Synthesis, molecular modeling and biological evaluation of chalcone thiosemicarbazide derivatives as novel anticancer agents

Zhang, Hongjia; Qian, Yanlong; Zhu, Da; Yang, Xuguang; Zhu, Hai‐Liang

doi:10.1016/j.ejmech.2011.07.016

Cited by 94 publications

(48 citation statements)

References 19 publications

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“…All the synthesized thiosemicarbazide compounds (1)(2)(3)(4)(5)(6)(7)(8) and the positive control chlorambucil were evaluated for their ability to antiproliferative activities against breast cancer cells. Although growth inhibition was concentration-dependent in either cell line, it was more pronounced at shorter times, in MDA-MB-231 than MCF-7 ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…4-Aryl/alkyl-1-(piperidin-4-yl)-carbonylthiosemicarbazides and 4-benzoyltiosemicarbazides used in this study (1)(2)(3)(4)(5)(6)(7)(8) were synthesized as described in our previous papers 12,13 . Calf thymus DNA, ethidium bromide (EtBr), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), genistein, netropsin were purchased from Sigma (St. Louis, MO).…”

Section: Reagents and Materialsmentioning

confidence: 99%

“…They comprise an intriguing class of chelating molecules which possess a wide range of beneficial medicinal properties and exhibit versatile structural features. They have been evaluated as antiviral, antibacterial and anticancer therapeutics over the last 50 years 1,2 . Although a number of reports are available on biological activity of thiosemicarbazides, study on topoisomerase activity is still scarcely explored.…”

Section: Introductionmentioning

confidence: 99%

“…Thiosemicarbazides, a large group of thiourea derivatives, exhibits various biological activities and have therefore attracted considerable pharmaceutical interest 1,2 . They comprise an intriguing class of chelating molecules which possess a wide range of beneficial medicinal properties and exhibit versatile structural features.…”

Section: Introductionmentioning

confidence: 99%

“…Inspired by these optimistic results, we have synthesized and investigated the antiproliferative activity of thiosemicarbazide derivatives (1)(2)(3)(4)(5)(6)(7)(8) (Figure 1) in both MDA-MB-231 and MCF-7 breast cancer cells and assessed their ability to act as inhibitors of topoisomerases I and II (topo I and II).…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity and topoisomerase I/II inhibition activity of novel 4-aryl/alkyl-1-(piperidin-4-yl)-carbonylthiosemicarbazides and 4-benzoylthiosemicarbazides

Siwek

Bielawska²,

Maciorkowska³

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of eight thiosemicarbazide derivatives was examined for cytotoxicity in breast cancer cell cultures. Among them, 4-benzoylthiosemicarbazides proved to be only slightly less potent than chlorambucil in both MDA-MB-231 and MCF-7 lines. In contrast, 4-aryl/ alkylthiosemicarbazides revealed significantly lower cytotoxicity effect. Subsequently, all titled compounds were tested as potential human topoisomerase I and II (topo I and topo II) inhibitors. Mechanistic studies revealed that tested thiosemicarbazides act as both topoisomerase I and topoisomerase II inhibitors. Among them, the best inhibitory activity was found for 4-benzoylthiosemicarbazides (1 and 2) with IC 50 at 50 mM against topo II.

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Section: Resultsmentioning

confidence: 99%

Section: Reagents and Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Cytotoxicity and topoisomerase I/II inhibition activity of novel 4-aryl/alkyl-1-(piperidin-4-yl)-carbonylthiosemicarbazides and 4-benzoylthiosemicarbazides

Siwek

Bielawska²,

Maciorkowska³

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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Evaluation of newly synthesized derivatives of bis(hydrazine‐1‐carbothioamide) and their metal complexes synthesized in bulk and nano size as potent anticancer agents

Taha

Saleh

Elhady

et al. 2019

Applied Organom Chemis

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A series of new metal complexes were synthesized in both bulk and nano size using green methods, starting with the reaction of (E)-N′-[(E)-2bromobenzylidene]-4-oxo-4-(piperidin-1-yl)but-2-enehydrazide with thiosemicarbazide and different metal halides such as CuI·2H 2 O, CuCl 2 ·2H 2 O, CoCl 2 ·2H 2 O, and ZnCl 2 ·2H 2 O, and metal nitrate such as Ga(NO 3 ) 3 ·2H 2 O.Structures of these metal complexes were confirmed using different spectroscopic methods, elemental analysis, electronic spectra, and microanalytical methods (scanning electron microscopy and transmission electron microscopy) for nano complexes. The distorted octahedral geometry for all complexes was suggested based on magnetic moments and electronic spectral studies. The cytotoxic activity of the compounds was investigated against human hepatocellular carcinoma (HepG2) and human colorectal carcinoma (HCT-116) cell lines. Most tested compounds had higher inhibitory activity than the standard vinblastine drug. Interestingly, the nano-sized Ga(III) complex 11 was the most potent compound against the two tested cell lines, with 50% inhibitory concentration (IC 50 ) of 2.56 μg/mL for HepG2, compared with the reference drug vinblastine (IC 50 15.6 μg/mL), and IC 50 4.64 μg/mL for HCT-116, compared with the standard (IC 50 13.9 μg/mL). The bioassay results helped us identify new potent and selective anticancer agents.

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Structural and biological studies of mononuclear metal (II) complexes containing hetero ligand based on 3‐acetylpyridine thiosemicarbazone

BenGuzzi,

S. Abubakr,

Hassan

2023

Applied Organom Chemis

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The Schiff base (3‐APT) was a bidentate ligand produced from the condensation between 3‐acetylpyridine and the amine group of thiosemicarbazide. Metal chelates were successfully obtained with formulas [Cu(3‐APT)2X]X, [Ni(3‐APT)2]X2.H2O and [Pd(3‐APT)X2] (where 3‐APT = 3‐acetylpyridine thiosemicarbazone and X = Cl−). The characterization was performed by various physicochemical tools. The studied (3‐APT) ligand had two donor sites through both azomethine nitrogen and thiocarbonyl sulfur. The characterization tools observed the presence of two different geometric shapes. The square planar structure in the case of both nickel (II) and palladium (II) chelates and the square pyramidal structure in the case of copper (II) complex. The characterization involved a 1HNMR study for the (3‐APT) ligand and its square planar Pd (II) and Ni (II) chelates. The density functional theory was used to structurally optimize the synthesized ligand and its chelates. The antibacterial activity was evaluated using different types of bacteria showing superior results. The breast (MCF‐7) cell line was selected to investigate the cytotoxic effect of formed compounds. The palladium (II) complex was the most cytotoxic effective compound with the least IC50 value. Further theoretical molecular docking study was performed to observe the active sites in the selected proteins during their interactions with our compounds.

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Synthesis, molecular modeling and biological evaluation of chalcone thiosemicarbazide derivatives as novel anticancer agents

Cited by 94 publications

References 19 publications

Cytotoxicity and topoisomerase I/II inhibition activity of novel 4-aryl/alkyl-1-(piperidin-4-yl)-carbonylthiosemicarbazides and 4-benzoylthiosemicarbazides

Cytotoxicity and topoisomerase I/II inhibition activity of novel 4-aryl/alkyl-1-(piperidin-4-yl)-carbonylthiosemicarbazides and 4-benzoylthiosemicarbazides

Evaluation of newly synthesized derivatives of bis(hydrazine‐1‐carbothioamide) and their metal complexes synthesized in bulk and nano size as potent anticancer agents

Structural and biological studies of mononuclear metal (II) complexes containing hetero ligand based on 3‐acetylpyridine thiosemicarbazone

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