Efficient synthesis of novel 1,10 phenanthroline-substituted imidazolium salts: Exploring their anticancer applications.

Autor: Çakır S; Department of Chemistry, Faculty of Science, Ege University, Bornova, 35100, Izmir, Turkey., Ilhan S; Department of Biology, Faculty of Engineering and Natural Sciences, Manisa Celal Bayar University, Manisa, Turkey., Atmaca H; Department of Biology, Faculty of Engineering and Natural Sciences, Manisa Celal Bayar University, Manisa, Turkey., Türkmen H; Department of Chemistry, Faculty of Science, Ege University, Bornova, 35100, Izmir, Turkey. Electronic address: hayatiturkmen@hotmail.com.
Jazyk: angličtina
Zdroj: European journal of medicinal chemistry [Eur J Med Chem] 2024 Nov 05; Vol. 277, pp. 116775. Date of Electronic Publication: 2024 Aug 13.
DOI: 10.1016/j.ejmech.2024.116775
Abstrakt: This study reports a new series of 1,10-phenanthroline-substituted imidazolium salts (1a-f), examining their design, synthesis, structure and anticancer activities. The structures of these salts (1a-f) were characterized using 1 H, 13 C NMR, elemental analysis, mass spectrometry and Fourier transform infrared (FT-IR) spectroscopies. The salts' cytotoxic activities were tested against cancer cell lines, specifically MCF-7, MDA-MB-231 and non-tumorigenic MCF-10A mammary cells. The study compared the impact of aliphatic and benzylic groups in the salts' structure on their anticancer activity. Screening results revealed that compound 1c, in particular, showed promising inhibitory activity against the growth of MDA-MB-231 breast cancer cells, with an IC 50 value of 12.8 ± 1.2 μM, indicating its potential as a chemotherapeutic agent. Cell apoptosis analysis demonstrated a tendency for compound 1c to induce early apoptosis in breast cancer cells. The stability/aquation of compound 1c was investigated using 1 H NMR spectroscopy and its binding modes with DNA were explored via UV-Vis spectroscopy. Additionally, the study investigated the interaction residues and docking scores of compound 1c and the reference drug doxorubicin against Bax and Bcl-2 proteins using molecular docking.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this article.
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Databáze: MEDLINE
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