Photodynamic therapy effect of morpholinium containing silicon (IV) phthalocyanine on HCT-116 cells

Yalçın, Can Özgür; Barut, Burak; Barut, Elif Nur; Demirbaş, Ümit; Dinçer, Tuba; Engin, Seçkin; Özel, Arzu; Sezen, Feride Sena

doi:10.1016/j.pdpdt.2020.101975

Cited by 10 publications

(6 citation statements)

References 43 publications

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“…Membranes were blocked and incubated with primary antibodies; anti‐cytochrome c (Cell Signaling; #11940S, (1 : 1000)), anti‐p53 (Cell signaling; #9282, (1 : 500)), anti‐caspase (Cell signaling; #9662, (1 : 1000)), and anti‐β‐actin (Sigma‐Aldrich, A5441, (1 : 3000)) antibody overnight at 4° C. After the primary antibody incubation, they were incubated with horseradish peroxidase (HRP) linked secondary antibody at room temperature for 1 h, and visualized with an enhanced chemiluminescence kit (ECL kit, Bio‐Rad). Densitometry results were normalized by β‐actin and expressed as % of the control group [45] …”

Section: Methodsmentioning

confidence: 99%

Insights into the Biological Activity and Cytotoxic Mechanism of Epimedium pubigerum

Seyhan,

Akkaya,

Kolci

et al. 2023

Chemistry & Biodiversity

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In this work, the phytochemical characterization, biological activity, and cytotoxic mechanism of aerial and rhizome methanol extracts (SME and RME) of Epimedium pubigerum were investigated to demonstrate its potential usage in the treatment of lung cancer. LC‐HRMS analysis, total phenolic/flavonoid content assay, DPPH radical scavenging assay, DNA interaction, cytotoxicity, and western blotting were investigated using different methods. Fumaric acid was found to be the most abundant compound in both extracts. SME and RME were cytotoxic on A549 cells concentration‐dependently. Also, in vitro scratch assay showed that SME and RME led to a significant anti‐migratory effect at 1 mg/mL. Cytochrome c, p53, and caspase 3 expression significantly increased in the presence of RME compared to the control. All of these results claimed that RME might be suggested as a theoretically more effective phytotherapeutic agent for lung cancer compared to the effect seen with the SME.

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Section: Methodsmentioning

confidence: 99%

Insights into the Biological Activity and Cytotoxic Mechanism of Epimedium pubigerum

Seyhan,

Akkaya,

Kolci

et al. 2023

Chemistry & Biodiversity

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“…[19,20] The interaction of compounds with DNA can prevent proliferation of cancerous cells by leading to cell death via apoptosis and necrosis. [21,22] Anticancer drugs are known to be able to cleave DNA with hydrolytic and oxidative pathway. [23,24] Phthalocyanines, which have strong nuclease capacity to DNA due to high singlet oxygen efficiency and especially water-soluble property, are crucial compounds for diagnostic usage in various in pharmacological and biological applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water‐soluble phthalocyanines containing 1‐methyl‐1H‐imidazole‐2‐thiol: Investigation of DNA nuclease, α‐glucosidase inhibitory, and photo‐physicochemical properties

Günsel

Kalkan

Atmaca

et al. 2021

Applied Organom Chemis

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In this work, we have presented on the synthesis and characterization of novel 3-(1-methyl-1H-imidazole-2-thiol)phthalonitrile (1) as a ligand and its nonperipherally (M = 2H (2), Zn(II) (3), and GaCl(III) ( 4)) phthalocyanines and their highly water-soluble hydrochloride derivatives (2a-4a), containing 1-methyl-1H-imidazole-2-thiol substituents. All compounds were supported by FT-IR, UV-Vis, 1 H-NMR, 13 C-NMR, and MALDI-TOF mass spectra. The molecular structure of the novel compound (1) and its intermolecular interactions have been elucidated by analyzing the results of X-ray diffraction measurements. In order to determine the supercoiled pBR322 plasmid DNA nuclease properties of compounds (2a-4a), agarose gel electrophoresis was used. The plasmid DNA nuclease did not observe without light irradiation on increasing concentrations (2a-4a). When irradiated at 10 and 20 J/cm 2 , the band intensities changed on agarose gel, displaying photonuclease activity on supercoiled pBR322 plasmid DNA of compounds (2a-4a); 4a had the highest photonuclease activities in a concentration-dependent manner at 10 and 20 J/cm 2 . The in vitro α-glucosidase inhibitory effects of compounds (2a-4a) were investigated to determine whether they can be used in potential agents for diabetes mellitus. Compounds (2a-4a) showed higher inhibitory effects than acarbose (63.03 ± 2.14 μM) against α-glucosidase enzyme. Lineweaver-Burk analysis showed that K m increased and V max remained the same on increasing concentrations of compounds (2a-4a). The finding results claimed that the compounds inhibited α-glucosidase enzyme via competitive manner. Dixon plots showed that K i values of compounds (2a-4a) were 14.70 ± 0.70, 11.20 ± 0.50, and 12.60 ± 0.20 μM, respectively. Besides, the effect of including metal ion on photochemical and photophysical features of the compounds was studied in DMSO and water, comparatively. The compounds gave high singlet oxygen quantum yields (Φ Δ = 0.86 for (4a), 0.77 for (3a), and 0.59 for (2a)) in DMSO. The results showed that the compounds are also very suitable for photodynamic therapy applications.

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“…[14] Thus, it irreversibly results in damage to the cell, inhibits the protein or DNA or RNA activities of the cell, and causes the death of cancer cells. [14,15] The interaction of the compounds with nucleic acid (DNA, RNA) is one of the most crucial targets for anticancer agents to understand their therapeutic mechanism in cancer treatment. [16][17][18] It has been reported that BODIPYs can interact with DNA via noncovalent binding modes.…”

Section: Introductionmentioning

confidence: 99%

“…[ 14 ] Thus, it irreversibly results in damage to the cell, inhibits the protein or DNA or RNA activities of the cell, and causes the death of cancer cells. [ 14,15 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water‐soluble BODIPY dyes and investigation of their DNA interaction properties and cytotoxicity/phototoxicity

Keleş

Barut

Yıldırım

et al. 2021

Applied Organom Chemis

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In this study, water‐soluble BODIPY dyes (BDPY‐4, BDPY‐5) bearing dimethylamino and diethylamino groups were synthesized for the first time. The DNA interaction and nuclease effect of two water‐soluble BODIPY dyes were examined using absorption, competitive binding experiments, and agarose gel electrophoresis. Then, cytotoxicity and phototoxicity of the compounds were determined against A549 cells by MTT cell viability assay. The ultraviolet–visible (UV–vis) spectra of BDPY‐4 and BDPY‐5 displayed hypochromism and absorption maxima shifted to the red region. In addition, Kb values of the compounds were calculated as 2.23 × 104 and 4.84 × 104 M−1, respectively. An high‐performance liquid chromatography (HPLC) instrument without a column was used to conduct competitive binding experiments for the first time. The approach prevented the decrease in the response due to dilution and enabled the analysis to be carried out in a short time. Upon increasing concentrations of the compounds, the emission intensity of EB‐DNA significantly decreased. These obtained results suggested that the compounds bound to CT‐DNA with intercalative mode. At the same time, the Stern–Volmer constants were determined as 1.80 × 106 and 1.79 × 106 M−1 for BDPY‐4 and BDPY‐5, respectively, which is coherent with intercalative binding mode. The compounds did not display noticeable photonuclease actions with light irradiation. BDPY‐4 and BDPY‐5 showed moderate phototoxic properties on light irradiation.

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Photodynamic therapy effect of morpholinium containing silicon (IV) phthalocyanine on HCT-116 cells

Cited by 10 publications

References 43 publications

Insights into the Biological Activity and Cytotoxic Mechanism of Epimedium pubigerum

Insights into the Biological Activity and Cytotoxic Mechanism of Epimedium pubigerum

Synthesis of water‐soluble phthalocyanines containing 1‐methyl‐1H‐imidazole‐2‐thiol: Investigation of DNA nuclease, α‐glucosidase inhibitory, and photo‐physicochemical properties

Synthesis of water‐soluble BODIPY dyes and investigation of their DNA interaction properties and cytotoxicity/phototoxicity

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