Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Novel Fluorinated Imidazolium Ionic Liquids: Eco-friendly, Facile and Efficient Construction, Characterization, in vitro Anticancer Activity, Toxicity and in silico Analysis
Corresponding Author(s) : Mouslim Messali
Asian Journal of Chemistry,
Vol. 32 No. 3 (2020): Vol 32 Issue 3
Abstract
An efficient and facile synthesis of novel fluorinated imidazolium-tagged ionic liquids under microwave irradiation is described. Novel prepared ionic liquids was identified and confirmed by spectroscopic and elemental analysis. Synthesized ionic liquids (1-12) was explored for their antiproliferative inhibition potency against three selected human cancer cell lines (MCF-7, HepG-2 and CACO2). Screening results have revealed that some tested ionic liquids exhibited promising activity compared with standard drugs, especially compounds 5 and 6 which consistently produced low IC50 values. Preliminary structure activity relationship (SAR) studies have been performed to identify the relation between molecular structure and activity. in silico Analysis of ionic liquids was carried out based on ADME, Lipinski rule, drug likeness, toxicity profiles and other physico-chemical properties. All compounds were safe in toxicity profile and computed LD50 values were in accepted range (2.55-2.89 mol/kg). in silico Results have shown that Lipinski rule of five was in accept range, except compound 1 and 2.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M.J. Earle and K.R. Seddon, Pure Appl. Chem., 72, 1391 (2000); https://doi.org/10.1351/pac200072071391
- H. Zhao, Y. Zhang and Z. Yuan, Aldrichim Acta, 454, 75 (2002); https://doi.org/10.1016/S0003-2670(01)01543-4
- F. El-Hajjaji, M. Messali, M.V.M. de Yuso, E. Rodríguez-Castellón, S. Almutairi, T.J. Bandosz and M. Algarra, J. Colloid Interface Sci., 541, 418 (2019); https://doi.org/10.1016/j.jcis.2019.01.113
- F. El-Hajjaji, M. Messali, A. Aljuhani, M.R. Aouad, B. Hammouti, M.E. Belghiti, D.S. Chauhan and M.A. Quraishi, J. Mol. Liq., 249, 997 (2018); https://doi.org/10.1016/j.molliq.2017.11.111
- F. Endres, ChemPhysChem, 3, 144 (2002); https://doi.org/10.1002/1439-7641(20020215)3:2<144::AIDCPHC144>3.0.CO;2-#
- A.F. Al-Ghamdi, M. Messali and S.A. Ahmed, J. Mater. Environ. Sci., 2, 215 (2011).
- T. Welton, Coord. Chem. Rev., 248, 2459 (2004); https://doi.org/10.1016/j.ccr.2004.04.015
- D.R. Macfarlane, M. Forsyth, P.C. Howlett, J.M. Pringle, J. Sun, G. Annat, W. Neil and E. Izgorodina, Acc. Chem. Res., 40, 1165 (2007); https://doi.org/10.1021/ar7000952
- P. Kubisa, Prog. Polym. Sci., 29, 3 (2004); https://doi.org/10.1016/j.progpolymsci.2003.10.002
- H. Qiu, S. Jiang, X. Liu and L.J. Zhao, J. Chromatogr. A, 1116, 46 (2006); https://doi.org/10.1016/j.chroma.2006.03.016
- R. Kawano, H. Matsui, C. Matsuyama, A. Sato, M.A.B.H. Susan, N. Tanabe and M. Watanabe, J. Photochem. Photobiol. Chem., 164, 87 (2004); https://doi.org/10.1016/j.jphotochem.2003.12.019
- A.H. Albalawi, W.S. El-Sayed, A. Aljuhani, S.M. Almutairi, N. Rezki, M.R. Aouad and M. Messali, Molecules, 23, 1727 (2018); https://doi.org/10.3390/molecules23071727
- M. Messali, M.R. Aouad, A.A. Ali, N. Rezki, T. Ben Hadda and B. Hammouti, Med. Chem. Res., 24, 1387 (2015); https://doi.org/10.1007/s00044-014-1211-x
- M. Messali, Molecules, 20, 14936 (2015); https://doi.org/10.3390/molecules200814936
- M. Messali, Acta Pharm., 65, 253 (2015); https://doi.org/10.1515/acph-2015-0028
- M. Messali, Arab. J. Chem., 9, S564 (2016); https://doi.org/10.1016/j.arabjc.2011.06.030
- M.I. Atta-Ur-Rahman and W.J. Thomsen, Bioassay Technique for Drug Development, Harwood Academic Publishers (2001).
- D.Y. Alawadi, H.A. Saadeh, H. Kaur, K. Goyal, R. Sehgal, T.B. Hadda, N.A. ElSawy and M.S. Mubarak, Med. Chem. Res., 24, 1196 (2014); https://doi.org/10.1007/s00044-014
- M. Messali, M. Aouad, W. El-Sayed, A. Al-Sheikh Ali, T.B. Hadda and B. Hammouti, Molecules, 19, 11741 (2014); https://doi.org/10.3390/molecules190811741
- M.H. Youssoufi, P.K. Sahu, P.K. Sahu, D.D. Agarwal, M. Ahmad, M. Messali, S. Lahsasni and T.B. Hadda, Med. Chem. Res., 24, 2381 (2015); https://doi.org/10.1007/s00044-014-1297-1
- B. Bennani, A. Kerbal, B.F. Baba, M. Daoudi, I. Warad, M. Aljofan, A.M. Alafeefy, V. Masand and T.B. Hadda, Med. Chem. Res., 22, 4798 (2013); https://doi.org/10.1007/s00044-012-0392-4
- D.E. Clark, J. Pharm. Sci., 88, 815 (1999); https://doi.org/10.1021/js980402t
- S. Singh and J. Singh, Med. Res. Rev., 13, 569 (1993); https://doi.org/10.1002/med.2610130504
References
M.J. Earle and K.R. Seddon, Pure Appl. Chem., 72, 1391 (2000); https://doi.org/10.1351/pac200072071391
H. Zhao, Y. Zhang and Z. Yuan, Aldrichim Acta, 454, 75 (2002); https://doi.org/10.1016/S0003-2670(01)01543-4
F. El-Hajjaji, M. Messali, M.V.M. de Yuso, E. Rodríguez-Castellón, S. Almutairi, T.J. Bandosz and M. Algarra, J. Colloid Interface Sci., 541, 418 (2019); https://doi.org/10.1016/j.jcis.2019.01.113
F. El-Hajjaji, M. Messali, A. Aljuhani, M.R. Aouad, B. Hammouti, M.E. Belghiti, D.S. Chauhan and M.A. Quraishi, J. Mol. Liq., 249, 997 (2018); https://doi.org/10.1016/j.molliq.2017.11.111
F. Endres, ChemPhysChem, 3, 144 (2002); https://doi.org/10.1002/1439-7641(20020215)3:2<144::AIDCPHC144>3.0.CO;2-#
A.F. Al-Ghamdi, M. Messali and S.A. Ahmed, J. Mater. Environ. Sci., 2, 215 (2011).
T. Welton, Coord. Chem. Rev., 248, 2459 (2004); https://doi.org/10.1016/j.ccr.2004.04.015
D.R. Macfarlane, M. Forsyth, P.C. Howlett, J.M. Pringle, J. Sun, G. Annat, W. Neil and E. Izgorodina, Acc. Chem. Res., 40, 1165 (2007); https://doi.org/10.1021/ar7000952
P. Kubisa, Prog. Polym. Sci., 29, 3 (2004); https://doi.org/10.1016/j.progpolymsci.2003.10.002
H. Qiu, S. Jiang, X. Liu and L.J. Zhao, J. Chromatogr. A, 1116, 46 (2006); https://doi.org/10.1016/j.chroma.2006.03.016
R. Kawano, H. Matsui, C. Matsuyama, A. Sato, M.A.B.H. Susan, N. Tanabe and M. Watanabe, J. Photochem. Photobiol. Chem., 164, 87 (2004); https://doi.org/10.1016/j.jphotochem.2003.12.019
A.H. Albalawi, W.S. El-Sayed, A. Aljuhani, S.M. Almutairi, N. Rezki, M.R. Aouad and M. Messali, Molecules, 23, 1727 (2018); https://doi.org/10.3390/molecules23071727
M. Messali, M.R. Aouad, A.A. Ali, N. Rezki, T. Ben Hadda and B. Hammouti, Med. Chem. Res., 24, 1387 (2015); https://doi.org/10.1007/s00044-014-1211-x
M. Messali, Molecules, 20, 14936 (2015); https://doi.org/10.3390/molecules200814936
M. Messali, Acta Pharm., 65, 253 (2015); https://doi.org/10.1515/acph-2015-0028
M. Messali, Arab. J. Chem., 9, S564 (2016); https://doi.org/10.1016/j.arabjc.2011.06.030
M.I. Atta-Ur-Rahman and W.J. Thomsen, Bioassay Technique for Drug Development, Harwood Academic Publishers (2001).
D.Y. Alawadi, H.A. Saadeh, H. Kaur, K. Goyal, R. Sehgal, T.B. Hadda, N.A. ElSawy and M.S. Mubarak, Med. Chem. Res., 24, 1196 (2014); https://doi.org/10.1007/s00044-014
M. Messali, M. Aouad, W. El-Sayed, A. Al-Sheikh Ali, T.B. Hadda and B. Hammouti, Molecules, 19, 11741 (2014); https://doi.org/10.3390/molecules190811741
M.H. Youssoufi, P.K. Sahu, P.K. Sahu, D.D. Agarwal, M. Ahmad, M. Messali, S. Lahsasni and T.B. Hadda, Med. Chem. Res., 24, 2381 (2015); https://doi.org/10.1007/s00044-014-1297-1
B. Bennani, A. Kerbal, B.F. Baba, M. Daoudi, I. Warad, M. Aljofan, A.M. Alafeefy, V. Masand and T.B. Hadda, Med. Chem. Res., 22, 4798 (2013); https://doi.org/10.1007/s00044-012-0392-4
D.E. Clark, J. Pharm. Sci., 88, 815 (1999); https://doi.org/10.1021/js980402t
S. Singh and J. Singh, Med. Res. Rev., 13, 569 (1993); https://doi.org/10.1002/med.2610130504