Synthesis, crystal structure, cytotoxicity study, DNA/protein binding and molecular docking of dinuclear copper(II) complexes

Bhunia, Apurba; Mistri, Soumen; Manne, Rajesh Kumar; Santra, Manas Kumar; Manna, Subal Chandra

doi:10.1016/j.ica.2019.03.022

Cited by 36 publications

(14 citation statements)

References 59 publications

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“…The values are comparable to other dinuclear copper(II) complexes. [46] Additionally, using the Stern-Volmer equation [Eq. (S4)], the quenching rate constants (K q ) were calculated taking an average intrinsic lifetime (τ 0 ) of 23 ns [47] and the suppression constants K s .…”

Section: Ct-dna Interaction Studies By Absorption and Fluorescence Spmentioning

confidence: 99%

Isoxazole‐Derived Aroylhydrazones and Their Dinuclear Copper(II) Complexes Show Antiproliferative Activity on Breast Cancer Cells with a Potentially Alternative Mechanism Of Action

et al. 2020

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This paper reports the design, synthesis and cytotoxicity studies of two new isoxazole‐derived aroylhydrazone ligands and their dinuclear copper(II) complexes. Compounds were fully characterized by various spectroscopic and analytical techniques. The molecular structures of four derivatives were confirmed by X‐ray crystallography. The stability of the ligands and the complexes in aqueous medium was monitored spectroscopically. Both the ligands and the complexes were shown to interact with calf thymus DNA (ct‐DNA). Additionally, structures containing a phenol pendant arm were significantly more cytotoxic than those carrying a pendant pyridine substituent, reaching sub‐micromolar IC50 values on the triple‐negative human breast cancer cell line MDA‐MB‐231. The metal chelation and transchelation ability of the compounds towards FeII, FeIII and ZnII ions was explored as a possible mechanism of action of these compounds.

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Section: Ct-dna Interaction Studies By Absorption and Fluorescence Spmentioning

confidence: 99%

Isoxazole‐Derived Aroylhydrazones and Their Dinuclear Copper(II) Complexes Show Antiproliferative Activity on Breast Cancer Cells with a Potentially Alternative Mechanism Of Action

et al. 2020

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“…Therefore, these processes must be taken into account to explain the experimental results. The importance of these transformations have been demonstrated for cisplatin, cis -[Pt(NH 3 ) 2 Cl 2 ], and oxaliplatin, [Pt(dach)(oxalato)], which, upon hydrolysis, lose the labile chloro and oxalato ligands, respectively, to form the active moieties cis -Pt(NH 3 ) 2 2+ and Pt(dach) 2+ that interact with DNA. , A similar situation was also observed with titanocene, Cp 2 TiCl 2 . , Other studies on Pt-, Au-, Ru-, and Rh-based potential drugs pointed in the same direction, identifying the active moieties involved in the ligand exchange or protein-metalation. − However, other facts must also be taken into account: polynuclear Au(III), Pd(II), and Pt(II) complexes have higher cytotoxicity than mononuclear species, − and many dimeric and polymeric copper compounds have been described as very promising candidates, − without considering their possible dissociation in mononuclear units that was demonstrated unambiguously in aqueous solution and coordinating solvents by EPR spectroscopy. − …”

Section: Introductionmentioning

confidence: 68%

Mo(VI) Potential Metallodrugs: Explaining the Transport and Cytotoxicity by Chemical Transformations

et al. 2022

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The transport and cytotoxicity of molybdenum-based drugs have been explained with the concept of chemical transformation, a very important idea in inorganic medicinal chemistry that is often overlooked in the interpretation of the biological activity of metal-containing systems. Two monomeric, [MoO2(L1)(MeOH)] (1) and [MoO2(L2)(EtOH)] (2), and two mixed-ligand dimeric MoVIO2 species, [{MoO2(L1–2)}2(μ-4,4′-bipy)] (3–4), were synthesized and characterized. The structures of the solid complexes were solved through SC-XRD, while their transformation in water was clarified by UV–vis, ESI-MS, and DFT. In aqueous solution, 1–4 lead to the penta-coordinated [MoO2(L1–2)] active species after the release of the solvent molecule (1 and 2) or removal of the 4,4′-bipy bridge (3 and 4). [MoO2(L1–2)] are stable in solution and react with neither serum bioligand nor cellular reductants. The binding affinity of 1–4 toward HSA and DNA were evaluated through analytical and computational methods and in both cases a non-covalent interaction is expected. Furthermore, the in vitro cytotoxicity of the complexes was also determined and flow cytometry analysis showed the apoptotic death of the cancer cells. Interestingly, μ-4,4′-bipy bridged complexes 3 and 4 were found to be more active than monomeric 1 and 2, due to the mixture of species generated, that is [MoO2(L1–2)] and the cytotoxic 4,4′-bipy released after their dissociation. Since in the cytosol neither the reduction of MoVI to MoV/IV takes place nor the production of reactive oxygen species (ROS) through Fenton-like reactions of 1–4 with H2O2 occurs, the mechanism of cytotoxicity should be attributable to the direct interaction with DNA that happens with a minor-groove binding which results in cell death through an apoptotic mechanism.

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“…Figure 5 depicts the absorption spectra of BSA in the presence of increasing concentrations of 14b (0–40 μM) that culminate in an increase in the intensity of the absorption band at 278 nm. Using these titration data, the apparent association constant (K app ) of the 14b with BSA has been determined using the following equation: [125]

true \frac{1}{A_{o b s} - A_{0}} = \frac{1}{A_{c} - A_{0}} + \frac{1}{K_{a p p} (() A_{c} - A_{0}) ([], c, o, m, p)}

…”

Section: Resultsmentioning

confidence: 99%

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

Ragheb

Abdelwahab

Darweesh

et al. 2022

Chemistry & Biodiversity

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The cyclocondensation reaction of aldehydes with dimedone and bis(6-aminopyrimidin-4-one) in acetic acid led to the formation of the corresponding bis (pyrimido[4,5-b]quinoline-4,6-diones) which are known as bis(sulfanediyl)bis(tetrahydro-5-deazaflavin) analogs in a single step. Also, bis(pyrimido[4,quinoline-4,6diones) which are linked to naphthyl core via phenoxymethyl linkage is prepared. The interactions of the synthesized compounds with DNA and bovine serum albumin (BSA) were studied. Gel electrophoresis assay was used to show the capability of the compounds to photocleave the supercoiled pBR322 plasmid DNA in UV-A (365 nm). Besides, the most photocleavable compound, bis(tetrahydropyrimido[4,5-b]quinoline-4,6-dione) linked to pyridin-3-yl at position-5 exhibits good binding affinities toward CT-DNA and BSA as supported by UV/VIS spectral studies. In addition to the experimental findings, a molecular docking simulation was performed to collect detailed binding data for this compound to both biomolecules.

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Synthesis, crystal structure, cytotoxicity study, DNA/protein binding and molecular docking of dinuclear copper(II) complexes

Cited by 36 publications

References 59 publications

Isoxazole‐Derived Aroylhydrazones and Their Dinuclear Copper(II) Complexes Show Antiproliferative Activity on Breast Cancer Cells with a Potentially Alternative Mechanism Of Action

Isoxazole‐Derived Aroylhydrazones and Their Dinuclear Copper(II) Complexes Show Antiproliferative Activity on Breast Cancer Cells with a Potentially Alternative Mechanism Of Action

Mo(VI) Potential Metallodrugs: Explaining the Transport and Cytotoxicity by Chemical Transformations

Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

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