Topoisomerase II inhibition activity of new square planar Ni(II) complexes containing N-substituted thiosemicarbazones: Synthesis, spectroscopy, X-ray crystallography and electrochemical characterization

Prabhakaran, R.; Sivasamy, R.; Angayarkanni, Jayaraman; Huang, Rui; Kalaivani, P.; Karvembu, Ramasamy; Dallemer, F.; Natarajan, K.

doi:10.1016/j.ica.2011.03.020

Cited by 47 publications

(24 citation statements)

References 75 publications

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“…The presence of a weak new band at 440 cm À1 is due to the formation of Ni-N linkage [1]. A medium intensity band appeared at 741 cm À1 due to C-S stretching indicates the coordination through the thiolate sulfur atom of the ligand [2].…”

Section: Resultsmentioning

confidence: 99%

“…When compared to the bonds between Ni1-S1 and Ni1-S2, which are 2.167 (13) and 2.163 (11) Å, respectively, the observed Ni1-N bonds are shorter. This is due to the strong p-interaction between nickel and imine nitrogen [2]. Information of hydrogen bonds of 1 are summarized in Table 5.…”

Section: H and 13 C Nmrmentioning

confidence: 99%

“…Derivatives of thiosemicarbazones and their metal complexes are well known for their wide range of biological activities that include antiproliferative, antibacterial, antitumor, antifungal, and antileukemic properties [1][2][3][4]. Previously, in our attempt to develop metal complexes with better cyto-selectivity, we have reported the cytotoxicity and topoisomerase inhibition activities of zinc complexes of thiosemicarbazones [5].…”

Section: Introductionmentioning

confidence: 99%

“…Several organometallic steroidal complexes containing ferrocenyl were synthesized by Top et al and the reported antiproliferative effect of these compounds on the hormone-independent prostate cancer cells PC-3 is stronger compared to the ferrocenyl derivative of the nonsteroidal antiandrogen nilutamide [17]. On the other hand, metal complexes containing thiosemicarbazones have demonstrated a wide range of biological activities including cytotoxic, antibacterial, antifungal, antitumor, and antileukemic properties [2,3,18]. The diversity of certain biological properties are increased dramatically by steroidal thiosemicarbazones [18].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP)

Heng

Sinniah

Teoh

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Testosterone thiosemicarbazone, L and its nickel (II) complex 1 were synthesized and characterized by using FTIR, CHN, (1)H NMR, and X-ray crystallography. X-ray diffraction study confirmed the formation of L from condensation of testosterone and thiosemicarbazide. Mononuclear complex 1 is coordinated to two Schiff base ligands via two imine nitrogens and two tautomeric thiol sulfurs. The cytotoxicity of both compounds was investigated via MTT assay with cisplatin as positive reference standard. L is more potent towards androgen-dependent LNCaP (prostate) and HCT 116 (colon). On the other hand, complex 1, which is in a distorted square planar environment with L acting as a bidentate NS-donor ligand, is capable of inhibiting the growth of all the cancer cell lines tested, including PC-3 (prostate). It is noteworthy that both compounds are less toxic towards human colon cell CCD-18Co. The intrinsic DNA binding constant (Kb) of both compounds were evaluated via UV-Vis spectrophotometry. Both compounds showed Kb values which are comparable to the reported Kb value of typical classical intercalator such as ethidium bromide. The binding constant of the complex is almost double compared with ligand L. Both compounds were unable to inhibit the action topoisomerase I, which is the common target in cancer treatment (especially colon cancer). This suggest a topoisomerase I independent-cell death mechanism.

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Section: Resultsmentioning

confidence: 99%

Section: H and 13 C Nmrmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP)

Heng

Sinniah

Teoh

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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show abstract

“…It was reported by Hall et al (1997) that nickel(II) complexes of thiosemicarbazones significantly inhibited topoisomerase II. Similarly, Prabhakaran et al (2011) showed that Ni(II) complexes containing N-substituted thiosemicarbazones considerably inhibited topoisomerase II.…”

Section: Discussionmentioning

confidence: 94%

Anticancer activities and mechanism of action of 2 novel metal complexes, C16H34N8O5Ag2Cd and C11H16N7O2Ag3Ni

Aydın¹,

Korkmaz²,

Teki̇n³

et al. 2014

Turk J Biol

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IntroductionCancer is considered the second most common disease causing death (Tuncer, 2008). It is estimated that 19.3 million new cancer cases will be detected per year by 2025. The incidence, morbidity, and mortality of cancer are expected to be much higher in developing countries such as Turkey. Efforts to cure cancer or reduce its occurrence will be significantly important (Tuncer, 2008).Although many anticancer drugs have been used to treat cancer, they have some limitations, such as side effects, tumor specificity, and tumor cell resistance (Roche, 2002). Therefore, new anticancer drug candidates with few or no side effects need to be developed as alternatives to current chemotherapeutic drugs. Metals and metal compounds have been used in medicine as antiprotozoal, antiulcer, antiarthritic, antimalarial, antimicrobial, and anticancer drugs (Avendańo, 2008). Nowadays, the application of metal complexes in medicine is being investigated very extensively. Thati et al. (2007) reported that silver complexes of coumarin derivatives possess anticancer activity against certain types of cancer. Zhu et al. (2003) reported that silver carboxylate dimers exert anticancer activity against human carcinoma cells. The phosphine Abstract: The discovery of anticancer activity in cisplatin triggered the development of novel drugs containing metals such as platinum or ruthenium. Extremely diverse structural chemistry and the interaction of metal complexes with biomolecules resulted in the exploration of novel metal complexes with drug potential. In the present study, the anticancer and cytotoxic activities and the mechanisms of action were investigated for C 16 H 34 N 8 O 5 Ag 2 Cd (AN1) and C 11 H 16 N 7 O 2 Ag 3 Ni (AN7), 2 newly synthesized dicyanidoargentate(I) complexes. The anticancer and cytotoxic activities of AN1 and AN7 on several cancer cell lines were tested by cell proliferation and cytotoxic activity assays, respectively. The apoptotic and replication inhibitory potentials of the compounds were investigated using terminal deoxynucleotidyl transferase dUTP nick and labeling (TUNEL) and DNA topoisomerase inhibition assays. AN1 and AN7 showed significant (P < 0.05) anticancer activity and lower cytotoxicity against all cell lines tested. The TUNEL assay results indicated that AN1 and AN7 may inhibit cell proliferation by inducing apoptosis. The compounds showed very significant DNA topoisomerase I inhibitory activity. Based on the results, it is suggested that compounds AN1 and AN7 are potential anticancer drug candidates.

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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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Topoisomerase II inhibition activity of new square planar Ni(II) complexes containing N-substituted thiosemicarbazones: Synthesis, spectroscopy, X-ray crystallography and electrochemical characterization

Cited by 47 publications

References 75 publications

Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP)

Synthesis of a DNA-targeting nickel (II) complex with testosterone thiosemicarbazone which exhibits selective cytotoxicity towards human prostate cancer cells (LNCaP)

Anticancer activities and mechanism of action of 2 novel metal complexes, C16H34N8O5Ag2Cd and C11H16N7O2Ag3Ni

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

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