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CATALYSIS LETTERS · 2013 ·Vol. 143 ·期 5 ·463-468 · IF 2.244

One-Pot Synthesis of 3,4-Dihydro-2(H)-Pyrimidinones Catalyzed by Reusable Acidic Choline-Based Ionic Liquids

Zhu Anlian,Li Qianqian,Li Lingjun,Wang Jianji

Abstract A series of choline-based ionic liquids (CIL) have been synthesized in this work. The results suggested that both the cations and the anions have significant influences on their properties such as thermostabilities, acidities and their performances for the synthesis of 3,4-dihydro-2(H)-pyrimidinones. The optimized catalytic system based on the CIL [DMEA][HSO 4 ] for the Biginelli reactions benefits from the wide substrates tolerance, benign reaction conditions, easy work-up procedures, and the feasible reusability of the ionic liquid. Graphical Abstract The thermostabilities, acidities, and the catalytic activities for the Biginelli reactions are all follows the sequence of [DMEA][HSO 4 ] > [Choline] [HSO 4 ] > [DMEA][H 2 PO 4 ] > [Choline] [H 2 PO 4 ] .

研究领域: 有机化学 · 催化化学 · 药物合成
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2014 · IF 2.423

Phase behaviour and microstructure of the micro-emulsions composed of cholinium-based ionic liquid, Triton X-100 and water

Yuanchao Pei,Yanjie Huang,Lin Li,Jianji Wang

In this paper, micro-emulsions composed of cholinium-based ionic liquids (ILs), octylphenol ethoxylate (Triton X-100) and water were prepared. These ternary systems were found to be stable over 12   months at room temperature. Their phase behaviour was investigated by using cloud titrations, and their microstructures were characterised by means of cyclic voltammetry and electrical conductance measurements at T   =   298.15   K. It was shown that the micro-emulsions exhibited IL-in-water, bi-continuous and water-in-IL microstructures. Dynamic light scattering data suggest that Triton X-100 forms micelles in water, which were swelled by the ILs added. Droplets with the size about 20   nm were formed in these IL-based micro-emulsions, and the droplet size increased with the increase of the IL concentrations. These IL-based micro-emulsions may have potential in drug delivery, chemical reactions and nanomaterial preparation as a new type of nanoreactors.

CAS / MDL: 13943-58-3
研究领域: 化学 · 材料科学
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2013 · IF 2.004

Synthesis and Thermophysical Properties of Biocompatible Cholinium-Based Amino Acid Ionic Liquids

Duan-Jian Tao,Zheng Cheng,Feng-Feng Chen,Zhang-Min Li,Na Hu,Xiang-Shu Chen

Nowadays the knowledge of thermodynamic properties for amino acid ionic liquids (AAILs) has been paramount for the design of many chemical processes. In this present work, a series of cholinium-based AAILs ([Ch][AA]) were synthesized by neutralization of choline hydroxide solution with five amino acids and then were characterized by 1H NMR, Fourier transform infrared (FT-IR), elemental analysis, thermogravimetry, and differential scanning calorimetry (DSC) analysis. Physico-chemical properties such as density, viscosity, refractive index, and conductivity were measured and correlated with the empirical equations in a wide temperature range. The thermal expansion coefficient values were also calculated from the acquired experimental density values. From the experimental data, it was found that the density, viscosity, and refractive index decreased while conductivity increased with the increase of temperature. The correlation results were proposed to be in good agreement with the experimental data, and optimal fitting parameters were presented. In addition, the coefficient of thermal expansion was considered to be independent of temperature in the range of (298.15 to 353.15) K.

研究领域: 化学工程 · 材料科学
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Drug Delivery and Translational Research · 2024 · IF 5.7

Choline-based ionic liquids enhance the dermal delivery of cyclosporine a for potential treatment of psoriasis

Li Yang,Yu Qin,Lu Yi,Ma Yanyun,Qi Jianping,Chen Zhongjian,Zhu Quangang,Wu Wei

Psoriasis is a prevalent chronic disease affecting 2–3% of the global population. Cyclosporine A (CyA) has been widely used with great promise in the treatment of moderate to severe psoriasis despite various side effects associated with its systemic administration. Topical administration of CyA circumvents systemic side effects; however, the poor water solubility and large molecular weight of CyA pose challenges for dermal delivery. In this study, choline-based ionic liquids (ILs) were used to enhance the dermal delivery of CyA for the potential treatment of psoriasis. All four ILs tested significantly improved the solubility of CyA, which was greater than that of the control group with dimethyl sulfoxide (DMSO) as a solubilizer (20%, w/w). The saturated solubility of CyA in two of the ILs, choline geranate ([Ch][Ge]) and choline ricinoleate ([Ch][Ra]), reached more than 90 mg/mL, and the solubilization capability of the ILs except [Ch][Ci] was resistant to water dilution. The negligible change in CyA content determined by high-performance liquid chromatography and the secondary structure detected by circular dichroism spectroscopy confirmed the stability of CyA in the ILs. At 4 h in the in vitro penetration test, the amount of CyA retained in the skin in the IL groups was slightly greater than that in the control group (20% DMSO). The water content of the ILs significantly affected their penetration ability. When the water content increased from 10 to 70%, the dermal delivery of CyA first increased, peaked at a water content of 30%, and then decreased. The dermal delivery ability of [Ch][Ge] and [Ch][Ra] with a water content of 70% was still comparable to that of 20% DMSO. Moreover, CyA-loaded ILs (0.5%, w/w) significantly relieved the symptoms of psoriasis in an imiquimod (IMQ)-induced mouse model, and the levels of inflammatory factors, including tumor necrosis factor α, interleukin 22 and interleukin 17, in the affected area were reduced by 71.7%, 75.6%, and 89.3%, respectively. The IL tested, choline sorbate ([Ch][So]), showed low cytotoxicity to human immortalized epidermal cells (HaCaT). After 7 days of consecutive application, [Ch][So] did not cause significant irritation. In conclusion, ILs demonstrate promising potential for the dermal delivery of CyA for the treatment of psoriasis. Graphical Abstract

CAS / MDL: 1634-04-4
研究领域: 药学 · 皮肤科 · 化学
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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2024 · IF 5.3

Enhanced transdermal delivery of insulin by choline-based ionic liquids

Yang Li,Qin Yu,Yi Lu,Haisheng He,Jianping Qi,Zongguang Tai,Zhongjian Chen,Quangang Zhu,Wei Wu

Ionic liquids (ILs) show promises as chemical penetration enhancers (CPEs) for transdermal delivery of macromolecular drugs. However, their high viscosity and strong drug-IL affinity may limit drug diffusion and release from the drug-loaded IL (one-step strategy). Herein, a two-step strategy was used by applying choline-based ILs as pretreatment agents followed by insulin solution to improve penetration. Insulin remained stable in the ILs and are released slowly from the IL matrices. In vitro and in vivo studies showed that two-step treatment enhanced insulin penetration compared to one-step treatment, with choline citrate ([Ch][Ci]) and choline geranate ([Ch][Ge]) performing the best. In a diabetic rat model, two-step treatment with [Ch][Ge] reduced blood glucose levels to below 80% within 8 h, while one-step treatment only maintained for 12 h. Trans-epidermal water loss and molecular dynamics simulations suggested that variations in release rates and skin condition accounted for the differences between the two strategies. Physical characterization confirmed that ILs enhanced transdermal delivery of insulin by permeabilizing stratum corneum and opening tight junctions. Preliminary safety assessment indicated mild irritation by [Ch][Ge], whereas [Ch][Ci] showed good biocompatibility. It is concluded that ILs hold potential in enhancing transdermal delivery of insulin.

研究领域: 药学 · 药物递送系统 · 生物物理学 · 药理学
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