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Öğe Design, synthesis, characterization, crystal structure, in silico studies, and inhibitory properties of the PEPPSI type Pd(II)NHC complexes bearing chloro/fluorobenzyl group(Academic Press Inc Elsevier Science, 2023) Gok, Yetkin; Taslimi, Parham; Sen, Betul; Bal, Selma; Aktas, Aydin; Aygun, Muhittin; Sadeghi, MortezaThis work contains synthesis, characterization, crystal structure, and biological activity of a new series of the PEPPSI type Pd(II)NHC complexes [(NHC)Pd(II)(3-Cl-py)]. NMR, FTIR, and elemental analysis techniques were used to characterize all (NHC)Pd(II)(3-Cl-py) complexes. Also, molecular and crystal structures of complex 1c were established by single-crystal X-ray diffraction. Regarding the X-ray studies, the palladium(II) atom has a slightly distorted square-planar coordination environment. Additionally, the enzyme inhibitory effect of new (NHC)Pd(II)(3-Cl-py) complexes (1a-1g) was studied. They exhibited highly potent inhibition effect on acetyl -cholinesterase (AChE), butyrylcholinesterase (BChE) and carbonic anhydrases (hCAs) (Ki values are in the range of 0.08 +/- 0.01 to 0.65 +/- 0.06 mu M, 10.43 +/- 0.98 to 22.48 +/- 2.01 mu M, 6.58 +/- 0.30 to 10.88 +/- 1.01 mu M and 6.34 +/- 0.37 to 9.02 +/- 0.72 mu M for AChE, BChE, hCA I, and hCA II, respectively). Based on the molecular docking, among the seven synthesized complexes, 1c, 1b, 1e, and 1a significantly inhibited AChE, BChE, hCA I, and hCA II enzymes, respectively. The findings highpoint that (NHC)Pd(II)(3-Cl-py) complexes can be considered as possible inhibitors via metabolic enzyme inhibition.Öğe Does postimplantation syndrome due to endovascular aneurysm repair increase mortality rate?(2020) Ozturk, Selen; Ozturk, Ibrahim; Yilmaz, Habip; Sen, BetulAim: Postimplantation syndrome diagnosed by high levels of white blood cell and c-reactive protein or fever is an inflammatory clinical finding after endovascular aneurysm repair. We aimed to analyze whether it can increase mortality rate or not.Material and Methods: A literature search was performed in electronic database, Pubmed, without date limitation. Trials that compare the rate of mortality between patients with postimplantation syndrome and controls were included. Date of articles and numbers of death in each groups were noted. The results of studies were evaluated by random or fixed effect model according to heterogeneity. Statistical analysis was performed by using Jamovi software.Results: After the database search, we attained in all 358 articles. After overview of titles and abstracts, we included 5 articles in the meta-analysis which contained 1283 patients and abided by inclusion criteria. In analysis, it was observed that there was no significant difference for mortality between patients with postimplantation syndrome and controls (OR: 0.27, 95% CI -0.27-0.81 and p=0.33. Studies included in the analysis were not heterogeneous (I2=6.63%). Possible publication bias was found (tau2:0.0). The weight of one of five studies with regard to results of analysis was 57.7%.Conclusion: We concluded that postimplantation syndrome cannot increase mortality, though it’s high development rate after endovascular aneurysm repair.Öğe Fluorinated benzimidazolium salts: Synthesis, characterization, molecular docking studies and inhibitory properties against some metabolic enzymes(Elsevier Science Sa, 2023) Zengin, Ramazan; Gok, Yetkin; Demir, Yeliz; Sen, Betul; Taskin-Tok, Tugba; Aktas, Aydin; Demirci, OzlemHere, a number of symmetric and unsymmetric N-heterocyclic carbene (NHC) precursors based on benzimidazol-2-ylidene are synthesized. The N-benzyl substituent in these compounds has an electron-withdrawing group (F) at the para position. The structure of these compounds was characterized using elemental analysis and various spectroscopic methods (FTIR and NMR). The molecular and crystal structures of compound 1f and compound 1h were unambiguously elucidated through single-crystal X-ray diffraction analysis. According to the X-ray studies, compound 1f exhibits the formation of a U-shaped molecule whereas compound 1h has a Z-shape formation. In addition, the enzyme inhibition activities of these compounds were investigated against acetylcholinesterase (AChE) and carbonic anhydrases (hCAs). They showed a highly potent inhibition effect on AChE and hCAs (Ki values are in the range of 14.84 +/- 1.91 to 174.80 +/- 23.60 nM for AChE, 22.41 +/- 1.93 to 188.67 +/- 27.05 nM for hCA I and 35.29 +/- 7.21 to 136.55 +/- 17.61 nM for hCA II). These results may contribute to the design and development of new drug candidates, particularly for treatment of some widespread disorders displayed in the world including Alzheimer's disease and glaucoma.Öğe New palladium complexes with N-heterocyclic carbene and morpholine ligands: Synthesis, characterization, crystal structure, molecular docking, and biological activities(Wiley, 2024) Behcet, Ayten; Taslimi, Parham; Sen, Betul; Taskin-Tok, Tugba; Aktas, Aydin; Gok, Yetkin; Aygun, MuhittinThis work includes the synthesis of a new series of palladium-based complexes containing both morpholine and N-heterocyclic carbene (NHC) ligands. The new complexes were characterized using NMR (1H and 13C), FTIR spectroscopic, and elemental analysis techniques. The crystal structure of complex 1b was obtained by utilizing the single-crystal X-ray diffraction method. X-ray studies show that the coordination environment of palladium atom is completed by the carbene carbon atom of the NHC ligand, the nitrogen atom of the morpholine ring, and a pair of bromide ligand, resulting in the formation of slightly distorted square planar geometry. All complexes were determined for some metabolic enzyme activities. Results indicated that all the synthetic complexes exhibited powerful inhibitory actions against all aims as compared to the control molecules. Ki values of new morpholine-liganded complexes bearing 4-hydroxyphenylethyl group 1a-e for hCA I, hCA II, AChE, BChE, and alpha-glycosidase enzymes were obtained in the ranges 0.93-2.14, 1.01-2.03, 4.58-10.27, 7.02-13.75, and 73.86-102.65 mu M, respectively. Designing of reported complexes is impacted by molecular docking study, and interaction with the current enzymes also proclaimed that compounds 1e (-12.25 kcal/mol for AChE and -11.63 kcal/mol for BChE), 1c (-10.77 kcal/mol and -9.26 kcal/mol for alpha-Gly and hCA II, respectively), and 1a (-8.31 kcal/mol for hCA I) are showing binding affinity and interaction from the synthesized five novel complexes.Öğe PEPPSI type Pd(II)NHC complexes bearing chloro-/fluorobenzyl group: Synthesis, characterization, crystal structures, ?-glycosidase and acetylcholinesterase inhibitory properties(Pergamon-Elsevier Science Ltd, 2021) Bal, Selma; Demirci, Ozlem; Sen, Betul; Taslimi, Parham; Aktas, Aydin; Gok, Yetkin; Aygun, MuhittinThis work reported the synthesis of a new PEPPSI (Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) type Pd(II)N-heterocyclic carbene (NHC) complexes bearing halo-benzyl (4-florobenzyl and 2-chloro-4-florobenzyl) group. These new complexes were synthesized from the florobenzyl / chlorofluorobenzyl substituted benzimidazolium salts, PdCl2 and pyridine. Characterizations of all the synthesized complexes were done using elemental analysis, H-1 NMR, C-13 NMR and FT-IR spectroscopy techniques. The molecular and crystal structures of the new PEPPSI type Pd(II)NHC complexes were determined by single-crystal X-ray diffraction method. X-ray studies show that molecular structures of three complexes comprise a palladium(II) atom with a slightly distorted square-planar coordination environment. These synthesized salts were found to be effective inhibitors for the alpha-glycosidase, and acetylcholinesterase (AChE) enzyme with K-i values in the range of 27.36 +/- 5.06-124.88 +/- 18.05 mu M for alpha-glycosidase, and 0.78 +/- 0.11-4.34 +/- 1.02 mu M for AChE, respectively. The significant group of drugs currently utilized for the therapy of Alzheimer's disease (AD) is acetylcholinesterase/cholinesterase inhibitor compounds. The first cholinesterase inhibitor licensed for symptomatic therapy of AD was tacrine. Inhibition acts of alpha-glycosidase enzyme by inhibitors tend to slow the breakdown and release of sugar molecules into the bloodstream and can be utilized as therapeutic factors in the therapy of obesity and diabetes. (C) 2021 Elsevier Ltd. All rights reserved.Öğe Plausible PEPPSI catalysts for direct C-H functionalization of furans and pyrroles(Elsevier, 2024) Munir, Naima; Gurbuz, Navin; Zafar, M. Naveed; Evren, Enes; Sen, Betul; Aygun, Muhittin; Ozdemir, IsmailThe worth of bi(hetero)arenes in ongoing medicinal and industrial research fields promotes their efficient synthesis by Pd-PEPPSI-bearing NHC spectator ligands encapsulated as site-selective direct C-H functionalization agents. Eight new asymmetric N-heterocyclic carbenes ligands and their plausible pyridine-assisted Pd (II) complexes are reported in this work. The synthesized compounds were thoroughly characterized by respective spectroscopic techniques, such as 1H, 13C, FTIR and elemental analysis. The structures of synthesized pro-ligand salts and complexes were determined by Single Crystal XRD. The on/off mechanism of pyridine assisted Pd-NHC complexes made them the best C-H functionalized catalysts for regioselective C5 arylated products. Five membered heterocyclic compounds such as 2-acetyl furan, furfuryl acetate and 1-methyl-2-pyrrole-carboxylaldehyde were treated with numerous aryl bromides under optimal catalytic reaction conditions. Furfuryl acetate was used for the first time as a substrate in the present research work. Interestingly, all the prepared catalysts possessed essential structural features that facilitated the formation of desired coupled products in quantitative yield with excellent selectivity.Öğe Silver N-heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes(Wiley, 2021) Bal, Selma; Demirci, Ozlem; Sen, Betul; Taskin Tok, Tugba; Taslimi, Parham; Aktas, Aydin; Gok, YetkinA series of the silver N-heterocyclic carbene (NHC) complexes have been synthesized from the reactions between benzimidazolium salts bearing fluorinated benzyl group and Ag2O via the deprotonation method. All Ag(I)NHC complexes were characterized by known spectroscopic techniques (H-1 nuclear magnetic resonance [NMR], C-13 NMR, and Fourier transform infrared [FT-IR]) and elemental analysis. The molecular structures of the two complexes were unambiguously elucidated through single-crystal X-ray diffraction analysis. Namely, X-ray studies show that the coordination geometry around the Ag(I) atom in the case of complex 2c is revealed to be almost linear with C-Ag-Cl angle, whereas in complex 2e, it appears as a nonlinear structure. The inhibitory profiles of these new complexes are investigated on some metabolic enzymes. Representatively, the most potent complex against human carbonic anhydrase isoenzymes I and II (hCAs I and II), 2d, was 1.8 times more potent than standard inhibitor acetazolamide against hCAs I and II. On the other hand, complexes 2c and 2b as most potent compounds against both cholinesterase enzymes was around 5 and 1.6 times more potent than tacrine against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively. The most active alpha-glucosidase inhibitor 2d had similar activity to acarbose as a standard inhibitor. Furthermore, it confirms its in vitro studies as a result of molecular docking studies for each enzyme with (i) binding energy and inhibition constant values and (ii) the definition of the best conformation and nonbonding interactions of the related complexes (2b, 2c, and 2d) against the different target proteins.Öğe A study about excellent xanthine oxidase inhibitory effects of new pyridine salts(Springer Wien, 2021) Yilmaz, Ulku; Noma, Samir Abbas Ali; Tok, Tugba Taskin; Sen, Betul; Gok, Yetkin; Aktas, Aydin; Ates, BurhanA series of pyridine salts were synthesized containing vitamin B3 (niacin), isonicotinonitrile, and non-substituted pyridine fragment from reactions of 1,3-dibromopropane, 1,4-dibromobutane, and 4,4 '-bis(chloromethyl)-1,1 '-biphenyl reactants with pyridines. The builds of pyridine salts were identified by dint of IR, H-1, and C-13 NMR spectroscopic techniques, and CHN analyses. Therewithal, the build of a compound was assigned via the X-ray single-crystal diffraction method. 1,3-Bis(3-cyanopyridine-1-ium-1-yl)propane dibromide crystallizes in the orthorhombic space group Ccce, with half of the cation molecule and one bromide anion in the asymmetric unit. Enzyme inhibitory properties of pyridine compounds were tested on the activities of xanthine oxidase (XO) and determined in the range from 0.394 to 0.623 mu M. All of the compounds inhibited enzyme more effectively than allopurinol that which is a standard drug. In addition, docking calculations were applied to investigate the binding properties and interactions of pyridine salts towards XO. Graphic abstractÖğe Synthesis, characterization and inhibitor properties of benzimidazolium salts bearing 4-(methylsulfonyl)benzyl side arms(Elsevier, 2023) Guzel, Abdussamat; Noma, Samir Abbas Ali; Sen, Betul; Kazanci, Ali; Taskin-Tok, Tugba; Kolac, Turgay; Aktas, AydinHerein, a series of N-heterocyclic carbene (NHC) precursors bearing sulfonyl moieties was prepared. 1-(4-(methylsulfonyl)benzyl)-3-alkylbenzimidazolium chloride salts were synthesized with the reaction of 1-alkylbenzimidazoles with 4-(methylsulfonyl)benzyl chloride. These compounds were characterized by using 1 H NMR, 13 C NMR, FT-IR spectroscopy and elemental analysis techniques. Molecular and crystal structures of compounds 2e and 2j were determined by using the single-crystal X-ray diffraction method. Furthermore, enzyme inhibitory properties of benzimidazolium salt were tested against xanthine oxidase (XO) and acetylcholinesterase (AChE), then determined the IC50 value range of XO were determined from 0.218 to 1.927 mu M, while the IC50 for AChE were determined from 1.328 to 5.22. Docking applications were used by using AutoDock4 in order to define the binding pose of the selected compounds, ( 2c, 2d and 2g ) and also to visualize the correlation of the generated optimal complexes. It is found that the compound 2g has good binding affinity (-11.24 kcal/mol) against AChE, on the other side, compound 2c shows the lowest binding energy (-8.32 kcal/mol) for the XO target. These findings and the defined compounds could be as potential agents to develop effective medicine for AChE and XO in the future.(c) 2022 Elsevier B.V. All rights reserved.Öğe Synthesis, characterization, crystal structure, ?-glycosidase, and acetylcholinesterase inhibitory properties of 1,3-disubstituted benzimidazolium salts(Wiley-V C H Verlag Gmbh, 2021) Bal, Selma; Demirci, Ozlem; Sen, Betul; Taslimi, Parham; Aktas, Aydin; Gok, Yetkin; Aygun, MuhittinChloro-/fluorobenzyl-substituted benzimidazolium salts were synthesized from the reaction of 4-fluorobenzyl/2-chloro-4-fluorobenzyl-substituted benzimidazole and chlorinated aromatic hydrocarbons. They were characterized using various spectroscopic techniques (Fourier-transform infrared and nuclear magnetic resonance) and elemental analysis. In addition, the crystal structures of the complexes 1a -d and 2b were determined by single-crystal X-ray diffraction methods. These compounds were crystallized in the triclinic crystal system with a P-1 space group. The crystal packing of all complexes is dominated by O-HMIDLINE HORIZONTAL ELLIPSISCl hydrogen bonds, which link the water molecules and chloride anions, forming a chloride-water tetrameric cluster. These synthesized salts were found to be effective inhibitors for alpha-glycosidase and acetylcholinesterase (AChE), with K-i values ranging from 45.77 +/- 6.83 to 102.61 +/- 11.56 mu M for alpha-glycosidase and 0.94 +/- 0.14 to 10.24 +/- 1.58 mu M for AChE. AChE converts acetylcholine into choline and acetic acid, thus causing the return of a cholinergic neuron to its resting state. Discovering AChE and alpha-glycosidase inhibitors is one of the important ways to develop new drugs for the treatment of Alzheimer's disease and diabetes.
