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The imidazolium salt (IS) and silver carbene complex (SCC) studied in this report are 3-(pyridin-2-ylmethyl)-1-(quinolin-2-ylmethyl)imidazolium chloride (1) and 3-(pyridin-2-ylmethyl)-1-(quinolin-2-ylmethyl)imidazole – silver acetate complex (2). It was anticipated that the anti-proliferative activity of 1 and 2 would be similar to other characterized ISs while having increased solubility. The SCC (2) was synthesized in order to simulate the ligand-metal coordination similar to that of cisplatin.
The success of the synthetic processes of 1 and 2 were determined by 1H NMR (300 MHz) spectroscopy. In addition, 1 was also characterized by 1H NMR (500 MHz) and 13C NMR (500 MHz) spectroscopy and mass spectrometry. The anti-proliferative activity of 1 was determined via MTT assay.
2-(Chloromethyl)pyridine and 1-(quinolin-2-ylmethyl)imidazole were dissolved in acetonitrile and successfully combined under reflux conditions to form 1. However, 1 exhibited limited anti-proliferative activity; an IC50 value of greater than 30 μM was obtained for both NCI-H460 and A549 cell lines. Likewise, 1 and silver acetate were dissolved in methylene chloride and successfully combined under anaerobic conditions to form 2. Compound 2, like 1, exhibited hygroscopic behavior.
Because 1 lacks anti-proliferative activity, further research should be focused on substituent families that have greater structural similarity to the ISs previously determined, via research, to exhibit great activity.
Dr. Wiley J. Youngs
Dr. Edward A. Evans
Dr. Teresa J. Cutright
Molnar, Cari E., "Synthesis, Characterization and Anti-Proliferative Activity of an Imidazolium Salt and its Silver Carbene Complex: Utilization of Picolyl and Quinolylmethyl Substituents" (2015). Williams Honors College, Honors Research Projects. 117.