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Öğe The anticholinesterase perspective of dimethoxyindole based benzenesulfonamides: Synthesis, biological investigation and molecular docking applications(John Wiley and Sons Inc., 2024) Bingül, Murat; Ercan, Selami; Boǧa, Mehmet; Arslan, Zehra; Tuneğ, Muhammed; Akocak, Süleyman; Bingül, Alev Arslantürk; Şengül, İbrahim Fazıl; Şahin, HasanDue to the well-known biological potential of benzenesulfonamides for the inhibition of specific enzymes, here in, we propose to investigate anticholinesterase efficiencies of five newly synthesized benzenesulfonamides incorporating dimethoxyindole tails. The targeted compounds were synthesized through the C7 position of the methyl 4,6-dimethoxy-1H-indole-2-carboxylate via Schiff-base reaction. The biological study was directed to identify the acetylcholinesterase (ACh) and butyrylcholinesterase (BCh) enzyme inhibitions. The molecular docking studies were also carried out to determine the possible poses of ligands 8 a–e in binding sites of enzymes and ligand-residue interactions. Molecular dynamics simulations, RMSD and RMSF plots, hydrogen bond analysis, per-residue energy decomposition and MM-PB(GB)/SA calculations were carried out investigate the potentials of the compounds towards the designated enzymes. It is important to note that all the synthesized compounds were found to be selective towards the BChE inhibition with a range of efficiencies. In addition to that the compound 8 a exhibited more potency than the standard Galanthamine with the value of 87.75 % for the same enzyme. The results could be valuable for the determination of new targets which are highly selective for BChE inhibition. The formation of hydrogen bonds and hydrophobic interactions with the residues located on the compounds were responsible for the binding free energy scores. The stability of all the compounds proved by molecular dynamics simulations were also promising for the further directions of the study.Öğe Antioxidant, acetylcholinesterase and butyrylcholinesterase inhibition profiles of histamine schiff bases(Turkish Chemical Society, 2019) Akocak, Süleyman; Lolak, Nabih; Tuneğ, Muhammed; Boǧa, MehmetIn this work, a series of histamine Schiff bases H(1-20) were assayed for antioxidant properties by using different bioanalytical methods such as DPPH-free radical scavenging assay, ABTS cation radical decolarization, cupric reducing antioxidant capacity (CUPRAC) and metal chelating methods. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition profiles were also assessed. In general, the synthesized compounds showed weak antioxidant activity against all tested methods, but some of them showed great inhibition potency against AChE and BChE enzymes. Specifically, compound H9 showed effective inhibition potency against both enzymes with percent inhibition of 97.03 and 93.64, respectively.Öğe Indolyl imine compounds as multi-target agents; synthesis, antidiabetic, anticholinesterase, antioxidant activities and molecular modeling(Elsevier B.V., 2024) Ceyhan, Sadık M.; Zengin, İrem Nur; Bingül, Murat; Şahin, Hasan; Boǧa, Mehmet; Sağlam, Mehmet F.; Kandemir, HakanA new range of indolyl imine system 3d-l has been successfully prepared from 4,6-dimethoxy-2,3-diphenyl-indole-7-carbaldehyde 2a and 4,6-dimethoxy-3-aryl-indole-7-carbaldehyde 2b-c via Schiff base reaction. The structure of targeted compounds was confirmed by 1H and 13C NMR, FT-IR, mass spectrometry and single crystal X-ray diffraction techniques. The indolyl imine derivatives were also subjected to in vitro antidiabetic activities employing ?-glucosidase and ?-amylase enzymes. In terms of antidiabetic investigation, the ?-glucosidase enzyme was found to be potential target due to the comparable inhibition concentrations with the standard acarbose and the compound 3e exhibited better potency than the standard. The anticholinesterase potency of the compounds was investigated towards the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. The compounds displayed moderate efficiency against the BChE enzyme with the best inhibition concentration of 30.48 ?M by the compound 3h. The antioxidant properties of final compounds were determined by DPPH radical scavenging, ABTS Cation Radical Decolarization and CUPRAC Cupric Reducing Antioxidant Capacity assay methods. The ABTS cation scavenging assay provided the best responses for the compounds and the candidates 3k and 3l were determined as promising targets for the antioxidant activity. Plausible binding mode and interaction of ligands with the selected enzyme have been studied by molecular docking, supporting the experimental results. In silico ADME showed high drug likeness of the synthesized compounds. © 2024 Elsevier B.V.Öğe Some heterocycles connected to substituted piperazine by 1,3,4-oxadiazole linker: Design, synthesis, anticholinesterase and antioxidant activity(Elsevier B.V., 2025) Kurt, Zuhal Kılıç; Konyar, Dilan; Okur, Hayati; Kaplan, Alevcan; Boǧa, MehmetAD is a multifactorial neurodegenerative disease that has caused morbidity and mortality on a global scale. Currently, there are only a few drugs used in the treatment of AD. Although many compounds that aim at new targets have reached clinical trials, none have been approved. However, discovering efficient drugs for AD treatment is one of the biggest challenges for pharmaceutical research and requires strong support. In this paper, we aim to design a series of indole, benzothiophene, and thiophene bearing 1,3,4-oxadiazole linker to the piperazine basic center and evaluate for their antioxidant and inhibitory activity against both cholinesterase enzymes. Among the compounds, 6a, 7b, and 8b exhibited moderate cationic radical scavenging activities with IC50 values ranging from 20.39 to 30.10 μM. The inhibitory activity results revealed that compounds 5c (IC50 for AChE = 53.91 μM and for BChE = 55.81 μM) and 6c (IC50 for AChE = 54.42 μM and BChE = 45.82 μM) bearing 2-fluorophenyl piperazine moiety showed both AChE and BChE inhibition with moderate IC50 values. To explore the binding properties of the target compounds into the active site of the enzyme, a molecular docking study was carried out using MOE software. The docking study showed that compound 6c targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE/BChE and formed important interactions with key residues. Moreover, theoretical physicochemical properties of the best active compound 6c were calculated by the SwissADME web service. It obeyed Lipinski's rule of five and had high GI absorption (gastrointestinal absorption) and good permeating to the blood-brain barrier (BBB). The compound 6c can be considered a promising compound and provides us directions for further research of anti-AD agent development.Öğe Sulphonamides incorporating 1,3,5-triazine structural motifs show antioxidant, acetylcholinesterase, butyrylcholinesterase, and tyrosinase inhibitory profile(Taylor and Francis Ltd, 2020) Lolak, Nabih; Boǧa, Mehmet; Tuneğ, Muhammed; Karakoç, Gulçin; Akocak, Suleyman; Supuran, Claudiu T.A series of 16 novel benzenesulfonamides incorporating 1,3,5-triazine moieties substituted with aromatic amines, dimethylamine, morpholine and piperidine were investigated. These compounds were assayed for antioxidant properties by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, 2,2`-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical decolarisation assay and metal chelating methods. They were also investigated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase, which are associated with several diseases such as Alzheimer, Parkinson and pigmentation disorders. These benzenesulfonamides showed moderate DPPH radical scavenging and metal chelating activity, and low ABTS cation radical scavenging activity. Compounds 2 b, 3d and 3 h showed inhibitory potency against AChE with % inhibition values of >90. BChE was also effectively inhibited by most of the synthesised compounds with >90% inhibition potency. Tyrosinase was less inhibited by these compounds.Öğe Synthesis of novel N-Acylhydrazones derived from 3,5-dinitrobenzohydrazide and evaluation of their anticholinesterase and antioxidant activities(Pleiades Publishing, 2024) Çakmak, Reşit; Çınar, Ercan; Başaran, Eyüp; Tuneğ, Gülsüm; İzgi, Sevcan; Boǧa, MehmetAbstract: Objective: In this study, it was aimed to determine the antioxidant activities and enzyme inhibition properties of newly synthesized N-acylhydrazone compounds (IIIa–IIIp) bearing an aryl sulfonate moiety. Methods: For this purpose, a series of hydrazone derivatives based on 3,5-dinitrobenzohydrazide (I) was synthesized for the first time and characterized by spectrometric methods (FT-IR, 1H NMR and 13C NMR) and elemental analysis. In vitro anticholinesterase activities of novel hydrazone derivatives were evaluated against acetyl- and butyrylcholinesterase (AChE and BChE) at 200 µM concentration. Moreover, the antioxidant potentials of the same molecules were determined by 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity and cupric ion reducing antioxidant capacity (CUPRAC) assays. Results: The obtained results displayed that some of the tested hydrazone compounds had varying enzyme inhibition and antioxidant activities. Discussion: In enzyme inhibition studies, N′-[2-{[4-fluorobenzensulfonyl]oxy}benzylidene]-3,5-dinitrobenzohydrazide (IIIb) with inhibition value 77.13 ± 0.14% showed the closest activity to the standard compound galanthamine with inhibition value 78.14 ± 0.65%. Compared to DPPH and ABTS assays, all of the molecules tested in CUPRAC assay showed antioxidant activities. The molecules tested in CUPRAC assay did not show as much activity as standard molecules (BHA, BHT and α-TOC). Conclusions: Compounds N′-[4-{[4-fluorobenzensulfonyl]oxy}benzylidene]-3,5-dinitrobenzohydrazide (IIIf) and N′-[4-{[4-methoxybenzensulfonyl]oxy}benzylidene]-3,5dinitrobenzohydrazide (IIIh) in this assay were determined to be the most active molecules.Öğe Synthesis, biologic properties, and molecular modeling studies of bis-indole based thiosemicarbazones(Springer, 2024) Ceyhan, Sadık M.; Bingül, Murat; Şahin, Hasan; Boǧa, Mehmet; Sağlam, Mehmet F.; Kandemir, Hakan; Şengül, İbrahim FazılThe Schiff base condensation reaction of thiosemicarbazides and methylene bridged 2,2′-bisindolylmethanes, prepared from the acid-catalyzed condensation of 3-aryl-4,6-dimethoxyindole-7-carbaldehydes and formaldehyde, produced a series of the targeted bis-indole based thiosemicarbazones. To explore the biological potential of the newly synthesized compounds, antidiabetic, anticholinesterase, and antioxidant activities were investigated. The structural derivatization carried out by the addition of bromophenyl ring at C3 position of the indole backbone increased the enzyme potency towards the anticholinesterase activity. Some of the targeted compounds showed selective the α-glucosidase enzyme inhibition activity. In addition to that, the inhibition concentrations were found to lower that the standard acarbose showing that they may be more efficient agents. Although most of the compounds were effective for the metal chelation capacities (CUPRAC), a couple of examples were found to be favorable for DPPH and ABTS assays. The presence of methyl substituted thiosemicarbazone tail with different indole back bones individually detected as promising targets for ABTS and DPPH activities. The compound methyl substituted thiosemicarbazone was also determined as the most potent agent with the 6 μM inhibition concentration toward CUPRAC assay. Molecular docking study was performed to support the experimental results. Graphical abstract: (Figure presented.)
