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Acetylphenyl-substituted imidazolium salts: synthesis, characterization, in silico studies and inhibitory properties against some metabolic enzymes
(Springer, 2023) Demirci, Ozlem; Tezcan, Burcu; Demir, Yeliz; Taskin-Tok, Tugba; Gok, Yetkin; Aktas, Aydin; Guzel, Bilgehan
Herein, we present how to synthesize thirteen new 1-(4-acetylphenyl)-3-alkylimidazolium salts by reacting 4-(1-H-imidazol-1-yl)acetophenone with a variety of benzyl halides that contain either electron-donating or electron-withdrawing groups. The structures of the new imidazolium salts were conformed using different spectroscopic methods (H-1 NMR, C-13 NMR, F-19 NMR, and FTIR) and elemental analysis techniques. Furthermore, these compounds' the carbonic anhydrase (hCAs) and acetylcholinesterase (AChE) enzyme inhibition activities were investigated. They showed a highly potent inhibition effect toward AChE and hCAs with K-i values in the range of 8.30 & PLUSMN; 1.71 to 120.77 & PLUSMN; 8.61 nM for AChE, 16.97 & PLUSMN; 2.04 to 84.45 & PLUSMN; 13.78 nM for hCA I, and 14.09 & PLUSMN; 2.99 to 69.33 & PLUSMN; 17.35 nM for hCA II, respectively. Most of the synthesized imidazolium salts appeared to be more potent than the standard inhibitor of tacrine (TAC) against AChE and Acetazolamide (AZA) against CA. In the meantime, to prospect for potential synthesized imidazolium salt inhibitor(s) against AChE and hCAs, molecular docking and an ADMET-based approach were exerted.
Antioxidant responses in Phanerochaete chrysosporium exposed to Astrazone Red FBL textile dye
(Wiley, 2013) Demirci, Ozlem; Hamamci, Dilek Asma
Interest in environmental-pollutant-induced oxidative stress and knowledge of the interactions between reactive oxygen species and cellular systems have increased in toxicology and microbial ecology considerably in recent decades. These reactive oxidants are produced by a variety of environmental sources: ionizing radiations, ultraviolet light, redox cycling drugs, hyperoxia, ischemia and redox-active xenobiotics or during metabolism of environmental pollutants, such as heavy metals in mining industries, dyes in wastewater of textile industries, pesticides and polycyclic hydrocarbons, i.e. foreign materials. In this study, the effect of dye on the antioxidative defence system of Phanerochaete chrysosporium was investigated, and we showed the ability of Phanerochaete chrysosporium to antioxidative response and defence system exposed to Astrazone Red FBL. Catalase, glutathione reductase, glutathione s-transferase activities and level of glutathione decreased, depending on the period of growth in each exposure to low and high concentration group (20 and 50?ppm) compared with the control group. Copyright (c) 2012 John Wiley & Sons, Ltd.
Design, Synthesis, Characterization, and Antitumor Activities of Benzimidazole-functionalized Organoruthenium Complexes Bearing Fluorine Group
(Bentham Science Publ Ltd, 2025) Pasahan, Ramazan; Demirci, Ozlem; Taskin, Irmak Icen; Pasahan, Aziz; Sever, Meryem Ruveyda; Gok, Yetkin; Aktas, Aydin
Background This work presents the synthesis of Ru(II)NHC complexes bearing a series of 4-fluorobenzyl group. These complexes have been characterized by a variety of spectroscopic methods (1H NMR, 13C NMR, and FTIR) and by elemental analysis techniques.Methods These complexes' antitumor activities against SH-SY5Y (human neuroblastoma) and HCT116 (human colon cancer) were investigated by 3-(4,5-dimethylthiazole-2-yl)-2,5-biphenyl tetrazolium bromide (MTT) assay.Results The results showed that all the synthesized complexes exhibited significant cytotoxic effect with low IC50 values 15 +/- 0.57, 15.26 +/- 0.71, 7.64 +/- 0.30, 27.66 +/- 0.36 and 14.45 +/- 0.84 (mu g/mL) respectively.Conclusion Furthermore, apoptosis assessed by double labeling with Annexin V-FITC/PI indicated that complexes 1b and 1d can effectively induce apoptosis and inhibit cell proliferation at the S phase in SH-SY5Y cells. Taken together, Ru(II)NHC complexes containing the 4-fluorobenzyl group have significant potential for the development of novel, highly effective anticancer agents.
Effects of endosulfan, thiamethoxam, and indoxacarb in combination with atrazine on multi-biomarkers in Gammarus kischineffensis
(Academic Press Inc Elsevier Science, 2018) Demirci, Ozlem; Guven, Kemal; Asma, Dilek; Ogut, Serdal; Ugurlu, Pelin
Studies addressing the toxicity of pesticides towards non-target organisms focus on the median lethal concentration and biochemical response of individual pesticides. However, when determining environmental risks, it is important to test the combined effects of pesticides, such as insecticides and herbicides, which are frequently used together in agricultural areas. Here we aimed to investigate the toxic effects of the combined use of the herbicide atrazine and the insecticides, endosulfan, indoxacarb, and thiamethoxam on Gammarus kischineffensis. To do this, we tested the activities of oxidative stress, detoxification, and neurotoxicity biomarkers. Compared to atrazine alone, we detected higher glutathione-S-transferase, catalase and superoxide dismutase activities (oxidative stress biomarkers) when atrazine was combined with either endosulfan or indoxacarb. However, higher IBR values were determined in organisms where pesticide mixtures were used according to individual use. Based on these results, mixtures of atrazine and other pesticides may cause synergistic effects and may be evidence of increased toxicity and oxidative stress.
Evaluation of the biochemical effects of an acetamiprid-based insecticide on a non-target species,Gambusia holbrooki
(Wiley, 2020) Demirci, Ozlem; Gungordu, Abbas
The toxic effects of an acetamiprid-based insecticide (ABI) onGambusia holbrookiwere evaluated after 24 and 96-h exposure periods. The 24 and 96-h median lethal concentration (LC50) values of ABI were determined as 75.9 and 42.2 mg/L active ingredient (AI)/L, respectively. In addition, the activity of five biochemical marker enzymes, including glutathione S-transferase (GST), glutathione reductase (GR), carboxylesterase (CaE), lactate dehydrogenase (LDH) and aspartate aminotransferase (AST) was measured after 24 and 96-h exposure to three different concentrations of the ABI to evaluate its sublethal effects. The acetamiprid concentrations in the exposure media were measured using liquid chromatography-tandem mass spectrometry. Our results showed that GST and LDH activities were increased and there were concentration-dependent changes in the integrated biomarker response (IBR) indexes after 24-h ABI exposure. However, the examined biomarkers were not useful for examining the effects of the ABI exposure for 96-h exposure periods, even at the highest concentration.
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, Ozlem
Here, 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.
Imidazol-2-ylidene-Pd-PEPPSI complexes containing 4-acetylphenyl side arm: Synthesis, characterization, crystal structure, and applications in Suzuki, Heck and Sonogashira reactions
(Elsevier Science Sa, 2025) Demirci, Ozlem; Celepci, Duygu Barut; Gok, Yetkin; Aktas, Aydin; Ayguen, Muhittin
This study presents the synthesis of new Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation (PEPPSI) type N-heterocyclic carbene (NHC)-Pd(II) complexes featuring a 4-acetylphenyl side arm, which demonstrate stability in the presence of air and moisture and function as homogeneous catalysts. All complexes were characterized using the elemental analysis technique and FTIR, 1H NMR, and 13C NMR spectroscopic methods. In addition, the molecular and crystal structures of the five complexes (2a, 2c, 2d, 2e, 2g) were determined by single crystal X-ray diffraction (SC-XRD). These complexes have been investigated for their catalytic abilities in the Suzuki-Miyaura cross-coupling reactions of aryl chlorides and bromides with aryl boronic acid derivatives, the Heck cross-coupling reactions of aryl bromides with styrene, and the cross-coupling reactions of aryl bromides with phenylacetylene. In addition, we investigated the catalytic activities of some complexes (2e, 2g) in the Sonogashira coupling reaction. The catalytic activities of these homogeneous catalysts in C-C coupling reactions were determined by varying various parameters such as solvent, base, temperature and time. They were found to be active catalysts under these conditions.
Imidazol-2-Ylidene-Silver(I) Complexes Bearing 4-Acetylphenyl Side Arm: Design, Synthesis, Characterization, Crystal Structure, and Inhibitory Properties Against Some Metabolic Enzymes
(Wiley, 2025) Demirci, Ozlem; Demir, Yeliz; Gok, Yetkin; Yakali, Gul; Taskin-Tok, Tugba; Muhammed, Muhammed Tilahun; Aktas, Aydin
Herein, the synthesis of silver(I)-N-heterocyclic carbene (Ag(I)NHC) complexes is presented. These complexes were synthesized from imidazolium salts and silver oxide via the deprotonation method. Ag(I)NHC complexes were characterized using various spectroscopic and analytical techniques, including FTIR, NMR, and elemental analysis. The single crystal structures of the complexes 1e and 1g were illuminated through x-ray crystallography. The study demonstrates that the geometrical characteristics of both complexes closely match those of previously described complexes with a comparable ligand structure. Acetylcholinesterase (AChE) inhibitors prevent the excessive breakdown of acetylcholine by acting on acetylcholinesterase in its neurotransmission. In this way, they help to improve cognitive functions in patients with AD. On the other hand, human carbonic anhydrase inhibitors (CAIs) have been used clinically for many years as antiepileptic, antiglaucoma, antimetastatic, antitumor, and diuretic agents. In this study, the enzyme inhibition abilities of seven imidazol-2-ylidene-silver(I) complexes bearing 4-acetylphenyl side arm were examined against AChE and hCAs. These molecules exhibited a highly potent inhibition effect on AChE and hCAs (Ki values are in the range of 16.27 +/- 1.81 to 130.79 +/- 11.98 nM for AChE, 13.22 +/- 1.88 to 182.14 +/- 33.93 nM for hCA I, and 12.72 +/- 1.99 to 62.36 +/- 9.21 nM for hCA II). Novel imidazol-2-ylidene-silver(I) complexes bearing 4-acetylphenyl side arms 1a-g displayed efficient inhibitory profiles for the examined metabolic enzymes. Docking was additionally performed to investigate the interactions of the current complexes 1a-g with hCA I, hCA II, and AChE proteins. It has been determined that compound 1d has activity against all the tested proteins, with the most effective interaction observed with hCA I. The pharmacokinetic properties of the three top potent complexes for each target against the related proteins were also examined using the SwissADME and pkCSM web tools. In the meantime, the stabilities of the complexes with the highest binding potential according to the docking study were assessed through molecular dynamics simulation. The AChE-1a complex was found to be the one with relatively high stability. Also, further energy computations were made by using the MD simulation results. The compounds have been estimated to bind strongly with their targets.
Imidazolium salts carrying two positive charges: design, synthesis, characterization, molecular docking, antibacterial and enzyme inhibitory activities
(Frontiers Media Sa, 2025) Demirhan, Ilter; Necip, Adem; Oner, Erkan; Gumuscu, Nalin; Demirci, Ozlem; Gok, Yetkin; Doni, Nebiye Yentur
Introduction The discovery of alternative drugs has gained importance due to the many side effects of these drugs used for treatment.Methods Herein, the synthesis of a series of unsymmetrical imidazolium salts containing 4-acetylphenyl/4-formylphenyl and bioactive heterocyclic groups such as morpholine, piperidine, pyrrole or pyridine was reported. 4-(1-H-imidazol-1-yl)acetophenone and 4-(1-H-imidazol-1-yl)benzaldehyde were used as salt precursors. Alkyl halides containing heterocyclic groups such as 2-morpholinoethyl hydrochloride, 2-pyrrolidinoethyl hydrochloride, 2-piperidinoethyl hydrochloride and pyridin-2-ylmethyl bromide hydrobromide were used. Thus, there are two positively charged nitrogens in the structure of these salts synthesized by the quaternization method. The structures of all salts were fully characterized by 1H, 13C NMR, FTIR spectroscopic and elemental analysis methods. the a series of imidazolium salts (1a-d and 2a-d) were designed, synthesized and fully characterized by spectroscopic methods.Results The inhibitory effect against AChE of the series compounds was evaluated as in vitro and in silico studies. The results indicated that the compounds showed remarkably potent inhibitory effects on AChE with K I values ranging from 0.63 +/- 0.04 mu M to 11.23 +/- 1.05 mu M and IC50 values spanning from 0.82 +/- 0.06 mu M to 14.75 +/- 0.82 mu M. The antimicrobial activities of the synthesized compounds were measured by inhibition of bacterial growth expressed as minimum inhibitory concentration (MIC) values. It was observed that the synthesized compounds exhibited antimicrobial activity especially against Gram negative bacteria. In addition, the results of molecular docking studies of bacteria supported our antimicrobial results.Conclusions The results suggested that the synthesized compounds showed the potential to be antimicrobial and acetylcholinesterase inhibitors.
New morpholine or triphenylphosphine-liganded palladium(II) N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, and anticancer activity
(Elsevier Science Sa, 2026) Gok, Yetkin; Ozkan, Gul; Kurucay, Ali; Ates, Burhan; Aktas, Aydin; Demirci, Ozlem; Aygun, Muhittin
A series of morpholine(Morp.)-liganded palladium(II) complexes (1a-c) and triphenylphosphine(PPh3)-liganded palladium(II) complexes (2a-c) bearing 4-fluorobenzyl substituted N-heterocyclic carbene (NHC) were synthesized from NHC-Pd(II)-pyridine and Morp./PPh3 by ligand exchange method. The new complexes were fully characterized using 1H NMR, 13C NMR, 19F NMR, 31P NMR, FTIR spectroscopy and elemental analysis techniques. Furthermore, single crystal X-ray diffraction was used to elucidate the structures of complexes 1a and 2b. The anticancer activities of the new complexes against MCF-7 (Human Breast Cancer) cell line were investigated. With an IC50 value of 37.54 for complex 1a, it can be said that it is more cytotoxic to MCF-7 cells compared to other complexes, while the least cytotoxicity was observed in complex 1b.
New silver N-heterocyclic carbene (NHC) complexes containing fluoro and acetyl groups: design, characterization, molecular docking studies, and inhibition properties against several metabolic enzymes
(Pergamon-Elsevier Science Ltd, 2026) Gok, Yetkin; Demir, Yeliz; Haroon, Muhammad; Sajid, Zaroon; Tezcan, Burcu; Aktas, Aydin; Demirci, Ozlem
This study presents the synthesis of acetyl-and fluorinated group-containing imidazol-2-ylidene silver complexes. The structures of the complexes obtained via deprotonation method were elucidated using spectroscopic techniques such as NMR, FTIR, and MS, as well as elemental analysis. In addition, the enzyme inhibition profiles of the synthesized Ag(I)-NHC complexes were thoroughly investigated against human carbonic anhydrase isoforms I and II (hCAs I and II), as well as acetylcholinesterase (AChE). Notably, compound 2f, bearing 2-chloro and 4-fluoro groups, exhibited superior inhibition potency against hCA I and AChE enzymes, with Ki values outperforming the reference inhibitors acetazolamide (AZA) and tacrine (TAC). These findings suggest that the dual halogenation pattern enhances both electrostatic and hydrophobic interactions within enzyme active sites. In addition, the cytotoxic activity of compound 2f was determined using MTT assays in SH-SY5Y (neuroblastoma), HCT-116 (colorectal carcinoma), and MCF-7 (breast adenocarcinoma) cell lines, yielding IC50 values of 35.63 +/- 0.84 mu M, 49.37 +/- 0.97 mu M, and 54.92 +/- 1.94 mu M, respectively. Further, we examined the inhibition potential of three most potent compounds (2a, 2e and 2f) with in silico molecular docking with three target proteins (hCA I, hCA II, and AChE). The binding energy score and ligand-protein interactions were indicating excellent inhibition potential of examined compounds. Overall, these results highlight the multi-target enzyme-blocking ability of 2f as a promising candidate for suppressing tumor growth.
Palladium(II) Complexes with N-Heterocyclic carbene and morpholine ligands: Synthesis, characterization, and their effects on herg1 potassium channel gene expression in the MCF-7 breast cancer cells
(Elsevier, 2026) Eroglu, Pelin; Gok, Yetkin; Izmirli, Merve; Demirci, Ozlem; Kazak, Canan
Acetylphenyl and various fluorinated alkyl-functionalized imidazol-2-ylidene carbene complexes of Pd(II) were prepared by the reaction of dibromo[1-(4-acetylphenyl)-3-(fluorinatedalkyl)imidazole-2-ylidene]pyridinepalladium(II) with morpholine in dichloromethane. The structures of the synthesized complexes were characterized using spectroscopic such as 1H, 13C, 19F NMR, and FT-IR and elemental analysis techniques. The Pd(II) complex 2d, incorporating an N-heterocyclic carbene (NHC) and morpholine ligand, was structurally characterized by Xray crystallography. The crystal packing reveals N-H & ctdot;Br hydrogen bonds, C-H & ctdot;F/O interactions, and C-F & ctdot;it stacking, forming a 3D network stabilized by supramolecular interactions. The cytotoxicity of the synthesized compounds (2a-f) was evaluated using the MCF-7 cell line. The anticancer activity of palladium complexes against MCF-7 cells was revealed with IC50 values ranging from 48.13-151.02 mu M. The effect of complex 2b on the gene expression of the hERG1 K+ channel was determined using the RT-qPCR method. hERG1 potassium channel gene expression decreased at the 50 mu M complex 2b concentration at 24 h.
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, Muhittin
This 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.
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, Yetkin
A 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.
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, Muhittin
Chloro-/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.

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