Mutagenicity of 1-Ethyl-2,4,5-triphenyl-1H-imidazole and Six Derivatives in Salmonella typhimurium

Year 2012, Volume: 25 Issue: 1, 1 - 8, 24.01.2012

Ferhan Korkmaz , Ferhan Korkmaz , Ayse Mercangoz

Abstract

Newly synthesized 1-Ethyl-2,4,5-triphenyl-1H-imidazole and its six derivatives were tested by Ames assay. In order to reveal the mutagenic activities of the compounds, two different mutant strains of Salmonella typhimurium (TA98 and TA100) were used in an Ames assay with/without S9 microsomal fraction from rat liver. It was found that the compounds have no mutagenic activities.

Keywords

1-Ethyl-2, 4, 5-triphenyl-1H-imidazole, Ames/Salmonella/Microsome assay, mutagenicity, predrug.

References

• Shirai, T., Ogawa, K., Takahashi, S., “Carcinogenic effect of mixtures of chemicals”, J. Toxicol. Pathol., 19: 1-13 (2006).
• Mortelmans, K., Zeiger, E., “The Ames/Salmonella/microsome mutagenicity assay”, Mutat. Res., 455: 29-60 (2000).
• Kho, R., Hodges, J.A., Hansen, M.R., Villar, H.O., “Ring systems in mutagenicty databases”, J. Med. Chem., 48: 6671-6678 (2005).
• Nii, H., Tsutsui, M., Kondo, J., Toyohira, Y., Ueno, S., Yanagihara, N., “Copper, zinc-superoxide dismutase enhances the mutagenicity in Salmonella typhimurium mEthyldipyrido[1,2-a:3’,2’-d] imidazole”, Mutat. Res., 653: 14-22 (2008). 2-amino-6
• Alaejos, M.S., Gonzalez, V., Afonso, A.M., “Exposure to heterocyclic aromatic amines from the consumption of cooked red meat and its effect on human cancer risk: A review”, Food Addit. Contam., 25(1): 2-24 (2007). [6] Inami, K., Okazawa, M., Mochizuki, M., “Mutagenicity of aromatic amines and amides with chemical models for cytochrome P450 in Ames assay”, Toxicol. in Vitro, 23: 986-991 (2009).
• Sarrif, A.M., Krahn, D.F., Donovan, S.M., O’neil R.M., “Evulation of hexamEthylphosphoramide for gene mutations in Salmonella typhimurium using plate incorporation, preincorporation and suspension assays”, Mutat. Res., 380: 167-177 (1997).
• Docherty, K.M., Habbeler, S.Z., Kulpa, C.F., Jr., “An assesment of ionic liquid mutagenicity using the Ames test”, Green Chem., 8: 560-567 (2006).
• Guzman, A., Garcia, C., Marin, A.P., Proudlock, R.J., Fernandez de Henestora, A.R., Ruiz, M.T., Tortajada, A., Lloyd, M., Marcos, R. “Evaluation of the phenyltetrahydropyridinyl butylazole-derived sigma- receptor ligand drug candidates”, Mutat. Res-Gen. Tox. En., 653: 91-98 (2008). of three
• Maertens, R.M., Gagne, R.W., Douglas, G.R., Zhu, J., White, P.A., “Mutagenic and carcinogenic hazard of settled house dust II: Salmonella mutagenicity”, Environ. Sci. Technol., 42: 1754-1760 (2008).
• Lah, B., Zinko, B., Tisler, T., Marinsek-Logar, R., “Genotoxicity detection in drinking water by Ames test, Zimmermann test and Comet assay”, Acta Chim. Slov., 52: 341-348 (2005).
• Gisela de, A., Umbuzeiro, A., Deborah, A., Roubicek, A., Petra, S.S., MariaInes, Z., Sato, A., “The Salmonella mutagenicity assay in a surface water quality monitoring program based on a 20- year survey”, Mutat. Res., 491: 119–126 (2001).
• Wollin, K.M., Görlitz, B.D., “Comparison of genotoxicity of textile dyestuffs in Salmonella mutagenicity assay, in vitro Micronucleus assay, and single cell gel/Comet assay”, J. Environ. Pathol., Toxicol. Oncol., 23(4): 267-278 (2004).
• Pitts Jr, J.N., Grosjean, D., Michke, T.M., Simmon, V.F., Poole, D., “Mutagenic activity of airborne particulate organic pollutants”, Toxicol. Lett., 1(2): 65-70 (1977).
• Vargas, V.M.F., Guidobono, R.R., Henriques J.A.P., “Genotoxicity of plant ectracts”, Mem. Inst. Oswaldo Cruz, Rio de Janeiro, 86(2): 67-70 (1991).
• Reid, K.A., Maes, J., Maes, A., Staden, J.V., Kimpe, N. D., Mulholland, D.A., Verchaeve, L., “Evaluation of the mutagenic and antimutagenic effects of South African plants”, J. Ethnopharmacol., 106: 44–50 (2006).
• Mercangöz, A.,
• Korkmaz-Aydoğdu, F.,
• “Determination of mutagenic activities of four
• derivatives of tri(substituted) phenyl imidazole in
• Salmonella typhimurium using the Ames assay”,
• Anadolu Univ. J. Sci. Technol., 5(1): 123-128 (2004).
• Puratchikody, A., Doble, M., “Antinociceptive and antiinflammatory activities and QSAR studies on 2- substituted-4,5-diphenyl-1H-imidazoles”, Med. Chem., 15: 1083–1090 (2007). Bioorg.
• Pérez-Rivera, A.A., Hu, T., Aardema, M. J., Nash, J.F., “Evaluation of the genotoxicity of the imidazole antifungal climbazole: Comparison to published results for other azole compounds”, Mutat. Res.-Gen. Tox. En., 672: 27–39 (2009).
• Khan, M.S., Siddiqui, S.A., Siddiqui, M.S.R.A., Goswami, U., Srinivasan, K.V., Khan M.I., “Antibacterial Activity of Synthesized 2,4,5- Trisubstituted Imidazole Derivatives”, Chem. Biol. Drug Des., 72: 197–204 (2008).
• Hrelia, P., Fimognari, C., Maffei, F., Brighenti, B., Garuti, “Synthesis, metabolism and structure–mutagenicity relationships of novel 4-nitro-(imidazoles and pyrazoles) in Salmonella typhimurium”, Mutat. Res., 397: 293–301 (1998). G.,
• Crozet, M.D., Botta, C., Gasquet, M., Curti, C., Remusat, V., Hutter, S., Chapelle, O., Azas, N., Méo, M.D., Vanelle, P., “Lowering of 5- nitroimidazole’s mutagenicity: Towards optimal antiparasitic pharmacophore”, Eur. Journal of. Med. Chem., 44: 653-659 (2009).
• Gümüş, F., Algül, Ö., Gökçen, E., Eroğlu, H., Diril, N., Gür, S., Özkul A., “Synthesis, cytotoxic activity on MCF-7 cell line and mutagenic activity of platinum(II) benzimidazole ligands”, Eur. J. Med. Chem., 38: 473-480 (2003). with 2-substituted
• Dean, B.J., Brooks, T.M., Hodson-Walker, G., “Genetic toxicology testing of 41 industrial chemicals”, Mutat. Res., 153: 57–77 (1984).
• Garner, R.C., Miller, E.C., Miller, J.A., “Liver microsomal metabolism of lotoxin B1 to reactive derivative toxic to Salmonella typhimurium TA 1530”, Cancer Res., 32: 2058– 2066 (1972).
• Maron, D.M., Ames, B.N., “Revised method for the Salmonella mutagenicity test” Mut. Res., 113: 173- 215 (1983).
• Forster, R., Blowers, S.D., Cinelli, S., Marquart, H. , Westendorf J., “Mutagenicity testing of imidazole and related compounds”, Mutat. Res., 298: 71-79 (1992).
• Voogd., C.E., Der-Steel, J.J., Jacobs, J.J.J.A.A., “Mutagenic Comparison of the mutagenic action of several nitroimidazoles and some imidazoles”, Mutat. Res., 66: 207-221 (1979).
• nitroimidazoles. IV:
• OECD SIDS, “Imidazole” SIDS Init. Asses. Rep. for SIAM17, Arona, Italy, (2003).
• Josephy, P.D., Gruz, P., Nohmi, T., “Recent advances genotoxicity assays”, Mutat. Res., 386: 1-23 (1997). of bacterial
• Aydoğan, G., Kutlu, M., “Mutagenic activities of ten imidazole derivates in Salmonella typhimurium”, Biologia, Bratislava, Sec. Cell. Mol. Biol., 62(1): 6- 12, (2007).