Drug‐derived surface‐active ionic liquids: a cost‐effective way to expressively increase blood‐stage antimalarial activity of primaquine

ChemMedChem ◽  
2021 ◽  
Author(s):  
Ana Teresa Silva ◽  
Isabel S. Oliveira ◽  
Joana Gomes ◽  
Luísa Aguiar ◽  
Diana Fontinha ◽  
...  
2020 ◽  
Vol 21 (15) ◽  
pp. 5334 ◽  
Author(s):  
Ana Teresa Silva ◽  
Lis Lobo ◽  
Isabel S. Oliveira ◽  
Joana Gomes ◽  
Cátia Teixeira ◽  
...  

Ionic liquids derived from classical antimalarials are emerging as a new approach towards the cost-effective rescuing of those drugs. Herein, we disclose novel surface-active ionic liquids derived from chloroquine and natural fatty acids whose antimalarial activity in vitro was found to be superior to that of the parent drug. The most potent ionic liquid was the laurate salt of chloroquine, which presented IC50 values of 4 and 110 nM against a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum, respectively, corresponding to an 11- and 6-fold increase in potency as compared to the reference chloroquine bisphosphate salt against the same strains. This unprecedented report opens new perspectives in both the fields of malaria chemotherapy and of surface-active ionic liquids derived from active pharmaceutical ingredients.


2021 ◽  
Vol 2 (4) ◽  
pp. 764-777
Author(s):  
Ana M. Ferreira ◽  
Ana Cláudia Leite ◽  
João A. P. Coutinho ◽  
Mara G. Freire

Chlorophylls and their derivatives have been extensively studied due to their unique and valuable properties, including their anti-mutagenic and anti-carcinogenic features. Nevertheless, high-purity-level chlorophylls extracted from natural sources are quite expensive because the methods used for their extraction have low selectivity and result in low yields. This study aimed to develop a “greener” and cost-effective technology for the extraction of chlorophylls from biomass using aqueous solutions of ionic liquids (ILs). Several aqueous solutions of ILs, with hydrotropic and surface-active effects were evaluated, demonstrating that aqueous solutions of surface-active ILs are enhanced solvents for the extraction of chlorophylls from spinach leaves. Operating conditions, such as the IL concentration and solid–liquid ratio, were optimized by a response surface methodology. Outstanding extraction yields (0.104 and 0.022 wt.% for chlorophyll a and b, respectively, obtained simultaneously) and selectivity (chlorophyll a/b ratio of 4.79) were obtained with aqueous solutions of hexadecylpyridinium chloride ([C16py]Cl) at moderate conditions of temperature and time. These extraction yields are similar to those obtained with pure ethanol. However, the chlorophyll a/b ratio achieved with the IL aqueous solution is higher than with pure ethanol (3.92), reinforcing the higher selectivity afforded by IL aqueous solutions as viable replacements to volatile organic compounds and allowing the obtainment of more pure compounds. Finally, the recovery and reuse of the solvent were evaluated by using a back-extraction step of chlorophylls using ethyl acetate. The results disclosed here bring new perspectives into the design of new approaches for the selective extraction of chlorophylls from biomass using aqueous solutions of surface-active ILs.


2019 ◽  
Vol 278 ◽  
pp. 145-155 ◽  
Author(s):  
Guowei Wang ◽  
Xiaoqing Xu ◽  
Yu Sun ◽  
Linghua Zhuang ◽  
Cheng Yao

2021 ◽  
Vol 19 ◽  
pp. 100369
Author(s):  
Dewi K.A. Kusumahastuti ◽  
Mariliis Sihtmäe ◽  
Villem Aruoja ◽  
Nicholas Gathergood ◽  
Anne Kahru
Keyword(s):  

RSC Advances ◽  
2016 ◽  
Vol 6 (58) ◽  
pp. 52781-52789 ◽  
Author(s):  
Juliusz Pernak ◽  
Kamil Czerniak ◽  
Agnieszka Biedziak ◽  
Katarzyna Marcinkowska ◽  
Tadeusz Praczyk ◽  
...  

A new family of herbicidal ionic liquids based on d-glucose and MCPA or 2,4-D anions has been synthesized and the physicochemical, surface active and herbicidal properties of the obtained salts were characterized.


2016 ◽  
Vol 69 (11) ◽  
pp. 1254 ◽  
Author(s):  
Jiequn Wu ◽  
Tianxiang Yin ◽  
Shaoxiong Shi ◽  
Weiguo Shen

The systematic investigation of the aggregation behaviours of newly synthesised surface-active ionic liquids 1-alkyl-3-methylimidazolium bis(2-ethylhexyl)sulfosuccinate ([Cnmim][AOT], n = 2, 3, 5, 6, 7) by various techniques is reported. The critical aggregation concentrations (CACs) and the standard Gibbs free energies of aggregation () were determined from measurements on conductivity, fluorescence, and surface tension, which suggested a stronger self-assembly ability in the bulk solution for [Cnmim][AOT] surfactants with longer alkyl chain cations. An interesting structure transition driven by the penetration of the imidazolium cation into the aggregate when n > 4 was found by analysis of the variations of the values of CAC, , the degree of counter ion binding (β), and the micropolarity (I1/I3) immediately after the CAC with changing alkyl chain length of the imidazolium cation, which was further confirmed by 1H NMR measurements.


2017 ◽  
Vol 121 (37) ◽  
pp. 8742-8755 ◽  
Author(s):  
Filipa A. Vicente ◽  
Inês S. Cardoso ◽  
Tânia E. Sintra ◽  
Jesus Lemus ◽  
Eduardo F. Marques ◽  
...  

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