Molecular hybrids integrated with imidazole and hydrazone structural motifs: Design, synthesis, biological evaluation, and molecular docking studies

Tapera, Michael; Kekeçmuhammed, Hüseyin; Sarıpınar, Emin; Doğan, Murat; Tüzün, Burak; Koçyiğit, Ümit M.; Çetin, Feyza Nur

doi:10.1016/j.molliq.2023.123242

Cited by 9 publications

(3 citation statements)

References 51 publications

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“…This is the liquid to use to store your Artemisia absinthium extract. [20] was used for these calculations. Several modules, including protein preparation [21,22], LigPrep [23,24], and Glide ligand docking [25,26] were employed in the molecular docking calculations.…”

Section: Methodsmentioning

confidence: 99%

Breast cancer Properties of Extract of Artemisia absinthium

2023

Proceeding Book of 3rd International Conference on Scientific and Academic Research ICSAR 2023

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Plants have been used for the treatment of various cancers since ancient times. Breast cancer is the second commonest global deadly menace. Natural plant extracts, herbal medicines, are generally accepted as safer drug substances than their synthetic counterparts. Artemisia absinthium, a perennial bushy plant, has traditionally been beneficial in diverse maladies, including hepatocyte overgrowth, hepatitis, gastritis, jaundice, wound healing, splenomegaly, dyspepsia, indigestion, bloating, stomach pain, anaemia and anorexia. It has also been known for its antioxidant, antifungal, antimicrobial, anthelmintic, anti-ulcer, anticarcinogenic, hepatoprotective, neuroprotective, antidepressant, analgesic, immunomodulatory, and cytotoxic properties. In this study, methanol extracts of powdered leaves of Artemisia absinthium was tried on breast cancer cells. The molecular content of the extract was determined by GC-MS. Chemical components were determinated for the Artemisia absinthium extract, and the inhibitory activities of these chemicals against the Crystal structure of breast cancer protein (PDB ID: 1A52 and 1JNX) downloaded from the Protein Data Bank site were compared.

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Section: Methodsmentioning

confidence: 99%

Breast cancer Properties of Extract of Artemisia absinthium

2023

Proceeding Book of 3rd International Conference on Scientific and Academic Research ICSAR 2023

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“…The software MOE was utilized for this docking analysis [28]. A ligand library was compiled using PubChem, and ligands were chosen for the docking studies based on their structural attributes and possible pharmacological signi cance [29]. The docking analyses revealed the possible binding locations of all ligands to the active site of 3LN1, and the stability of the protein-ligand complexes was also assessed.…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Molecular docking and DFT study of 4-difluoromethyl pyrazole derivatives as cyclooxygenase-2 inhibitor

Khan,

Hussain,

Mubarik

et al. 2024

Preprint

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We applied molecular docking simulations and DFT to examine the binding interactions of 4-difluoromethyl pyrazole derivatives (3a-3h). We assessed the potential binding mechanisms and strengths of derivatives within the receptor's binding site. By methodical simulations, we elucidated the characteristics and interactions towards binding capacities. Proposed compounds were subjected to molecular docking with the major protease (PDB:3LN1) to assess binding affinities. In designed compounds (3a-3h), 3a and 3f show the highest docking score, leading to high affinity toward 3LN1. An energy score of -6.9765 Cal/mol of ligand 3g suggests a strong and advantageous binding affinity, with the negative number indicating stability. The reactivity parameters, FMO, and MEP of the drugs were estimated by DFT calculations. The strong affinity of 3a and 3f was attributed to the existence of three hydrogen bonds and several hydrophobic interactions between the drug and the essential amino acid residues of the receptor. Ultimately, the molecular docking findings were illustrated using the estimated molecule electrostatic potential data using DFT. All these characteristics showed varying degrees of influence on the binding affinity of these compounds with the active protein locations.

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“…[6,7] Imidazole has been recognized as a significant type of heterocyclic framework in the field of drug discovery. Imidazole derivatives have been reported to exhibit a diverse range of [a] H. Kekeçmuhammed biological activities, such as anticancer, [8,9] antibacterial, [10] antiviral [11] antitubercular, [12] antiepileptic [13] and antifungal agents. [14] It is hypothesized that molecules with an imidazole ring exhibit noteworthy bioactivity because of the high polarity properties of imidazole.…”

Section: Introductionmentioning

confidence: 99%

The Suppressive Effect of Novel Hydrazones‐Tethered Imidazoles in HCT‐116 and HT‐29 Colorectal Cancer Cells: Synthesis, Biological Activity and Molecular Modeling Studies

Kekeçmuhammed,

Tapera,

Şahin

et al. 2024

ChemistrySelect

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A series of hybrid compounds containing both the imidazole ring and the hydrazone moiety have been synthesized. Synthesized compounds were characterized by various spectral techniques, including FT‐IR, 1H‐NMR, 13C‐NMR, and HRMS. The compounds were evaluated for their antiproliferative activities on colorectal cancer cells HCT‐116 and HT‐29 in a time‐dependent manner. Among them, some compounds exhibited remarkable anti‐cancer activity with a less cytotoxic effect on non‐cancerous cell lines, especially HRK‐2 with IC50 value of 1.35±0.18 μM in HCT‐116 cells and HRK‐5 with IC50 value of 2.67±0.61 μM in HT‐29 cells. Investigations of colon cancer cell death were performed, and the most active compounds were found to trigger cell death via nuclear localization and induce S phase arrest of the colon cancer cell. Moreover, molecular modeling studies for the synthesized compounds was performed to predict their binding affinities toward the active site of BCL‐2. The findings of the molecular modeling investigations were highly consistent with those of the cytotoxicity results.

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Molecular hybrids integrated with imidazole and hydrazone structural motifs: Design, synthesis, biological evaluation, and molecular docking studies

Cited by 9 publications

References 51 publications

Breast cancer Properties of Extract of Artemisia absinthium

Breast cancer Properties of Extract of Artemisia absinthium

Molecular docking and DFT study of 4-difluoromethyl pyrazole derivatives as cyclooxygenase-2 inhibitor

The Suppressive Effect of Novel Hydrazones‐Tethered Imidazoles in HCT‐116 and HT‐29 Colorectal Cancer Cells: Synthesis, Biological Activity and Molecular Modeling Studies

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