Evaluation of the effects of newly synthesized metallophthalocyanines on breast cancer cell lines with photodynamic therapy

Bostancı, Hayrani Eren; Bilgiçli, Ahmet T.; Güzel, Emre; Günsel, Armağan; Hepokur, Ceylan; Çimen, Behzat; Yaraşir, M. Nilüfer

doi:10.1039/d2dt01912d

Cited by 7 publications

(4 citation statements)

References 38 publications

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“…When the literature information was scanned, it was stated that the amount of DMSO added in cell culture studies could be a maximum of 0.5 % of the total volume. [51] All synthesized compounds were tested at a maximum dose of 100 μM on each cell line, and cell viability percentages were determined. Cisplatin, a chemotherapeutic drug, was included as a negative control.…”

Section: Anticancer Activitymentioning

confidence: 99%

Synthesis and Characterization of Oxime Derivatives and their Some Transition Metal Complexes with Thiadiazole Groups: Biological Activities, and Molecular Docking Studies of the Ligands

Otaiwi,

Mirghani,

Bostancı

et al. 2024

ChemistrySelect

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This study involved the synthesis and investigation of the anticancer and antioxidant capabilities of six newly developed ligands generated from 1,3,4‐thiadiazole and diphenyl ether keto oxime which has never been synthesized before, together with their transition metal complexes. The obtained ligands were characterized using elemental analysis, FTIR, 1H NMR, 13C NMR, and mass spectroscopy. Polymeric complexes of the obtained ligands were synthesized by reacting all ligands with MCl2.nH2O (M: Mn2+/Co2+)/Ni2+/Cu2+)) salts. The polymeric complexes′ structures were determined using elemental analysis, ICP‐AES, FTIR spectroscopy, UV‐vis spectroscopy, magnetic susceptibility analysis, and thermogravimetric analysis. Subsequently, the ligands were examined for their anticancer properties. To achieve this objective, the HT‐22 cell line, which consists of healthy mouse hippocampus neuronal cells, is utilized as the control group. Additionally, the MCF7 (breast cancer), MDA‐MB‐231 (breast cancer), C6 (rat glioma), HT‐29 (colon cancer), and A549 (lung carcinoma) cell lines are employed in cell culture research as representatives of cancerous cell lines. Based on the cell culture investigations, some of the synthesized ligands showed moderate to good anti‐cancer activity, especially for both colon cancer and brain tumors. Finally, a molecular docking analysis was conducted utilizing MOE software to ascertain the binding affinity between the synthesized ligands and the specific proteins of interest.

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Section: Anticancer Activitymentioning

confidence: 99%

Synthesis and Characterization of Oxime Derivatives and their Some Transition Metal Complexes with Thiadiazole Groups: Biological Activities, and Molecular Docking Studies of the Ligands

Otaiwi,

Mirghani,

Bostancı

et al. 2024

ChemistrySelect

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“…For this reason, UV–vis spectroscopy is frequently used to examine the physical properties of Pcs . In general, two bands of Pcs are detected in the UV–vis electronic absorption spectra, which is the best evidence for phthalocyanine compounds. − The bands in the 600–700 nm region were exhibited to the Q-band transition, principally 1a 1u → 1e g * from Gouterman’s 4-orbital model . The other bands are called Soret or B bands between 300 and 400 nm in the UV region.…”

Section: Resultsmentioning

confidence: 99%

Combination of Light and Ultrasound: Exploring Sono–Photochemical Activities of Phthalocyanine-Based Sensitizers

et al. 2023

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Recently, there has been increasing interest in photodynamic therapy (PDT) compared to traditional methods (immunotherapy, surgery, chemotherapy, or radiotherapy) in the treatment of cancer. Also, sonodynamic therapy (SDT) is a non-invasive therapeutic modality that enables high tissue penetration by triggered ultrasound (US). Phthalocyanines (Pcs) are known as one of the most important classes of sensitizers used in PDT and SDT. Motivated by these facts, in this study, to assess potentials for sono-PDT (SPDT), the preparation of peripherally substituted metal-free (2), zinc (3), and indium (4) Pcs was completed by 3-methoxybenzyloxy substituents. The resulting compounds were characterized by applying spectroscopic techniques including 1 H NMR, FT-IR, UV−vis, and MS. In sono−photochemical studies, the calculated singlet oxygen quantum yield (Φ Δ ) values were 0.68 for ZnPc (3) and 0.83 for InPc (4) after light irradiation; these values increased to 0.81 for 3 and 0.94 for 4 after combination US and light irradiation. The obtained data proved that the singlet oxygen production increased considerably by changing the method from light irradiation to US/light. This research will enrich the literature on increasing singlet oxygen production by the SPDT method. Theoretical calculations based on density functional theory (DFT) give further explanations of the optical and (photo)chemical processes behind the singlet oxygen generation. Our calculations are able to provide the energy of the excited states with excellent agreement with the experimental results, and they also allow us to understand and predict the activity of these Pcs based on their excited states and a clear enhancement of the spin−orbit coupling (SOC) when a metal center is included in the Pcs. This work thus exploits new insights into the advanced sono-photodynamic properties of potential sensitizers for efficient SPDT applications.

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“…With the flow cytometry studies described previously, 73 the two most active treatments on cancer cells ( 3a and 3b ) were listed, how they were directed to apoptosis with Annexin V dye and where the cell cycle was stopped with the necessary kit. The results obtained are shown in Figures 4 and 5 .…”

Section: Results and Discussionmentioning

confidence: 99%

Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I–II Inhibition Properties, and In Silico Studies

Faris,

Bostancı,

Özcan

et al. 2024

ACS Omega

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Imidazole derivatives display extensive applications in pharmaceutical chemistry and have been investigated as bioactive compounds for medicinal chemistry. In this study, besides the starting materials (3a−c and 4a−c), synthesis, characterization, and biological activity studies were conducted on a total of 18 compounds, nine of which are known and the other nine are original. The compounds investigated in the study are a series of alkyl (7−15) and aryl (16−24) ether derivatives bearing substituted phenyl and imidazole rings, which were characterized using various methods including 1 H NMR, 13 C NMR, FT-IR analysis, elemental analysis, and mass spectroscopy. Computeraided drug design studies have been carried out to predict the biological activities of compounds. Besides DFT calculations, the binding affinities of the compounds to EGFR, VEGFR2, FGFR1, HSP90, hCA I, and hCA II were investigated. Additionally, druglikeness and ADME analyses were performed on the compounds. Anticancer, antioxidant, and enzyme inhibition activity tests were performed in biological activity studies on the synthesized compounds. Among the synthesized compounds, compounds 17 and 19− 24 generally exhibited inhibition profiles against the widespread cytosolic hCA I isozyme with IC 50 values ranging from 4.13 to 15.67 nM and cytosolic hCA II isozyme with IC 50 values ranging from 5.65 to 14.84 nM. L929 (mouse fibroblast cell line) was used as the control healthy cell line, and MCF7 (breast cancer), C6 (rat glioblastoma), and HT-29 (colon cancer) cells were used in cell culture studies as cancer cell lines. Before the study on cancer cells, all compounds were examined on healthy cells, and their cytotoxicity was determined. As a result of these data, studies continued with six compounds determined to be nontoxic. On cancerous cells, it was determined that compounds 3a, 3b, 4a, 4b, 4c, and 7 had cytotoxic effects on both colon cancer and brain tumors. It was found that compound 3b had a more toxic effect than cisplatin on the glioma cell line with an IC 50 value of 10.721 ± 0.38 μM, and compound 3a had a more toxic effect on the colon cancer cell line with an IC 50 value of 20.88 ± 1.02 μM. However, it was determined that the same compounds did not have a statistically significant effect on breast cancer. Flow cytometry studies also showed that when the IC 50 dose of compound 3b was applied to the C6 cell line, the cells tended to early and late apoptosis. Additionally, it has been shown by flow cytometry that the cell cycle stops in the G0/G1 phase. A similar effect was observed in the colon cancer cell line with compound 3a. Compound 3b caused early and late apoptosis of the colon cancer cell line with the applied IC 50 dose and stopped the cell cycle in the G0/G1 phase. Finally, the FRAP method studied all synthesized compounds' antioxidant effects. According to the measured antioxidant power results, it was determined that no compound had a more effective reducing power than vitamin E.

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Evaluation of the effects of newly synthesized metallophthalocyanines on breast cancer cell lines with photodynamic therapy

Abstract: In this study, the new phthalonitrile derivative 3-(4-(3-oxobutyl)phenoxy)phthalonitrile (1) and its non-peripheral metallophthalocyanine derivatives [Zinc(II) (2), Copper(II) (3), Cobalt (II) (4), Manganese (III) (5), Gallium (III) (6), and Indium (III)...

Cited by 7 publications

References 38 publications

Synthesis and Characterization of Oxime Derivatives and their Some Transition Metal Complexes with Thiadiazole Groups: Biological Activities, and Molecular Docking Studies of the Ligands

Synthesis and Characterization of Oxime Derivatives and their Some Transition Metal Complexes with Thiadiazole Groups: Biological Activities, and Molecular Docking Studies of the Ligands

Combination of Light and Ultrasound: Exploring Sono–Photochemical Activities of Phthalocyanine-Based Sensitizers

Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I–II Inhibition Properties, and In Silico Studies

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