the real sample analysis. The optimized method was successfully applied to access content safety of selected PAHs for 24 kinds of commercial rice available in Malaysia.

Matched MeSH terms: Ionic Liquids/chemistry
Fulltext A Kinetic Approach of DPPH Free Radical Assay of Ferulate-Based Protic Ionic Liquids (PILs)

Ahmad NA, Jumbri K, Ramli A, Abd Ghani N, Ahmad H, Lim JW

Molecules, 2018 Dec 05;23(12).
PMID: 30563037 DOI: 10.3390/molecules23123201

The antiradical efficiency (AE) and kinetic behavior of a new ferulate-based protic ionic liquids (PILs) were described using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay. The reduction of the DPPH free radical (DPPH•) was investigated by measuring the decrease in absorbance at 517 nm. The time to reach steady state for the reaction of parent acid (ferulic acid) and synthesized PILs with DPPH• was continuously recorded for 1 h. Results revealed that the AE of 2-butylaminoethanol ferulate (2BAEF), 3-dimethylaminopropanol ferulate (3DMAPF) and 3-diethylaminopropanol ferulate (3DEAPF) PILs have improved compared to ferulic acid (FA) as the reaction class changes from low to medium. This attributed to the strong hydrogen abstraction occurred in the PILs. Furthermore, these PILs were found to have a good kinetic behavior compared to FA due to the high rate constant (k₂) (164.17, 242.84 and 244.73 M-1 s-1, respectively). The alkyl chain length and more alkyl substituents on the nitrogen atom of cation were believed to reduce the cation-anion interaction and speed up the hydrogen atom transfer (HAT) and electron transfer (ET) mechanisms; hence, increased rate constant was observed leading to a strong antioxidant activity of the synthesized PILs.

Matched MeSH terms: Ionic Liquids/chemistry*
Isolation of C-phycocyanin from Spirulina platensis microalga using Ionic liquid based aqueous two-phase system

Chang YK, Show PL, Lan JC, Tsai JC, Huang CR

Bioresour Technol, 2018 Dec;270:320-327.
PMID: 30241065 DOI: 10.1016/j.biortech.2018.07.138

An aqueous two-phase system (ATPS) with ionic liquids (ILs) was used for the isolate of C-phycocyanin (CPC) from Spirulina platensis microalga. Various imidazolium ILs and potassium salts were studied. The effect of ILs-ATPS on the extraction efficiency of CPC was also studied. The experimental parameters like pH, loading volume, algae concentration, temperature, and alkyl chain length of IL were well-covered in this report. The experimental results showed that the extraction efficiency, the partition coefficient, and the separation factor for CPC were 99%, 36.6, and 5.8, respectively, for an optimal pH value of 7 and a temperature of 308 K. The order of extraction efficiency for CPC using IL-ATPS was: 1-octyl-3-methylimidazolium bromide (C8MIM-Br) > 1-hexyl-3-methylimidazolium bromide (C6MIM-Br) > 1-butyl-3-methylimidazolium bromide (C4MIM-Br). The isolation process followed the pseudo second-order kinetic model and the thermodynamic results were obviously spontaneous.

Matched MeSH terms: Ionic Liquids/chemistry
Ionic liquid as a potential solvent for preparation of collagen-alginate-hydroxyapatite beads as bone filler

Iqbal B, Sarfaraz Z, Muhammad N, Ahmad P, Iqbal J, Khan ZUH, et al.

J Biomater Sci Polym Ed, 2018 07;29(10):1168-1184.
PMID: 29460709 DOI: 10.1080/09205063.2018.1443604

In this study, collagen/alginate/hydroxyapatite beads having different proportions were prepared as bone fillers for the restoration of osteological defects. Ionic liquid was used to dissolve the collagen and subsequently the solution was mixed with sodium alginate solution. Hydroxyapatite was added in different proportions, with the rationale to enhance mechanical as well as biological properties. The prepared solutions were given characteristic bead shapes by dropwise addition into calcium chloride solution. The prepared beads were characterized using FTIR, XRD, TGA and SEM analysis. Microhardness testing was used to evaluate the mechanical properties. The prepared beads were investigated for water adsorption behavior to ascertain its ability for body fluid uptake and adjusted accordingly to the bone cavity. Drug loading and subsequently the antibacterial activity was investigated for the prepared beads. The biocompatibility was assessed using the hemolysis testing and cell proliferation assay. The prepared collagen-alginate-HA beads, having biocompatibility and good mechanical properties, have showed an option of promising biologically active bone fillers for bone regeneration.

Matched MeSH terms: Ionic Liquids/chemistry*
Ionic-Liquid-Based Paclitaxel Preparation: A New Potential Formulation for Cancer Treatment

Chowdhury MR, Moshikur RM, Wakabayashi R, Tahara Y, Kamiya N, Moniruzzaman M, et al.

Mol Pharm, 2018 06 04;15(6):2484-2488.
PMID: 29762034 DOI: 10.1021/acs.molpharmaceut.8b00305

Paclitaxel (PTX) injection (i.e., Taxol) has been used as an effective chemotherapeutic treatment for various cancers. However, the current Taxol formulation contains Cremophor EL, which causes hypersensitivity reactions during intravenous administration and precipitation by aqueous dilution. This communication reports the preliminary results on the ionic liquid (IL)-based PTX formulations developed to address the aforementioned issues. The formulations were composed of PTX/cholinium amino acid ILs/ethanol/Tween-80/water. A significant enhancement in the solubility of PTX was observed with considerable correlation with the density and viscosity of the ILs, and with the side chain of the amino acids used as anions in the ILs. Moreover, the formulations were stable for up to 3 months. The driving force for the stability of the formulation was hypothesized to be the involvement of different types of interactions between the IL and PTX. In vitro cytotoxicity and antitumor activity of the IL-based formulations were evaluated on HeLa cells. The IL vehicles without PTX were found to be less cytotoxic than Taxol, while both the IL-based PTX formulation and Taxol exhibited similar antitumor activity. Finally, in vitro hypersensitivity reactions were evaluated on THP-1 cells and found to be significantly lower with the IL-based formulation than Taxol. This study demonstrated that specially designed ILs could provide a potentially safer alternative to Cremophor EL as an effective PTX formulation for cancer treatment giving fewer hypersensitivity reactions.

Matched MeSH terms: Ionic Liquids/chemistry
Study of the antimicrobial activity of cyclic cation-based ionic liquids via experimental and group contribution QSAR model

Ghanem OB, Shah SN, Lévêque JM, Mutalib MIA, El-Harbawi M, Khan AS, et al.

Chemosphere, 2018 Mar;195:21-28.
PMID: 29248749 DOI: 10.1016/j.chemosphere.2017.12.018

Over the past decades, Ionic liquids (ILs) have gained considerable attention from the scientific community in reason of their versatility and performance in many fields. However, they nowadays remain mainly for laboratory scale use. The main barrier hampering their use in a larger scale is their questionable ecological toxicity. This study investigated the effect of hydrophobic and hydrophilic cyclic cation-based ILs against four pathogenic bacteria that infect humans. For that, cations, either of aromatic character (imidazolium or pyridinium) or of non-aromatic nature, (pyrrolidinium or piperidinium), were selected with different alkyl chain lengths and combined with both hydrophilic and hydrophobic anionic moieties. The results clearly demonstrated that introducing of hydrophobic anion namely bis((trifluoromethyl)sulfonyl)amide, [NTF2] and the elongation of the cations substitutions dramatically affect ILs toxicity behaviour. The established toxicity data [50% effective concentration (EC50)] along with similar endpoint collected from previous work against Aeromonas hydrophila were combined to developed quantitative structure-activity relationship (QSAR) model for toxicity prediction. The model was developed and validated in the light of Organization for Economic Co-operation and Development (OECD) guidelines strategy, producing good correlation coefficient R2 of 0.904 and small mean square error (MSE) of 0.095. The reliability of the QSAR model was further determined using k-fold cross validation.

Matched MeSH terms: Ionic Liquids/chemistry
Adsorption of malachite green from aqueous solution by using novel chitosan ionic liquid beads

Naseeruteen F, Hamid NSA, Suah FBM, Ngah WSW, Mehamod FS

Int J Biol Macromol, 2018 Feb;107(Pt A):1270-1277.
PMID: 28965968 DOI: 10.1016/j.ijbiomac.2017.09.111

Chitosan ionic liquid beads were prepared from chitosan and 1-butyl-3-methylimidazolium based ionic liquids to remove Malachite Green (MG) from aqueous solutions. Batch adsorption experiments were carried out as a function of initial pH, adsorbent dosage, agitation time and initial MG concentration. The optimum conditions were obtained at pH 4.0, 0.008g of adsorbent dosage and 20min of agitation time were utilized in the kinetic and isotherm studies. Three kinetic models were applied to analyze the kinetic data and pseudo-second order was found to be the best fitted model with R2>0.999. In order to determine the adsorption capacity, the sorption data were analyzed using the linear form of Langmuir, Freundlich and Temkin equations. The isotherm was best fitted by Langmuir isotherm model. The maximum adsorption capacity (qmax) obtained from Langmuir isotherm for two chitosan beads 1-butyl-3-methylimidazolium acetate A and 1-butyl-3-methylimidazolium B are 8.07mgg-1 and 0.24mgg-1 respectively.

Matched MeSH terms: Ionic Liquids/chemistry*

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