Biological properties of hexadeca-substituted metal phthalocyanines bearing different functional groups

Farajzadeh, Nazli; Özdemir, Sadin; Tollu, Gülşah; Bayır, Zehra Altuntaş; Koçak, Makbule Burkut

doi:10.1016/j.jinorgbio.2022.111888

Cited by 29 publications

(19 citation statements)

References 81 publications

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“…The DPPH free radical scavenging test, which is frequently used as a basic screening technique to evaluate the anti-radical activity of different substances, is an easy-to-use, low-cost, and highly effective technique. 38–41 Different concentrations of BPI derivatives (12.5, 25, 50, 100, and 200 mg L −1 ) were tested to determine their radical scavenging ability. Evaluation of the scavenging capacities of the compounds was made by comparing the results of Trolox and ascorbic acid used as standard.…”

Section: Resultsmentioning

confidence: 99%

Glycerol group substituted bis(2-pyridylimino)isoindoline (BPI) complexes: synthesis, characterization and investigation of their biological properties

Kaşıkçı,

Katırcı,

Özdemir

et al. 2023

Dalton Trans.

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Section: Resultsmentioning

confidence: 99%

Glycerol group substituted bis(2-pyridylimino)isoindoline (BPI) complexes: synthesis, characterization and investigation of their biological properties

Kaşıkçı,

Katırcı,

Özdemir

et al. 2023

Dalton Trans.

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“…In this work, DNA was completely fragmented in the presence of zinc (II) phthalocyanines at all tested concentrations. [ 32 ] All of these results revealed that different substituted groups have an effect on DNA damage.…”

Section: Resultsmentioning

confidence: 99%

DNA interaction, cytotoxic and phototoxic properties of new water‐soluble zinc (II) phthalocyanines

Bıyıklıoğlu

Baş

Altun

et al. 2022

Applied Organom Chemis

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In this paper, we have synthesized water‐soluble peripherally tetra and octa‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) groups substituted zinc (II) phthalocyanines (DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ). Also, we have investigated ct‐DNA binding, supercoiled plasmid DNA cleavage properties of DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ by using spectrophotometric and electrophoretic methods. On the other hand, cytotoxic and phototoxic effects of DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ were examined using (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay on human lung adenocarcinoma (A549) cell lines. In UV–Vis absorption studies, hypochromism was observed about 18% for DM‐C6‐ZnQ and 57% for o‐DM‐C6‐ZnQ on addition of increasing concentrations of ct‐DNA. The intrinsic binding constant (Kb) values of DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ were 3.82 (±0.14) × 104 M−1 and 2.34 (±0.05) × 105 M−1, respectively. The supercoiled plasmid DNA cleavage studies showed that DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ had no DNA damage actions in the dark. On the other hand, they caused DNA damage depending on the light dose. In the MTT assay, the compounds had low cytotoxic properties on A549 cell lines, but they showed significant phototoxic actions. These results reveal that the compounds interact with DNA and have phototoxic properties; it has been determined that they have the potential to be photosensitizing agents for photodynamic therapy.

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“…DPPH (2,2-diphenyl-1-picrylhydrazyl) assay which is a common method in determining the antioxidant activities, [2,44] were carried out in this study. The radical scavenging ability of the tested compounds was monitored by measuring the decrease in UV absorption at 517 nm.…”

Section: Dpph Radical Scavenging Activitymentioning

confidence: 99%

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

et al. 2023

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This study describes the synthesis and characterization of peripherally and non‐peripherally substituted copper(II) and cobalt(II) phthalocyanines bearing tetraethyleneglycol monomethyl ether chains. In addition, the metal‐free and zinc(II) phthalocyanine derivatives were prepared according to the referred procedure. All newly synthesized phthalocyanines were characterized using some spectroscopic techniques such as elemental analysis and fourier transform infrared, ultraviolet‐visible, and mass spectroscopies. The effects of solvent type and concentration on aggregation properties of phthalocyanines were studied, as well. The biological activities of a series of these peripherally and non‐peripherally tetra‐substituted phthalocyanines were investigated. The effects of the central metal ion and the position of the substituent on biological activities of phthalocyanines were also compared. When the antioxidant activities of the synthesized molecules were evaluated by the 2,2‐diphenyl‐1‐picrylhydrazyl method, 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatocobalt(II) (63.17±0.012 %) showed the highest activity. The highest reducing power activity was obtained with the 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) molecule. In the antibacterial activity studies using the disc diffusion method, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy) ethoxy)ethoxy)ethoxy]phthalocyaninatocopper(II) exhibited the highest inhibition activity on both gram negative (18±0.23 mm) and gram positive (23±0.07 mm) strains. On the other hand, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy) ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatozinc(II) compounds presented hemolytic activity against sheep blood in the hemolytic activity studies. The results confirmed that the synthesized molecules demonstrated average antioxidant activity compared to standard antioxidants. 2,9/10,16/17,23/24‐Tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatocopper(II), 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxy ethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11, 15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy) ethoxy]phthalocyaninatozinc(II) complexes could remarkably inhibit S. aureus and CuPc‐1 complex E. coli growth.

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Biological properties of hexadeca-substituted metal phthalocyanines bearing different functional groups

Cited by 29 publications

References 81 publications

Glycerol group substituted bis(2-pyridylimino)isoindoline (BPI) complexes: synthesis, characterization and investigation of their biological properties

Glycerol group substituted bis(2-pyridylimino)isoindoline (BPI) complexes: synthesis, characterization and investigation of their biological properties

DNA interaction, cytotoxic and phototoxic properties of new water‐soluble zinc (II) phthalocyanines

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

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