Structure elucidation {spectroscopic, single crystal X-ray diffraction and computational DFT studies} of new tailored benzenesulfonamide derived Schiff base copper(II) intercalating complexes: Comprehensive biological profile {DNA binding, pBR322 DNA cleavage, Topo I inhibition and cytotoxic activity}

Afsan, Zeenat; Roisnel, Thierry; Tabassum, Sartaj; Arjmand, Farukh

doi:10.1016/j.bioorg.2019.103427

Cited by 39 publications

(17 citation statements)

References 87 publications

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“…The shape index of complex 1 depicted red concave regions corresponding to CÀ HÀ π interactions which gives an indication of the presence of aromatic stacking interactions, whereas the electron density present around the different molecular interactions is represented by the curvedness surface. [34] The 2-dimensional fingerprint representations of complex 1 provide both qualitative and quantitative information regarding the contributions to Hirshfeld surfaces ensuing from different intermolecular interactions (Figure S6).…”

Section: Hirshfield Surface Analysismentioning

confidence: 99%

Chromone‐Appended Zn(II) tRNA‐Targeted Potential Anticancer Chemotherapeutic Agent: Structural Details, in vitro ct‐DNA/tRNA Binding, Cytotoxicity Studies And Antioxidant Activity

et al. 2022

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A 3-formyl-chromone-appended zinc(II) intercalator drug candidate of the formulation [bis(chromone)(H 2 O) 2 Zn(II)] was prepared as a potent anticancer agent and thoroughly characterized by multi-spectroscopic and single X-ray crystallographic studies. Preliminary binding studies of complex 1 with ct-DNA/tRNA were carried out employing various complementary biophysical techniques and the corroborative results of these experiments suggested strong binding propensity via intercalation binding mode towards ct-DNA/tRNA therapeutic targets, with higher preference for tRNA as quantified by binding constant { K b , K and K sv } parameters. The cleavage studies with pBR322 DNA were performed which implied that 1 cleaved the DNA by hydrolytic cleavage pathway which was further validated by T4 religation assay. Moreover, 1 was found to exhibit the tRNA cleavage behavior in a concentration and time-dependent manner. The cytotoxicity of complex 1 was evaluated against Huh-7, DU-145 and the PNT2 cell lines by MTT assay. A dose-dependent growth inhibition of the Huh-7 and DU-145 cells at low micromolar concentrations was observed and in another set of experiments, lipid peroxidation & glutathione (GSH) depletion were induced in the presence of the tested drug candidate. Interestingly, drug candidate 1 demonstrated selective cytotoxic activity for the DU-145 cancer cell line with LC 50 value of 3.2 μM which was further visualized by confocal microscopy.

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Section: Hirshfield Surface Analysismentioning

confidence: 99%

Chromone‐Appended Zn(II) tRNA‐Targeted Potential Anticancer Chemotherapeutic Agent: Structural Details, in vitro ct‐DNA/tRNA Binding, Cytotoxicity Studies And Antioxidant Activity

et al. 2022

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“…Calculated HOMO-LUMO energy gap (ΔE) of complexes (0.33, 0.38, and 0.36 eV) was lower than free ligands (1.20 eV); these are attributed to after complexation of Cu 2+ , and there is a disruption of internal charge transfer that leads to changes in electronic properties. [79][80][81] By analyzing HOMO and LUMO energy values, we found the [Cu-P1] 3+ with the smallest HOMO-LUMO energy gap (ΔE), so complex Cu-P1 is the most active, [82,83] then which showed the best DNA binding and antitumor activity.…”

Section: Dft Calculation Analysismentioning

confidence: 99%

DNA interactive and selective anticancer activity studies of copper(II) complexes decorated water‐soluble porphyrin

Zhang

Hou

et al. 2020

Applied Organom Chemis

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Cancer is one of the diseases that seriously threaten the health of peoples. As a representative of metal drugs, cisplatin has considerable promise for the treatment of cancer. However, side effects are one of major problems for cisplatin due to their poor selectivity for cancer cells. We report here, for the first time, the syntheses of three new water‐soluble porphyrin‐modified copper(II) complexes Cu‐P1, Cu‐P2, and Cu‐P3. Results from calf thymus DNA (ct‐DNA)‐binding efficiency tests show that three copper(II) complexes could obviously interact with ct‐DNA and Cu‐P1 characterized the strongest bound performance. Besides, their function on anticancer against A549, H1975, HepG2, and T47D cells were analyzed, they show the best anticancer activity against lung cancer cells H1975, Cu‐P1 exhibited the greatest cytotoxic effect among the series, and the ligand L was less active against cancer cells. Furthermore, the cytotoxicities of ligand L, complexes Cu‐P1, Cu‐P2, Cu‐P3, and cisplatin were further evaluated against the breast cells Hs 578Bst and complexes more negligible cytotoxicity than ligand L and cisplatin. The anticancer mechanism is discussed by flow cytometer. Then, density functional theory (DFT) calculations analysis further proved the biological activities of the target compounds. Therefore, preliminary research suggests that these copper(II) complexes can inhibit human malignancy cells.

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“…DNA interacts with the drug by the charged sugar-phosphate groups, through its base pairs that was named intercalation and through minor and major groove binding [28]. Intercalation is the strong binding mode between different biomolecules and DNA [29] [11]. Intercalation mode of interaction was rst time proposed by Lerman and he also predicted that planer molecules show intercalation mode of interaction with DNA [30].…”

Section: Introductionmentioning

confidence: 99%

Study of Interactions Between 3-benzoyl-4-hydroxy-2-methyl-2H-1, 2-benzothiazine and Human DNA by Theoretical, Spectroscopic and Viscometric measurements

et al. 2022

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From the last few years mode of interactions between drugs and DNA is an attractive research area as it bridges chemistry, molecular biology and medicinal science. Interactions between small heterocyclic molecules and human DNA is a noteworthy feature in pharmacology for investigation of drugs mechanism and designing of more effective and target speci c drugs with fewer side effects. The present research work focuses on the theoretical investigations of 3-benzoyl-4-hydroxy-2-methyl-2H-1, 2-benzothiazine (SASA) by using Gaussian (16W) software to predict optimized geometry, HOMO-LUMO gap, bond length, bond angle, dihedral angle, electronic and vibrational spectra. Possible reaction site observed in SASA was C 7, C 9 and C 18 as these atoms show maximum charge density.Later the interactions of SASA with human DNA was explored spectroscopic investigations and viscometric investigations at physiological buffers of pH of 4.7 (stomach pH) and 7.4 (blood pH) respectively. Maximum absorbance between SASA-DNA complex was observed in buffer solution of pH 3.4 at wavelength of 370nm, whereas at 7.4 has maximim absorbance between. Spectroscopic results re ects the bathochromic and hyperchromic shift succeeding the addition of human DNA. During viscosity measurement, intercalation and electrostatic mode of interaction were detected at low and high concentration of drug in solution respectively. Increase in the value of rate constant was observed with the increase in concentration of drug. Larger values of rate constant were observed at pH 7.4 in comparison to pH 3.5. Rate constant, thermodynamic parameters and viscometric analysis prefers the intake of SASA via blood.

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Cited by 39 publications

References 87 publications

Chromone‐Appended Zn(II) tRNA‐Targeted Potential Anticancer Chemotherapeutic Agent: Structural Details, in vitro ct‐DNA/tRNA Binding, Cytotoxicity Studies And Antioxidant Activity

Chromone‐Appended Zn(II) tRNA‐Targeted Potential Anticancer Chemotherapeutic Agent: Structural Details, in vitro ct‐DNA/tRNA Binding, Cytotoxicity Studies And Antioxidant Activity

DNA interactive and selective anticancer activity studies of copper(II) complexes decorated water‐soluble porphyrin

Study of Interactions Between 3-benzoyl-4-hydroxy-2-methyl-2H-1, 2-benzothiazine and Human DNA by Theoretical, Spectroscopic and Viscometric measurements

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