A large library of hydrophobic imidazolium salts has been synthesized and characterized, and several of the compounds have displayed moderate to high antitumor activity against a variety of non-small cell lung cancer cell lines – NCI-H460, NCI-A549, NCI-H1975 and HCC827 – in vitro. The efficacy appears to be strongly related to the inclusion of aromatic, planar substituents in the N1 and N3 positions of the imidazole ring and the overall hydrophobic nature of the salts. Substiuents of this nature have included derivitzied naphthylmethyl and quinolylmethyl groups. The inhibitory concentration (IC50) values of these imidazolium salts, as determined by the MTT assay, fall in a clinically achievable range and are comparable to current cancer therapeutics, i.e. cisplatin. The imidazole molecule presents a template that can be modified by standard synthetic techniques, allowing the chemist to easily modify the properties of the imidazolium salts so as to probe structure-activity relationships or add beneficial solubilizing or targeting groups to the salts. We report the synthesis, characterization, and in vitro anticancer activity of select imidazolium salts from our library, demonstrating their potential as new therapeutic agents for the treatment of non-small cell lung cancers.

Synthesis, characterization, and in vitro anticancer activity of quinolylmethyl- and napthylmethyl-substituted imidazolium salts

249th National Meeting (2015)

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