Synthesis, characterization, and biological activity of monoand bisimidazolium salts

N,N'-substituted imidazolium salts are incredibly versatile compounds that have found applications across a variety of fields. They can be chemically modified through straightforward procedures, allowing for the synthesis of imidazolium salts with vastly differing properties. This dissertation explores the potential biological applications of mono- and bisimidazolium salts as new chemotherapeutic agents for the treatment of non-small cell lung carcinomas (NSCLC) and as chemical exfoliating agents for the treatment of recurrent urinary tract infections.;Chapter I of this dissertation reviews the basic nomenclature and structure of imidazolium salts. Past and current research toward the biological applications of imidazolium salts and their use as precursors to N-heterocyclic carbene complexes is summarized.;Chapter II explores the activity of a series of monoimidazolium salts against a panel of NSCLC cell lines. The treatment of lung cancer remains frustratingly difficult, and lung cancer maintains one of the highest mortality rates among cancer types. Current treatment options are only marginally effective and are plagued by severe side effect profiles or eventual resistance of the cancers to treatment. Therefore, there is a pressing need to develop new chemotherapeutic agents for the treatment of lung cancer. In this chapter, the in vitro antiproliferative activity of monoimidazolium salts against several NSCLC lines are determined by the MTT cell viability assay. The degree of apoptotic cell death is investigated by the use of the Annexin V-FITC/PI apoptosis detection assay, and possible imidazolium salt interactions with DNA are probed by a fluorescent intercalator displacement assay.;Chapter III focuses on the synthesis of a series of bisimidazolium salts designed to mimic the activity of the bisintercalating agent echinomycin. The in vitro antiproliferative activity of these bisimidazolium salts and their potential interactions with DNA were determined by the appropriate assays mentioned above.;Chapter IV assesses the ability of monosubstituted imidazolium salts to serve as novel small-molecule urinary bladder exfoliants. The primary agent currently used in preclinical studies of various urological conditions, the peptide protamine sulfate, has limited translational potential to human studies due to concerns including systemic adverse reactions and bladder tissue injury. The effects of imidazolium salts on bladder epithelial cells are determined in both in vitro and in vivo models by a variety of methods. Their potential for use in the eradication of chronically resident Escherichia coli. .