Spectrophotometric, voltammetric and cytotoxicity studies of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)-substituted derivatives: A combined experimental–computational study

Akgemci, Emine Guler; Saf, Ahmet Özgür; Tasdemir, Halil Ugur; Türkkan, Ercan; Bingöl, Haluk; Turan, Suna Özbaş; Akkiprik, Mustafa

doi:10.1016/j.saa.2014.09.087

Cited by 11 publications

(7 citation statements)

References 33 publications

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“…The DpT group of compounds, which includes Dp44mT and DpC, were derived from an analysis of structural activity associations over a period of 20 years and were derived from assessment of the pyridoxal isonicotinoyl hydrazone analogue group of agents (17)(18)(19)(20). Since the derivation of DpT compounds, numerous types of biological activity, including antiviral, antibacterial, antitumor, anti-leprosy, anti-tubercular and anti-malarial activities, were reported in multiple studies (21)(22)(23)(24)(25). The N1NH(CS)N 4 H structure is the key active structure, and is necessary for the biological activity of the compound.…”

Section: Discussionmentioning

confidence: 99%

In vitro assessment of the role of DpC in the treatment of head and neck squamous cell carcinoma

Zeng

et al. 2018

Oncol Lett

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The present study aimed to investigate the antitumor efficacy of di-2-pyridylketone-4-cyclohexyl-4-methyl-3-thiosemicarbazone (DpC) and di-2-pyridylketone-4,4,-dimethyl-3-thiosemicarbazone (Dp44mT) on head and neck squamous cell carcinoma (HNSCC) cells. The proliferation and apoptosis of HNSCC cells treated with the iron chelators DpC and Dp44mT were detected. The mechanism of DpC-induced apoptosis on HNSCC cells was investigated. The human HNSCC cell lines FaDu, Cal-27 and SCC-9 were cultured and exposed to gradient concentrations of DpC and Dp44mT. A Cell Counting Kit-8 assay was used to detect the viability of FaDu, Cal-27, SCC-9 cells. Double staining with annexin V and propidium iodide was performed for the detection of the proportion of apoptotic FaDu, Cal-27 and SCC-9 cells following treatment. The nuclear damage to Cal-27 cells that were treated with DpC was detected by Hoechst staining. Finally, western blot analysis was used to detect the expression of proteins associated with the DNA damage pathway in Cal-27 cells that were treated with DpC. The CCK-8 assay showed that treatment with DpC and Dp44mT was able to markedly inhibit the viability of FaDu, Cal-27 and SCC-9 cells in a concentration-dependent manner. In comparison to Dp44mT, treatment with DpC exhibited a more effective inhibitory effect on the viability of HNSCC cells. The proportion of apoptotic cells detected by flow cytometry increased in a dose-dependent manner in all cell lines following DpC and Dp44mT treatment, with the proportion of apoptotic HNSCC cells induced by DpC treatment being significantly higher compared with Dp44mT (P<0.05). The results of Hoechst staining revealed that the nuclei of Cal-27 cells exhibited morphological changes in response to DpC treatment, including karyopyknosis and nuclear fragmentation. The expression of DNA damage-associated proteins, including phosphorylated (p)-serine-protein kinase ATM, p-serine/threonine-protein kinase Chk1 (p-Chk-1), p-serine/threonine-protein kinase ATR (p-ATR), p-Chk-2, poly (ADP-ribose) polymerase, p-histone H2AX, breast cancer type 1 susceptibility protein, p-tumor protein P53, increased with increasing concentration of DpC in Cal-27 cells. Treatment with DpC and Dp44mT markedly inhibited cell viability and increased the apoptotic rates in human HNSCC cells in a concentration-dependent manner. DpC exhibited a stronger antitumor effect compared with Dp44mT, potentially inducing the apoptosis of HNSCC cells via the upregulation of DNA damage repair-associated proteins.

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Section: Discussionmentioning

confidence: 99%

In vitro assessment of the role of DpC in the treatment of head and neck squamous cell carcinoma

Zeng

et al. 2018

Oncol Lett

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“…Zn(HMAT)2 was synthesized (Scheme 1) according to our previous article (18,19). The possible structure of the complex is given in Scheme 1 (20,21)…”

Section: Synthesis Of Zn(hmat)2mentioning

confidence: 99%

“…UV-Vis spectra of HMAT and Zn(HMAT)2 (in DMF) was presented in Figure 3. In the UV-Vis spectrum of HMAT, the band at 305 nm belongs to azomethine π→π* transitions, whereas the absorption at 355 nm corresponds to thioamide n→π* transitions (19). After the complexation, the first band associated with the carbonyl and azomethine group was observed at 296 nm due to π→π* transitions (30).…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

“…Bovine serum albumin (BSA), which is the protein in the blood, take place in many researches due to its low cost (16), structural homology to human serum albumin and stability (17). Synthesis method of 2-hydroxy-5methoxyacetophenone thiosemicarbazone based Zn(II) complex and its application studies such as evaluation of anticancer activity in breast cancer cell lines, carbonic anhydrase inhibition and microbiological analysis results were included in our previous study (18,19). In addition, the investigation of binding properties CT-DNA and BSA with the compound have been presented in this article.…”

Section: Introductionmentioning

confidence: 99%

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CT-DNA/BSA Binding Studies of Thiosemicarbazone-Derivated Zn(II) Complex

Uçar

Fındık

Akgemci

2022

Cumhuriyet Science Journal

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“…The substituent of phenolic groups at N4 position enhances the biological significance of thiosemicarbazones [13]. Likewise, substitution at N4 position accelerates the antiproliferative capacity of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone [14] and 2-pyridinecarboxaldehyde thiosemicarbazone metal complexes [15].…”

Section: Biological Importance Of Semicarbazones and Thiosemicarbazonesmentioning

confidence: 99%

Biological Applications of Co(II) and Ni(II) Complexes of Semicarbazones and Thiosemicarbazones

Jain¹,

Kumar²,

Chandra³

2018

Asian J. Chem.

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Spectrophotometric, voltammetric and cytotoxicity studies of 2-hydroxy-5-methoxyacetophenone thiosemicarbazone and its N(4)-substituted derivatives: A combined experimental–computational study

Cited by 11 publications

References 33 publications

In vitro assessment of the role of DpC in the treatment of head and neck squamous cell carcinoma

In vitro assessment of the role of DpC in the treatment of head and neck squamous cell carcinoma

CT-DNA/BSA Binding Studies of Thiosemicarbazone-Derivated Zn(II) Complex

Biological Applications of Co(II) and Ni(II) Complexes of Semicarbazones and Thiosemicarbazones

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