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Öğe Comparative chemical and biological evaluation of Urtica dioica extracts obtained by methanol and hexane: antioxidant, cytotoxic, apoptotic, and antimicrobial potentials(Bmc, 2025) Ugur, Yilmaz; Menevse, Irem Nur; Dundar, Muhammed; Karci, Huseyin; Zengin, Rukiye; Guzel, AbdussamatBackground Urtica dioica L. is a widely utilized medicinal plant with potential antioxidant, cytotoxic, and antimicrobial properties. Methods This study aimed to investigate its multi-target biological activities across four cell lines (A549, MDA-MB-231, HCT116, and BEAS-2B) while evaluating the impact of two extraction solvents (acidified methanol and hexane) on activity outcomes. Results The acidified methanolic extract exhibited higher total phenolic (61.25 +/- 3.07 mg GAE/g) and flavonoid (51.20 +/- 2.01 mg CE/g) content, correlating with superior antioxidant activity (DPPH: 84.36 +/- 1.50 mg TE/g; CUPRAC: 174.04 +/- 9.54 mg TE/g). In contrast, the hexane extract demonstrated stronger cytotoxicity across cancer cell lines (IC50: 3.10-4.12 mu g/mL), along with significant induction of apoptosis and G0/G1 cell cycle arrest, despite lower antioxidant capacity. In addition, both extracts increased the protein levels of p21 and cleaved caspase-3, suggesting involvement of cell cycle inhibition and activation of intrinsic apoptotic signalling pathways. Moderate antimicrobial activity was also observed, with inhibition zones ranging from 7 to 10 mm across bacterial and fungal strains. Conclusions These findings highlight the bioactive potential of U. dioica and the critical role of extraction solvent in modulating its total phenolic and flavonoid contents and biological effects. The observed upregulation of p21 and cleaved caspase-3 further supports the notion that U. dioica extracts may exert antiproliferative activity through p21-mediated cell cycle control and caspase-dependent apoptosis. Further in vivo studies and mechanistic investigations are needed to confirm these observations and clarify their potential therapeutic relevance.Öğe Direct arylation (hetero-coupling) of heteroarenes via unsymmetrical palladium-PEPPSI-NHC type complexes(Pergamon-Elsevier Science Ltd, 2021) Nawaz, Zahid; Gurbuz, Nevin; Zafar, Muhammad Naveed; Tahir, Muhammad Nawaz; Ashfaq, Muhammad; Karci, Huseyin; Ozdemir, IsmailThe growing interest of industry in the field of bi(hetero)arenes compounds, motivated us to synthesize these compounds via homogeneous catalytic route by using Pd PEPPSI-type complexes through direct arylation. In this work, the five new Pd PEPPSI-type complexes bearing NHC spectator ligands were synthesized and characterized by a bunch of spectroscopic techniques. Further confirmations of structural details were provided by a single crystal X-ray diffraction study of one pro-ligand and one complex. All these newly synthesized Pd-carbene complexes were found significantly active as catalysts toward direct arylation of five members heterocyclic compounds such as n-propylthaizole, 2-acetylfurane and 2-acetylthiophene with aryl bromides derivatives. These catalysts give significantly good results within two hours with just 1 mol % catalyst loading.Öğe Exploring the antimicrobial potential of new selenium- N-heterocyclic carbene complexes and their benzimidazolium salts: synthesis, characterization, biological evaluation, and docking insights(Springer Int Publ Ag, 2025) Boualia, Boutheina; Sandeli, Abd el-Krim; Boulebd, Houssem; Karci, Huseyin; Dundar, Muhammed; Ozdemir, Ilknur; Gurbuz, NevinThe present work, describes the synthesis and antimicrobial evaluation of new selenium-NHC adducts (3a-e) and their corresponding benzimidazolium salts (2a-e). Specific synthetic approaches were employed, resulting in compounds with satisfactory stability under humid and aerated conditions. Characterization by spectroscopic methods confirmed structural changes upon selenium incorporation. Biological evaluations revealed varying antimicrobial and antifungal activities among the synthesized compounds. The results indicated that the benzimidazolium salts exhibited significantly enhanced antimicrobial and antifungal activities compared to reference agents. For instance, compound 2a demonstrated an IC50 value of 6.25 mu g/mL against Candida albicans, which was comparable to the reference Caspofungin (6.25 mu g/mL). Similarly, compound 2e demonstrated strong antibacterial activity against Staphylococcus aureus, with an IC50 value of 0.8 mu g/mL, significantly outperforming the reference Ampicillin (1.56 mu g/mL). In contrast, the selenium-NHC adducts exhibited moderate to minimal activity, with compound 3e showing the highest IC50 value of 25 mu g/mL against Staphylococcus aureus, but failing to surpass the activity of the reference agent. To explore the potential mechanism of action, molecular docking studies were conducted against Escherichia coli DNA gyrase and CYP51. The molecular docking results demonstrate that synthesized compounds exhibit significant binding affinity against both enzymes, indicating antibacterial and antifungal potential. These binding affinities suggest that these molecules could be effective dual-action antimicrobial agents.Öğe N-alkylbenzimidazole silver(I) complexes: Synthesis, biological evaluation and molecular docking study(Pergamon-Elsevier Science Ltd, 2024) Ari, Erkan; Sahin, Neslihan; Ustun, Elvan; Dundar, Muhammed; Karci, Huseyin; Ozdemir, Lknur; Koc, AhmetA series of N-alkylbenzimidazole silver(I) complexes were synthesized and fully characterized by FT-IR, Mass, 1H, 13C{1H} NMR spectroscopy, and elemental analysis. Synthesized N-alkylbenzimidazole silver(I) complexes were investigated for their antimicrobial activities against bacteria Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and the fungal strains Candida albicans and Candida glabrata. All the complexes (2a-f) showed higher antimicrobial activity against bacteria than fungi strains. In particular, complexes 2b and 2e showed comparable activity to Ampicillin against Escherichia coli. Also, all complexes showed better activity than Ampicillin against Pseudomonas aeruginosa. The complex 2e showed remarkable activity against Candida albicans (12.5 mu g/mL) and Candida glabrata (25 mu g/mL). The molecules that were first optimized by DFT-based calculation methods were also analyzed by molecular docking methods against DNA gyrase of E. Coli, CYP51 from Candida glabrata, and Penicillin Binding Protein-3.Öğe Novel benzimidazolium salts and their silver(I)-N-heterocyclic carbene complexes: synthesis, characterization and their biological properties(Taylor & Francis Ltd, 2023) Belhi, Zeyneb; Karci, Huseyin; Dundar, Muhammet; Gurbuz, Nevin; Ozdemir, Ilknur; Koc, Ahmet; Cheriti, AbdelkrimThis study was conducted to synthesize and characterize 1,3-dialkyl-5,6-dimethyl-benzimidazolium salts and their silver complexes. Four novel silver(I)-N-heterocyclic carbene complexes were synthesized and characterized by mass analyses, FT-IR and NMR spectroscopy. The biological capacity of the synthesized compounds was evaluated in vitro for their antimicrobial and antitumor activities. The minimum inhibitory concentration (MIC) of the 1,3-dialkyl-5,6-dimethyl-benzimidazolium salts and their complexes was determined for E. coli, P. aeruginosa, S. aureus, C. glabrata and C. albicans in vitro through BMD (Broth Microdilution). The results indicated that silver(I)-NHC complexes exhibit antimicrobial activity. In particular, complex 3c presented a significant broad-spectrum antimicrobial activity. The anticancer properties of the synthesized compounds were evaluated against MCF-7, HCT116, SH-SY5Y and BEAS-2B cell lines. Anticancer activity measurements were carried out according to the Alamar Blue assay. Efficacy was established by comparison of the salts and silver compounds with cisplatin.Öğe Novel N-heterocyclic carbene silver(I) complexes: Synthesis, structural characterization, antimicrobial and cytotoxicity potential studies(Elsevier Science Sa, 2025) Karaca, Emine Ozge; Mizrak, Ebru; Gurbuz, Nevin; Cetinkaya, Erdem; Karci, Huseyin; Dundar, Muhammed; Ozdemir, IlknurIn this study, a new series of 1-(2-ethylhexyl)-3-(alkyl)-5,6-dimethylbenzimidazol-2-ylidene]silver(I) complexes has been synthesized and investigated their in vitro antibacterial, antifungal and anticancer properties. All molecules were characterized by 1H NMR, 13C NMR, and IR spectroscopy techniques. In vitro antimicrobial activity of the synthesized compounds investigated in this work was tested against the reference strains: Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 29213) and Pseudomonas aeruginosa (ATCC 27853), Candida albicans (ATCC MYA-2876) and Candida glabrata (ATCC 2001). Anticancer properties of samples were evaluated against A549, HCT116 and BEAS-2B cells lines. All silver-NHC complexes showed antibacterial activity against the tested bacterial and fungal strains.Öğe Silver (I)-N-heterocyclic carbene complexes: Synthesis and characterization, biological evaluation of Anti-Cholinesterase, anti-alpha-amylase, anti-lipase, and antibacterial activities, and molecular docking study(Elsevier Science Sa, 2021) Sandeli, Abd El-Krim; Khiri-Meribout, Naima; Benzerka, Saida; Gurbuz, Nevin; Dundar, Muhammed; Karci, Huseyin; Bensouici, ChawkiA series of novel silver(I)-N-heterocyclic carbene complexes have been prepared and fully characterized by spectroscopic methods and X-ray crystallographic analyses. The biological capacity of the synthesized compounds was evaluated in vitro for their anti-microbial, anti-cholinesterase, anti-lipase, anti-diabetic activities in search of potent inhibitors compound. All compounds were tested against two types of fungi and three bacterias. The results proved that most compounds indicated moderate to excellent activity against all types of bacteria and fungi except compound 2f that didn't show any antibacterial activity. The synthesized compound's capacity to inhibit the enzymes AChE, BChE, Lipase, and alpha-amylase were evaluated. The results showed that silver(I)-NHC complexes 3a-f are effective against all types of enzymes. The highest activity was reported toward AChE, BChE, and alpha-amylase enzymes, and at a lower rate against Lipase enzyme compared to the references drug. In contrast, benzimidazolium salts 2a-f, which showed significant inhibitory activity against AChE and BChE enzymes, while all salts were not active against both Lipase and alpha-amylase enzymes. Molecular docking simulations using AutoDock, have been performed of the new compounds as a representative set of our molecules into AChE and BChE enzymes for lead optimization of the binding interaction template of the most active inhibitors docked into the active site of their relevant AChE and BChE enzymes inhibitors.Öğe Synthesis of new imidazolidine derivatives: Characterization, anti-cancer potential and molecular docking(Elsevier, 2025) Slimani, Ichraf; Karci, Huseyin; Dundar, Muhammed; Ustun, Elvan; Ozdemir, Lknur; Gurbuz, Nevin; Koc, AhmetCreating safe and effective anticancer pharmaceuticals with an imidazolidine heterocyclic ring was the goal of this project. Starting with 1-(2-hydroxypropyl)imidazoline and N, N-dimethylformamide dimethyl acetal, substituted-imidazolidine derivatives (3a-h) have been generated. The anti-tumor potential of the imidazolidine derivatives (3a-h) was further investigated using the human colon cancer cell line HCT116 and the human neuroblastoma cell line SH-SY5Y. All of the synthesized compounds, except for All synthesized compounds, except for the salt 3f (1-(2-hydroxypropyl)-3-(3,4,5-trimethoxybenzyl) imidazolinium chloride) which was not active against the HCT116 cancer cell line, were active against the two cell lines. According to the results of biological tests, the inhibitory concentration (IC50) values ranged from 45.44 mu M to 663.73 mu M. The salt 3 g showed the highest anticancer effect, particularly against the HCT116 cancer cell line, with a selectivity index reaching 2.75. Also, optimized molecules were analyzed by molecular docking methods against crystal structures of Vascular Endothelial Growth Factor Receptors (VEGFR2) and Cytochrome P450 17A1, and their binding affinities, interaction details and inhibition constants were determined. The molecules were additionally evaluated for possible drug-likeness and bioavailability scores which include absorption, distribution, metabolism, excretion and toxicity aspects.Öğe Synthesis, characterization, and anticancer potential of novel NHC ligands and their selenium complexes: a combined in vitro and in silico investigation(Royal Soc Chemistry, 2025) Boualia, Boutheina; Sandeli, Abd el-Krim; Evren, Enes; Ozdemir, Ismail; Karci, Huseyin; Dundar, Muhammed; Ozdemir, IlknurWe report herein the efficient synthesis of new benzimidazolium salts (A1-A6) and their corresponding selenium-NHC complexes (B1-B6), along with the evaluation of their cytotoxicity profiles against two cancer cell lines (HCT116 and SH-SY5Y) and one normal cell line (BEAS-2B). The findings revealed that the benzimidazolium salts (A1-A6) exhibited significantly higher cytotoxicity toward all tested cell lines compared to their selenium derivatives (B1-B6). Among them, compounds A3, A4, and A5 showed the most potent cytotoxic effects, with IC50 values ranging from 3.09 to 26.12 mu M, approximately ten times lower than that of cisplatin. However, these compounds also exhibited relatively low IC50 values in normal BEAS-2B cells, although still higher than those observed in the cancer cell lines, indicating a preferential cytotoxicity toward cancer cells. Structure-activity relationship analysis revealed that the benzimidazolium core acts as the pharmacophore of these compounds, while substitution on the aromatic ring-particularly with bulky groups-enhances cytotoxicity. Conversely, incorporation of the selenium atom was found to markedly reduce or even eliminate cytotoxicity up to concentrations of 800 mu M. Further in silico studies were conducted to gain a deeper understanding of the molecular structures and chemical reactivity of these compounds. In addition, molecular docking studies against PARP-1 and tubulin highlighted the strong inhibitory potential of the most active compounds (A3, A4, and A5) toward both targets, suggesting their potential involvement in the observed cytotoxic effects. Overall, these investigations propose benzimidazolium salts A3, A4, and A5 as promising anticancer agents and highlight the selenium derivatives as non-toxic selenium-based NHC complexes. Further studies should be undertaken to optimize the biological activity of these compounds and to enhance their selectivity toward cancer cells.Öğe Sythesis, characterisation, anticancer and antimicrobial activity of Ag-N-heterocyclic carbene complexes containing benzimidazole derivatives(Elsevier Science Sa, 2024) Karci, Huseyin; Dundar, Muhammed; Nawaz, Zahid; Ozdemir, Lknur; Gurbuz, Nevin; Koc, Ahmet; Ozdemir, IsmailTo prepare a novel series of silver(I) complexes, the interaction of benzimidazolium salts having their two nitrogen atoms substituted by bulky groups with Ag2O in DCM has been carried out. Their structures were characterized by elemental analyses, 1H NMR, 13C NMR, elemental analysis, and IR spectroscopy techniques. Further, the antimicrobial and antifungal activities properties of both the salts and their silver(I)-NHC complexes were tested against positive and negative bacteria using the Clinical and Laboratory Standards Institute (CLSI) and the European Committee for Antimicrobial Susceptibility Testing (EUCAST) respectively. The results show that silver complexes are effective against E. coli, P. aeruginosa and S. aureus bacterial species with moderate to high activity, and their minimum inhibitory concentrations ranging from 25 to 400 mu g/Ml. It was also observed that 3b compound, which has the best antifungal properties among the synthesized compounds, showed high antimicrobial activity when all bacterial species were taken into account. In addition, the salts and complexes were then evaluated for their ability to inhibit the proliferation of four different cancer cell lines (A549, MCF-7, HCT116, SH-SY5Y and BEAS-2B cells lines). AlamarBlue assay demonstrated that the salts and complexes exhibited potent cytotoxicity towards all cancer lines. 2c compound showed the highest cytotoxic activity against BEAS-2B, A549 and MCF-7 cell lines. Except for 2c, compounds 3d, 3e and 3f showed cytotoxic activity at the lowest concentrations against MCF7 cell line.The study highlights the importance of N-heterocyclic carbene ligands in the development of silver-based drugs with anticancer properties.Öğe Tris(benzimidazole)(nitrato)silver(I) complexes: Synthesis, catalytic activities, and biological evaluation(Elsevier, 2026) Boubakri, Lamia; Hallab, Wissem; Karci, Huseyin; Attour, Anis; Dundar, Muhammed; Ozdemir, Lknur Lknur; Gurbuz, NevinIn this study new N-alkylbenzimidazole derivatives 1a-e and their related tris(benzimidazole)(nitrato)silver(I) complexes 2a-e were prepared and characterized by FT-IR, 1H,13C{1H} NMR spectroscopy, and elemental analysis, which support the proposed structures. Further confirmations of structural details were provided by a single-crystal X-ray. A single crystal of tris(N-alkylbenzimidazole)(nitrato)silver(I) 2e shows that the coordination geometry around Ag slightly distorted tetrahedral geometry. Further, the synthesized compounds were evaluated for their antimicrobial activities against bacteria Escherichia coli, P. aeruginosa, S. aureus, and the fungal strains C. albicans and C. glabrata. The results indicated that the activity shown by the tested compounds, especially against Gram-negative bacteria, is valuable for the development of new treatment options against these microorganisms. Especially, the drug development potential of N-alkyl-5,6-dimethylbenzimdazole 1b and complexes 2b, 2c, and 2e showing the highest antimicrobial activity. Also, the alkylbenzimidazole substituent 1b and 1e and the Tris(1-alkylbenzimidazole)silver(I) 2c showed remarkable activity against fungi strains. Complexes 2a, 2b, 2c, 2d, and 2e also showed high cytotoxicity. The synthesized complexes demonstrated higher cytotoxicity relative to Cisplatin across all tested cell lines. Furthemore, a mild catalytic protocol for benzaldehyde, amine, and phenylacetylene coupling (A3-coupling) allows for the selective synthesis of propargyl amines using N-alkylbenzimidazole silver(I) nitrate catalysts with conversion of 100 %. The present approach is environmentally benign and water is generated as the sole by product.
