Synthesis and Characterization of Imidazolium Salt Derivatives for Anti-Tumor Activity

Author

Ryan W. Pearce, University of Akron Main CampusFollow

Date of Last Revision

2023-05-02 15:13:36

Major

Chemistry

Degree Name

Bachelor of Science

Date of Expected Graduation

Summer 2015

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.

Research Sponsor

Wiley J. Youngs, PhD

First Reader

Leah P. Shriver, PhD

Second Reader

Kim C. Calvo, PhD

Recommended Citation

Pearce, Ryan W., "Synthesis and Characterization of Imidazolium Salt Derivatives for Anti-Tumor Activity" (2015). Williams Honors College, Honors Research Projects. 214.
https://ideaexchange.uakron.edu/honors_research_projects/214