Novel biologically active metallophthalocyanines as promising antioxidant-antibacterial agents: Synthesis, characterization and computational properties

Günsel, Armağan; Kobyaoğlu, Abdullah; Bilgiçli, Ahmet T.; Tüzün, Burak; Büşra, Tosun; Arabacı, Gülnur; Yaraşir, M. Nilüfer

doi:10.1016/j.molstruc.2019.127127

Cited by 43 publications

(18 citation statements)

References 45 publications

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“…Thus, phthalocyanines have been investigated in many high technological applications such as liquid crystal, [ 6 ] dye‐sensitized photovoltaic solar cells, [ 7 ] chemical sensors, [ 8 ] organic electronics, [ 9 ] and nonlinear optics [ 10 ] and is still under investigation. Phthalocyanines are also used in antimicrobial, [ 11 ] antioxidant, [ 12 ] and photodynamic therapy applications because of their photosensitizer properties. [ 13 ] The ability of phthalocyanines to generate singlet oxygen makes them promising for photodynamic therapy.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Bilgiçli

Hepokur

et al. 2021

Applied Organom Chemis

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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.

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Section: Introductionmentioning

confidence: 99%

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Bilgiçli

Hepokur

et al. 2021

Applied Organom Chemis

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“…Our results were similar to several studies about the antibacterial activities of the phthalocyanine compounds. [64][65][66][67] 3.8 | Theoretical results…”

Section: Antibacterial Propertiesmentioning

confidence: 99%

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

Bilgiçli

Kandemir

Tüzün

et al. 2021

Applied Organom Chemis

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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 ultravioletvisible (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 (K sv ) of Ag + ions against ZnPc(3) was found using the Stern-Volmer equation. The binding constant (K a ) 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

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“…There are many theoretical methods to compare the biological activities of molecules. [57][58][59][60][61] Among them, the most effective and important method is molecular docking, which compares biological activities from the numerical values of the parameters obtained by the interaction of molecules with enzymes. Molecules were initially optimized using the Gaussian software program.…”

Section: Enzymes Studiesmentioning

confidence: 99%

In vitro inhibitory effects of some acetophenone derivatives on some metabolic enzymes and molecular docking

Taslimi

2020

Archiv der Pharmazie

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Novel biologically active metallophthalocyanines as promising antioxidant-antibacterial agents: Synthesis, characterization and computational properties

Cited by 43 publications

References 45 publications

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

Synthesis of (4R)‐2‐(3‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies

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

In vitro inhibitory effects of some acetophenone derivatives on some metabolic enzymes and molecular docking

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