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    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, Morteza
    This 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.
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    Novel 2-methylimidazolium salts: Synthesis, characterization, molecular docking, and carbonic anhydrase and acetylcholinesterase inhibitory properties
    (Academic Press Inc Elsevier Science, 2020) Bal, Selma; Kaya, Ruya; Gok, Yetkin; Taslimi, Parham; Aktas, Aydin; Karaman, Muhammet; Gulcin, Ilhami
    In this work, structures of different imidazolium compounds were designed and synthesized. These compounds were synthesized from 2-methylimidazole and alkyl/aryl halides. Their structures were characterized by using H-1 NMR, C-13 NMR, FTIR spectroscopic techniques. All the synthesized compounds were tested for their inhibition activities on different enzymes. Inhibition experiments gave good and moderate results, proving their activities of these compounds as anticholinergics potential. These obtained novel 2-methylimidazolium salts (1a-e and 2a-e) molecules were effective inhibitors of the carbonic anhydrase I and II isozymes (hCA I and II) and acetylcholinesterase (AChE) enzymes with Ki values in the range of 26.45 +/- 6.49-77.60 +/- 9.53 nM for hCA I, 27.87 +/- 5.00-86.61 +/- 5.71 nM for hCA II, and 1.15 +/- 0.19-8.89 +/- 0.49 nM for AChE, respectively. AChE enzyme inhibitors are the most common drugs applied in the therapy of diseases such as senile dementia, Alzheimer's disease, ataxia, Parkinson's disease, and among others.
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    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.
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    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.
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    Synthesis and characterization of some Schiff bases, their metal complexes and thermal, antimicrobial and catalytic features
    (Springer, 2015) Bal, Selma; Orhan, Betul; Connolly, Joseph Donald; Digrak, Metin; Koytepe, Suleyman
    Two pyridine carboxaldehyde-derived schiff bases and their copper, nickel and manganese complexes have been synthesized, characterized by spectroscopic and thermal analyses. For the antimicrobial activity experiments, the microorganisms B. megaterium, K. pneumoniae, E. coli, P. aeruginasa, S. aureus, B. subtilis and E. aerogenes have been used. Nickel and copper complex compounds of ligand L-2 were recorded as the most effective coordination compounds as antimicrobial. Catalytic activity results revealed that the both manganese and nickel complexes were moderately more effective for the oxidation reactions of cyclohexene and styrene.
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    Synthesis of carbazole-derived ligands and their metal complexes: characterization, thermal, catalytic, and electrochemical features
    (Springer Wien, 2016) Bal, Selma; Koytepe, Suleyman; Connolly, Joseph D.
    Heading from N-ethylcarbazole, two novel carbazole-derived imine compounds and their copper, cobalt, and nickel complexes have been synthesized. Their open structures have been proposed on the basis of various spectroscopic analyses. All the synthesized compounds have also been examined for their catalytic, thermal, and electronic features. Good or moderate results have been obtained for the catalytic activities of the synthesized complexes. Thermal features showed that the coordination compounds can be used in many organic reactions like oxidation reactions depending on high temperatures. Electronic features of these newly synthesized compounds have also been reported for the first time with this paper.
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    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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    Synthesis, characterization, crystal structure, biological activities, and molecular docking study of the (NHC)Pd(II)(Morp) (NHC: N-heterocyclic carbene, Morp: Morpholine) complexes
    (Pergamon-Elsevier Science Ltd, 2024) Aktas, Aydin; Taslimi, Parham; Bal, Selma; Celepci, Duygu Barut; Gok, Yetkin; Taskin-Tok, Tugba; Aygun, Muhittin
    In this paper, a new palladium -based (NHC)Pd(II)(Morp) complexes (NHC: N -heterocyclic carbene, Morp: morpholine) were prepared. The NHC ligand in these complexes bears the 2-chloro-4-fluorobenzyl group. All complexes were fully characterized by 1 H, 13 C NMR, FTIR spectroscopic and elemental analysis methods. The crystal structure of complex 1f has been determined by using single-crystal X-ray diffraction. Furthermore, all complexes were investigated for their ability to inhibit enzymes. All complexes exhibited highly potent inhibition effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes (K i values are in the range of 97.84 +/- 8.97 to 132.28 +/- 11.63 mu M and 18.24 +/- 2.08 to 39.08 +/- 5.28 mu M for AChE and BChE, respectively). Designing of reported complexes is impacted by molecular docking study, because with molecular docking study, it will lead to future researches by illuminating the interaction mechanism of complexes 1a , 1b , 1c and 1f with potential activity against target AChE and BChE enzymes at molecuar level.