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

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

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 eff...

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Published in:Journal of oral pathology & medicine Vol. 50; no. 5; pp. 470 - 477
Main Authors: Campos, Paloma Santos, Menti, Luiza Deitos, Pazutti, Luise, Bortoli, Natália Ângela, Ferreira, Leonildo Alves, Wyk, Juanita Lizele, Darkwa, James, Schrekker, Henri Stephan, Lamers, Marcelo Lazzaron
Format: Journal Article
Language:English
Published: Denmark Wiley Subscription Services, Inc 01-05-2021
Subjects:
Anions
Apoptosis
Bioactive compounds
Biological activity
Carcinoma, Squamous Cell - drug therapy
Cations
Cell adhesion
Cell death
Cell proliferation
Chloride
Chlorides
Cisplatin
Dentistry
Head and Neck Neoplasms
Humans
Imidazole
ionic liquids
Keratinocytes
Mouth Neoplasms - drug therapy
Oral cancer
Oral squamous cell carcinoma
Salts
spheroids
Squamous cell carcinoma
Squamous Cell Carcinoma of Head and Neck
Tumor cell lines
Tumor cells
apoptosis
ionic liquids
spheroids
oral cancer
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Summary: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.
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ISSN:0904-2512
1600-0714
DOI:10.1111/jop.13146