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Öğe Alkyl chain modified metalophthalocyanines with enhanced antioxidant-antimicrobial properties by doping Ag+ and Pd2+ ions(Elsevier, 2022) Alici, Esma Hande; Bilgicli, Ahmet T.; Tuzun, Burak; Gunsel, Armagan; Arabaci, Gulnur; Yarasir, M. NiluferIn this study, we report the synthesis and characterization of peripheral alkyl chain-substituted metalophthalocyanines [CuPc (3) , ZnPc (4) , and CoPc (5) ] as optically sensitive substances with antifungal and antibacterial properties. Synthesized compounds were characterized by using common spectroscopic methods such as H-1 NMR, C-13 NMR, FT-IR, MALDI-TOF, fluorescence, and UV-Vis spectroscopy. Aggregation behaviors of phthalocyanines in the presence of Ag+ and Pd2+ ions were investigated by UV-Vis and fluorescence spectroscopy. The quenching capacity of Ag+ and Pd2+ ions for (4) was calculated from the Stern-Volmer equation and was found to be 9.76 x 10(4) mol/L and 2.86 x 10(5) mol/L for Pd2+ and Ag+ ions, respectively. The binding stoichiometry (n) and binding constant (K-a) of (4) for Ag+and Pd2+ ions were calculated by the changed Benesi-Hildebrand equation. K-a value of (4) for Ag+ and Pd2+ ions are 2.57 x 10(9) M-1 and 1.44 x 10(8) M-1 , respectively. The binding ratio of (4) for Ag+ and Pd2+ ions is 1.83 and 1.68, respectively. The morphological features of phthalocyanine derivatives were examined before and after the Ag + or Pd(2+)ions treatment by scanning electron microscopy (SEM). In addition, the antioxidant efficiencies of newly synthesized metalophthalocyanines and their Ag+ and Pd2+ ion-doped aggregates were evaluated using different methods such as DPPH free radical scavenging, iron ion chelating, and reducing power activities. The chemical and biological activities of phthalonitrile and its metalophthalocyanines were also evaluated by DFT and molecular docking calculations. Finally, the antifungal and antibacterial efficiencies of newly synthesized beta-substituted phthalocyanines and their Ag+ and Pd2+ ion-doped forms were investigated using macrobroth dilution and disk diffusion methods. (c) 2022 Elsevier B.V. All rights reserved.Öğe Novel biologically active metallophthalocyanines as promising antioxidant-antibacterial agents: Synthesis, characterization and computational properties(Elsevier, 2020) Gunsel, Armagan; Kobyaoglu, Abdullah; Bilgicli, Ahmet T.; Tuzun, Burak; Tosun, Busra; Arabaci, Gulnur; Yarasir, M. NiluferThis study reports on the synthesis and characterization of non-peripherally tetrasubstituted zinc(II), copper(II) and cobalt(II) phthalocyanines with 4-(trifluoromethylthio)phenoxy substituents. Synthesized compounds were characterized by FT-IR, H-1 NMR, MALDI mass, elemental analysis and UV-Vis spectroscopic methods. By using some parameters obtained from quantum chemical calculations, the activity of the studied ligand (1) against metal atoms was investigated. Based on the obtained results, the NMR, IR and UV-Vis spectra of the ligand (1) in different phases were compared with experimental results. Also, theorical and experimental UV-Vis spectrum values of metallophthalocyanines (2-4) were investigated. Additionally, the possible use of all synthesized metallophthalocyanines for antioxidant and antibacterial agents were investigated. The obtained results showed that CoPc (4) had very good antioxidant activities among others. Although all of the tested metallophthalocyanines (2-4) had some antibacterial activities, ZnPc (2) had the best antibacterial effect against five different bacteria among other metallophthalocyanines tested. (C) 2019 Elsevier B.V. All rights reserved.Öğe 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, GulnurThis 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.Öğe The Water-Soluble Peripheral Substituted Phthalocyanines as Corrosion Inhibitors for Copper in 0.1 N HCl: Gravimetric, Electrochemical, SEM-EDS, and Quantum Chemical Calculations(Maik Nauka/Interperiodica/Springer, 2020) Akin, Mustafa; Gunsel, Armagan; Bilgicli, Ahmet T.; Tuzun, Burak; Arabaci, Gulnur; Saki, Neslihan; Yarasir, M. NiluferCorrosion inhibition effects of water-soluble peripheral substituted cobalt, copper and zinc metallophthalocyanines (CoPc(1), CuPc(2)and ZnPc(3)) on the copper metal in 0.1 N HCl were investigated by using gravimetric, electrochemical, SEM-EDS analysis and quantum chemical calculations. On the electrochemical investigations and gravimetric analysis the highest inhibitor efficiency was obtained with CoPc(1)at 1 x 10(-2)mol/L concentration. SEM-EDS results indicated parallel results and oxygen atom content increased in the order of ZnPc(3), CuPc(2)and CoPc(1). According to the quantum chemical calculations, following corrosion inhibition efficiency ranking was obtained: CoPc(1)> CuPc(2)> ZnPc(3).
