DNA interaction and anticancer properties of new peripheral phthalocyanines carrying tosylated 4-morpholinoaniline units

Yalazan, Halise; Barut, Burak; Ertem, Beytullah; Yalçın, Can Özgür; Ünver, Yasemin; Özel, Arzu; Ömeroğlu, İpek; Durmuş, Mahmut; Kanteki̇n, Hali̇t

doi:10.1016/j.poly.2019.114319

Cited by 22 publications

(13 citation statements)

References 54 publications

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“…In addition, high cell concentrations are used for the iNOS assay; in the present study, the cytotoxicity tests of RAW 264.7 cells were performed following the iNOS assay. It has been reported that the cytotoxic activity of doxorubicin progressively decreases depending on the cell density (62) Low dark cytotoxicity of Pcs has been reported before due to the absence of reactive oxygen species, and the results from the present study are in agreement with other studies (33,63,64). Therefore, their phototoxic effects should be studied to evaluate their anticancer potential.…”

Section: Resultssupporting

confidence: 93%

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Assessment of in vitro Cytotoxic, iNOS, Antioxidant and Photodynamic Antimicrobial Activities of Water‐soluble Sulfonated Phthalocyanines

Akın¹,

Şaki

Güzel

et al. 2021

Photochem & Photobiology

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In recent years, much effort has been devoted to the development of effective anticancer agents. In this manner, the utilization of water‐soluble sulfonated phthalocyanines is crucial for many cancer cell lines. In this study, phthalonitrile and metallophthalocyanine compounds linked by benzenesulfonic acid groups have been prepared. Antimicrobial behaviors of those compounds were investigated by performing disk diffusion and photodynamic assays on gram‐positive and negative bacteria. Indium phthalocyanine (InClPc) (3) showed inhibition activity against B. cereus, B. subtilis and S. aureus with disk diffusion assay. Also, gallium and indium phthalocyanines (2 and 3) exhibited inhibitory activity on both gram‐positive and ‐negative microorganisms after light activation. Increasing the inhibitor concentration and light exposure time increased the inhibition activity for both molecules. GaClPc (2) demonstrated the maximum reducing power capacity among studied compounds, and CoPc (4) showed even better DPPH radical scavenging ability than the standard molecule Trolox at 2000 µg mL−1 concentration. The dose‐dependent effect of compounds on cytotoxicity was studied against cancer cells PANC‐1, MDA‐MB‐231, HepG2, A549, HeLa, CaCo‐2 and non‐tumorigenic cells HEK‐293. All compounds showed no significant cytotoxic effect on any cell line up to the highest treated concentration at 50 µg mL−1. However, all phthalocyanines had significant nitric oxide inhibition activity, and only in copper phthalocyanine (CuPc) (5), the MTT IC50 value was reached on LPS‐activated RAW 264.7 macrophage cells. The lowest inducible nitric oxide synthase (iNOS) IC50 values were defined as 6 ± 1 μg mL−1 and 7 ± 0.5 μg mL−1 for CuPc (5) and InClPc (3), respectively.

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Section: Resultssupporting

confidence: 93%

“…Also, new alternative anticancer methods should be investigated due to the deficiencies of known treatment methods of cancer. The anticancer effects of Pcs and their conjugates have been demonstrated by photodynamic therapy (33,34). Therefore, they are potential anticancer agents and further investigation should be conducted.…”

Section: Introductionmentioning

confidence: 99%

Assessment of in vitro Cytotoxic, iNOS, Antioxidant and Photodynamic Antimicrobial Activities of Water‐soluble Sulfonated Phthalocyanines

Akın¹,

Şaki

Güzel

et al. 2021

Photochem & Photobiology

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“…Peripherally tetra-substituted zinc(II) phthalocyanine containing tosylated 4-morpholinoaniline units displayed DNA cleavage activity. 77 These results support the achievements that were obtained in this study. It was reported that the newly synthesized complexes bind either to the major or minor groove of DNA or make external contact (electrostatic binding).…”

Section: Dna Cleavage Activitysupporting

confidence: 89%

The design and synthesis of metallophthalocyanine–gold nanoparticle hybrids as biological agents

et al. 2022

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“…Yalazan et al . (78) investigated the DNA cleavage activity of new peripheral phthalocyanines bearing tosylated 4‐morpholinoaniline units using pBR322 plasmid DNA. The peripheral zinc (II) phthalocyanine showed DNA nuclease ability.…”

Section: Resultsmentioning

confidence: 99%

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Farajzadeh

Özdemir

Gonca

et al. 2021

Photochem & Photobiology

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As thiazoles and fluorinated groups are well known as active species of hybrid pharmaceutical agents, this study aimed to evaluate the synergic effect of these groups on the biological features of phthalocyanines for the first time in the hope of discovering efficient pharmaceutical agents. Therefore, a new phthalonitrile derivative namely 4‐(2‐(4‐methylthiazol‐5‐yl)ethoxy)‐5‐(4‐(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal‐free (2)/metal phthalocyanines (3‐5) were prepared and characterized using various spectroscopic techniques. Solubility of new phthalocyanines (2‐5) was examined in a series of polar and nonpolar solvents. Additionally, sono/photochemical methods were applied to examine the photophysical and sono/photochemical properties of new zinc phthalocyanine to measure its potential as a probable material for sono/photodynamic therapies. The antioxidant activities of compounds (1‐5) were evaluated using the DPPH scavenging activity method and the highest radical scavenging activity was obtained 92.13% (200 mg L−1) for manganese phthalocyanine. All the phthalocyanines demonstrated high DNA nuclease activity, as well. The antimicrobial activities of compounds (1‐5) were investigated using disk diffusion and microdilution methods. The phthalocyanines exhibited effective microbial cell inhibition activity against Escherichia coli (E. coli). Antimicrobial photodynamic therapy activity was investigated against E. coli by LED irradiation. Compounds (2‐5) acted as photosynthesizers. Also, they displayed significant biofilm inhibition activity against Staphylococcus aureus (S. aureus) and Pseudomonas aeruginosa (P. aeruginosa).

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DNA interaction and anticancer properties of new peripheral phthalocyanines carrying tosylated 4-morpholinoaniline units

Cited by 22 publications

References 54 publications

Assessment of in vitro Cytotoxic, iNOS, Antioxidant and Photodynamic Antimicrobial Activities of Water‐soluble Sulfonated Phthalocyanines

Assessment of in vitro Cytotoxic, iNOS, Antioxidant and Photodynamic Antimicrobial Activities of Water‐soluble Sulfonated Phthalocyanines

The design and synthesis of metallophthalocyanine–gold nanoparticle hybrids as biological agents

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

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