Copper(<scp>ii</scp>) complexes with tridentate halogen-substituted Schiff base ligands: synthesis, crystal structures and investigating the effect of halogenation, leaving groups and ligand flexibility on antiproliferative activities

Kordestani, Nazanin; Rudbari, Hadi Amiri; Fernandes, Alexandra R.; Raposo, Luís R.; Luz, André; Baptista, Pedro V.; Brunò, Giuseppe; Scopelliti, Rosario; Fateminia, Zohreh; Micale, Nicola; Tumanov, Nikolay; Wouters, Jan; Kajani, Abolghasem Abbasi; Bordbar, Abdol‐Khalegh

doi:10.1039/d0dt03962d

Cited by 32 publications

(20 citation statements)

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“…Apart from this, the Cu-N py bond distance of complexes L 1 CuCl-L 4 CuCl falls within the range of the reported data for the copper(II) complexes containing a pyridyl ligand. [47][48][49][50][51] Intrigued by the difference in the molecular structures of the copper(II) complexes L 1 CuCl-L 4 CuCl due to the length of the pyridyl arm, we aim to investigate the difference in the binding modes and reactivity pattern of the nitrite anion bound to the L 1 Cu + and L 2 Cu + fragments. However, only L 1 Cu (O 2 N) crystallizes in the monoclinic space group P21/c and has a mononuclear structure as shown in Fig.…”

Section: Papermentioning

confidence: 99%

Nitric oxide generation study of unsymmetrical β-diketiminato copper(ii) nitrite complexes

et al. 2022

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Section: Papermentioning

confidence: 99%

Nitric oxide generation study of unsymmetrical β-diketiminato copper(ii) nitrite complexes

et al. 2022

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“…On the other hand, transition-metal complexes are being used in pharmaceutical and medicinal chemistry since the discovery of cisplatin . Several coordination compounds of metal ions (chromium, cobalt, copper, manganese, molybdenum, palladium, ruthenium, tungsten, vanadium, and zinc) have been applied in the treatment of various diseases owing to their antimicrobial and antioxidant, − anticancer, , antiproliferative, , anti-inflammatory, DNA binding and cytotoxicity, ,,, antitumor, and antidiabetic activities. Studies also indicated that Zn(II) complexes exhibit anti-inflammatory, antidiabetic, antioxidant, and antimicrobial activities, , whereas Cu(II) complexes exhibited promising antimicrobial, antioxidant, antiviral, DNA binding, ,, and antiproliferative activities.…”

Section: Introductionmentioning

confidence: 99%

“…Several coordination compounds of metal ions (chromium, cobalt, copper, manganese, molybdenum, palladium, ruthenium, tungsten, vanadium, and zinc) have been applied in the treatment of various diseases owing to their antimicrobial and antioxidant, − anticancer, , antiproliferative, , anti-inflammatory, DNA binding and cytotoxicity, ,,, antitumor, and antidiabetic activities. Studies also indicated that Zn(II) complexes exhibit anti-inflammatory, antidiabetic, antioxidant, and antimicrobial activities, , whereas Cu(II) complexes exhibited promising antimicrobial, antioxidant, antiviral, DNA binding, ,, and antiproliferative activities. Previous studies of a zinc(II) complex of quinoline derivative ligand indicated an in vitro biological screening effect tested against four bacterial strains, Escherichia coli and Pseudomonas aeruginosa (Gram-negative) as well as Staphylococcus aureus and Bacillus subtilis (Gram-positive).…”

Section: Introductionmentioning

confidence: 99%

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Damena

Alem

Zeleke³

et al. 2022

ACS Omega

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In the present work, two novel complexes of zinc(II) and copper(II) were synthesized from the ligand 2-((2-hydroxyethyl)amino)quinoline-3-carbaldehyde ( H 2 L ) in a 1:2 metal-to-ligand ratio in methanol. The complexes were characterized by UV–visible spectroscopy, fluorescence spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy-energy-dispersive X-ray spectroscopy (SEM-EDX), mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy, and thermogravimetric analysis (TGA) experimental techniques and density functional theory (DFT) calculations. The spectral data revealed that the mono-deprotonated ( HL ) ligand acted as a bidentate ligand, which bound to both Zn(II) and Cu(II) ions via the nitrogen atom of the amine (N–H) and the hydroxyl (O–H) groups through the deprotonated oxygen atom. Formation constants and thermal analysis indicated that both metal complexes are stable up to 100 °C with thermodynamically favored chemical reactions. The Cu(II) complex showed antibacterial activities with the zones of inhibition of 20.90 ± 2.00 mm against Pseudomonas aeruginosa , 19.69 ± 0.71 mm against Staphylococcus aureus , and 18.58 ± 1.04 mm against Streptococcus pyogenes . These results are relatively higher compared with the Zn(II) complex at the same concentration. The minimum inhibitory concentration (MIC) results for the complexes also showed similar trends against the three bacteria. On the other hand, radical scavenging activities of both Cu(II) and Zn(II) complexes showed half-maximal inhibitory concentrations (IC 50 ) of 4.72 and 8.2 μg/mL, respectively, while ascorbic acid (a positive control) has a value of 4.28 μg/mL. The Cu(II) complex exhibited better communication with the positive control, indicating its potential use for biological activities. The calculated and in silico molecular docking results also strongly support the experimental results.

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“…Moreover, copper-containing complexes or materials also behave as bearers of high thermal and electrical conductivity, or catalytic and sensory features. As examples, the following papers could be mentioned to show the current strives on the design of copper(II) complexes showing some of the above mentioned properties, mainly the antiproliferative one [ 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. To date, one of the most intensively studied groups of copper(II) complexes in terms of their possible clinical use as anticancer agents is the copper(II) complexes called Casiopeínas ® , whose composition can be expressed by the formulas [Cu( N – N )( N – O )] + and/or [Cu( N – N )( O – O )] + , where ( N – N ) represents an aromatic heterocyclic diimine, such as 2,2′-bipyridine (bpy) or 1,10-phenanthroline (phen), ( N – O ) and ( O – O ) stands for an amino acid, and acetylacetone, respectively [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Copper(II) Complexes Containing Natural Flavonoid Pomiferin Show Considerable In Vitro Cytotoxicity and Anti-inflammatory Effects

Vančo

Trávníček

Hošek

et al. 2021

IJMS

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A series of new heteroleptic copper(II) complexes of the composition [Cu(L)(bpy)]NO3·2MeOH (1), [Cu(L)(dimebpy)]NO3·2H2O (2), [Cu(L)(phen)]NO3·2MeOH (3), [Cu(L)(bphen)]NO3·MeOH (4), [Cu(L)(dppz)]NO3·MeOH (5) was prepared, where HL = 3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-ene-1-yl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, (pomiferin) and bpy = 2,2'-bipyridine, dimebpy = 4,4ʹ-dimethyl-2,2ʹ-bipyridine, phen = 1,10-phenanthroline, bphen = 4,7-diphenyl-1,10-phenanthroline, and dppz = dipyrido[3,2-a:2',3'-c]phenazine. The complexes were characterized using elemental analysis, infrared and UV/Vis spectroscopies, mass spectrometry, thermal analysis and conductivity measurements. The in vitro cytotoxicity, screened against eight human cancer cell lines (breast adenocarcinoma (MCF-7), osteosarcoma (HOS), lung adenocarcinoma (A549), prostate adenocarcinoma (PC-3), ovarian carcinoma (A2780), cisplatin-resistant ovarian carcinoma (A2780R), colorectal adenocarcinoma (Caco-2) and monocytic leukemia (THP-1), revealed the complexes as effective antiproliferative agents, with the IC50 values of 2.2–13.0 μM for the best performing complexes 3 and 5. All the complexes 1–5 showed the best activity against the A2780R cells (IC50 = 2.2–6.6 μM), and moreover, the complexes demonstrated relatively low toxicity on healthy human hepatocytes, with IC50 > 100 μM. The complexes were evaluated by the Annexin V/propidium iodide apoptosis assay, induction of cell cycle modifications in A2780 cells, production of reactive oxygen species (ROS), perturbation of mitochondrial membrane potential, inhibition of apoptosis and inflammation-related signaling pathways (NF-κB/AP-1 activity, NF-κB translocation, TNF-α secretion), and tested for nuclease mimicking activity. The obtained results revealed the corresponding complexes to be effective antiproliferative and anti-inflammatory agents.

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Copper(ii) complexes with tridentate halogen-substituted Schiff base ligands: synthesis, crystal structures and investigating the effect of halogenation, leaving groups and ligand flexibility on antiproliferative activities

Abstract: To investigate the effect of different halogen substituents, leaving groups and the flexibility of ligand on the anticancer activity of copper complexes, sixteen copper(II) complexes with eight different tridentate Schiff-base...

Cited by 32 publications

References 61 publications

Nitric oxide generation study of unsymmetrical β-diketiminato copper(ii) nitrite complexes

Nitric oxide generation study of unsymmetrical β-diketiminato copper(ii) nitrite complexes

Novel Zinc(II) and Copper(II) Complexes of 2-((2-Hydroxyethyl)amino)quinoline-3-carbaldehyde for Antibacterial and Antioxidant Activities: A Combined Experimental, DFT, and Docking Studies

Copper(II) Complexes Containing Natural Flavonoid Pomiferin Show Considerable In Vitro Cytotoxicity and Anti-inflammatory Effects

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