Synthesis of oleanolic acid hydrazide-hydrazone hybrid derivatives and investigation of their cytotoxic effects on A549 human lung cancer cells

Şenol, Halil; Berre, Mercümek; Büşra, Şahin Rabia; Burak, Kapucu Halil; Hacıosmanoğlu, Ebru

doi:10.1016/j.rechem.2022.100317

Cited by 9 publications

(1 citation statement)

References 65 publications

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“…They can be formed when the NNH 2 group replaces the oxygen in aldehydes or ketones. Hydrazone derivatives have a broad range of pharmaceutical activities and are already being used in the market as anticancer, antiproliferative, antimicrobial, anti-inflammatory, and antiviral agents [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

et al. 2022

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To understand whether previously synthesized novel hydrazone and oxadiazole derivatives have promising anticancer effects, docking studies and in vitro toxicity assays were performed on A-549, MDA-MB-231, and PC-3 cell lines. The antiproliferative properties of the compounds were investigated using molecular docking experiments. Each compound’s best-docked poses, binding affinity, and receptor-ligand interaction were evaluated. Compounds’ molecular weights, logPs, TPSAs, abilities to pass the blood-brain barrier, GI absorption qualities, and CYPP450 inhibition have been given. When the activities of these molecules were examined in vitro, for the A-549 cell line, hydrazone 1e had the minimum IC50 value of 13.39 μM. For the MDA-MB-231 cell line, oxadiazole 2l demonstrated the lowest IC50 value, with 22.73 μM. For PC-3, hydrazone 1d showed the lowest C50 value of 9.38 μM. The three most promising compounds were determined as compounds 1e, 1d, and 2a based on their minimum IC50 values, and an additional scratch assay was performed for A-549 and MDA-MB-231 cells, which have high migration capacity, for the three most potent molecules; it was determined that these molecules did not show a significant antimetastatic effect.

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Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

et al. 2022

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New Anthranilic Acid Hydrazones as Fenamate Isosteres: Synthesis, Characterization, Molecular Docking, Dynamics & in Silico ADME, in Vitro Anti‐Inflammatory and Anticancer Activity Studies

Şenol

Cagman

Katmerlikaya

et al. 2023

Chemistry & Biodiversity

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In this study, twenty new anthranilic acid hydrazones 6–9 (a–e) were synthesized and their structures were characterized by Fourier‐transform Infrared (FT‐IR), Nuclear Magnetic Resonance (1H‐NMR – 13C‐NMR), and High‐resolution Mass Spectroscopy (HR‐MS). The inhibitory effects of the compounds against COX‐II were evaluated. IC50 values of the compounds were found in the range of >200–0.32 μM and compounds 6e, 8d, 8e, 9b, 9c, and 9e were determined to be the most effective inhibitors. Cytotoxic effects of the most potent compounds were investigated against human hepatoblastoma (Hep‐G2) and human healthy embryonic kidney (Hek‐293) cell lines. Doxorubicin (IC50: 8.68±0.16 μM for Hep‐G2, 55.29±0.56 μM for Hek‐293) was used as standard. 8e is the most active compound, with low IC50 against Hep‐G2 (4.80±0.04 μM), high against Hek‐293 (159.30±3.12), and high selectivity (33.15). Finally, molecular docking and dynamics studies were performed to understand ligand‐protein interactions between the most potent compounds and COX II, Epidermal Growth Factor Receptor (EGFR), and Transforming Growth Factor beta II (TGF‐βII). The docking scores were calculated in the range of −10.609–−6.705 kcal/mol for COX‐II, −8.652–−7.743 kcal/mol for EGFR, and −10.708–−8.596 kcal/mol for TGF‐βII.

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Novel thiosemicarbazone and thiazolidin‐4‐one derivatives containing vanillin core: Synthesis, characterization, and anticancer activity studies

Tokalı

Şenol

Katmerlikaya

et al. 2023

Journal of Heterocyclic Chem

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Cancer is one of the most common and lethal disease in the world, therefore, patients need new and potent anticancer agents for treatment. In this study, starting from vanillin, 24 new compounds, which are 12 thiosemicarbazone (4a‐h, 5i‐j, 6k) and 12 thiazolidin‐4‐one (7a‐h, 8i‐j and 9k) derivatives, were synthesized and characterized by Nuclear Magnetic Resonance (NMR), High‐Resolution Mass Spectroscopy (HRMS), and Fourier‐transform Infrared (FTIR) techniques. In vitro cytotoxic effects were investigated on CCD‐1079Sk human healthy fibroblast and MDA‐MB‐231 human breast cancer cell lines. For MDA‐MB‐231, molecules showed IC50 in ranging of 88.08 ± 0.027–16.54 ± 0.031 μM (Doxorubicin: 61.70 ± 0.021 μM) and for CCD‐1079Sk, molecules showed IC50 in ranging of 192.36 ± 0.018–13.58 ± 0.035 μM (Doxorubicin:52.01 ± 0.028 μM). Compounds 6k and 7f were found most selective and potent anticancer agents compared to Doxorubicin used as a standard drug.

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Synthesis of oleanolic acid hydrazide-hydrazone hybrid derivatives and investigation of their cytotoxic effects on A549 human lung cancer cells

Cited by 9 publications

References 65 publications

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

Cytotoxic Activity and Docking Studies of 2-arenoxybenzaldehyde N-acyl Hydrazone and 1,3,4-Oxadiazole Derivatives against Various Cancer Cell Lines

New Anthranilic Acid Hydrazones as Fenamate Isosteres: Synthesis, Characterization, Molecular Docking, Dynamics & in Silico ADME, in Vitro Anti‐Inflammatory and Anticancer Activity Studies

Novel thiosemicarbazone and thiazolidin‐4‐one derivatives containing vanillin core: Synthesis, characterization, and anticancer activity studies

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