Anticancer potential and through study of the cytotoxicity mechanism of ionic liquids that are based on the trifluoromethanesulfonate and bis(trifluoromethylsulfonyl)imide anions

Kuczak, Micha; Musiał, Małgorzata; Malarz, Katarzyna; Rurka, Patryk; Zorębski, Edward; Musioł, Robert; Dzida, Marzena; Mrozek-Wilczkiewicz, Anna

doi:10.1016/j.jhazmat.2021.128160

Cited by 15 publications

(11 citation statements)

References 74 publications

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“…65,69 Pyridinium, ammonium, and other ILs have also been reported to have anticancer activity. 120–122 Aljuhani et al showed anticancer activities of a series of pyridinium ILs on two lung cancer cell lines (A549 and H-1229), and the maximum rate of proliferation inhibition was 99.69%. 123 Bourakadi et al evaluated the antitumor activity of a series of 3-methyl-1-alkyl-2-(thiazol-4-yl) benzimidazol-3-ium ILs against four human tumor cell lines: HT29 (colon), K652 (Leukemia), MDA-MB231, and SKBR3 (breast) and established the antitumor prospect of ILs based on thiabendazole.…”

Section: Therapeutic Components and Mechanismmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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Section: Therapeutic Components and Mechanismmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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“…[31,32] In last decade anticancer studies of imidazolium, phosphonium, chloine, benzalkonium, ammonium, and pyrrolidium-based ionic liquids had been studied on different cancer cells like Hepatocarcinoma, Brain cancer cells, Human embryonic kidney, colon carcinoma, cervical cancer, melanoma. [33][34][35][36][37][38][39][40][41][42][43][44][45] Our research group has interest on development of third generation of ionic liquids as anti-cancer drugs. Hence, we have reported in-silico and in-vitro studies on tumor cell using derivatives of 1,3benzodioxole based ionic liquid.…”

Section: Introductionmentioning

confidence: 99%

“…The third generation of ionic liquids is well known for biological activities such as anticancer, antifungal, antibacterial, and so on [31,32] . In last decade anticancer studies of imidazolium, phosphonium, chloine, benzalkonium, ammonium, and pyrrolidium‐based ionic liquids had been studied on different cancer cells like Hepatocarcinoma, Brain cancer cells, Human embryonic kidney, colon carcinoma, cervical cancer, melanoma [33–45] . Our research group has interest on development of third generation of ionic liquids as anti‐cancer drugs.…”

Section: Introductionmentioning

confidence: 99%

1,3‐Benzodioxole Tagged Lidocaine Based Ionic Liquids as Anticancer Drug: Synthesis, Characterization and In Silico Study

et al. 2023

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Skin cancer is by far the most frequent type of cancer in humans which gradually increases day by day. Numerous treatments are traditionally and conventionally available in the market but due to various factors such as high dose, high cost, adverse side effects, and so on. So, these treatments require novel routes of action and target drugs that can overcome these drawbacks. As per the ritual of our research group to design a new drug for mankind, we have synthesized derivatives of 1,3‐Benzodioxole tagged lidocaine‐based ionic liquid in the present work and characterized using techniques like 1H, 13C NMR, and infrared spectroscopy. The in‐silico studies were conducted which provided information regarding the binding mode of active 1,3‐benzodioxole‐derived ILs with the tubulin protein (1TUB) receptor. The binding affinity for [Pip‐Lid]OAc and [Pip‐Lid]OTf are −384.47 kJ/mol and −355.74 kJ/mol respectively. The properties of these ionic liquids like ADMET, blood‐brain barrier permeability, and drug‐likeliness proved the potency of the given compound for the treatment of skin cancer. Briefly, the current study showed the good anticancer potential of synthesized ionic liquids against skin cancer.

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“…The study concentrates on modeling the gas-ionic liquid partition coefficients for three organic compounds hexane, cyclohexane and benzene in the series of ionic liquids with common bis(trifluoromethylsulfonyl)imide ([Tf2N] − ) anion using linear and non-linear QSPR methods. [Tf2N] + ILs are being extensively studied for various applications, for example as a media for supercapacitors [ 63 ], a heavy metal adsorbent [ 64 ], an anticancer agent [ 65 ] and gas solvent in sensors [ 66 ] among many other applications [ 67 , 68 , 69 ]. Variation in ionic counterpart makes it possible more specifically to understand how molecular interactions of partitioning by the ionic liquid and how to enable finding the application-appropriate ionic liquid.…”

Section: Introductionmentioning

confidence: 99%

Machine Learning Quantitative Structure–Property Relationships as a Function of Ionic Liquid Cations for the Gas-Ionic Liquid Partition Coefficient of Hydrocarbons

Toots

Sild

Leis

et al. 2022

IJMS

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Ionic liquids (ILs) are known for their unique characteristics as solvents and electrolytes. Therefore, new ILs are being developed and adapted as innovative chemical environments for different applications in which their properties need to be understood on a molecular level. Computational data-driven methods provide means for understanding of properties at molecular level, and quantitative structure–property relationships (QSPRs) provide the framework for this. This framework is commonly used to study the properties of molecules in ILs as an environment. The opposite situation where the property is considered as a function of the ionic liquid does not exist. The aim of the present study was to supplement this perspective with new knowledge and to develop QSPRs that would allow the understanding of molecular interactions in ionic liquids based on the structure of the cationic moiety. A wide range of applications in electrochemistry, separation and extraction chemistry depends on the partitioning of solutes between the ionic liquid and the surrounding environment that is characterized by the gas-ionic liquid partition coefficient. To model this property as a function of the structure of a cationic counterpart, a series of ionic liquids was selected with a common bis-(trifluoromethylsulfonyl)-imide anion, [Tf2N]−, for benzene, hexane and cyclohexane. MLR, SVR and GPR machine learning approaches were used to derive data-driven models and their performance was compared. The cross-validation coefficients of determination in the range 0.71–0.93 along with other performance statistics indicated a strong accuracy of models for all data series and machine learning methods. The analysis and interpretation of descriptors revealed that generally higher lipophilicity and dispersion interaction capability, and lower polarity in the cations induces a higher partition coefficient for benzene, hexane, cyclohexane and hydrocarbons in general. The applicability domain analysis of models concluded that there were no highly influential outliers and the models are applicable to a wide selection of cation families with variable size, polarity and aliphatic or aromatic nature.

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Anticancer potential and through study of the cytotoxicity mechanism of ionic liquids that are based on the trifluoromethanesulfonate and bis(trifluoromethylsulfonyl)imide anions

Cited by 15 publications

References 74 publications

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

1,3‐Benzodioxole Tagged Lidocaine Based Ionic Liquids as Anticancer Drug: Synthesis, Characterization and In Silico Study

Machine Learning Quantitative Structure–Property Relationships as a Function of Ionic Liquid Cations for the Gas-Ionic Liquid Partition Coefficient of Hydrocarbons

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