A Profile of the Biological Activity of Functionalized Benzimidazolium Ionic Liquids

DOI:

https://doi.org/10.37285/ijpsn.2020.13.5.9

Authors

  • Paul Metilda
  • P Jebha Starling

Abstract

Now-a-days, the pharmaceutical industries were facing many challenges that impose the need to develop innovative and effective therapies. Hence, the investigation of effective therapies for cancer is an actual goal of every pharmaceutical industries. Recently, Ionic Liquids (ILs) have been considered as potential target in scientific community because of their unique performance in various fields. Moreover, numerous combinations made between the cation and the anion, which can be tuned the physicochemical and biological properties of ILs. Especially, these ionic liquids play a vital role for designing new drugs and producing potent bioactivity. Herein we synthesized a series of benzimidazolium based ionic liquids with different functional groups and their structure was confirmed by FT-IR, 1H NMR, 13C NMR as well as High resolution Mass spectroscopy technique antimicrobial activity of ILs were screened by five bacterial and fungal strains which was measured in terms of zone of inhibition. All the compounds were found to be effective against all bacterial species and fungi Candida albicans. Moreover, the total antioxidant capacity of ILs has been evaluated by Phosphomolybdenum method. The report indicates that kojic acid functionalized ILs exhibited significant antioxidant activity. In addition, antitumor activity of these compounds has been analyzed using human ovarian cancer cell line SK-OV-3, human prostate cancer cell line DU-145 and human leukemia cancer cell line K-562. The data obtained from antitumour studies showed that an excellent activity of ester functionalized ionic liquid confirms that can be used as an anticancer agent. However, ester functionalized and kojic acid functionalized ILs possess biologically active against the tested strains

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Keywords:

Benzimidazolium based ionic liquids, Antimicrobial activity, Total antioxidant capacity, Antitumor activity, Kojic acid functionalized ionic liquids

Downloads

Published

2020-09-15

How to Cite

1.
Metilda P, Starling PJ. A Profile of the Biological Activity of Functionalized Benzimidazolium Ionic Liquids. Scopus Indexed [Internet]. 2020 Sep. 15 [cited 2024 Dec. 21];13(5):5120-3. Available from: https://ijpsnonline.com/index.php/ijpsn/article/view/1119

Issue

Section

Research Articles

References

Arjmand F, Mohani B and Ahmad S (2005). Synthesis, antibacterial, antifungal activity and interaction of CT-DNA with a new benzimidazole derived Cu (II) complex. Eur J Med Chem 40(11): 1103-1110.

Berman J, Halm K, Adkison K and Shaffer J (1997). Simultaneous pharmacokinetic screening of a mixture of compounds in the dog using API LC/MS/MS analysis for increased throughput. J Med Chem 40(6): 827-829.

Bicaz K and Rogers RD (2010). Confused ionic liquid ions—a ‘‘liquification’’ and dosage strategy for pharmaceutically active salts. Chem Commun. 46(8): 1215-1217.

Chauhan V, Singh S and Bhadani A (2012). Synthesis, characterization and surface properties of long chain beta-hydroxy-gamma-alkyloxy-Nmethylimidazolium surfactants. Colloids Surf A 395: 1-9.

Davis JH (2004). Task-specific ionic liquids. Chem Lett 33(9): 1072-1077.

Fang S, Jin Y, Yang L, Hirano S, Tachibana K and Katayama S (2011). Functionalized ionic liquids based on quaternary ammonium cations with three or four ether groups as new electrolytes for lithium battery. Electrochim Acta 56(12): 4663-4671.

Fei Z, Geldbach TJ, Zhao D and Dyson PJ (2006). From dysfunction to bis-function: On the design and applications of functionalised ionic liquids. Chem Eur J 12(8): 2122-2130.

Ferraz R, Costa-Rodrigues J, Fernandes M.H, Santos MM, Marrucho IM, Rebelo LP, Prudêncio C, Noronha JP, Petrovski Z and Branco LC (2015). Antitumor Activity of Ionic Liquids Based on Ampicillin. Chem Med Chem 10(9): 1480-1483.

Garcia MT, Ribosa I, Perez L, Manresa A and Comelles F (2013). Aggregation behav-ior and antimicrobial activity of ester-functionalized imidazolium- andpyridinium-based ionic liquids in aqueous solution. Langmuir 29(8): 2536-2545.

Hajiopur AR and Rafiee F (2015). Recent progress in ionic liquids and their applications in organic synthesis. Org Prep Proced Int 47(4): 249-308.

Hough WL, Smiglak M, Rodriguez H, Swatloski RP, Spear SK, Daly DT, Pernak J, G risel JE, Carliss RD, Soutullo MD, Davis JH and Rogers RD (2007). The third evolution of ionic liquids: active pharmaceutical ingredients. New J Chem 31(8): 1429-1436.

Karna M, Lahtinen M and Valkonen J (2009). Preparation and characterization of new low melting ammonium-based ionic liquids with ether functionality. J Mol Struct 922(1-3): 64-76.

Kumar RA, Papaıconomou N, Lee J-M, Salminen J, Clark DS and Prausnitz JM (2009). In vitro cytotoxicities of ionic liquids: effect of cation rings, functionalgroups, and anions. Environ Toxicol 24(4): 388-395.

Kumar S, Kumar D, Manjusha D, Saroha K, Singh N and Vashishta B (2008). Antioxidant and free radical scavenging potential of Citrullus colocynthis (L.) Schrad. methanolic fruit extract. Acta Pharm 58(2): 215-220.

Kumar V and Malhotra SV (2010a). Antitumor Activity of Ionic Liquids on Human Tumor Cell Lines. Pharmaceuticals 8: 91-102.

Li QL, Huang J, Wang Q, Jiang N, Xia CQ, Lin HH, Wua J and Yu XQ (2006). Monometallic complexes of 1,4,7,10-tetaazacyclo-dodecane containing an imidazolium side: Synthesis, characterization, and their interaction with plasmid DNA. Bio org Med Chem 14(12): 4151-4157.

Li X, Ma J and Wang J (2015). Cytotoxicity, oxidative stress, and apoptosis in HepG2 cells induced by ionic liquid 1-methyl-3-octylimidazolium bromide. Ecotoxicol Environ Saf 120: 342–348.

Malhotra SV and Kumar V (2010b). A profile of the in vitro anti-tumor activity of imidazolium-based ionic liquids. Bioorg Med Chem Lett 20(2): 581-585.

Marrucho IM, Branco LC and Rebelo LPN. Ionic liquids in pharmaceutical applications. Annu Rev Chem Biomol Eng 5: 527-546.

Monteiro MJ, Camilo FF, Ribeiro MCC and Torresi RM (2010). Ether-bond-containing ionic liquids and the relevance of the ether bond position to transport properties. J Phys Chem B 114(39): 12488-12494.

Morrissey S, Pegot B, Coleman D, Garcia MT, Ferguson D Quilty B and Gathergood N (2009). Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: a step towards greener ionic liquids. Green Chem 11(4): 475-483.

Pernak J, Kalewska J, Ksycifiska H and Cybulski J (2001). Synthesis and anti-microbial activities of some pyridinium saltr with alkoxymethyl hydrophobic group. Eur J Med Chem 36 (11-12): 899-907.

Pernak J, Sobaszkiewicz K and Foksowicz-Flaczyk J (2004). Ionic liquids with symmetrical dialkoxymethyl-substituted imidazolium cations. Chem Eur J 10(14): 3479-3485.

Plechkova NV and Seddon KR (2008). Applications of ionic liquids in the chemical industry. Chem Soc Rev 37: 123-150.

Sanderson CJ and Wilson DV (1971). A simple method for coupling proteins to insoluble polysaccharides. Immunology 20(6): 1061-1065.

Sarilmiser K and Oner ET (2014). Investigation of anti-cancer activity of linear and aldehyde-activated levan from Halomonas smyrnensis AAD6T. Biochem Eng Journal 92(15): 28-34.

Shamshina JL, Kelley SP, Gurau G and Rogers RD (2015). Chemistry: Develop Ionic Liquid Drugs. Nature 528(7581): 188-189.

Sreejayan N and Rao MN (1997). Nitric oxide scavenging by curcuminoids. J Pharm Pharmacol 49(1): 105-107.

Sroka Z and Cisowski W (2003). Hydrogen peroxide scavenging, antioxidant and antiradical activity of some phenolic acids. Food Chem Toxicol 41(6): 753-758.

Wang X Q, Yu L, Jiao J J, Zhang HN, Wang R and Chen H (2012). Aggregation behavior of COOH-functionalized imidazolium-based surface active ionic liquids in aqueous solution. J Mol Liq 173: 103-107.

Welton T (1999). Room-temperature ionic liquids: Solvents for synthesis and catalysis. Chem Rev 99(8): 2071-2084.

Yansong Z and Tobias B (2015). Application of Ionic Liquids in Solar Cells and Batteries: A Review. Curr Org Chem 19(11): 556-566.

Zhou C, Wang F, Chen H, Li M, Qiao F, Liu Z, Hou Y, Wu C, Fan Y, Liu L, Wang S and Wang Y (2016). Selective Antimicrobial Activities and Action Mechanism of Micelles Self-Assembled by Cationic Oligomeric Surfactants. App Mate & Inter 8(6): 4242-4249.