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Öğe Anticancer, antioxidant, DFT calculations, and docking studies of some new peptide-indole conjugates(Acg Publications, 2024) Kucukbay, Hasan; Gonul, Zeynep; Kurucay, Ali; Ates, Burhan; Boulebd, Houssem; Kucukbay, F. ZehraIn this study, the structures of six new peptide-indole derivatives were elucidated through spectroscopic and analytical methods following their synthesis. In addition to their anticancer and antioxidant properties, density functional theory (DFT) calculations and docking studies were conducted for the compounds. According to the obtained results, compounds 1 and 3 were identified as the most active against the MCF-7 cell line, with IC50 values of 8.72 and 5.86 mu g/mL, respectively. Conversely, compounds 4 and 1 were found to be the most active against the A549 cell line, with IC50 values of 15.43 and 16.10 mu g/mL, respectively. When compared to standard antioxidants using both the DPPH and iron reduction power assays, the compounds did not exhibit significant antioxidant activity. The molecular geometry and electronic properties of the synthesized peptide-indole derivatives were investigated through theoretical calculations using the Density Functional Theory (DFT) method. Molecular docking studies were also conducted to investigate the binding modes of the synthesized compounds within the active sites of EGFR enzyme.Öğe Bridged NHC-Pd(II) complexes: Synthesis, DFT calculations, molecular docking, and investigation of catalytic and biological activities(Elsevier Science Sa, 2024) Firat, Tuba; Bugday, Nesrin; Yasar, Seyma; Boulebd, Houssem; Mansour, Lamjed; Koko, Waleed S.; Hamdi, NaceurSix palladium(II) ( 3a -f ) complexes of the type [Pd 2 ( mu-Cl) 2 (NHC)] were prepared by transmetallation of the corresponding Ag-NHC and [PdCl 2 (CH 3 CN) 2 ] complexes, and their structures were successfully characterised by 1 H NMR, 13 C NMR, HRMS, FTIR and elemental analysis. Density functional theory (DFT) calculations were also realised for the complexes. The prepared complexes were assessed for their catalytic activity in the C -H arylation of 2-isobuthylthiazole as well as for their biological activities. As results, these complexes were found to be potent catalysts in the creation of C5-arylated 2-isobuthylthiazole derivatives via C -H bond activation reaction. Furthermore, biological activity analysis revealed that complex 3a exhibits high cytotoxicity towards both human colon carcinoma cell lines (HCT-116) and hepatocellular carcinoma cell lines (HepG-2) with IC 50 values of 4.2 and 9.3 mu MmL -1 , respectively. Complex 3b also showed antioxidant activity comparable to that of BHT through DPPH and ABTS assays. Both complexes 3d and 3f also showed significant inhibitory activity towards the AChE enzyme with IC 50 values of 5.06 and 2.52 mu MmL -1 , respectively. Finally, all complexes showed excellent antiparasitic activity, with 3b exhibiting strong antileishmanial activity against both L. major promastigotes and amastigotes. The interaction between the most cytotoxic complexes and DNA, envisaged as a potential mechanism of toxicity, was explored by means of docking studies. In summary, these prepared complexes have the potential to serve as potent catalysts for the synthesis of arylated 2-isobutylthiazole and biologically active agents, paving the way for numerous prospects in the fields of medicinal chemistry and organic synthesis.Öğe Exploring the anticancer potential of new 3-cyanopyridine derivatives bearing N-acylhydrazone motif: Synthesis, DFT calculations, cytotoxic evaluation, molecular modeling, and antioxidant properties(Wiley, 2024) Kadi, Ibtissem; Sekerci, Guldeniz; Boulebd, Houssem; Zebbiche, Zineddine; Tekin, Suat; Benarous, Khedidja; Serseg, Talia3-Cyanopyridine derivatives are known for exhibiting excellent anticancer activity due to their strong capability to inhibit various biological targets, including Pim-1 kinase, survivin, and tubulin polymerization. On the other hand, N-acylhydrazones (NAH) are known to be a very versatile motif in medicinal chemistry and drug design. Based on these data, we report in this paper, the synthesis of novel 3-cyanopyridines incorporating N-acyl hydrazine scaffold, the evaluation of their cytotoxicity on the breast (MCF-7) and ovarian (A-2780) cancer cell lines and their antioxidant properties. Excluding 4a and 4d, all tested molecules exhibited high cytotoxicity against A-2780, with IC50 values ranging from 1.14 to 1.76 mu M. Conversely, only four molecules 3d, 4b, 4c, and 4d demonstrated cytotoxicity against MCF-7, with IC50 values ranging from 1.14 to 3.38 mu M. On the other hand, all the tested molecules exhibited a moderate antioxidant capacity in both the DPPH and metal chelation assays. Docking and molecular dynamics studies revealed that 2d, 3d, and 4d are potential inhibitors of tubulin and the oe strogen receptor, which may explain their high cytotoxicity. These results are promising to study these newly synthesized 3-cyanopyridine-N-acylhydrazones in depth for use as potential anticancer candidates. A series of novel N-acetylhydrazone motifs-containing 3-cyanopyridine derivatives were synthesized, and their anticancer properties against MCF-7 and A2780 cancer cell lines, along with their antioxidant capacities, were investigated under in vitro conditions. Additionally, density functional theory (DFT) calculations and molecular modeling were conducted in silico. imageÖğe 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 Microwave Synthesis, Evaluation, and Docking Study of Amino Acid Derivatives of 7-Chloroquinoline: Exploring Cytotoxic and Antioxidant Potentials(Amer Chemical Soc, 2026) Ezugwu, James A.; Kucukbay, Fatumetuzzehra; Oz, Samet; Keskin, Tuba; Boulebd, Houssem; Tekin, Suat; Kucukbay, HasanNew carbamate and amino acid derivatives of 7-chloroquinoline were synthesized and characterized using FTIR, 1H NMR, 13C NMR, and HRMS analysis. The synthesized compounds were obtained through a benzotriazole-mediated approach via microwave synthesis and evaluated for antioxidant and anticancer activities. All the synthesized compounds have antioxidant properties though less than those of the standard. Cytotoxic activities of new 7-chloroquinolinyl benzyl amino carbamate derivatives were accessed using LNCaP (Lymph Node Carcinoma of the Prostate), A2780 (human ovarian cancer), and MCF-7 (breast cancer) cell lines. For cytotoxicity research, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay was used. The synthesized compounds were subjected to a cell viability assay, and following a 24 h treatment, the IC50 values were determined. Among all the tested compounds, compound 4b demonstrated comparable antitumor activity against LNCaP, A2780, and MCF-7 cell lines when compared to the standard drug docetaxel with IC50 values of 6.61, 2.81, and 5.69 mu g/mL for LNCaP, A2780, and MCF-7 cell lines, respectively. A molecular docking study targeting the beta-tubulin enzyme revealed that compounds 4a, 4b, and 5b exhibit a high affinity for the taxane binding site and may mimic the action of docetaxel.Öğe New benzimidazolium N-heterocyclic carbene precursors and their related Pd-NHC complex PEPPSI-type: Synthesis, structures, DFT calculations, biological activity, docking study, and catalytic application in the direct arylation(Elsevier, 2022) Sandeli, Abd El-Krim; Boulebd, Houssem; Khiri-Meribout, Naima; Benzerka, Saida; Bensouici, Chawki; ozdemir, Namik; Gurbuz, NevinNew benzhydryl-5,6-dimethyl-(3-methylbenzyl)benzimidazolium salt as N-heterocyclic carbene precursors and their related new Pd-NHC complex PEPPSI-type with the general formula [PdBr2(NHC)(pyridine)] were prepared and theoretically studied. Quantum chemistry computations at the B3LYP/6-311G(d,p)/LANL2DZ level were used to examine the molecular structure, electronic characteristics, and chemical reactivity of the ligand and its Pd complex. Further, the structural characterization of the complex (c) was determined by a single-crystal X-ray diffraction study, which supports the proposed structures and offered a more detailed structural characterization. In addition, their biological activity against. cholinesterase enzymes were also determined. The new compounds were tested against two enzymes (AChE and BChE), furthermore, docking studies were carried out in order to gain a better understanding of the bonding modes of L and COP in the active sites of AChE and BChE enzymes. The new salt and Pd-NHC complex PEPPSI-type were fully characterized by spectroscopic and analytical methods. The new Pd-catalysts based N-heterocyclic carbene ligand PEPPSI-Type was applied by the direct arylation process of five-membered heteroaromatics such as thiophene, and furan derivatives with various (hetero)aryl bromides in the presence of 1 mol% catalyst, using KOAc as a co-catalyst. The results showed that the new Pd-NHC complex is an effective catalyst. (C) 2021 Elsevier B.V. All rights reserved.Öğe Pd-NHC complex catalyzed C-H bond activation reactions of caffeine and 2-isobuthylthiazole(Elsevier, 2022) Bugday, Nesrin; Khan, Siraj; Yasar, Sedat; Bulut, Fatih; Boulebd, Houssem; Karabiyik, Hande; Karabiyik, HasanA series of new Pd-NHC complexes were synthesized, characterized, and utilized as catalysts on 8-(hetero)ary-lation of xanthines and C-5 (hetero)arylation of 2-isobuthylthiazole. All the synthesized derivatives were characterized by NMR, Q-TOF-LC/MS, FTIR, and X-ray (for 4a, 5a, and 5b) analysis. In addition, DFT calculations and computational NBO studies for Pd-NHC complexes were examined, and HOMO and LUMO energy levels and electron density of each Pd-NHC complex were defined. 4a-c and 5a-b complexes showed good catalytic activity in C-H bond activation reactions. DFT studies have also been conducted to examine the reaction mechanism following the CMD pathway. Complex 5a was chosen as a representative catalyst for the reaction of unsubstituted phenyl with caffeine and 2-isobuthylthiazole. Although the delta E values of the complexes are so close, slight difference in the catalytic activity were observed for 4a-c and 5a-b. Since this low delta E value facilitates the oxidative addition reaction of (hetero)aryl bromides, thanks to this catalytic system, new 8-(hetero)aryl xan-thines and 5-(hetero)aryl thiazole derivatives could be synthesized with high yields and low catalyst loading.Öğe Preparation, DFT calculations, docking studies, antioxidant, and anticancer properties of new pyrazole and pyridine derivatives(Wiley, 2022) Zebbiche, Zineddine; Sekerci, Guldeniz; Boulebd, Houssem; Kucukbay, Fatumetuzzehra; Tekin, Suat; Tekin, Zehra; Kucukbay, HasanSeven novel pyrazole derivatives (4a-g) and four novel starting compounds incorporating substituted pyridine moieties were synthesized successfully. Cell viability assay for the tested compounds was performed, and the inhibitory concentrationlogarithmic 50 (LogIC(50)) values of the compounds were calculated after a 24-h treatment. Four of the examined compounds (3d, 3g, 4f, and 4g) showed comparable cytotoxic activity against CaCo-2 compared to the standard drug docetaxel at 0.1 and 1 mu M concentrations. Although the LogIC(50) of docetaxel was -0.678 mu M for CaCo-2 cells at 24 h, the LogIC(50) values of compounds were -0.794, -0.567, -0.657, and -0.498 respectively. Five of the compounds (2d, 2g, 3d, 3g and 4e) showed comparable cytotoxic activity against MCF-7 at 0.1 mu M concentration compared to docetaxel (p < 0.05). Docking studies revealed the compounds have a good affinity to the active site of the human topoisomerase II beta enzyme. The antioxidant capacities of all compounds were determined using both 1,1-diphenyl-2-picrylhydrazyl and metal chelation methods. Although the compounds did not show significant antioxidant activity, relatively effective are compounds 3c, 3d, and 3g, which are hydrazine derivatives with approximately 50% antioxidant activity of standard antioxidants at concentrations of 62.5 and 125 mu g/ml.Öğe Synthesis, Cytotoxicity, Antioxidant Activity, DFT Calculations, and Docking Studies of New Pyridine-Malonate Derivatives as Potential Anticancer Agents(Taylor & Francis Ltd, 2023) Kadi, Ibtissem; Guldeniz, Sekerci; Boulebd, Houssem; Zebbiche, Zineddine; Tekin, Suat; Kucukbay, Fatumetuzzehra; Gonul, ZeynepA series of new pyridine-malonate derivatives were synthesized and fully characterized by 1HNMR, 13CNMR, FTIR, and elemental analysis. Their molecular geometry and chemical reactivity have been investigated using DFT calculations. The cytotoxicity of all synthesized compounds was assessed against two human cancer cell lines (MCF-7 and A-2780) using the MTT assay. Among them, compounds 2a, 2c, 2e, and 2g showed comparable or more potent cytotoxicity toward the MCF-7 cells than the reference drug docetaxel (IC50 = 0.34-0.47 vs. 0.50 mu M). In contrast, only compound 2g showed more potent cytotoxicity against the A-2780 cell line compared to the standard (IC50 = 0.36 vs. 0.42 mu M). The docking study revealed a good affinity for the active site of the human topoisomerase-II beta enzyme, which may explain the promising cytotoxicity of these classes of molecules. The radical scavenging activity of the respective compounds was studied using DPPH radical scavenging assay and it was found that most of the compounds are moderate DPPH radical scavengers compared to the standard drugs BHA and BHT.Öğe Synthesis, DFT calculations, and investigation of catalytic and biological activities of back-bond functionalized re-NHC-Cu complexes(Wiley, 2024) Yagmurlu, Ayse; Bugday, Nesrin; Yasar, Seyma; Boulebd, Houssem; Mansour, Lamjed; Koko, Waleed S.; Hamdi, NaceurFive copper complexes (3a-e) stabilized by ring-expanded back-bond functionalized N-heterocyclic carbene ligands (re-NHCs) were produced in the glovebox by reacting free re-NHC with CuI precursor. The potential of these re-NHC-Cu complexes as catalysts on the synthesis of mono- and di-(1,4-disubstituted-1,2,3-triazoles) by Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reactions was investigated. Various spectroscopic approaches were utilized to completely characterize the structures of the re-Cu-NHC complexes. Furthermore, density functional theory (DFT) calculations were carried out to get further insights into their molecular geometry and CuAAC reaction mechanism. The re-NHC-Cu complexes showed high activity on the CuAAC reaction in an open-air atmosphere at rt. The Gibbs free energies as well as the optimized geometries of the intermediates and the transition states of the determining step of the reactions catalyzed by 3a, 3e, and 3b complexes were computed. Complex 3e was found to be the most efficient catalyst among these re-NHC-Cu complexes. Additionally, re-Cu-NHC complexes were investigated for their biological activities, including antiproliferative, antioxidant, AChE and TyrE inhibition, and antiparasitic activity. The results showed that the 3b, 3d, and 3e complexes possessed strong antiproliferative activity against human colon carcinoma (HCT-116) and moderate cytotoxic activity against hepatocellular carcinoma (HepG-2) cell lines. In addition, effective selective antileishmanial effects were observed for the 3e compound against both promastigotes and amastigotes stages of L. major with an IC50 value of 0.027 and 0.39 mu M mL-1, respectively. These results demonstrate that these compounds are promising candidates for the treatment of colorectal cancer and leishmaniasis. re-NHC-Cu complexes have been synthesized and used as catalyst on CuAAC reactions. imageÖğe Synthesis, in vitro, and in silico studies of novel poly-heterocyclic compounds bearing pyridine and furan moieties as potential anticancer agents(Elsevier, 2023) Kadi, Ibtissem; Sekerci, Güldeniz; Boulebd, Houssem; Zebbiche, Zineddine; Tekin, Suat; Kucukbay, Hasan; Kucukbay, FatümetüzzehraThirteen novel poly-heterocyclic compounds containing pyridine and furan moieties were synthesized and fully characterized by H-1 NMR, 1(3)C NMR, FTIR, and elemental analysis. The optimized geometry of the most stable conformation of the synthesized compounds was determined at the DFT/B3LYP level of theory. Frontier molecular orbitals, molecular electrostatic potential, and atoms in molecules analysis were performed to better understand the electronic properties, reactivity, and intermolecular interactions. The cytotoxicity of all compounds was assessed In vitro against MCF-7 and A-2780 cell lines using the MTT assay. Among them, compounds 2c, 3c, 3d, 4a, and 4c at 0.1 mu M concentration showed more potent cytotoxicity against the MCF-7 cells than the reference drug docetaxel. On the other hand, compounds 2c, 3a, 3c, and 4c are more cytotoxic against the A-2780 cell line compared to the standard at the same concentration. The docking studies revealed an excellent affinity for the active site of the human topoisomeraseII ss enzyme, which may explain the promising cytotoxicity of these classes of molecules. The in silico evaluation of ADMET parameters indicated good pharmacokinetic properties of all the investigated compounds. (c) 2022 Elsevier B.V. All rights reserved.Öğe Synthesis, structures, DFT calculations, and catalytic application in the direct arylation of five-membered heteroarenes with aryl bromides of novel palladium-N-heterocyclic carbene PEPPSI-type complexes(Royal Soc Chemistry, 2021) Sandeli, Abd el-Krim; Khiri-Meribout, Naima; Benzerka, Saida; Boulebd, Houssem; Gurbuz, Nevin; Ozdemir, Namik; Ozdemir, IsmailA new series of Pd-catalysts based on an N-heterocyclic carbene PEPPSI-type ligand (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation) with the general formula [Pd(H)Br2(NHC)(pyridine)] was synthesized and fully characterized via spectroscopic analytical methods. Further, the structural characterization of 3a, 3b, and 3d was performed via single-crystal X-ray diffraction, which supported the proposed structures and offered a more detailed structural characterization. Additionally, the electronic, vibrational, thermodynamic, and optical properties of 3a, as a representative molecule, were confirmed utilizing density functional theory (DFT) calculations. The experimental molecular geometry of the ground state of complex 3a was compared with the minimized structure obtained from DFT calculations. The B3LYP functional in conjunction with the LANL2DZ basis set for the palladium atom and the 6-311G(d,p) basis set for the hydrogen, carbon, nitrogen, and bromine atoms were used for all calculations. The frontier molecular orbitals and molecular electrostatic potential were also analyzed and discussed. Due to the significant interest in halo-substituted arylated heteroarenes in organic chemistry, the catalytic activity of these Pd(II)-NHC PEPPSI-type complexes were evaluated via the direct arylation of five-membered heteroaromatics such as thiophene, furan, and thiazole derivatives with various (hetero)aryl bromides in the presence of 1 mol% catalyst. The results showed that all new Pd-NHC complexes are effective catalysts, which exhibited very good catalytic activity and gave C-H activation selectively at the C(5)-position of 2-acetyl furan and 2-acetyl thiophene.
