Synthesis and structure of a new ternary monocopper(II) complex containing mixed ligands of 2,2′‐diamino‐4,4′‐bithiazole and picrate:<i>in vitro</i>anticancer activity, molecular docking and reactivity towards DNA

Wang, Xiling; Zheng, Kang; Wang, Ling-Yang; Li, Yan‐Tuan; Wu, Zhi‐Yong; Yan, Cui‐Wei

doi:10.1002/aoc.3497

Cited by 7 publications

(2 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The binding ability of complexes to DNA is investigated through molecular docking procedures. Here, the E2 regulatory protein binding DNA targets (PDB ID: 423D) are considered for the calculations [ 80 , 81 ]. The regulatory signals of the virus are dependent on the nucleotides that are involved in protein binding along with the deformation ability of the corresponding target DNA region.…”

Section: Resultsmentioning

confidence: 99%

“…It can also be observed that complex 1 forms three explicit hydrogen bonds with DG7, DA17, and DG19 residues, while complex 2 has only one hydrogen bond with DC18 residue which could be the reason for the stronger interaction observed in the case of complex 1 over complex 2. e binding ability of complexes to DNA is investigated through molecular docking procedures. Here, the E2 regulatory protein binding DNA targets (PDB ID: 423D) are considered for the calculations [80,81].…”

Section: Molecular Docking Studies On Metal Complexes Binding To E2mentioning

confidence: 99%

See 1 more Smart Citation

Oxoperoxovanadium Complexes of Hetero Ligands: X‐Ray Crystal Structure, Density Functional Theory, and Investigations on DNA/BSA Interactions, Cytotoxic, and Molecular Docking Studies

Kothandan

Thirumoorthy

Rodríguez‐Diéguez

et al. 2022

Bioinorganic Chemistry and Applications

View full text Add to dashboard Cite

Oxoperoxovanadium (V) complexes [VO (O)2 (nf) (bp)] (1) and [VO (O)2 (ox) (bp)] (2) based on 5-nitro-2-furoic acid (nf), oxine (ox) and 2, 2′ bipyridine (bp) bidentate ligands have been synthesized and characterized by FT-IR, UV-visible, mass, and NMR spectroscopic techniques. The structure of complex 2 shows distorted pentagonal-bipyramidal geometry, as confirmed by a single-crystal XRD diffraction study. The interactions of complexes with bovine serum albumin (BSA) and calf thymus DNA (CT-DNA) are investigated using UV-visible and fluorescence spectroscopic techniques. It has been observed that CT-DNA interacts with complexes through groove binding mode and the binding constants for complexes 1 and 2 are 8.7 × 103 M−1 and 8.6 × 103 M−1, respectively, and BSA quenching constants for complexes 1 and 2 are 0.0628 × 106 M−1 and 0.0163 × 106 M−1, respectively. The ability of complexes to cleave DNA is investigated using the gel electrophoresis method with pBR322 plasmid DNA. Furthermore, the cytotoxic effect of the complexes is evaluated against the HeLa cell line using an MTT assay. The complexes are subjected to density functional theory calculations to gain insight into their molecular geometries and are in accordance with the results of docking studies. Furthermore, based on molecular docking studies, the intermolecular interactions responsible for the stronger binding affinities between metal complexes and DNA are discussed.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Molecular Docking Studies On Metal Complexes Binding To E2mentioning

confidence: 99%

Oxoperoxovanadium Complexes of Hetero Ligands: X‐Ray Crystal Structure, Density Functional Theory, and Investigations on DNA/BSA Interactions, Cytotoxic, and Molecular Docking Studies

Kothandan

Thirumoorthy

Rodríguez‐Diéguez

et al. 2022

Bioinorganic Chemistry and Applications

View full text Add to dashboard Cite

show abstract

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

Gurudevaru

Gopalakrishnan

Senthilkumar

et al. 2017

Applied Organom Chemis

View full text Add to dashboard Cite

Mononuclear and dinuclear copper(II) complexes with thiophenecarboxylic acid, [Cu(3‐TCA)2(2,2′‐bpy)] (1), [Cu(3‐Me‐2‐TCA)2(H2O)(2,2′‐bpy)] (2), [Cu(5‐Me‐2‐TCA)2(H2O)(2,2′‐bpy)] (3) and [Cu2(2,5‐TDCA)(DMF)2(H2O)2(2,2′‐bpy)2](ClO4)2 (4) (where 3‐TCA = 3‐thiophenecarboxylic acid; 3‐Me‐2‐TCA = 3‐methyl‐2‐thiophenecarboxylic acid; 5‐Me‐2‐TCA = 5‐methyl‐2‐thiophenecarboxylic acid; 2,5‐TDCA = thiophene‐2,5‐dicarboxylic acid; 2,2′‐bpy = 2,2′‐bipyridyl; DMF = N,N‐dimethylformamide), were synthesized. Compounds 1–4 were extensively characterized using both analytical and spectroscopic methods. Additionally, the solid‐state structures of 1 and 4 were unambiguously established from single‐crystal X‐ray diffraction studies. The hexacoordinated Cu(II) centre in 1 (CuO4N2) is a distorted octahedral geometry whereas the pentacoodinated 4 (CuO3N2) has distorted square pyramidal geometry. Compounds 1 and 4 exhibit intermolecular hydrogen bonding which leads to the formation of two‐ and three‐dimensional supramolecular architectures, respectively. Spectrophotometric and computational investigations suggest that these compounds bind with DNA in minor groove binding such that Kb = 4.9 × 105 M−1 and Ksv = 3.4 × 105 M−1, and binding score of −5.26 kcal mol−1. The binding affinity of these complexes to calf thymus DNA is in the order 2 > 3 > 4 > 1. Methyl‐substituted thiophene ring increases the DNA binding affinity whereas unsubstituted thiophene ring DNA binding rate is reduced. The methyl group on the thiophene ring would sterically hinder π–π stacking of the ring with DNA base pairs, and subsequently they are involved in hydrophobic interaction with the DNA surface rather than partial intercalative interaction. Compounds 1–4 show pronounced activity against B16 mouse melanoma skin cancer cell lines as measured by MTT assay yielding IC50 values in the micromolar concentration range. The compounds could prove to be efficient anti‐cancer agents, since at a concentration as low as 2.1 μg ml−1 they exerted a significant cytotoxic effect in cancer cells whereas cell viability was not affected in normal cells.

show abstract

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Ghasemi

Behzad

Khaleghian

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

Two new mixed-ligand complexes with general formula [Cu(SB)(L')]ClO 4(1 and 2) were synthesized and characterized by different spectroscopic and analytical techniques including Fourier transform infrared (FT-IR) and UV-Vis spectroscopy and elemental analyses. The SB ligand is an unsymmetrical tridentate NN'O type Schiff base ligand that was derived from the condensation of 1,2-ethylenediamine and 5-bromo-2-hydroxy-3-nitrobenzaldehyde. The L' ligand is pyridine in (1) and 2,2 0 -dimethyl-4,4 0 -bithiazole (BTZ) in (2). Crystal structure of (2) was also obtained. The two complexes were used as anticancer agents against leukemia cancer cell line HL-60 and showed considerable anticancer activity. The anticancer activity of these complexes was comparable with the standard drug 5-fluorouracil (5-FU). Molecular docking and pharmacophore studies were also performed on DNA (PDB:1BNA) and leukemia inhibitor factor (LIF) (PDB:1EMR) to further investigate the anticancer and anti-COVID activity of these complexes. The molecular docking results against DNA revealed that (1) preferentially binds to the major groove of DNA receptor whereas (2) binds to the minor groove. Complex (2) performed better with 1EMR. The experimental and theoretical results showed good correlation. Molecular docking and pharmacophore studies were also applied to study the interactions between the synthesized complexes and SARS-CoV-2 virus receptor protein (PDB ID:6LU7). The results revealed that complex (2) had better interaction than (1), the free ligands (SB and BTZ), and the standard drug favipiravir.anticancer, COVID-19, mixed-ligand, molecular docking, unsymmetrical Schiff base CCDC number 2089608 contains the supplementary crystallographic data for complex (2). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif (supporting information).

show abstract

Synthesis and structure of a new ternary monocopper(II) complex containing mixed ligands of 2,2′‐diamino‐4,4′‐bithiazole and picrate:in vitroanticancer activity, molecular docking and reactivity towards DNA

Cited by 7 publications

References 57 publications

Oxoperoxovanadium Complexes of Hetero Ligands: X‐Ray Crystal Structure, Density Functional Theory, and Investigations on DNA/BSA Interactions, Cytotoxic, and Molecular Docking Studies

Oxoperoxovanadium Complexes of Hetero Ligands: X‐Ray Crystal Structure, Density Functional Theory, and Investigations on DNA/BSA Interactions, Cytotoxic, and Molecular Docking Studies

Synthesis and structural and DNA binding studies of mono‐ and dinuclear copper(II) complexes constructed with ─O and ─N donor ligands: Potential anti‐skin cancer drugs

Synthesis and characterization of two new mixed‐ligand Cu(II) complexes of a tridentate NN'O type Schiff base ligand and N‐donor heterocyclic co‐ligands: In vitro anticancer assay, DNA/human leukemia/COVID‐19 molecular docking studies, and pharmacophore modeling

Contact Info

Product

Resources

About