<i>α</i>- or <i>β</i>-Substituted functional phthalocyanines bearing thiophen-3-ylmethanol substituents: synthesis, characterization, aggregation behavior and antioxidant activity

Bilgiçli, Ahmet T.; Tekin, Yusuf Kenan; Alıcı, Esma Hande; Yaraşir, M. Nilüfer; Arabacı, Gülnur; Kandaz, Mehmet

doi:10.1080/00958972.2015.1080361

Cited by 22 publications

(8 citation statements)

References 35 publications

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“…The method of scavenging DPPH free radicals has been used to assess the antioxidant activity of the ligand and isolated solid complexes. [55] The results of the inhibition ratio for DPPH was registered in Table S6. The results is compared to those of traditional antioxidants.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Structural elucidation, molecular modeling, and biological and antioxidant studies of phenanthroline/nicotinamide metals complexes

El‐Shwiniy

El-Wahed

Saeed

et al. 2021

Applied Organom Chemis

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Three new cobalt (II), nickel (II), and copper (II) complexes [M (nicotinamide)(phenanthroline)(H2O)3]Cl2·3H2O (where M: Co (II), Ni (II) and Cu (II)) have been prepared and characterized by elemental analysis, Fourier transform infrared (FT‐IR), and ultraviolet/visible (UV–Vis) spectroscopy as well as thermal analysis. The molar conductance measurements proved that the complexes were electrolytes. The results obtained from FT‐IR confirm that the metal atoms were coordinated by one nitrogen atom from nicotinamide (NA) ligand, two nitrogen atoms from phenanthroline (Phen), and three oxygen atoms from three different water molecules. The complexes have octahedral structure. thermogravimetry (TGA) and its differential (DTG) analyses confirmed the suggested stereochemistry. Coats–Redfern and Horowitz–Metzger equations were used to calculate kinetic and thermodynamic parameters. Molecular modeling calculations confirm the structural geometry of the complexes, and the data indicate that the complexes are soft with respect to ligands where absolute softness (σ) varied from 5.34 to 13.33 eV, whereas σ for NA and Phen are 5.34 and 8.19 eV, respectively. The ligands and their complexes were assayed for their in vitro antimicrobial activities against some bacterial and fungal strains; the data showed that the complexes were active against some bacterial species compared with NA and Phen. Moreover, complexes and ligands revealed excellent antioxidant properties and could be useful in fighting the free radicals which occur in close connection with cancerous cells.

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Section: Antioxidant Activitymentioning

confidence: 99%

Structural elucidation, molecular modeling, and biological and antioxidant studies of phenanthroline/nicotinamide metals complexes

El‐Shwiniy

El-Wahed

Saeed

et al. 2021

Applied Organom Chemis

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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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“…Absorbance in UV-Visible region was recorded in DMF solution using UV-Visible spectrometer. The 1 H and 13 C NMR of the ligand was recorded on a Bruker instrument employing TMS as internal reference and DMSO -DMF as solvent. The mass spectral study of the ligand was carried out using LC mass spectrometer.…”

Section: Methodsmentioning

confidence: 99%

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2018

IJPSR

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ABSTRACT:A novel Mannich base ligand 1-(2,5-dioxopyrrolidin-1-yl) (4-hydroxy phenyl)methyl)thiourea (PSTU) and its Manganese (II) and Cobalt (II) complexes have been synthesized and characterized by elemental analysis, molar conductance measurements, magnetic susceptibility measurements, FT-IR, 1 H NMR and 13C NMR spectroscopic studies. The antimicrobial activities and antioxidant activities of the free ligand and its metal complexes were also performed. The results revealed enhanced antimicrobial activities against Bacillus subtilis (gram+ive) and Escherichia coli (gram-ive bacteria) and also significant antioxidant activity. In addition, DNA binding properties of the ligand and its metal complexes have been investigated by UV-Visible absorption spectroscopy, viscosity measurements, emission spectra and gel electrophoresis, which suggest that the metal complexes act as efficient DNA binders. The results shown that the nuclease activity Co(II) complex was effective which could induce scission of pBr322 super coiled DNA effectively to linear form in presence of H 2 O 2 as oxidizing agent.

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α- or β-Substituted functional phthalocyanines bearing thiophen-3-ylmethanol substituents: synthesis, characterization, aggregation behavior and antioxidant activity

Cited by 22 publications

References 35 publications

Structural elucidation, molecular modeling, and biological and antioxidant studies of phenanthroline/nicotinamide metals complexes

Structural elucidation, molecular modeling, and biological and antioxidant studies of phenanthroline/nicotinamide metals complexes

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

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