The anti-tumor effects of imidazolium salts on oral squamous cell carcinoma

Paloma Santos de Campos, Luiza Deitos Menti, Luise Pazutti, Natália Ângela Bortoli, Leonildo Alves Ferreira, Juanita Lizele van Wyk, James Darkwa, Henri Stephan Schrekker, Marcelo Lazzaron Lamers

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


Background: Imidazolium salts (IS), ionic derivatives of neutral imidazoles, have properties that can be adjusted by structural modifications to their cations and anions, which makes this particular class of compounds a promising option for developing biologically active compounds. The anti-tumor effects of the IS 1-n-butyl-3-methylimidazolium chloride (C4MImCl), 1-n-decyl-3-methylimidazolium chloride (C10MImCl), 1-n-hexadecyl-3-methylimidazolium chloride (C16MImCl), 1-n-hexadecyl-2,3-dimethylimidazolium chloride (C16M2ImCl), 1-n-octadecyl-3-methylimidazolium chloride (C18MImCl), 1-n-hexadecyl-3-methylimidazolium methanesulfonate (C16MImMeS), and 1-n-hexadecyl-2,3- dimethylimidazolium methanesulfonate (C16M2ImMeS) on oral squamous cell carcinoma (OSCC) have been studied here. Methods: Oral squamous cell carcinoma cells (CAL27) were incubated with increasing IS doses and then submitted to proliferation (2D), cell death (2D) and spheroid assay (3D). Results: The IS anti-tumor effect was dependent on both its N-alkyl chain length and anion, whereby C16MImCl proved to be more effective in combination for inhibiting cell proliferation and cell-cell adhesion, outperforming the methylated C16M2ImCl derivative and, most importantly, the gold standard—cisplatin. In addition, C16MImCl had little effect on keratinocytes and more pronounced effects on more aggressive tumor cells. It also exhibited similar effects on inducing cell death when compared to Cisplatin. This compound spread to a greater area of the tumor sphere and produced an enhanced number of apoptotic and necrotic cells in the tumor cell line, demonstrating only a small rise in the healthy cells. Conclusion: These data indicate that the effect of C16MlmCl on OSCC is promising, as it is selective for cancer cells.

Original languageEnglish
Pages (from-to)470-477
Number of pages8
JournalJournal of Oral Pathology and Medicine
Issue number5
Publication statusPublished - May 2021


  • apoptosis
  • ionic liquids
  • oral cancer
  • spheroids

ASJC Scopus subject areas

  • Pathology and Forensic Medicine
  • Oral Surgery
  • Otorhinolaryngology
  • Cancer Research
  • Periodontics


Dive into the research topics of 'The anti-tumor effects of imidazolium salts on oral squamous cell carcinoma'. Together they form a unique fingerprint.

Cite this