The Study of Cytotoxicity of an Imidazolium Based Ionic Liquid on MCF-7 Cell Line

Subject Areas : Journal of Chemical Health Risks

Elham Sajadiyeh ¹ , Masoumeh Tabatabaee ² , SayedMorteza Seifati ³ , Zohreh Derikvend ⁴

1 - Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Irann
2 - Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran
3 - Department of Biology, Ashkezar Branch, Islamic Azad University, Ashkezar, Iran
4 - Department of Chemistry, Khorramabad Branch, Islamic Azad University, Khorramabad, Iran

Received: 2019-12-22 Accepted : 2020-11-23 Published : 2021-03-01

Keywords: Cytotoxicity, MCF-7 Cell Line, IImidazolium Ionic Liquids, IC50 values,

Abstract :

Ionic liquids are liquid in wide range and could be applied in many fields. These compounds can be used as solvents for inorganic and organic synthesis and show biological activities. 1-ethyl-3-Methylimidazolium bromide (1) as an ionic liquid has been synthesized from the reaction of 1-methylimidazole and ethylbromide in toluene as solvent and under refluxed condition. The prepared compound was characterized by 1H-NMR, IR spectroscopy and elemental analyses. The effect of cytotoxicity of -ethyl-3-Methylimidazolium bromide (ion liquid)on the MCF-7 cell line has been investigated. The cytotoxic activity of synthesis compound was assessed by the MTT colorimetric method in vitro assay performed in human MCF-7 breast carcinoma cell line. Dose effect of compound was investigated and results showed that the cytotoxic effect was dose-dependent. The decrease of concentration of ion liquid was followed by markedly increase of tumor cell viability. The cytotoxicity of 1-ethyl-3-Methylimidazolium bromide, expressed as IC50values after 48 h incubation. This value was 2.91 mM for mcf-7 cell line.

References:

1. Filippov A., Munavirov B., Glavatskih S., Shah F.U.,  Antzutkin O.N., 2020. Diffusion of Ions in Phosphonium Orthoborate Ionic Liquids Studied by 1H and ¹¹B Pulsed Field Gradient NMR. 8, article 119. 

2. Naz S., Uroos M., Asim A.M., Muhammad N.,   Shah F.U., 2020. One-Pot Deconstruction and Conversion of Lignocellulose into Reducing Sugars by Pyridinium Based Ionic Liquid Metal Salt System. Front Chem., 8, Article 236.

3. Pérez S.A., Montalbán M.G.,Carissimi G., Licence P.,Víllora G., 2020. In vitro cytotoxicity assessment of monocationic and dicationic pyridinium-based ionic liquids on HeLa, MCF-7, BGM and EA. hy926 cell lines. J Hazard Mater. 385, 121513.

4. Muthayala M.K., Chhikara B.S., Parang K., Kumar A., 2012. Ionic Liquid-Supported Synthesis of Sulfonamides and Carboxamides. ACS Comb Sci. 14, 60−65.

5. Ahmed E., Ruck M, 2011. Chemistry of polynuclear transition-metal complexes in ionic liquids. Dalton Trans. 40, 9347–9357.

6. Wasserscheid P., Welton T., Ionic Liquids-New "Solutions" for Transition Metal Catalysis. Wiley-VCH, New York, 2007.

7. Visser A.E., Swatloski R.P., Reichert W.M., Mayton R., Sheff S., Wierzbicki A., Davis J.H.,  Rogers R.D., 2002.  Task-specific ionic liquids incorporating novel cations for the coordination and extraction of Hg²⁺ and Cd²⁺: synthesis, characterization, and extraction studies. Environ Sci Technol. 36, 2523–2529.

8. Papageorgiou N., Athanassov Y., Armand M., Bonhôte P., Pettersson H., Azam A., Grätze M.,  1996. The performance and stability of ambient temperature molten salts for solar cell applications. J Electrochem Soc. 143, 3099–3108.

9. Hallett J. P., Welton T., 2011. Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. Chem Rev. 111, 3508–3576.

10. Tang S., A. Babai A., Mudring A.V., 2008. Europium based ionic liquids as luminescent soft materials. Angew Chem. 120, 7743–7746.

11. Babai A., Mudring A.V., 2006. The Octanuclear Europium Cluster [bmpyr]₆[Eu₈(μ₄ O)(μ₃ OH)₁₂(μ₂ OTf)₁₄ (μ₁ Tf)₂](HOTf)_1.5 Obtained from the Ionic Liquid [bmpyr][OTf. Z Anorg Allg Chem. 632, 1956–1958.

12. Jin K., Huang X., Pang L., Li J., Appel A., Wherland S., 2002. [Cu(I)(bpp)]BF4: the first extended coordination network prepared solvothermally in an ionic liquid solvent. Chem Commun. 2872–2873.

13. Reichert W.M., Holbrey J.D.,  Vigour K.B., Morgan T.D., Broker G.A., Rogers R.D., 2006. Approaches to crystallization from ionic liquids: Complex solvents–complex results or, a strategy for controlled formation of new supramolecular architectures. Chem Commun. 4767–4779.

14. Holbrey J.D., Vigour K.B., Reichert W.M., Rogers R.D., 2006. The structure of [Co(H-tptz)Cl₃]·H₂O (tptz=2,4,6-tri(2-pyridyl)-1,3,5-triazine) prepared by crystallization from the ionic liquid, N-butyl-N-methyl-pyrrolidinium bis(trifluoromethanesulfonyl)imide. J Chem Crystallogr. 36, 799–804.

15. Zhu X.W., Ge H.L., Cao Y.B., 2016. Mixture cytotoxicity assessment of ionic liquids and heavy metals in MCF-7 cells using mixtox. Chemosphere. 163, 544-51.

16. Kristina R., Železnjak J., Bubalo M.C., Redovniković I.R., Slivac I., Srček V.G., 2016. Comparative in vitro study of cholinium-based ionic liquids and deep eutectic solvents toward fish cell line. Ecotoxicology and Environmental Safety. 131, 30-36.

17. Wojciech S., Hackenberg F., Müller-Bunz H., Tacke M., 2014, Synthesis and cytotoxicity studies of p-benzyl substituted NHC–copper (I) bromide derivatives. Polyhedron. 80, 3-9.

18. Kumar R.A., Papaïconomou N., Lee J.M., Salminen J., Clark D.S., Prausnitz J.M., 2009. In vitro cytotoxicities of ionic liquids: effect of cation rings, functional groups, and anions. Environ Toxicol. 4, 388-395.

19. Sekhon B.S., 2011. Ionic liquids: Pharmaceutical and Biotechnological Applications. Asian J Pharm Biol Res, 1, 395-411.

20. Borowiecki P., Milner-Krawczyk M., Brzezińka D., Wielechowska M., Plenkiewicz J., 2013. Synthesis and Antimicrobial Activity of Imidazolium and Triazolium Chiral Ionic Liquids. Eur J Org Chem. 712–720.

21. Kaushik N.K., Attri P., Kaushik N., Choi E.H., 2012. Synthesis and Antiproliferative Activity of Ammonium and Imidazolium Ionic Liquids against T98G Brain Cancer Cells. Molecules. 17, 13727-13739.

22. Messali M., Aouad M.R., Ali A.A.S., Rezki N., Hadda T.B., Hammouti B., 2015. Synthesis, characterization, and POM analysis of novel bioactive imidazolium-based ionic liquids. Med Chem Res. 24, 1387–1395.

23. Dzyuba S.V., Kollar K. D., Sabnis S.S., 2009. Synthesis of Imidazolium Room-Temperature Ionic Liquids. J Chem Edu. 86, 856-857.

24. Rajathi K., Rajendran A., 2013, Synthesis, Characterization and Biological Evaluation of Imidazolium Based Ionic Liquids. J Chem.  2, 36-41.

25. Mosmann T., 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays.  J Immunol Meth. 165, 55–63.