Zinc complex of tryptophan appended 1,4,7,10-tetraazacyclododecane as potential anticancer agent: Synthesis and evaluation

Adhikari, Anupriya; Kumari, Neelam; Adhikari, Manish; Kumar, Nitin; Tiwari, Anjani K.; Shukla, Alok Kumar; Mishra, Anil K.; Datta, Anupama

doi:10.1016/j.bmc.2017.04.035

Cited by 27 publications

(8 citation statements)

References 48 publications

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“…In addition to the expected biological properties of the Schiff base compounds, [30][31][32][33][34][35] binding the cobalt, copper and zinc atoms to this unit make these complexes a good prospect for biologically active compounds [36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] (31)(32)(33)(34)(35) for zinc, 36-40 for cobalt, 41-45 for copper). For the study of the biological activities of new ligand (H 3 L Br ) and its complexes 1-3, docking calculations were run to investigate the possibility of interaction between these compounds with nine protein targets, including: BRAF kinase, cathepsin B (CatB), DNA gyrase, histone deacetylase (HDAC7), recombinant human albumin (rHA), ribonucleotide reductases (RNR), thioredoxin reductase (TrxR), thymidylate synthase (TS), topoisomerase II (Top II).…”

Section: Introductionmentioning

confidence: 99%

Theoretical and experimental investigation of anticancer activities of an acyclic and symmetrical compartmental Schiff base ligand and its Co(ii), Cu(ii) and Zn(ii) complexes

et al. 2018

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Section: Introductionmentioning

confidence: 99%

Theoretical and experimental investigation of anticancer activities of an acyclic and symmetrical compartmental Schiff base ligand and its Co(ii), Cu(ii) and Zn(ii) complexes

et al. 2018

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“…Also shrinking of the cells followed by clustering and fragments formation takes place (Figures and ). These results suggest that the complexes mediated cell death take place due to apoptosis which is activated by fragmentation and damage to the DNA . The resulted values suggest that the 1 and 2 show a significant inhibitory potency against the proliferation of the cell line in a dose‐dependent manner (IC 50 = 19–23 μM).…”

Section: Resultsmentioning

confidence: 90%

Zinc(II)‐N₂O₂ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity

Neelakantan¹,

Balakrishnan²,

Balamurugan³

et al. 2018

Applied Organom Chemis

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The alkyne arms containing zinc(II) N2O2 ligation complexes (1) and (2) were prepared from 2,2′‐{cyclohexane‐1,2‐diylbis[nitrilo(E)methylylidene]}bis[5‐(prop‐2‐yn‐1‐yloxy)phenol] (L1) and 2,2′‐{1,2‐phenylenebis[nitrilo(E)methylylidene]}bis[5‐(prop‐2‐yn‐1‐yloxy)phenol] (L2) and characterized by analytical and various spectral techniques. The molecular geometry of 1 and 2 was optimized by Density Functional Theory (DFT) at B3LYP/6‐311G(d,p) level and compared with literature. The complexes are stable in solution, and their solution structure was assessed using NMR and ESI‐MS spectroscopy. Topological analysis of the electron density and nature of the bonding in the complexes has been determined by using Bader's AIM method. The interaction and binding modes of calf thymus DNA (CT‐DNA) with complexes (1 and 2) were investigated by using absorption and emission spectral and viscometric studies. The nuclease activity investigated through gel electrophoresis reveals that 1 and 2 exhibits a significant DNA cleavage activity via a hydrolytic pathway and is further confirmed by an experiment performed in the presence of T4 ligase. The protein binding ability of 1 and 2 with bovine serum albumin (BSA) protein evaluated show good protein binding propensity. In‐vitro cytotoxicity of the complexes has shown significant activity against human brain tumor (U87 MG) and breast carcinoma (BT20) cancer cell lines. The comet assay has been used to determine the extent of DNA fragmentation in cancer cells. The phosphatase activity investigated through kinetic measurements establishes that the zinc complexes possess significant hydrolytic efficiency and follow the order 2 > 1. The DFT calculations have also been carried out to support the proposed mechanistic pathway of catalytic activity.

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“…Zn(II) complexes have also been demonstrated to trigger DNA damage [50]. It has been shown that Zn cation induces micronuclei in human leucocytes in the same range of concentrations and not in a dose-dependent manner [51].…”

Section: Discussionmentioning

confidence: 99%

6-Methoxyquinoline complexes as lung carcinoma agents: induction of oxidative damage on A549 monolayer and multicellular spheroid model

et al. 2019

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The aim of this work was to study the antitumor effects and the mechanisms of toxic action of a series of 6-methoxyquinoline (6MQ) complexes in vitro. The Cu(II) and Zn(II) complexes (Cu6MQ and Zn6MQ) are formulated as M(6MQ) 2 Cl 2 ; the Co(II) and Ag(I) compounds (Co6MQ and Ag6MQ) are ionic with formulae [Ag(6MQ) 2 ] + NO 3 − and H(6MQ) + [Co(6MQ) Cl 3 ] − (where H(6MQ) + is the protonated ligand). We found that the copper complex, outperformed the Co(II), Zn(II) and Ag(I) complexes with a lower IC 50 (57.9 µM) in A549 cells exposed for 24 h. Cu6MQ decreased cell proliferation and induced oxidative stress detected with H 2 DCFDA at 40 µM, which reduces GSH/GSSG ratio. This redox imbalance induced oxidative DNA damage revealed by the Micronucleus test and the Comet assay, which turned into a cell cycle arrest at G2/M phase and induced apoptosis. In multicellular spheroids, the IC 50 values tripled the monolayer model (187.3 µM for 24 h). At this concentration, the proportion of live/dead cells diminished, and the spheroids could not proliferate or invade. Although Zn6MQ also decreased GSH/GSSG ratio from 200 µM and the cytotoxicity is related to oxidative stress, the induction of the hydrogen peroxide levels only doubled the control value. Zn6MQ induced S phase arrest, which relates with the increased micronucleus frequency and with the induction of necrosis. Finally, our results reveal a synergistic activity with a 1:1 ratio of both complexes in the monolayer and multicellular spheroids.

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Zinc complex of tryptophan appended 1,4,7,10-tetraazacyclododecane as potential anticancer agent: Synthesis and evaluation

Cited by 27 publications

References 48 publications

Theoretical and experimental investigation of anticancer activities of an acyclic and symmetrical compartmental Schiff base ligand and its Co(ii), Cu(ii) and Zn(ii) complexes

Theoretical and experimental investigation of anticancer activities of an acyclic and symmetrical compartmental Schiff base ligand and its Co(ii), Cu(ii) and Zn(ii) complexes

Zinc(II)‐N₂O₂ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity

6-Methoxyquinoline complexes as lung carcinoma agents: induction of oxidative damage on A549 monolayer and multicellular spheroid model

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Zinc complex of tryptophan appended 1,4,7,10-tetraazacyclododecane as potential anticancer agent: Synthesis and evaluation

Cited by 27 publications

References 48 publications

Theoretical and experimental investigation of anticancer activities of an acyclic and symmetrical compartmental Schiff base ligand and its Co(ii), Cu(ii) and Zn(ii) complexes

Theoretical and experimental investigation of anticancer activities of an acyclic and symmetrical compartmental Schiff base ligand and its Co(ii), Cu(ii) and Zn(ii) complexes

Zinc(II)‐N2O2ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity

6-Methoxyquinoline complexes as lung carcinoma agents: induction of oxidative damage on A549 monolayer and multicellular spheroid model

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Product

Resources

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Zinc(II)‐N₂O₂ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity