Cytotoxicity estimation of ionic liquids based on their effective structural features

Fatemi, M.; Izadiyan, Parisa

doi:10.1016/j.chemosphere.2011.04.021

Cited by 122 publications

(66 citation statements)

References 27 publications

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“…The model input data are the target values of molecular descriptor projections. The chemometric models are linear models, and applied here based on their expected robustness and improved prediction when compared to classical least squares multivariate models [9][10][11][12] . The first tested model is Principal Component Regression (PCR) given by Eq.…”

Section: Resultsmentioning

confidence: 99%

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Chemometric versus Random Forest Predictors of Ionic Liquid Toxicity

Kurtanjek

2015

Chem.Biochem.Eng.Q.

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The objective of this work was a comparative analysis of the standard chemometric and decision tree(s) models for prediction of biological impact of ionic liquids (ILs) for various combinations of cations and anions. The models are based on molecular descriptors for combinations of the following cations: imidazole, pyridinium, quinolinium, ammonium, phosphonium; and anions: BF 4 , Cl, PF 6 , Br, CFNOS, NCN 2 , C 6 F 18 PBF 4 , C 6 F 18 P. The derived data matrix is decomposed by singular value decomposition of the cation and anion matrices into corresponding first ten components, each accounting for 99.5 % of the corresponding total variances. Biological impact data, i.e. molecular level toxicity, are based on acetylcholinestarase inhibition experimental data provided in MERCK Ionic Liquids Biological Effects Database. Applied were the following models: Principal component regression (PCR), partial least squares (PLS), and decision tree(s) model. The model performances were compared by ten-fold validation. Obtained were the following Pearson regression coefficients R 2 : PCR 0.62, PLS 0.64, and for decision tree forest RFDT 0.992. The decision tree(s) models significantly outperformed chemometric models for numerical predictions of EC 50 concentrations and the classification of ILs into four levels of toxicities.

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Section: Resultsmentioning

confidence: 99%

“…ties, as for example, viscosity, given in literature [12][13][14] . A possible explanation is due to high dispersion of the experimental data EC 50 involved in measurement of the biological effect of ILs.…”

Section: F I G 1 -Comparison Between the Test Samples For Measured mentioning

confidence: 99%

Chemometric versus Random Forest Predictors of Ionic Liquid Toxicity

Kurtanjek

2015

Chem.Biochem.Eng.Q.

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“…For example, small anions as hydrophilic Cl -remained in solution, whereas a more hydrophobic anion like PF 6 formed a film at the lipid /water boundary. Furthermore, the hydrolysis of fluorinated anion and formation of fluorides, potent inhibitors of Na + K + ATPase (an enzyme which participates in the maintainance of the cell's static electric potential and which regulates cellular transport volume), also contribute to their higher toxicity (11).…”

Section: Ionic Liquidsmentioning

confidence: 99%

Toxicity mechanisms of ionic liquids

Bubalo

Radošević

Redovniković

et al. 2017

Archives of Industrial Hygiene and Toxicology

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Over the past three decades a growing awareness of environmental protection prompted the development of so-called green and sustainable technologies. Therefore, academic and wider community intensively explores new chemicals and safer, more energy efficient processes based on a rational compromise between economic, social, and environmental requirements. Due to low volatility and stability, ionic liquids emerged as a potential replacement for traditional volatile and harmful organic solvents. Various studies have been carried out to validate the green character of ionic liquids, whereby data published suggest that these compounds, due to their relatively high toxicity and poor biodegradability, could have an extremely negative impact on the environment. This paper presents the current knowledge on the toxicity of ionic liquids, with a special emphasis on the mechanisms by which this group of compounds causes changes in the morphology and physiology of organisms at different organisational levels of the ecosystem.

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“…Their activity is such that one is no longer dependant on the nature of the anion to ensure high product yields -the iodide 26 can promote the formation of 6 in >90% yield at just 1 mol% loading. We also note with interest that Fatemi and Izadiyan 13 have very recently suggested that ILsymmetry is linked to cytotoxicity to rat luekemia cell lines; with less symmetrical salts in general proving more cytotoxic than more symmetrical counterparts.…”

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confidence: 99%

“…While it should be noted that 7/7a have not been directly observed experimentally, this hypothesis can account all of the data obtained thus far. [6][7][8] While 4 was shown to be catalytically active and completely non-toxic to 20 sample microorganisms (8 bacteria and 12 fungi), 8 we were nevertheless aware that the utility and potential environmental impact of these systems could be significantly improved if: (a) catalytic activity could be increased significantly (so that less of the material would be required for use in synthetic applications) and (b) the tetrafluoroborate counteranion [9][10][11][12][13] (which is a sine qua non for high activity in catalysts such as 4) could be replaced with a less hydrolytically unstable 14 substitute.…”

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confidence: 99%

A new generation of aprotic yet Brønsted acidic imidazolium salts: low toxicity, high recyclability and greatly improved activity

et al. 2013

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a Catalysts which have low antimicrobial toxicity and are aprotic, yet which can act as Brønsted acidic catalysts in the presence of protic additives have been developed. The catalysts are recyclable, considerably more active (i.e. can be used at 10-50 times lower loadings) and of broader scope than their antecedent generation.Since Forbes and Davis reported the design of a class of phosphonium-and imidazolium ion-based ionic liquids (e.g. 1, Fig. 1A) equipped with a pendant acidic sulfonic acid moiety, interest in Brønsted acidic ionic liquids (BAILs) has gathered considerable pace.1,2 These materials afford the practitioner the flexibility of a system which combines strong acidity with the traditional advantages 3 associated with the use of nonvolatile ionic liquids. Subsequently two other strategies for the design of acidic imidazolium-ion based ionic liquids (ILs) were reported: the protonated imidazole conjugate acids 3o,4 (i.e. 2) and traditional imidazolium-ion based ILs which incorporate acidic counteranions (i.e. 3). 5 While these systems have found application in a wide-range of acid-catalysed reactions, the potential uncertainties from an environmental standpoint (to the best of our knowledge the toxicity and biodegradation profiles of these materials have yet to be established) and potential storage difficulties associated with the fact that these materials are strongly Brønsted acidic, remain. We therefore became interested in the design of aprotic salts which could serve as acidic catalysts only when used in conjunction with an additive. These materials hold promise as catalysts which can be designed to be readily storable and of minimal toxicity/environmental impact, the catalytically useful acidity of which could be controlled in an 'on-off' fashion. In short, these catalysts would be acidic only when required.Our inspiration for this work came from the serendipitous discovery that N-alkyl pyridinium ions could catalyse the acetalisation of benzaldehyde in the absence of any discernible acidic species in solution. 6,7 It was later demonstrated that this phenomenon also occurred in the case of N-alkyl imidazolium ions, which allowed the design of a suite of demonstrably low antimicrobial toxicity salts (of which 4, Fig. 1A, proved the most active) capable of promoting the acetalisation of aldehydes (inter alia) at low catalyst loadings (e.g. 5-10 mol%, Fig. 1B). 8a Along the same lines, we recently demonstrated that triazolium ion-based species could act in a similar fashion at loadings of 1-2 mol%. 8b It was proposed that the low resonance stabilisation energy of the imidazolium ion would allow

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Cytotoxicity estimation of ionic liquids based on their effective structural features

Cited by 122 publications

References 27 publications

Chemometric versus Random Forest Predictors of Ionic Liquid Toxicity

Chemometric versus Random Forest Predictors of Ionic Liquid Toxicity

Toxicity mechanisms of ionic liquids

A new generation of aprotic yet Brønsted acidic imidazolium salts: low toxicity, high recyclability and greatly improved activity

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