Abstract
Carbazoles and imidazole represent two important classes of heterocycles which exhibit diverse biological activities such as antitumor properties. In this study, imidazole (C1-C3) and carbazole (C4 and C5) derivatives were evaluated for their cytotoxic activity against three human cancer cell lines namely, MCF7 (human breast cancer), HT29 (human colon cancer), and HeLa (human cervical cancer). Carbazole derivatives (C4 and C5) with IC50 < 10 µM showed greater cytotoxic effect than imidazole derivatives (C1-C3). Furthermore, all compounds exhibited better anticancer activity against MCF-7 than other two cell lines (HT-29, HeLa) and compound C4 was the most potent compound with the IC50 values of 2.5, 5.4 and 4.0 µM, against MCF-7, Hela and HT-29 cell lines, respectively. Physicochemical properties of compounds were calculated and their correlation with the IC50 values on MCF-7 cell line investigated. Surface area and polarizability of compounds showed good correlation by R2 = 0.8396 and R2 = 0.834, respectively. Docking studies of these compounds were also performed on the DNA as proposed target to comprehend their binding interactions and binding energies. The docking energy of compounds ranged from - 11.32 to -13.48 kcal/mol. Compound C3 with energy of -13.48 kcal/mol had the highest docking energy. Docking results indicated that these compounds (C1-C5) had strong affinity in binding to the DNA.
 
 KEY WORDS: Imidazole, Carbazole, Molecular docking, Cancer, MTT assay
 
 Bull. Chem. Soc. Ethiop. 2020, 34(2), 377-384
 DOI: https://dx.doi.org/10.4314/bcse.v34i2.14
Highlights
Cancer after the cardiovascular problems is one of the most spread and mortal disease in the world
All heterocyclic compounds were evaluated against three cell lines including MCF7, HT-29 and HeLa by standard MTT assay method (Table 2)
The IC50 values on MCF-7 cell line and physicochemical properties of compounds were plotted and the results showed that surface area and polarizability had good correlation than the other physicochemical properties
Summary
Cancer after the cardiovascular problems is one of the most spread and mortal disease in the world. Salerno and co-workers designed and synthesized novel imidazole derivatives based on azalanstat and investigated their antiproliferative properties in prostate ((DU-145, PC3, LnCap) and breast cancer cell lines (MDA-MB-231, and MCF-7) [8] Based on these premises and importance of imidazole and carbazole heterocyclic nucleuses in medicinal chemistry, we investigated imidazole and carbazole derivatives, which were synthesized recently [9,10,11], for cytotoxic activity. Physicochemical properties of compounds, to indicate their correlation with the IC50 values on MCF-7 cell line, were calculated. Docking study of these compounds was carried out to determine the best binding mode and binding energies of these compounds with DNA as proposed targets. The grid box parameters of 1BNA were 60×74×120 points in x, y, and z directions. gpf and dpf as grid and docking parameter files were built by AutoDock Tools
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