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    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, Halit
    The 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.
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    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, Halit
    The 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.
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    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, Halit
    In 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.
  • Küçük Resim
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    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, Halit
    Phthalonitrile 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.