Quantitative structure–activity relationship (QSAR) prediction of (eco)toxicity of short aliphatic protic ionic liquids

Peric, Brezana; Sierra, Jordi; Martí, Esther; Cruañas, Robert; Garau, M. A.

doi:10.1016/j.ecoenv.2015.02.027

Cited by 67 publications

(23 citation statements)

References 23 publications

(26 reference statements)

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“…Biological activity of ILs was shown to depend on their hydrophilicity and hydration state/hydration number. [8][9][10][11] Starting from the assumption 'more polar-less toxic', lower cytotoxicity of ILs with polar groups was presumed, which was thus tested. Accordingly, the aim of this study was to assess the anticancer potential of imidazolium-based ionic liquids with salicylate anion in human cancer cell lines using the MTT cell viability assay, as well as antimicrobial potential of these compounds against several bacterial and Candida strains by the standard double diluted antimicrobial procedure.…”

Section: Introductionmentioning

confidence: 99%

Anticancer and antimicrobial properties of imidazolium based ionic liquids with salicylate anion

et al. 2020

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Ionic liquids (ILs) are well known for their physicochemical properties that recommend them for many purposes. However, many ILs are not environmentally friendly. Bearing these facts in mind, a series of imidazoliumand salicylate-based ILs with low general toxicity were designed and their pharmacological potential studied. Herein, their antiproliferative effect against human cancer cell lines and antimicrobial activity on selected Gram-positive and Gram-negative bacteria and Candida strains are presented. ILs with 1-butyl--3-methylimidazolium or imidazolium cation (IL 1 and compound 5), with the lowest dipole moments and highest lipophilicity, exerted highest cytotoxicity against colon and/or lung cancer cells, manifesting high selectivity to the normal cells. The most non-polar IL with the 1-butyl-3-methylimidazolium cation expressed the strongest anticancer potential, but it was also toxic against normal cells, although its cytotoxicity was less than the cytotoxic effect of commercially used chemotherapeutic agents. The same compounds, IL 1 and compound 5, expressed modest effect on the bacterial strain that causes serious lung diseases and pulmonary infections (Staphylococcus aureus) or which are included in colon cancer formation (Esherichia coli and Enterococcus faecalis). Salicylate itself was toxic against lung cancer cell line A549 and affected some Candida strains.

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Section: Introductionmentioning

confidence: 99%

Anticancer and antimicrobial properties of imidazolium based ionic liquids with salicylate anion

et al. 2020

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“…41 Finally, we have employed an additional external dataset of eight compounds (not used for developing the models), but for judging the true external predictivity of the models. 42 2.2 Development of predictive QSTR models 2.2.1 Dataset division and descriptor pre-treatment. Variance and correlation based criteria were implemented for the thinning of the descriptor pool giving predictor variables with a variance >0.0001 and an inter-correlation (r) among descriptors <0.95.…”

Section: The Dataset and Descriptorsmentioning

confidence: 99%

Development of predictive QSAR models for Vibrio fischeri toxicity of ionic liquids and their true external and experimental validation tests

et al. 2016

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Despite possessing an interesting chemical nature and tuneable physicochemical properties, ionic liquids (ILs) must have their ecotoxicity tested in order to be commercialized. The water solubility of ILs allows their easy access to the aquatic compartment of the ecosystem creating a potential hazard to aquatic organisms. Hence, it is relevant to design ionic liquids with lower toxicity while keeping the desired properties of interest. Considering the possibility of an enormous number of combinations of different cations and anions, a rational guidance for the structural design of ionic liquids is essential in order to prioritize the synthesis as well as testing of selected molecules only. Predictive in silico models, such as quantitative structure-activity relationship (QSAR) models, can play a pivotal role in exploring the important chemical attributes contributing to the response activity. These models may then lead to the design of novel ionic liquids. The present study aims at developing predictive QSAR models for the ecotoxicity of ionic liquids using the bacteria Vibrio fischeri as an indicator response species. Instead of a single model, here we have used multiple models to capture more complete structural information of ionic liquids for toxicity towards Vibrio fischeri. The derived chemical attributes have been implemented in designing new analogues, some of which have been synthesized and had their ecotoxicity tested for the same model organism. The predictive QSAR models reported here can be used for ecotoxicity prediction of new IL chemicals and for data-gap filling. Moreover, the synthesized low-toxic ILs could be considered for evaluation as well as for application in suitable processes serving the purpose of industry and academia.

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“…With the same approach, Das and Roy (2014a) developed a model with R 2 of 0.918 (training set) and 0.861 (test set). Peric et al (2015) developed a model for aliphatic protic ILs using the group contribution method. Basant et al (2015) suggested nonlinear models based on machine-learning approaches; i.e., cascade correlation network (CCN) and support vector machines (SVMs).…”

Section: Introductionmentioning

confidence: 99%

Interpretation of toxicological activity of ionic liquids to acetylcholinesterase inhibition via in silico modelling

Cho

Yun

2016

Chemosphere

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Quantitative structure–activity relationship (QSAR) prediction of (eco)toxicity of short aliphatic protic ionic liquids

Cited by 67 publications

References 23 publications

Anticancer and antimicrobial properties of imidazolium based ionic liquids with salicylate anion

Anticancer and antimicrobial properties of imidazolium based ionic liquids with salicylate anion

Development of predictive QSAR models for Vibrio fischeri toxicity of ionic liquids and their true external and experimental validation tests

Interpretation of toxicological activity of ionic liquids to acetylcholinesterase inhibition via in silico modelling

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