Date of Graduation

Summer 2015

Document Type

Honors Research Project

Degree Name

Bachelor of Science

Major

Chemistry

Research Sponsor

Wiley J. Youngs, PhD

First Reader

Leah P. Shriver, PhD

Second Reader

Kim C. Calvo, PhD

Abstract

Several aldehydes (butanal, pentanal, hexanal, 4-hydroxybenzaldehyde) were reacted with 1,3-bis(naphthalen-2-ylmethyl)-imidazolium bromide (1) to produce novel C2 substituted imidazolium salts for the potential use against non-small cell lung cancer in humans. Compounds 2-(1-hydroxypentyl)-1,3-bis(naphthalen-2-ylmethyl)-imidazolium bromide (3) and 2-(1-hydroxyhexyl)-1,3-bis(naphthalen-2-ylmethyl)-imidazolium bromide (5) were successfully synthesized with structures supported by NMR and mass spectrometry. Characterization by 1H NMR showed evidence of 1 in both compounds. The tumor cell growth inhibition of 3 against non-small cell lung cancer lines NCI-A549, NCI-H460, HCC827, and NCI-H1975 was tested and found to be comparable to cisplatin as measured by MTT assay. Compounds were compared by their IC50 values against a panel of human cancer cell lines. The IC50 values for 3 were: 9 μM for A549 cells, 7 μM for H460 cells, 5 μM for HCC827 cells, and 3 μM for H1975 cells. Cisplatin had IC50 values in the range of 3-8 μM for these cell types, indicating that our compound had similar efficiency to a current chemotherapeutic agent. Similar IC50 values for 1 in the literature suggest C2 substituents may not significantly affect tumor cell growth inhibition.1 This may allow for different functional groups to be substituted at the C2 position in order to optimize properties such as water solubility and toxicity while not hindering therapeutic benefits.

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