Anticancer and biological properties of new axially disubstituted silicon phthalocyanines

Farajzadeh, Nazli; Kuşçulu, Nilgün Güler; Yenilmez, H. Yasemin; Bahar, Dilek; Bayır, Zehra Altuntaş

doi:10.1039/d2dt01033j

Cited by 9 publications

(9 citation statements)

References 83 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…50,51 The investigation of the DNA cleavage activity of different metal complexes such as metal phthalocyanines can help design novel advanced drugs, especially for the fight against cancers and bacteria. 52,53 In this study, stock samples of compounds (1-3-QSi) were prepared in DMSO and their pBR322 DNA cleavage activities were examined by performing agarose gel electrophoresis. The obtained results are shown in Fig.…”

Section: Dna Cleavage Assaymentioning

confidence: 99%

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

et al. 2022

View full text Add to dashboard Cite

show abstract

Section: Dna Cleavage Assaymentioning

confidence: 99%

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Various substituents can be added to the peripheral, non-peripheral or axial positions of the Pc ring to make it soluble. [22][23][24][25][26] For example, Pcs with high solubility in water become bioactive substances and benefit from a wide variety of biological properties. In recent years, our group has focused on the synthesis and biological applications of water-soluble phthalocyanines.…”

Section: Introductionmentioning

confidence: 99%

“…The diversity in the uses of Pcs is highly dependent on their solubility. Various substituents can be added to the peripheral, non‐peripheral or axial positions of the Pc ring to make it soluble [22–26] . For example, Pcs with high solubility in water become bioactive substances and benefit from a wide variety of biological properties.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2023

View full text Add to dashboard Cite

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.

show abstract

“…[33][34][35][36] Among the axially substituted Pcs, silicon phthalocyanines (SiPcs) exhibit excellent biological properties owing to the unusual six-coordinated silicon (IV) ion and the possibility of symmetrically or unsymmetrically replacement of different axial ligands. [37,38] Generally, amine, carboxylic, or sulfonic groups result in water-soluble phthalocyanines. [39][40][41] Also, axially substituted phthalocyanines exhibit less aggregation which is required for most industrial and medicinal applications.…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, axially substituted phthalocyanines bearing various ligand(s) on the metal center have attracted attention in recent years [33–36] . Among the axially substituted Pcs, silicon phthalocyanines (SiPcs) exhibit excellent biological properties owing to the unusual six‐coordinated silicon (IV) ion and the possibility of symmetrically or unsymmetrically replacement of different axial ligands [37,38] . Generally, amine, carboxylic, or sulfonic groups result in water‐soluble phthalocyanines [39–41] .…”

Section: Introductionmentioning

confidence: 99%

Silicon Phthalocyanines as Anti‐infectious, Antioxidant, and Anticancer Agents

Yenilmez¹,

Farajzadeh²,

Tollu³

et al. 2023

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

This study reports the synthesis of three silicon phthalocyanines (SiPc1–3) bearing 2‐dimethylaminoethoxy, 2‐[2‐(dimethylamino)ethoxy]ethoxy, or 2‐{2‐[2‐(dimethylamino)ethoxy]ethoxy}ethoxy on axial positions. Also, their quaternized derivatives (SiPcQ1–3) were prepared. The effect of ligand length on the biological features of water‐soluble silicon phthalocyanines (SiPcQ1–3) was investigated. The highest antimicrobial activity was obtained 32 μg/mL for SiPcQ1 against double‐distilled water, E. hirae, and E. faecalis. The growth inhibition percentages of compounds SiPcQ1–3 were obtained 100 %, 100 %, and 85.14 %, respectively. The highest biofilm inhibition activity was obtained 86.16 % for 250 mg/L SiPcQ3 against S. aureus. The E. coli growth inhibition activities of 50 mg/L compounds SiPcQ1–3 ranged from 60.17 % to 87.53 % and their activities increased (73.46 %–95.37 %) by the enhancement of the concentration. The E. coli viability inhibition activities of SiPcQ1–3 were concentration‐dependent. The DNA cleavage and binding properties of SiPcQ1–3 were studied using pBR322 DNA and CT‐DNA, respectively. Besides, the toxicity of SiPcQ1–3 was examined against the human colon cancer cell line (DLD‐1). The IC50 values of compounds (SiPcQ1–3) were obtained between 10.12 and 27.06 μM in the dark, however, these values were calculated between 12.32 and 22.17 μM under the light. SiPcQ3 exhibited the highest in vitro anticancer activity against the tested cell.

show abstract

Anticancer and biological properties of new axially disubstituted silicon phthalocyanines

Abstract: This study reports the synthesis of three novel axially disubstituted silicon phthalocyanines (1-3-Si) and their quaternized phthalocyanines (1-3-QSi). The resulting compounds were characterized by applying spectroscopic techniques including 1H NMR,...

Cited by 9 publications

References 83 publications

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

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

Silicon Phthalocyanines as Anti‐infectious, Antioxidant, and Anticancer Agents

Contact Info

Product

Resources

About