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Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Letter Article

Ionic Liquids with Anti-Candida and Anticancer Dual Activity as Potential N-Myristoyltransferase Inhibitors

Author(s): Larysa Metelytsia, Maria Trush, Ivan Semenyuta, Sergiy Rogalsky, Oleksandr Kobzar, Larisa Kalashnikova, Volodymyr Blagodatny and Diana Hodyna*

Volume 16, Issue 7, 2020

Page: [1036 - 1041] Pages: 6

DOI: 10.2174/1573407215666191007120402

Price: $65

Abstract

Background: Currently, a study on the relationship between candidiasis and cancer has been conducted. Until recent years, the opportunistic fungus C. albicans is mainly associated with cancer processes and is able to stimulate carcinogenesis and metastasis.

Methods: A number of ionic liquids as potential anticancer and anti-Candida agents have been investigated based on modern theoretical and experimental data about the relationship between oncopathology and candida infection.

Results: The analysis of the received experimental results demonstrates that ionic liquid with alkyl chain length of 6 carbon atoms (C6) has not shown anti-Candida activity. The indicators of its cytotoxicity ІС50 (28,617μМ) and MTC (9,050 μМ) against HEP-2 tumor cell line were also very low. Compounds with alkyl chain length C12 have shown high potential of anti-Candida activity and anticancer properties.

Conclusion: Based on the obtained results, сompound 4 (C12C1IM-Cl) is proposed for further study as a potential double-acting agent with high anticancer and anti-Candida activities. N-myristoyltransferase is presented and used for docking as a potential molecular target responsible for the dual anti-Сandidа and anticancer activities of studied ionic liquids.

Keywords: Ionic liquids, N-myristoyltransferase, docking, anticancer, anti-Candida, oncopathology.

Graphical Abstract

[1]
Utreja, D.; Sarbjit, V.; Manpreet Kaur, S. Schiff Bases and their metal complexes as anti-cancer agents: A review. Curr. Bioact. Compd., 2015, 11(4), 215-230.
[http://dx.doi.org/10.2174/1573407212666151214221219]
[2]
De Oliveira, M.G.; Figueredo, A.S.; De Aquino, G.L.B.; Leopoldino, A.M.; Da Silva, V.B.; Taft, C.A.; De Paula da Silva, C.H.T. In Silico Design of phenylbenzamide derivatives coupled to pyrimidines as Novel hnRNP K ligands against cancer. Curr. Bioact. Compd., 2014, 10(3)
[http://dx.doi.org/10.2174/157340721003141013142614]
[3]
Fait, M.E.; Da Costa, H.P.S.; Freitas, C.D.T.; Bakás, L.; Morcelle, S.R. Antifungal activity of arginine-based surfactants. Curr. Bioact. Compd., 2019, 15(3), 351-359.
[http://dx.doi.org/10.2174/1573407214666180131161302]
[4]
De Azambuja, G.O.; Svetaz, L.; Goncalves, I.L.; Corbelini, P.F.; Von Poser, G.L.; Kawano, D.F.; Zacchino, S.; Eifler-Lima, V.L. In vitro antifungal activity of dihydropyrimidinones/thiones against Candida albicans and Cryptococcus neoformans. Curr. Bioact. Compd., 2019, 15(6), 648-655.
[http://dx.doi.org/10.2174/1573407214666180926115745]
[5]
Sinha, M.; Kaur, B.; Kaur, A.; Kuletha, S.; Singh, K.; Bhatia, R. Anticancer activity of aminoacid linked novel 4-Methylumbelliferone derivatives. Curr. Bioact. Compd., 2019, 15(1), 51-62.
[http://dx.doi.org/10.2174/1573407213666170210143503]
[6]
Limsitthichaikoon, S.; Priprem, A.; Damrongrungruang, T.; Limphirat, W.; Kukhetpitakwong, R. improvement of chemical stability and activities of anthocyanins by complexation. Curr. Bioact. Compd., 2016, 12, 17-24.
[http://dx.doi.org/10.2174/1573407212666160210225758]
[7]
Kenneth, V.I. Infections in cancer patients with solid tumors: A review. J. Infect. Dis. Ther., 2017, 6(1), 69-83.
[http://dx.doi.org/10.1007/s40121-017-0146-1]
[8]
Choi, J.; Lee, B.; Park, S.A. Epidemiological study on Candida Species in patients with cancer in the intensive care unit. Osong Public Health Res. Perspect., 2017, 8(6), 384-388.
[http://dx.doi.org/10.24171/j.phrp.2017.8.6.05]
[9]
Garrett, W.S. Cancer and the microbiota. Science, 2015, 348(6230), 80-86.
[http://dx.doi.org/10.1126/science.aaa4972]
[10]
Oikonomopoulou, K.; Brinc, D.; Kyriacou, K.; Diamandis, E.P. Infection and cancer: Revaluation of the hygiene hypothesis. Clin. Cancer Res., 2013, 19(11), 2834-2841.
[http://dx.doi.org/10.1158/1078-0432.CCR-12-3661]
[11]
Trush, M.M.; Semenyuta, I.V.; Vdovenko, S.I.; Rogalsky, S.P.; Lobko, E.O.; Metelytsia, L.O. Synthesis, spectroscopic and molecular docking studies of imidazolium and pyridinium based ionic liquids with HSA as potential antimicrobial agents. J. Mol. Struct., 2017, 1137, 692-699.
[http://dx.doi.org/10.1016/j.molstruc.2017.02.079]
[12]
Hodyna, D.; Kovalishyn, V.; Rogalsky, S.; Blagodatnyi, V.; Metelytsia, L. Imidazolium ionic liquids as potential anti-candida inhibitors: QSAR modeling and experimental studies. Curr. Drug Discov. Technol., 2016, 13(2), 109-119.
[http://dx.doi.org/10.2174/1570163813666160510122201]
[13]
Hodyna, D.; Kovalishyn, V.; Rogalsky, S.; Blagodatnyi, V.; Petko, K.; Metelytsia, L. Antibacterial activity of imidazolium-based ionic liquids investigated by QSAR modeling and experimental studies. Chem. Biol. Drug Des., 2016, 88(3), 422-433.
[http://dx.doi.org/10.1111/cbdd.12770]
[14]
Prasad, K.K.; Toraskar, M.P.; Kadam, V.J. N-myristoyltransferase: A novel target. Mini Rev. Med. Chem., 2008, 8(2), 142-149.
[http://dx.doi.org/10.2174/138955708783498159]
[15]
Zhao, C.; Ma, S. Recent advances in the discovery of N-myristoyltransferase inhibitors. ChemMedChem, 2014, 9(11), 2425-2437.
[http://dx.doi.org/10.1002/cmdc.201402174]
[16]
Selvakumar, P.; Lakshmikuttyamma, A.; Shrivastav, A.; Das, S.; Dimmock, J.; Sharma, R. Potential role of N-myristoyltransferase in cancer. Prog. Lipid Res., 2007, 46(1), 1-36.
[http://dx.doi.org/10.1016/j.plipres.2006.05.002]
[17]
Li, T.; Jing, C.; Gao, K.; Yue, W.; Li, S. Cytotoxicity of 1-dodecyl-3-methylimidazolium bromide on HepG2 cells. Genet. Mol. Res., 2015, 14(4), 13342-13348.
[http://dx.doi.org/10.4238/2015.October.26.31]
[18]
Malhotra, S.V.; Kumar, V. A profile of the in vitro anti-tumor activity of imidazolium-based ionic liquids. Bioorg. Med. Chem. Lett., 2010, 20(2), 581-585.
[http://dx.doi.org/10.1016/j.bmcl.2009.11.085]
[19]
Garcia, M.T.; Ribosa, I.; Perez, L.; Manresa, A.; Comelles, F. Aggregation behaviour and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution. Langmuir, 2013, 29, 2536-2545.
[http://dx.doi.org/10.1021/la304752e]
[20]
Garcia, M.T.; Ribosa, I.; Perez, L.; Manresa, A.; Comelles, F. Self assembly and antimicrobial activity of long-chain amide functionalized ionic liquids in aqueous solution. Coll. Surf. B., 2014, 123, 318-325.
[http://dx.doi.org/10.1016/j.colsurfb.2014.09.033]
[21]
Dzyuba, S.V.; Bartsch, R.A. Efficient synthesis of 1-alkyl(aralkyl)-3-methyl(ethyl)imidazolium halides: Precursors for room-temperature ionic liquids. J. Heterocycl. Chem., 2001, 38, 265-268.
[http://dx.doi.org/10.1002/jhet.5570380139]
[22]
Bauer, A.W.; Kirby, W.M.; Sherris, J.C.; Turck, M. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Pathol., 1966, 45, 493-496.
[http://dx.doi.org/10.1093/ajcp/45.4_ts.493]
[23]
Semenyuta, I.; Kovalishyn, V.; Tanchuk, V.; Pilyo, S.; Zyabrev, V.; Blagodatnyy, V.; Trokhimenko, O.; Brovarets, V.; Metelytsia, L. 1,3-Oxazole derivatives as potential anticancer agents: Computer modeling and experimental study. Comput. Biol. Chem., 2016, 65, 8-15.
[http://dx.doi.org/10.1016/j.compbiolchem.2016.09.012]
[24]
Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belew, R.K.; Goodsell, D.S.; Olson, A.J. Autodock4 and AutoDockTools4: Automated docking with selective receptor flexiblity. J. Comput. Chem., 2009, 16, 2785-2791.
[http://dx.doi.org/10.1002/jcc.21256]
[25]
http://www.rcsb.org/structure/1IYL [Accessed May, 2018].
[26]
Stewart, J. MOPAC Stewart Computational Chemistry, HTTP://OpenMOPAC.net [Accessed May, 2018].
[27]

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