Pyridine-2-Carbaldehyde Thiosemicarbazonecopper System: Extending Some Findings to Other Thiosemicarbazone and Coordination Compounds

García–Tojal, Javier; Gil‐García, Rubén; Gómez-Saiz, Patricia; Ugalde, Marı́a

doi:10.2174/1877944111101020189

Cited by 20 publications

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“…In general, the coordination of a-N-pyridyl TSCs to certain metal ions [e.g. Cu(II), Pt(II), Pd(II), Ni(II)] can result in complexes with increased anticancer activity and different mechanisms of action [13]. Especially Cu(II) complexes of TSCs often show enhanced antitumor effect where it is generally assumed that their efficacy is frequently based on intracellular reductant-induced reactive oxygen species (ROS) formation [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

A comparative study of α- N -pyridyl thiosemicarbazones: Spectroscopic properties, solution stability and copper(II) complexation

Dömötör

May

Pelivan

et al. 2018

Inorganica Chimica Acta

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The effects of methyl substituents at different positions on the 2-formylpyridine thiosemicarbazone (FTSC) core structure on various physico-chemical properties were investigated. Proton dissociation processes, aqueous solution stability, isomer distribution in different solvents, fluorescence properties and lipophilic character of FTSC, pyridine-2-carboxaldehyde N 4 ,N 4-dimethylthiosemicarbazone (PTSC), 2acetylpyridine thiosemicarbazone (AcFTSC) and 2-acetylpyridine N 4 ,N 4-dimethylthiosemicarbazone (AcPTSC) were studied and compared under the same conditions. There are more and more indications that Cu(II) ions play an important role in the biological activity of anticancer thiosemicarbazones. Therefore, the complex formation equilibria of FTSC with Cu(II) ions were studied by pH-potentiometry, UV-visible spectrophotometry and electron paramagnetic resonance (EPR) spectroscopy to determine stoichiometry, stability constants and solution structures of the complexes formed in aqueous solution (with 30% DMSO). Mono-ligand complexes in different protonation states were identified such as [CuLH] 2+ , [CuL] + and [CuL(OH)] with (N pyridyl ,N,S)(H 2 O), (N pyridyl ,N,S À)(H 2 O) and (N pyridyl ,N,S À)(OH) coordination modes, respectively. At ligand excess two kinds of isomers of a bis complex [CuL 2 ] were detected at pH > 7, in which binding of the ligands via (N pyridyl ,N,S À)(N) and (N pyridyl ,N,S À)(S À) donor sets is probable at the equatorial positions. Based on the stability data, [CuL] + complexes of the aN -pyridyl thiosemicarbazones are predominant at pH 7.4 at 1:1 metal-to-ligand ratio possessing such high solution stability that their decomposition is not likely even at biologically relevant micromolar concentrations. In addition, FTSC and all methylated derivatives investigated show similar Cu(II) binding abilities which is in contrast to the respective Fe(II)/(III) complexes where terminal dimethylation distinctly increases the solution stabilities.

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Section: Introductionmentioning

confidence: 99%

A comparative study of α- N -pyridyl thiosemicarbazones: Spectroscopic properties, solution stability and copper(II) complexation

Dömötör

May

Pelivan

et al. 2018

Inorganica Chimica Acta

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“…Many TSCs including Triapine and DpC exhibit excellent chelating properties with biologically-relevant transition metal ions, such as iron(II/III), copper(II) and zinc(II). 17 The coordination of these tridentate TSCs to metal ions might result in metal complexes with enhanced anticancer properties and altered modes of action. Because malignant cells require higher amounts of essential metal ions than normal cells as a consequence of their high metabolism and proliferation levels, coordination of metal ions could be a strategy to traffick TSCs into cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Copper(ii) thiosemicarbazone complexes induce marked ROS accumulation and promote nrf2-mediated antioxidant response in highly resistant breast cancer cells

et al. 2017

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A series of water-soluble sodium salts of 3-formyl-4-hydroxybenzenesulfonic acid thiosemicarbazones (or sodium 5-sulfonate-salicylaldehyde thiosemicarbazones) containing different substituents at the terminal nitrogen atom (H, Me, Et, Ph) and their copper(ii) complexes have been prepared and characterised by elemental analysis, spectroscopic techniques (IR, UV-vis, H NMR), ESI mass spectrometry, X-ray crystallography and cyclic voltammetry. The proligands and their copper(ii) complexes exhibit moderate water solubility and good stability in aqueous environment, determined by investigating their proton dissociation and complex formation equilibria. The copper(ii) complexes showed moderate anticancer activity in established human cancer cell lines, while the proligands were devoid of cytotoxicity. The anticancer activity of the copper(ii) complexes correlates with their ability to induce ROS accumulation in cells, consistent with their redox potentials within the biological window, triggering the activation of antioxidation defense mechanisms in response to the ROS insult. These studies pave the way for the investigation of ROS-inducing copper(ii) complexes as prospective antiproliferative agents in cancer chemotherapy.

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“…Thiosemicarbazones (TSCs) are sulfur-containing organic substances whose biological properties have been extensively studied [1][2][3][4][5][6][7][8], in particular their activities against microbial diseases as malaria, small-pot, influenza, leishmaniasis or chagas [9][10][11][12][13][14], neurological pathologies [15,16] and cancer [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36]. Different biological targets have been identified, like DNA [37][38][39], RNA [40] and several enzymes as RNA-dependent DNA polymerases [41], xanthine oxidoreductase [42], thioredoxin reductase [43,44], topoisomerase IIa [45][46][47] or s...…”

Section: -Introductionmentioning

confidence: 99%

“…cells/well filled with 200 μL of medium) for 24 h under basal conditions and then exposed for other 24 h to different concentrations of the treatments( 2,4,6,8,10,20,25,50 μg per mL of medium of each treatment HPTSC, HPTSC*, 1 and 2) or just DMEM for the not treated cells (NT). Then, MTT reagent dissolved in PBS was added to the wells at a final concentration of 0.5 mg/mL of DMEM and the plate was maintained in the incubator for 2 h. After incubation for 2 h with the MTT solution, the medium was removed and 200 μL DMSO were added to each well.…”

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confidence: 99%

Revisiting the thiosemicarbazonecopper(II) reaction with glutathione. Activity against colorectal carcinoma cell lines

García–Tojal

Gil‐García

Fouz

et al. 2018

Journal of Inorganic Biochemistry

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Thiosemicarbazones (TSCs), and their copper derivatives, have been extensively studied mainly due to the potential applications as antitumor compounds. A part of the biological activity of the TSC-Cu complexes rests on their reactivity against cell reductants, as glutathione (GSH). The present paper describes the structure of the [Cu(PTSC)(ONO)] compound (1) (HPTSC=pyridine-2-carbaldehyde thiosemicarbazone) and its spectroscopic and magnetic properties. ESI studies performed on the reaction of GSH with 1 and the analogous [{Cu(PTSC*)(ONO)}] derivative (2, HPTSC*=pyridine-2-carbaldehyde 4N-methylthiosemicarbazone) show the absence of peaks related with TSC-Cu-GSH species. However GSH-Cu ones are detected, in good agreement with the release of Cu ions after reduction in the experimental conditions. The reactivity of 1 and 2 with cytochrome c and myoglobin and their activities against HT-29 and SW-480 colon carcinoma cell lines are compared with those shown by the free HPTSC and HPTSC* ligands.

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Pyridine-2-Carbaldehyde Thiosemicarbazonecopper System: Extending Some Findings to Other Thiosemicarbazone and Coordination Compounds

Cited by 20 publications

References 0 publications

A comparative study of α- N -pyridyl thiosemicarbazones: Spectroscopic properties, solution stability and copper(II) complexation

A comparative study of α- N -pyridyl thiosemicarbazones: Spectroscopic properties, solution stability and copper(II) complexation

Copper(ii) thiosemicarbazone complexes induce marked ROS accumulation and promote nrf2-mediated antioxidant response in highly resistant breast cancer cells

Revisiting the thiosemicarbazonecopper(II) reaction with glutathione. Activity against colorectal carcinoma cell lines

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