Anticancer and antimicrobial properties of imidazolium based ionic liquids with salicylate anion

Abstract

Ionic liquids (ILs) are well known for their physicochemical properties that recommend them for many purposes. However, many ILs are not environmentally friendly. Bearing these facts in mind, a series of imidazoliumand salicylate-based ILs with low general toxicity were designed and their pharmacological potential studied. Herein, their antiproliferative effect against human cancer cell lines and antimicrobial activity on selected Gram-positive and Gram-negative bacteria and Candida strains are presented. ILs with 1-butyl--3-methylimidazolium or imidazolium cation (IL 1 and compound 5), with the lowest dipole moments and highest lipophilicity, exerted highest cytotoxicity against colon and/or lung cancer cells, manifesting high selectivity to the normal cells. The most non-polar IL with the 1-butyl-3-methylimidazolium cation expressed the strongest anticancer potential, but it was also toxic against normal cells, although its cytotoxicity was less than the cytotoxic effect of commercially used chemotherapeutic agents. The same compounds, IL 1 and compound 5, expressed modest effect on the bacterial strain that causes serious lung diseases and pulmonary infections (Staphylococcus aureus) or which are included in colon cancer formation (Esherichia coli and Enterococcus faecalis). Salicylate itself was toxic against lung cancer cell line A549 and affected some Candida strains.

In Vitro Anticancer and Antivirus Activities of Cyano- and Bis(Trifluoromethylsulfonyl)imide-Based Ionic Liquids

“…Additionally, one can note based on Wang et al results that the structure of the cation (ammonium, pyridinium, or imidazolium) with a similar number of -CH 2 - groups attached to nitrogen does not influence toxicity toward HeLa cells significantly, which is consistent with our previous observation for NHDF cell lines even if aliphatic quaternary ammonium ILs have been reported to be less hazardous in many other cytotoxicity studies . However, importantly, not only does the elongation of the alkyl chain length exert influence but also cation/anion functionalization may play a role, as clearly seen in the results presented by Jovanovic-Santa et al or Ferraz et al (see Table S1). Ferraz et al showed that ILs with hydroxyl-functionalized cations ([C 2 OHC 1 im] + ) are much more cytotoxic against HepG2 cells than ILs with nonfunctionalized cations ([C 2 C 1 im] + ).…”

“…These results stay in contrast with the conclusion presented in a very recently published review that polar substituents reduce toxicity . On the other hand, cytotoxicity data toward HeLa and A549 cell lines (see again Table S1) reported by Jovanovic-Santa et al are consistent with this rule. The results are different for each cell line.…”

The Impact of [C16Pyr][Amp] on the Aggressiveness in Breast and Prostate Cancer Cell Lines

“…The third generation of ILs is a fusion of physical, chemical, and biological properties and provides improved water solubility and permeability, low toxicity, and better bioavailability [ 12 , 14 ]. The promising anticancer properties of these agents toward malignant cell lines of several tumor models have already been described [ 12 , 17 , 43 , 44 , 45 , 46 ]. The combination of ILs with chemotherapeutic agents has also been studied, with promising results in terms of reducing chemotherapy toxicity [ 47 , 48 , 49 ].…”

Density Functional Method Study on the Cooperativity of Intermolecular H-bonding and π-π+ Stacking Interactions in Thymine-[Cnmim]Br (n = 2, 4, 6, 8, 10) Microhydrates

“…Ionic liquids (ILs) have been widely used in many fields due to their large variety and unique properties, which are a class of liquid compounds consisting of a bulky organic cation and relatively small anion and provided with excellent properties such as very low vapor pressure, nonvolatility, nonflammability, high thermal and electrochemical stability, and have been touted as greener alternatives to the conventional organic solvents [ 1 , 2 , 3 ]. However, the ILs create hazards to the natural environment and various biological levels of organization [ 4 , 5 , 6 ], which are indicated by the inhibition of enzymatic activity (e.g., acetylcholinesterase [ 7 , 8 , 9 ], the antioxidant enzyme of the animal liver [ 10 , 11 , 12 ]), the antimicrobial activity (e.g., Vibrio fischeri [ 13 ], Escherichia coli [ 14 , 15 ]), the phytotoxicity to aqueous and terrestrial plants [ 16 , 17 ] (e.g., Lemna minor [ 18 ], Ulva lactuca [ 19 ], Hordeum vulgare [ 20 , 21 ]), and the toxicity to invertebrates (e.g., Daphnia magna [ 13 , 22 , 23 ], Caenorhabditis elegans [ 24 ]) as well as vertebrates (e.g., Rana nigromaculata [ 25 ], Danio rerio [ 26 ], rat pheochromocytoma PC12 [ 27 , 28 ], even to human cell lines including human colon carcinoma CaCo-2 and HT-29 [ 29 ], IPC-81 [ 30 ], human cervical cancer HeLa [ 31 ], human lung carcinoma A549 [ 32 ], and so on. Furthermore, it was found that all the tested systems have shown distinctive susceptibilities by ILs at different levels.…”