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Öğe Chalcone-based schiff bases: Design, synthesis, structural characterization and biological effects(Elsevier B.V., 2025) Yalazan, Halise; Koç, Damla; Aydın Köse, Fadime; Akgül, Muhammed İsmail; Fandaklı, Seda; Tüzün, Burak; Taslimi, Parham; Kantekin, HalitThe presented work describes the synthesis, characterization, and biological effects of three new Schiff base compounds (SOH-F/Cl/Br) and their phthalonitrile derivatives (SCN-F/Cl/Br). The structures of all synthesized compounds were elucidated by NMR, FT-IR, and mass spectroscopic methods. Enzyme results were obtained at the nanomolar level. Cytotoxic activity of novel compounds was evaluated against neuroblastoma (SH-SY₅Y) and mouse fibroblast (NIH-₃T₃) cell lines using MTT. It has been determined that all tested molecules have a powerful cytotoxic effect; IC₅₀ values were under 10 µM against SH-SY₅Y cells. Among all compounds, the lowest IC₅₀ value was observed in SCN-Br (1.798 ± 0.036 µM). Moreover, the IC₅₀ concentration of SCN-Br (12.79 ± 0.33 µM) in healthy NIH-₃T₃ cells was significantly higher than in cancerous cells. The activity comparison of the studied six molecules was made with both DFT calculations and molecular docking calculations. Various proteins that are hCA I protein (PDB ID: ₂CAB), hCA II protein (PDB ID: ₅AML), and SH-SY₅Y protein (PDB ID: ₇LQZ, ₅WIV, and ₂F₃₇) were used in molecular docking calculations. After this comparison, ADME/T calculations were used to analyze the molecules to be used as drugs.Öğe Chlorine-thymol substituted silicon (IV) phthalocyanines: Synthesis, characterization, and in vitro acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) inhibitory effect(John Wiley and Sons Ltd, 2024) Aktaş Kamiloğlu, Ayşe; Arslan, Tayfun; Tekin, Aşkın; Kantekin, Halit; Acar, İrfanIn this study, novel chlorine-thymol derivatives (1,3-bis(4-chloro-2-isopropyl-5 methylphenoxy)propan-2-ol (Thy-OHI) and 2-[2-(4-chloro-2-isopropyl-5-methylphenoxy)ethoxy]ethanol (Thy-OHII)) and axially di-4-chloro-2-isopropyl-5-methylphenoxy (Thy-SiPc), 1,3-bis(4-chloro-2-isopropyl-5-methylphenoxy)propanoxy (Thy-OHI-SiPc), and 2-[2-(4-chloro-2-isopropyl-5-methylphenoxy)ethoxy]ethanoxy (Thy-OHII-SiPc) substituted silicon phthalocyanine compounds were obtained, and their structures were elucidated by the combination of various methods such as NMR, IR, UV–Vis, and MS. The inhibitory effects of these compounds (Thy-OHI, Thy-OHII, Thy-SiPc, Thy-OHI-SiPc and Thy-OHII-SiPc), synthesized for the first time, on cholinesterase enzymes (AChE and BChE) were investigated in the laboratory environment. In the studies, notably Thy-OHI-Si and thymol derivative ligand Thy-OHII displayed significant inhibition against AChE and BChE.Öğe Development of pyrimidine-substituted schiff base and their axially silicon phthalocyanines as inhibitors of acetylcholinesterase and butyrylcholinesterase for alzheimer's disease therapy(John Wiley and Sons Ltd, 2025) Aktaş Kamiloğlu, Ayşe; Arslan, Tayfun; Tekin, Aşkın; Kantekin, HalitIn this study, axially substituted silicon (IV) phthalocyanine complexes containing pyrimidine-substituted Schiff bases were synthesized and characterized. The Schiff bases (Pyr-1 and Pyr-2) were synthesized through a condensation reaction between pyrimidine derivatives and appropriate aldehydes, followed by their coordination with silicon (IV) to form the corresponding phthalocyanine complexes (Pyr-1-SiPc and Pyr-2-SiPc). The synthesized Schiff bases (Pyr-1 and Pyr-2) and silicon (IV) phthalocyanine derivatives (Pyr-1-SiPc and Pyr-2-SiPc) were subsequently tested in vivo for their inhibitory effect on the enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). A substantial number of these compounds exhibited pronounced inhibitory activity against both enzymes. Notably, among the phthalocyanines and their precursor compounds, the most intriguing were identified as submicromolar selective inhibitors of AChE and BChE, with IC50 values of 4.26 μM and 6.46 μM, respectively.Öğe New chalcone-substituted metallophthalocyanines: Synthesis, characterization, and investigation of their properties(Sage Publications, 2020) Kamiloğlu, Ayşe Aktaş; Karaca, Hüseyin; Çelik, Gonca; Acar, İrfan; Kantekin, HalitThe synthesis of novel metallophthalocyanines (M = Zn, Mg, and Co) derived from (E)-3-(3-bromophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one and (E)-3-(3-fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one is achieved. These complexes and the synthesized novel phthalonitrile derivatives are characterized by FTIR, 1H NMR, 13C NMR, UV-Vis, mass spectrometry, and elemental analysis. The aggregation properties of the metallophthalocyanines ZnPc, MgPc, and CoPc are investigated in different solvents and at different concentrations in dimethyl formamide. The electrochemical behavior is also investigated. The cyclic voltammograms give one oxidation reaction for all the bromo-derived metallophthalocyanines and one reduction reaction for all the fluoro-derived metallophthalocyanines. Fe3+, Cd2+, Hg2+, Cu2+, Ni2+, and Co2+ ions are titrated fluorometrically with the phthalocyanines. The bromo- and fluoro-substituted phthalocyanine compounds show different effects on the metal ion titrations.Öğe Octa- and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and in vitro antimicrobial activity(Taylor & Francis Inc, 2020) Kamiloğlu Aktaş , Ayşe; Direkel, Şahin; Yalazan, Hadise; Kantekin, Halit; Acar, İrfanIn this study, the novel phthalonitrile derivatives1and2weresynthesized. Tetra-substituted metal-free1a(H2Pc) and metalloph-thalocyanines (ZnPc1b,CoPc1cand CuPc1d) bearing four per-ipheral 4-allyl-2,6-dimethoxyphenol (methoxy-eugenol) groupsand octa-substituted metal-free2aand metallophthalocyanines(ZnPc2b,CoPc2cand CuPc2d) bearing eight peripheralmethoxy-eugenol group were synthesized. All new synthesizedcompounds are characterized by IR,13Cf1HgNMR (for1and2),UV-Vis (for1a–2d) and mass spectroscopy. Antimicrobial activitiesof the synthesized phthalonitrile derivatives (1and2) andphthalocyanine compounds1a–2dwere determined by microdi-lution broth method against nine different bacteria and one yeastspecies. In this study, CoPc (2c) compound, which has eight per-ipheral 4-allyl-2,6-dimethoxyphenol, had the highest antibacterialactivity (minimum inhibitory concentration [MIC]¼312lg/mL). Inaddition,1b,1d,2band2dwere found to be effective on atleast three different bacterial species at different concentrations(MIC¼1250–5000lg/mL).Shigella flexneriwere the most affectedbacteria, but none of the compounds were effective against fun-gal isolate.Öğe Photophysical, photochemical properties of chalcone substituted Zinc(II) and Magnesium(II) metallophthalocyanines bearing thiophene units(Springer, 2022) Kamiloğlu, Ayşe; Ömeroğlu, İpek; Yalazan, Halise; Durmuş, Mahmut; Çelik, Gonca; Kantekin, HalitThe novel thiophene-chalcone compound (2), phthalonitrile derivatives bearing thiophene-chalcone group (3 and 4) and their zinc (II) (ZnPcs) (3a and 4a) and magnesium (II) (MgPcs) (3b and 4b) phthalocyanine compounds were synthesized in this study. The structure of all these new compounds were elucidated by spectroscopic techniques like IR, 1 H NMR, 13 C NMR (for compounds 2, 3 and 4), MALDI–TOF mass and UV-Vis. The fuorescence quantum yields and lifetimes (photophysical properties), and the singlet oxygen and photodegradation quantum yields (photochemical properties) of thiophene bearing chalcone substituted ZnPcs (3a and 4a) and MgPcs (3b and 4b) were studied in DMSO (dimethylsulfoxide) to determine if they are convenient photosensitizers for photodynamic therapy (PDT) applications.Öğe Synthesis and characterization of metallophthalocyanine with morpholine containing Schiff base and determination of their antimicrobial and antioxidant activities(Elsevier Science SA, 2019) Ünlüer, Dilek; Kamiloglu, Ayşe Aktaş; Direkel, Şahin; Bektaş, Ersan; Kantekin, Halit; Sancak, KemalIn this work, novel metallophthalocyanine compounds (M = Zn, Cu, Co) bearing four 2-methoxy-4-{(Z)-[(4-morpholin-4-ylphenyl) imino] methyl} phenol at the peripheral positions were sythesized starting from the new phthalonitrile derivative (2). These new compounds (2-5) have been characterized by a combination of FT-IR, H-1 NMR (for compounds 2 and 3), C-13 NMR (for compound 2), UV-Vis (for compounds 3,4 and 5) and mass spectrophotometry techniques. Antioxidant activities of the metallophthalocyanines were investigated by using DPPH free radical scavenging assay and FRAP (ferric ion reducing antioxidant power) method. The antimicrobial activity of the synthesized metallo phthalocyanine compounds (3-5) were determined against the selected different six standart bacteria isolates by microdilution broth assay with Alamar Blue Dye. Most affected bacteria from the compounds were standard E. coli and S. typhimurium (MIC 625 mu g/ml). Standart Y. enterocolitica and S. aureus have been less affected by the compounds (MIC 10.000 mu g/ml). (C) 2019 Published by Elsevier B.V.Öğe Synthesis and in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes activity of aldehyde and schiff base substituted cobalt (II), copper (II), and zinc (II) phthalocyanines(John Wiley and Sons Ltd, 2024) Yalazan, Halise; Kamiloğlu, Ayşe Aktaş; Tekin, Askın; Arslan, Tayfun; Kantekin, HalitIn this work, a series of aldehyde-substituted phthalocyanine compounds (1, 3, and 5) were prepared by the cyclotetramerization of the 4-(5-(diethylamino)-2-formylphenoxy) phthalonitrile (a) and the corresponding metal salts. Schiff base-substituted phthalocyanines (2, 4, and 6) were derived from an aldehyde-substituted phthalocyanine (1, 3, and 5) via the reaction of aldehyde-substituted phthalocyanines with an amine reagent. The compounds that were obtained were characterized using FT-IR, 1H {13C} NMR, UV–Vis, and MS spectra (a and 1–6). The inhibitory qualities of synthesized aldehyde and Schiff base-substituted complexes against the enzymes butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) were assessed. The majority of phthalocyanines exhibited strong enzyme-inhibiting properties. Out of the six produced phthalocyanines, 3 and 4 displayed the most intriguing profiles as submicromolar selective AChE inhibitors (IC50 = 0.060 ?M), whereas 1 demonstrated the most potent BChE inhibitor (IC50 = 0.024 ?M). The aggregation studies of CoPcs, CuPcs, and ZnPcs (1–6) were also carried out in this work.Öğe Synthesis, spectroscopic, and photophysicochemical behavior of Zn(II) and Mg(II) phthalocyanine– chalcone conjugates(Taylor and Francis Ltd., 2021) Aktaş Kamiloğlu , Ayşe; Yalazan, Halise; Durmuş, Mahmut; Çelik, Gonca; Ömeroğlu, İpek; Acar, İrfan; Kantekin, HalitPhthalonitrile derivatives (8, 9, and 10) bearing different chalcone groups and their zinc(II) (ZnPcs) (8a, 9a, and 10a) and magnesium(II) (MgPcs) (8b, 9b, and 10b) complexes were prepared. The new compounds (5, 8–10, 8a–10a, and 8b–10b) were characterized by a combination of spectroscopic techniques, such as FT-IR, 1H NMR, 13C NMR (for 5, 8, 9, and 10), UV–Vis (for metallophthalocyanines), and MALDI-TOF mass spectra, and by elemental analysis (5, 8, 9, and 10). The aggregation behavior and photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen and photodegradation quantum yields) properties of different chalcone-substituted peripheral ZnPcs (8a, 9a, and 10a) and MgPcs (8b, 9b, and 10b) were investigated in dimethylsulfoxide (DMSO) to determine whether they are photosensitizers for photodynamic therapy (PDT) applications. The peripheral tetra-substituted MgPc (9b) showed longer lifetime than other compounds and unsubstituted ZnPc. The tetra-substituted ZnPc (9b) produced higher fluorescence quantum yield than the unsubstituted ZnPc and its chalcone-substituted counterparts. The ZnPcs (8a, 9a, and 10a) and MgPcs (8b, 9b, and 10b) showed low singlet oxygen production, but they showed quite high photostability, except MgPc 10b.
