Synthesis, characterization, crystal structure and cytotoxic properties of thiosemicarbazide Ni(II) and Zn(II) complexes

Kumar, S. Mathan; Rajesh, Jegathalaprathaban; Anitha, K.; Dhahagani, K.; Marappan, M.; Gandhi, Namita; Rajagopal, Gurusamy

doi:10.1016/j.saa.2015.01.080

Cited by 14 publications

(4 citation statements)

References 46 publications

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“…Thiosemicarbazone derivatives exhibit important biological activities [ 11 ], such as antibacterial [ 12 ], antimalarial, [ 13 ] and antitumor activities [ 14 ]. The antiproliferative properties of thiosemicarbazones have been attributed to their ability to chelate metal ions because of the presence of an NNS (Nitrogen–Nitrogen–Sulfur) tridentate set of donor atoms that bind not only iron, but also copper [ 15 , 16 , 17 ], molybdenum [ 18 ], nickel [ 16 , 19 ], zinc [ 17 , 19 ], and ruthenium [ 20 ]. The thiosemicarbazone-metal complexes are lipophilic and pass through the cell membrane to release the metal intracellularly.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Almeida

Lafayette

Silva

et al. 2015

IJMS

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In this work, the acridine nucleus was used as a lead-compound for structural modification by adding different substituted thiosemicarbazide moieties. Eight new (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide derivatives (3a–h) were synthesized, their antiproliferative activities were evaluated, and DNA binding properties were performed with calf thymus DNA (ctDNA) by electronic absorption and fluorescence spectroscopies. Both hyperchromic and hypochromic effects, as well as red or blue shifts were demonstrated by addition of ctDNA to the derivatives. The calculated binding constants ranged from 1.74 × 104 to 1.0 × 106 M−1 and quenching constants from −0.2 × 104 to 2.18 × 104 M−1 indicating high affinity to ctDNA base pairs. The most efficient compound in binding to ctDNA in vitro was (Z)-2-(acridin-9-ylmethylene)-N-(4-chlorophenyl) hydrazinecarbothioamide (3f), while the most active compound in antiproliferative assay was (Z)-2-(acridin-9-ylmethylene)-N-phenylhydrazinecarbothioamide (3a). There was no correlation between DNA-binding and in vitro antiproliferative activity, but the results suggest that DNA binding can be involved in the biological activity mechanism. This study may guide the choice of the size and shape of the intercalating part of the ligand and the strategic selection of substituents that increase DNA-binding or antiproliferative properties.

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Section: Introductionmentioning

confidence: 99%

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Almeida

Lafayette

Silva

et al. 2015

IJMS

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“…The electronic absorption spectra of 3-TFT was recorded in ethanol (1x10 -6 M) as solvent with cut-off point at 205 nm. Peak at 235 nm is attributed to the π→π* transition for phenyl ring chromophore [7]. The broad peak at 318 nm is assigned as overlapped of both n→π* and π→π* electronic transitions of thiocarbonyl (C=S) and azomethine carbon (C=N) chromophores.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Electrical Conductivity of N-(3-(Trifluoromethyl)Benzylidine)Thiosemicarbazide towards Dyes Sensitized Solar Cell

Osman

Farizal

Ishak

et al. 2018

DDF

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Organic compound containing thiosemicarbazide moiety has been successfully synthesized. The new synthesized dyes, N-(3-(Trifluoromethylbenzaldehyde)benzylidine thiosemi- carbazide (3-TFT) was characterized by spectroscopic technique namely, CHNS elemental analysis, Fourier Transform Infra-Red analysis (FT-IR), UV-Visible analysis (UV-Vis),1H and13C Nuclear Magnetic Resonance (NMR). The thin films of this dye have been prepared using a spin coating technique and deposited on indium tin oxide (ITO) glass substrate. The main highlight was an electrical conductivity of thin films which was measured using four point probing system in a range of light intensity, 25 Wm-2until 200Wm-2. The potential electrical conductivity of 3-TFT dye was found gradually increased until reached the maximum conductivity values of 0.1489 Scm-1at light intensity of 100 Wm-2in the most diluted concentration at 1x10-5M.

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“…12,13 Consequently the data obtained for each complex showed the quality of the results with minimum concentration (5 μM) and shorter incubation period (24 h) when compared to the results of similar observations. 12,31,32 CONCLUSIONS In this study, the coordinating ability of the nine thiosemicarbazone-based copper(II) complexes C1-C9 was derived from three sulfur-containing ligands H(L1)-H(L3) with copper and diimine co-ligands. It was concluded that the copper(II) bis complexes C1-C3 coordinated to the central metal copper through two molecules, deprotonated thiolic sulfur and azomethine nitrogen.…”

Section: In Vitro Cytotoxic Evaluation By the Mtt Assaymentioning

confidence: 99%

Synthesis and efficacy of copper(II) complexes bearing N(4)-substituted thiosemicarbazide and diimine co-ligands on plasmid DNA and HeLa cell lines

Rajendran¹,

Periyasamy²,

Kamatchi

et al. 2020

JSCS

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This present work deals with the synthesizes of nine novel thiosemicarbazone copper(II) complexes {[Cu(L) 2 ]Cl C3, [Cu(L)(bpy)]Cl C4-C6, [Cu(L) (phen)]Cl C7-C9 (where, L = H(L1)-H(L3), H(L1) = (E)-N-methyl-2-(1-phenyl-2-((5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)thio)ethylidene)hydrazinecarbothioamide, H(L2) = (E)-N-ethyl-2-(1-phenyl-2-((5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)thio)ethylidene) hydrazinecarbothioamide, H(L3) = (E)-N-phenyl-2-(1-phenyl-2-((5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)thio)ethylidene) hydrazinecarbothioamide, bpy = 2,2′-bipyridyl and phen = 1,10-phenanthroline) with improved pharmacological results. The synthesized complexes were characterized by various spectral-analytical techniques. The structure of the copper(II) complexes C1-C9 was proposed by EPR spectroscopy. It confirmed the square planar coordination around Cu(II) complexes. The antibacterial screening of the complexes revealed that complexes C7 and C8 demonstrated significant activity against Gram-positive (B. thuringiensis) and Gram-negative (E. coli) bacteria. The concentration-dependent DNA cleavage activity of supercoiled (SC) pUC18 DNA exhibited complete DNA degradation effect on complex C6 at a minimum concentration of 40 μM. In vitro cytotoxic results showed that the mixed ligand copper(II) complexes C4, C5 and C7 exhibited higher effects on human cervical cancer cell lines, HeLa, when compared to cisplatin. Hence, the results obtained from each biological screening indicated the superior biological efficacy of the mixed ligand copper(II) complexes bearing diimine moieties. It could be considered as a promising alternative to an existing anticancer drug.

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Synthesis, characterization, crystal structure and cytotoxic properties of thiosemicarbazide Ni(II) and Zn(II) complexes

Cited by 14 publications

References 46 publications

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Synthesis, DNA Binding, and Antiproliferative Activity of Novel Acridine-Thiosemicarbazone Derivatives

Synthesis and Electrical Conductivity of N-(3-(Trifluoromethyl)Benzylidine)Thiosemicarbazide towards Dyes Sensitized Solar Cell

Synthesis and efficacy of copper(II) complexes bearing N(4)-substituted thiosemicarbazide and diimine co-ligands on plasmid DNA and HeLa cell lines

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