Synthesis and antiproliferative activity of ammonium and imidazolium ionic liquids against T98G brain cancer cells

Molecules

Volumn 17, Issue 12, 2012, Pages 13727-13739

  Kaushik, Nagendra Kumar ^a   Attri, Pankaj ^a   Kaushik, Neha ^a   Choi, Eun Ha ^a  

^a Kwangwoon University   (South Korea)

Author keywords

HEK non malignant cells; Ionic liquid; T98G brain cancer cells

Indexed keywords

IMIDAZOLE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; BRAIN TUMOR; CELL DEATH; CELL PROLIFERATION; CELL STRAIN HEK293; CELL SURVIVAL; DRUG EFFECT; HUMAN; PATHOLOGY; SYNTHESIS; TUMOR CELL LINE;

BRAIN NEOPLASMS; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; HEK293 CELLS; HUMANS; IMIDAZOLES; IONIC LIQUIDS; QUATERNARY AMMONIUM COMPOUNDS;

EID: 84871558645     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171213727     Document Type: Article

References (37)

1. Stoimenovski, J.; MacFarlane, D.R.; Bica, K.; Rogers, R.D. Crystalline vs. ionic liquid salt forms of active pharmaceutical ingredients: A position paper. Pharm. Res. 2010, 27, 521-526.
2. Rogers, R.D.; Seddon, K.R. Ionic Liquids: Industrial Applications to Green Chemistry; ACS Symp. Ser.: Washington, DC, USA, 2002.
3. Hough, W.L.; Smiglak, M.; Rodriguez, H.; Swatloski, R.P.; Spear, S.K.; Daly, D.T.; Pernak, J.; Grisel, J.E.; Carliss, R.D.; Soutullo, M.D.; et al. The third evolution of ionic liquids: Active pharmaceutical ingredients. New J. Chem. 2007, 31, 1429-1436.
4. Yu, M.; Wang, S.-H.; Luo, Y.-R.; Han, Y.-W.; Li, X.-Y.; Zhang, B.-J.; Wang, J.-J. Effects ofthe1-Alkyl-3-methylimidazolium bromide ionic liquids on the antioxidant defense system of Daphnia magna. Ecotox. Environ. Saf. 2009, 72, 1798-1804.
5. Attri, P.; Venkatesu, P. Influence of protic ionic liquids on the structure and stability of succinylated Con A. Int. J. Biol. Macromol. 2012, 51, 119-128.
6. Attri, P.; Venkatesu, P.; Kumar, A. Water and a protic ionic liquid acted as refolding additives for chemically denatured enzymes. Org. Biomol. Chem. 2012, 10, 7441-7636.
7. Hough-Troutman, W.L.; Smiglak, M.; Griffin, S.; Reichert, W.M.; Mirska, I.; Jodynis-Liebert, J.; Adamska, T.; Nawrot, J.; Stasiewicz, M.; Rogers, R.D.; et al. Ionic liquids with dual biological function: Sweet and anti-microbial, hydrophobic quaternary ammonium-based salts. New J. Chem. 2009, 33, 26-33.
8. Pernak, J.; Goc, I.; Mirska, I. Antimicrobial activities of protic ionic liquids with lactate anion. Green Chem. 2004, 6, 323-329.
9. Demberelnyamba, D.; Kim, K.-S.; Choi, S.; Park, S.Y.; Lee, H.; Kim, C.J.; Yoo, I.D. Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. Bioorg. Med. Chem. 2004, 12, 853-857.
10. Pernak, J.; Sobaszkiewicz, K.; Mirska, I. Anti-microbial activities of ionic liquids. Green Chem. 2003, 5, 52-56.
11. Pernak, J.; Feder-Kubis, J. Synthesis and properties of chiral ammonium-based ionic liquids. Chem. Eur. J. 2005, 11, 4441-4449.
12. Pernak, J.; Sobaszkiewicz, K.; Foksowicz-Flaczyk, J. Ionic liquids with symmetrical dialkoxy methyl-substituted imidazolium cations. Chem. Eur. J. 2004, 10, 3479-3485.
13. Kumar, V.; Malhotra, S.V. Study on the potential anti-cancer activity of phosphonium and ammonium-based ionic liquids. Bioorg. Med. Chem. Lett. 2009, 19, 4643-4646.
14. Stock, F.; Hoffman, J.; Ranke, J.; Ondruschka, B.; Jastorff, B. Effects of ionic liquids on the acetylcholinesterase- A structure-Activity relationship consideration. Green Chem. 2004, 6, 286-290.
15. Skladanowski, A.C.; Stepnowski, P.; Kleszczynski, K.; Dmochowska, B. AMP deaminase in vitro inhibition by xenobiotics A potential molecular method for risk assessment of synthetic nitro- and polycyclic musks, imidazolium ionic liquids and N-glucopyranosyl ammonium salts. Environ. Toxicol. Pharmacol. 2005, 19, 291-296.
16. Hosseinzadeh, F.; Mahkam, M.; Galehassadi, M. Synthesis and characterization of ionic liquid functionalized polymers for drug delivery of an anti-inflammatory drug. Des. Monomers Polym. 2012, 15, 379-388.
17. Malhotra, S.V.; Kumar, V. A profile of the in-vitro antitumor activity of imidazolium-based ionic liquids. Bioorg. Med. Chem. Lett. 2010, 20, 581-585.
18. Fujita, K.; MacFarlane, D.R.; Forsyth, M. Protein solubilising and stabilising ionic liquids. Chem. Commun. 2005, 4804-4806.
19. Von Hagen, J.; Michelsen, U. Use of ionic liquids for protein extraction. U.S. Patent US7470778B2, 2008.
20. Fujita, K.; Forsyth, M.; MacFarlane, D.R.; Reid, R.W.; Elliott, G.D. Unexpected improvement in stability and utility of cytochrome c by solution in biocompatible ionic liquids. Biotechnol. Bioeng. 2006, 94, 1209-1213.
21. Fujita, K.; MacFarlane, D.R.; Forsyth, M.; Yoshizawa-Fujita, M.; Murata, K.; Nakamura, N.; Ohno, H. Solubility and stability of cytochrome c in hydrated ionic liquids: Effect of Oxo acid residues and kosmotropicity. Biomacromolecules 2007, 8, 2080-2086.
22. Schöfer, S.H.; Kaftzik, N.; Wassrescheid, P.; Kragl, U. Enzyme catalysis in ionic liquids: Lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chem. Commun. 2001, 425-426.
23. Ranke, J.; Stolte, S.; Stormann, R.; Arning, J.; Jastorff, B. Design of sustainable chemical products-the example of ionic liquids. Chem. Rev. 2007, 107, 2183-2206.
24. Carson, L.; Chau, P.K.W.; Earle, M.J.; Gilea, M.A.; Gilmore, B.F.; Gorman, S.P.; McCann, M.T.; Seddon, K.R. Antibiofilm activities of 1-Alkyl-3-methylimidazolium chloride ionic liquids. Green Chem. 2009, 11, 492-497.
25. Shaw, G.; Morse, S.; Ararat, M.; Graham, F.L. Preferential transformation of human neuronal cells by human adenoviruses and the origin of HEK 293 cells. FASEB J. 2002, 16, 869-871.
26. Attri, P.; Reddy, P.M.; Venkatesu, P.; Kumar, A.; Hofman, T. Measurements and Molecular Interactions for N,N-dimethylformamide with Ionic Liquid Mixed Solvents. J. Phys. Chem. B 2010, 114, 6126-6133.
27. Attri, P.; Venkatesu, P.; Kumar, A. Temperature effect on the molecular interactions between ammonium ionic liquids and N,N-dimethylformamide. J. Phys. Chem. B 2010, 114, 13415-13425.
28. Attri, P.; Venkatesu, P.; Hofman, T. Temperature dependence measurements and structural characterization of trimethyl ammonium ionic liquids with a highly polar solvent. J. Phys. Chem. B 2011, 115, 10086-10097.
29. Kaushik, N.K.; Kim, Y.H.; Han, Y.G.; Choi, E.H. Effect of jet plasma on T98G human brain cancer cells. Curr. Appl. Phys. 2013, 13, 176-180.
30. Wahab, R.; Kaushik, N.K.; Verma, A.K.; Mishra, A.; Hwang, I.H.; Yang, Y.B.; Shin, H.S.; Kim, Y.S. Fabrication and growth mechanism of ZnO nanostructures and their cytotoxic effect on human brain tumor U87, cervical cancer HeLa, and normal HEK cells. J. Biol. Inorg. Chem. 2011, 16, 431-442.
31. Mishra, A.; Jung, H.; Park, J.W.; Kim, H.K.; Kim, H.; Stang, P.J.; Chi, K.W. Anticancer activity of self-Assembled molecular rectangles via arene-ruthenium acceptors and a new unsymmetrical amide ligand. Organometallics 2012, 31, 3519-3526.
32. Kaushik, N.K.; Kim, H.S.; Chae, Y.J.; Lee, Y.N.; Kwon, G.C.; Choi, E.H.; Kim, I.T. Synthesis and anticancer activity of di(3-thienyl)methanol and di(3-thienyl)methane. Molecules 2012, 17, 11456-11468.
33. Kaushik, N.K.; Uhm, H.S.; Choi, E.H. Micronucleus formation induced by dielectric barrier discharge plasma exposure in brain cancer cells. Appl. Phys. Lett. 2012, 100, 0841021-0841024.
34. Organic Chemistry Portal. Available online: http://www.organic-chemistry. org/prog/peo/ (accessed on 6-13 October 2012).
35. Tekto, I.V. Computing chemistry on the web. Drug Discov. Today 2005, 10, 1497-1500.
36. Wenlock, M.C.; Austin, R.P.; Barton, P.; Davis, A.M.; Leeson, P.D. A comparison of physicochemical property profiles of development and marketed oral drugs. J. Med. Chem. 2003, 46, 1250-1256.
37. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug. Del. Rev. 2001, 4, 3-26.