DNA/Protein Binding, Molecular Docking, and in Vitro Anticancer Activity of Some Thioether-Dipyrrinato Complexes

Gupta, Rakesh; Sharma, Gunjan; Pandey, Rampal; Kumar, Amit; Koch, Biplob; Li, Pei‐Zhou; Xu, Qiang; Pandey, Daya Shankar

doi:10.1021/ic401662d

Cited by 150 publications

(71 citation statements)

References 115 publications

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“…Thus, the observed more negative FEB values suggest an effective binding affinity, which correlates well with the experimental DNA binding results. The more negative relative binding energy of complex 2 indicates its higher DNA binding affinity than the other complexes, because 2 shows strong hydrophobic interactions with right‐handed DNA . Thus, we can conclude that there is a mutual complement between spectroscopic techniques and molecular docking modelling, which substantiates our experimental results, and provides further evidence of intercalative binding.…”

Section: Resultssupporting

confidence: 85%

Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine‐containing macrocyclic binuclear copper(II) complexes

Karthick¹,

Karthikeyan

Korrapati

et al. 2016

Applied Organom Chemis

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A series of new macrocyclic binuclear copper(II) complexes of the type [Cu2L1–5(ClO4)](ClO4) (1–5) were synthesized by template condensation between precursor compounds 2,6‐bis(4‐aminoethylpiperazin‐1‐ylmethyl)‐4‐substituted phenols and 2,6‐diformyl‐4‐substituted phenols. The synthesized precursors and complexes were characterized using regular physicochemical techniques. The rate constant values obtained for the hydrolysis of 4‐nitrophenylphosphate were in the range 1.83 × 10−2–4.19 × 10−2 min−1. Antioxidant studies against 2,2′‐diphenyl‐1‐picrylhydrazyl revealed the antioxidant potency of the synthesized complexes. Binding studies of the complexes with calf thymus DNA were conducted using electronic, viscometric and voltammetric techniques, and the obtained results suggested a non‐covalent groove mode of binding. The oxidative cleavage of pBR322 DNA in the presence of co‐reactant H2O2 and radical scavengers showed single strand scission and involvement of H2O2 radical in the cleavage process. Molecular docking studies were performed to insert complexes into the crystal structures of 1BNA and VEGFR kinase at active sites to determine the possible binding mode and predominant binding interactions. In vitro cytotoxicity of the complexes was tested against human epidermoid carcinoma cells (A431) by MTT assay, which revealed the effective anticancer activity of the complexes. Live cell and fluorescent imaging of A431 cells showed that the complexes induce cell death through apoptosis.

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Section: Resultssupporting

confidence: 85%

Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine‐containing macrocyclic binuclear copper(II) complexes

Karthick¹,

Karthikeyan

Korrapati

et al. 2016

Applied Organom Chemis

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“…Molecular visualization of the docked complexes was performed on the Molegro virtual viewer platform. The default parameters were used for the docking calculation with correlation type shape only, FFT mode at 3D level, grid dimension of 6 with receptor range 180 and ligand range 180 with twist range 360 and distance range 40 32 …”

Section: Expirimentalmentioning

confidence: 99%

Synthesis, characterization, CT‐DNA binding and docking studies of novel selenated ligands and their palladium complexes

Kumar

et al. 2020

Applied Organom Chemis

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A novel selenated Schiff base (S)‐L1H has been synthesized from (2S)‐1‐(benzylselanyl)‐3‐phenylpropan‐2‐amine which upon reduction formed a reduced Schiff base (S)‐L2H. Palladium (II) complexes (S)‐1 and (S)‐2 of ligands (S)‐L1H and (S)‐L2H respectively were successfully synthesized. The structures of all four compounds were thoroughly identified by analytical and various spectroscopic techniques. The absolute molecular structures of the above two complexes were further confirmed by single crystal X‐ray diffraction. Both (S)‐L1H and (S)‐L2H coordinated as monobasic ((S)‐L1–2), chelating, tridentate (Se,N,O−) ligands resulting in the complexes of composition (S)‐[PdCl(L1/2)] [(S)‐1/2]. In the crystals of complexes (S)‐1 and (S)‐2, there were moderate to strong Se⋯O, CH⋯Cl and CH⋯O types of intermolecular secondary interactions. CT‐DNA binding activity of these selenium‐containing ligands and their palladium complexes bearing a Pd–Se bond have been evaluated for the first time by performing electronic absorption titration and fluorescence emission quenching using CT‐DNA‐EB and viscometric experiments. These ligands and complexes exhibited remarkable DNA binding activity as shown by their intrinsic DNA binding constants (Kb) and Stern–Volmer constants (Ksv) in the ranges 5.2–9.9 × 104 and 3.6–4.7 × 104, respectively. The viscosity of CT‐DNA decreases with increasing concentration of these compounds. The results of the DNA‐binding studies revealed that all of the compounds interact with DNA at a minor groove which was further confirmed by molecular docking studies.

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“…The hypochromic shifts in the electronic spectra indicate intercalation of the complexes in CT‐DNA . The isosbestic points in the titration curve (at 375 nm for 1 and at 280 and 390 nm for 2 ) indicate the presence of more than two species in the medium …”

Section: Resultsmentioning

confidence: 99%

DNA/Protein Binding, Molecular Docking and Cytotoxicity Studies of Piperazinyl‐Moiety‐Based Copper(II) Complexes

et al. 2018

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Copper(II) complexes {[Cu(HL)(ClO4)(H2O)](ClO4)⋅3H2O} (1), {[Cu(HL)(m‐phth)]⋅5H2O} (2) and {[Cu(HL)(NCS)]2(ClO4)2⋅2H2O} (3) (HL=2‐{[2‐(1‐piperazinyl)ethylimino]methyl}phenol; m‐phth=1,3‐benzenedicarboxylate] have been synthesized and characterized by structural determination and spectroscopic studies. The mononuclear square pyramidal complex 1 resulted from the reaction of HL with copper perchlorate hexahydrate. Then mononuclear square planar complex 2 and dinuclear thiocyanato bridged complex 3 were obtained by reacting 1 with disodium 1,3‐benzenedicarboxylate (Na2(m‐phth)) and potassium thiocyanate, respectively. The interactions of 1–3 with CT‐DNA / serum albumins were investigated by UV‐visible absorption and fluorescence spectroscopy. The intrinsic binding constants of 1, 2 and 3 with CT‐DNA were calculated as 1.44 (±0.13) × 105, 4.86 (±0.11) × 105 and 4.51 (±0.16) × 105 L mol−1, respectively. Study of the interactions of 1–3 with human serum albumin (HSA) / bovine serum albumin (BSA) showed that all the complexes could quench intrinsic fluorescence of HSA and BSA through a static quenching process. Molecular docking technique was utilised to confirm the mode of interaction of complexes with CT‐DNA / serum albumin. Anticancer activities of the complexes have been tested using human breast cancer cell lines MCF7 and MBA‐MB‐231. Among the complexes studied 3 shows the higher cytotoxic activity and growth inhibition of cancer cells via induction of apoptotic cell death.

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DNA/Protein Binding, Molecular Docking, and in Vitro Anticancer Activity of Some Thioether-Dipyrrinato Complexes

Cited by 150 publications

References 115 publications

Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine‐containing macrocyclic binuclear copper(II) complexes

Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine‐containing macrocyclic binuclear copper(II) complexes

Synthesis, characterization, CT‐DNA binding and docking studies of novel selenated ligands and their palladium complexes

DNA/Protein Binding, Molecular Docking and Cytotoxicity Studies of Piperazinyl‐Moiety‐Based Copper(II) Complexes

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