An investigation on the DNA/protein binding, DNA cleavage and in vitro anticancer properties of SNO pincer type palladium(II) complexes with N-substituted isatin thiosemicarbazone ligands

Muralisankar, Mathiyan; Basheer, Sabeel M.; Haribabu, Jebiti; Bhuvanesh, Nattamai; Karvembu, Ramasamy; Sreekanth, Anandaram

doi:10.1016/j.ica.2017.05.044

Cited by 56 publications

(18 citation statements)

References 53 publications

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“…The IR spectrum of the ligand displayed band around 3414, 3315 and 3180 cm −1 , which are assigned to pyridine attached NH, terminal NH and thiocarbonyl attached NH groups, respectively. After complexation, stretching frequency of the thiocarbonyl group adjacent to –NH was disappeared and other two bands were unaltered, which strongly evidencing the ligand coordination with all the metal(II) ions in the deprotonated thiol form . The formation of a new peaks were observed in the complexes in the range of 1506–1565 cm −1 due to ʋ(N=C).…”

Section: Resultsmentioning

confidence: 88%

“…It also has been known that the influence on the biological activity of the metal complexes can be brought about by the nature of the metal ion, its oxidation state, and the number and type of ligands bound to improve the potentiality of the drugs . We have been very much interested in studying the variable coordination behaviour of thiosemicarbazone ligands and their metal complexes towards various biological applications …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Structural, Biological Evaluation, Molecular Docking and DFT Studies of Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) Complexes bearing Heterocyclic Thiosemicarbazone ligand

Konakanchi

Haribabu

Prashanth

et al. 2018

Applied Organom Chemis

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A new ligand, 2‐aminonicotinaldehyde N‐methyl thiosemicarbazone (ANMTSC) and its metal complexes [Co(II) (1); Ni(II) (2); Cu(II) (3); Zn(II) (4); Cd(II) (5) or Hg(II) (6)] were synthesized. The compounds were characterized by analytical methods and various spectroscopic (infrared, magnetic, thermal, 1H, 13C NMR, electronic and ESR) tools. The structure of ANMTSC ligand was confirmed by single crystal X‐ray diffraction study. The spectral data of metal complexes indicate that the ligand acts as mononegative, bidentate coordination through imine nitrogen (N) and thiocarbonyl sulphur (S−) atoms. The proposed geometries for complexes were octahedral (1–2), distorted octahedral (3) and tetrahedral (4–6). Computational details of theoretical calculations (DFT) of complexes have been discussed. The compounds were subjected to antimicrobial, antioxidant, antidiabetic, anticancer, ROS, studies and EGFR targeting molecular docking analysis. Complex 5 has shown excellent antibacterial activity and the complexes 2 and 5 have shown good antifungal activity. The complexes 1 and 4 displayed good antioxidant property with IC50 values of 11.17 ± 1.92 μM and 10.79 ± 1.85 μM, respectively compared to standard. In addition, in vitro anticancer activity of the compounds was investigated against HeLa, MCF‐7, A549, IMR‐32 and HEK 293 cell lines. Among all the compounds, complex 4 was more effective against HeLa (IC50 = 10.28 ± 0.69 μM), MCF‐7 (IC50 = 9.80 ± 0.83 μM), A549 (IC50 = 11.08 ± 0.57 μM) and IMR‐32 (10.41 ± 0.60 μM) exhibited superior anticancer activity [IC50 = 9.80 ± 0.83 (4) and 9.91 ± 0.37 μM (1)] against MCF‐7 compared with other complexes.

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Section: Resultsmentioning

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural, Biological Evaluation, Molecular Docking and DFT Studies of Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) Complexes bearing Heterocyclic Thiosemicarbazone ligand

Konakanchi

Haribabu

Prashanth

et al. 2018

Applied Organom Chemis

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“…The coordination of the Cu(II) and Ni(II) ions to the ligands through the azomethine group (C=N) was confirmed by the slight shift in the vibration to lower wavenumbers (1590 cm −1 ) compared to that of the free ligands (1615 cm −1 ). The band at ∼850 cm −1 assigned to the ν (C=S) vibration in the ligands was shifted to a lower wavenumber of ∼835 cm −1 in the complexes, indicating the sulphur was involved in coordination to the metal ion [14, 31, 32]. Thus, the TSCs act in a tridentate manner with an NNS system coordinating through the nitrogen atoms of the azomethine group and the pyrazine ring and the sulphur atom of the thioamide group.…”

Section: Resultsmentioning

confidence: 99%

Cu(II) and Ni(II) Complexes with New Tridentate NNS Thiosemicarbazones: Synthesis, Characterisation, DNA Interaction, and Antibacterial Activity

Polo-Cerón

2019

Bioinorganic Chemistry and Applications

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This paper reports the synthesis and detailed characterisation of copper(II) and nickel(II) complexes with tridentate thiosemicarbazone ligands H2L1 and H2L2 derived from 2-acetylpyrazine. The ligands and their metal complexes were characterised by different physicochemical techniques, including elemental and thermogravimetric analysis; UV-Vis, IR, 1H-NMR, and 13C-NMR spectroscopy; molar conductance measurements; and mass spectrometry. The crystal structure of the H2L1 ligand was determined by single crystal X-ray diffraction studies. The spectral data showed that the thiosemicarbazone behaves as an NNS tridentate ligand through the nitrogen atoms of the azomethine group and pyrazine ring and the sulphur atom of the thioamide group. Elemental and thermal analyses indicated that the obtained metal complexes had a 1 : 1 stoichiometry (metal-ligand). The interactions between these complexes and calf thymus DNA (CT-DNA) were studied by electronic absorption and viscosity measurements. The activities of these compounds against oxidative DNA cleavage were examined by agarose gel electrophoresis. Cu(II) and Ni(II) complexes can wind DNA strands through groove interactions and promote strand breakage of the plasmid pmCherry under oxidative stress conditions. Moreover, all the complexes could interact more strongly with DNA than could with the free ligands. Finally, the antibacterial activities of the ligands and their complexes were determined by in vitro tests against Gram-positive bacterial strains (S. aureus ATCC 25923, L. monocytogenes ATCC 19115, and B. cereus ATCC 10876) and Gram-negative bacterial strains (E. coli ATCC 25922, S. typhimurium ATCC 14028, and K. pneumoniae ATCC BAA-2146) using the broth microdilution method. The metal complexes showed greater antimicrobial activities than the precursor ligands against some of the microorganisms.

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“…Thiosemicarbazones can act as NS [37] bidentate, NN S [38] and ONS [39] tridentate or ONN S [40] tetradentate chelators, forming either neutral [41] or cationic [42,43], mononuclear [44,45] or polynuclear [46][47][48] systems with different metal ions. Complexes of V(IV) [49], Mn(II) [50], Fe(III) [38,51], Co(III) [52], Ni(II) [53][54][55][56], Cu(II) [28,57,58], Zn(II) [48], Ga(III) [59,60], Ru(II/III) [61][62][63][64][65][66][67][68][69], Pd(II) [70][71][72][73][74], In(III) [75], Re(I) [76,77], Pt(II) [78], Au(III) [79], Hg(II) [80], Ag(I) [81] and Sn(IV) [39] exhibit higher cytotoxicity and anti...…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones

et al. 2020

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Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (1, -NH2; 2, -NHMe; 3, -NHEt) have been prepared and characterized. In both the X-ray structures of 1 and 3, two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in 1a and nitrate in 1b) or in the co-ligand (water in 3a and methanol in 3b). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes 1 and 3 confirmed the presence of such different species in the solution. The electrochemical behavior of the pro-ligands and of the complexes was investigated, as well as their biological activity. Complexes 2 and 3 exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes 2 and 3 also showed a high selectivity towards cancerous cell lines with respect to non-cancerous cell lines and were able to circumvent cisplatin resistance. Via the Transmission Electron Microscopy (TEM) imaging technique, preliminary insights into the biological activity of copper complexes were obtained.

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An investigation on the DNA/protein binding, DNA cleavage and in vitro anticancer properties of SNO pincer type palladium(II) complexes with N-substituted isatin thiosemicarbazone ligands

Cited by 56 publications

References 53 publications

Synthesis, Structural, Biological Evaluation, Molecular Docking and DFT Studies of Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) Complexes bearing Heterocyclic Thiosemicarbazone ligand

Synthesis, Structural, Biological Evaluation, Molecular Docking and DFT Studies of Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) Complexes bearing Heterocyclic Thiosemicarbazone ligand

Cu(II) and Ni(II) Complexes with New Tridentate NNS Thiosemicarbazones: Synthesis, Characterisation, DNA Interaction, and Antibacterial Activity

Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones

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