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  • Küçük Resim
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    Octa-substituted Zinc(II), Cu(II), and Co(II) phthalocyanines with 1-(4-hydroxyphenyl)propane- 1-one: Synthesis, sensitive protonation behaviors, Ag(I) induced H-type aggregation properties, antibacterial– antioxidant activity, and molecular docking studies
    (18 June 2021) Bilgiçli, Ahmet T.; Kandemir, Tugberk; Arıduru, Rana; Günsel, Armagan; Abak, Çagla; Yarasir, M. Nilüfer; Arabaci, Gulnur
    This study shows the synthesis and characterization of 4,5-bis(4-propionylphenoxy) phthalonitrile (2) and its octa-substituted phthalocyanine derivatives [ZnPc(3), CuPc(4), and CoPc(5)]. A combination of standard spectroscopic techniques has characterized the newly synthesized phthalonitrile derivative and phthalocyanines. The aggregation behaviors of new octa-substituted phthalocyanines have been evaluated by ultraviolet– visible (UV-vis) spectroscopy. The metal ion-sensitive behaviors of new octa-substituted phthalocyanines in the presence of soft metal ions have been performed by UV-vis and fluorescence spectrophotometer. The quenching efficiency (Ksv) of Ag+ ions against ZnPc(3) was found using the Stern–Volmer equation. The binding constant (Ka) and binding stoichiometry (n) of ZnPc(3) with Ag+ ions were calculated using the modified Benesi–Hildebrand equation. Sensitive protonation behaviors of octa-substituted phthalocyanines have been investigated by titration experiments as well as computational calculations. The ZnPc(3) and CuPc(4) were exhibited H-type aggregation behaviors toward Ag+ ions. However, the protonation of octa-substituted zinc and copper phthalocyanine during the titration with HCl caused J-type selfaggregation properties. In vitro antioxidant properties of the new compounds were investigated by the radical scavenging ability of 1,1-diphenyl- 2-picrylhydrazyl (DPPH), chelating ability to ferrous ions, and reducing power methods. Additionally, in vitro antibacterial activities of the octa-substituted phthalocyanines were determined. Finally, optimized structures of novel compounds [(2), ZnPc(3), CuPc(4), and CoPc(5)] were obtained on the HF (Hartree–Fock), B3LYP (Becke, 3-parameter, Lee-Yang-Parr), M06–2X methods with 3–21 g, 6–31 g and SDD basis set. Then, biological activities of novel phthalonitrile and its phthalocyanine derivatives toward breast, liver, and lung cancer proteins were compared with molecular docking studies.
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    Synthesis of (4R)-2-(3-hydroxyphenyl)thiazolidine- 4-carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies
    (9 March 2021) Bilgiçli, Ahmet T.; Bilgicli, Hayriye Genc; Hepokur, Ceylan; Günsel, Armağan; Zengin, Mustafa; Yarasir, M. Nilüfer; Tüzün, Burak
    In this study, firstly, (4R)-2-(3-hydroxyphenyl)thiazolidine-4-carboxylic acid (1) and (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (2) were prepared. Then, the novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) bearing thiazolidine groups in peripheral positions were synthesized using by compound (2). The synthesized new compounds (1–5) were characterized by the combination of standard spectroscopic methods such as FT-IR, 1H NMR, 13C NMR, UV–Vis spectral data, and MALDI-TOF. Aggregation behaviors of peripheral tetra-substituted metallophthalocyanines were investigated in dimethyl sulfoxide (DMSO) media. Fluorescence properties and fluorescence quantum yield of the new type zinc phthalocyanine (3) were performed in DMSO at room temperature. The anticancer activity of novel type metallophthalocyanines bearing thiazolidine groups in peripheral positions were investigated on rat glioma cancer (C6), human prostate carcinoma (DU-145), and normal human lung fibroblast (WI-38) cell lines. Finally, the biological and chemical activities of (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine- 4-carboxylic acid (2) and its novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) have been compared with many parameters obtained using theoretical methods that are the Gaussian software and molecular docking.
  • Küçük Resim
    Öğe
    Tetra-substituted phthalocyanines bearing thiazolidine derivatives: synthesis, anticancer activity on different cancer cell lines, and molecular docking studies
    (5th October 2021) M. Nilüfer Yarasir; Bilgiçli, Ahmet T.; Hepokur, Ceylan; Bilgicli, Hayriye Genc; Tüzün, Burak; Günsel, Armağan; Mısır, Sema; Zengin, Mustafa; Yarasir, M. Nilüfer
    In the first step, (4R)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid (c) and 2-(2-(3,4-dicyanophenoxy) phenyl)thiazolidine-4-carboxylic acid (1) were prepared. Then, the peripherally tetra-substituted metallophthalocyanines [ZnPc (2), CuPc (3), and CoPc (4)] were synthesized by using 1. The structures of the obtained compounds were characterized by common spectroscopic methods. Aggregation behaviors of the tetra-substituted metallophthalocyanines (2–4) were investigated by UV-Vis and fluorescence spectroscopy in the presence/absence of soft metal ions. The electronic spectra of the newly synthesized metallophthalocyanines [ZnPc (2), CuPc (3), and CoPc (4)] were analyzed by the Bayliss method. The fluorescence quantum yield of diamagnetic ZnPc (2) was obtained in DMSO at room temperature. Also, the anticancer activity of the newly synthesized metallophthalocyanine derivatives was studied on C6, DU-145, and WI-38 cell lines and investigated using six concentrations (3.125; 6.25; 12.5; 50; 75; 100 μg L−1). The cell cycle and apoptosis analyses of CuPc (3) were performed. In addition, the chemical and biological activities of 2-(2-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (1) and its novel type metallophthalocyanines [ZnPc (2), CuPc (3), and CoPc (4)] were compared with many parameters obtained from the Gaussian software and molecular docking methods.