Synthesis and structure of new dicopper(II) complexes bridged by N-(2-hydroxy-5-methylphenyl)-N′-[3-(dimethylamino)propyl]oxamide with in vitro anticancer activity: A comparative study of reactivities towards DNA/protein by molecular docking and experimental assays

Zheng, Kang; Yan, Meixing; Li, Yan‐Tuan; Wu, Zhi‐Yong; Yan, Cui‐Wei

doi:10.1016/j.ejmech.2015.12.042

Cited by 20 publications

(6 citation statements)

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“…In the past few years, several other dicopper(II) complexes have been synthesized and studied regarding their anticancer properties. Some authors demonstrated the DNA binding − and/or DNA cleavage ,,,, abilities of these compounds. Very recently, Cao et al proved that alteration of the chelating arms on the ligands allows for regulation of the reactivity of their dinuclear copper(II) complexes toward DNA .…”

Section: Introductionmentioning

confidence: 99%

“…In this sense, the authors reported new complexes with IC 50 values in the micromolar range for HepG2 cancer cells. 35−39 Additionally, remarkable activities have been described in the HeLa and A549, 35 SMMC-7721, 39 and MGC-803 and BEL-7404 43 cell lines. In other studies, the compounds have shown even lower IC 50 values, in the nanomolar range, when tested in HeLa and Caco-2, 41 as well as in U937 42 and MCF7, 48 cells.…”

Section: ■ Introductionmentioning

confidence: 99%

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Binucleating Hydrazonic Ligands and Their μ-Hydroxodicopper(II) Complexes as Promising Structural Motifs for Enhanced Antitumor Activity

et al. 2019

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Very few inorganic antineoplastic drugs have entered the clinic in the last decades, mainly because of toxicity issues. Because copper is an essential trace element of ubiquitous occurrence, decreased side effects could be expected in comparison with the widely used platinum anticancer compounds. In the present work, two novel hydrazonic binucleating ligands and their μ-hydroxo dicopper-(II) complexes were prepared and fully characterized. They differ by the nature of the aromatic group present in their aroylhydrazone moieties: while H 3 L1 and its complex, 1, possess a thiophene ring, H 3 L2 and 2 contain the more polar furan heterocycle. X-ray diffraction indicates that both coordination compounds are very similar in structural terms and generate dimeric arrangements in the solid state. Positive-ion electrospray ionization mass spectrometry analyses confirmed that the main species present in a 10% dimethyl sulfoxide (DMSO)/water solution should be [Cu 2 (HL)(OH)] + and the DMSO-substituted derivative [Cu 2 (L)(DMSO)] + . Scattering techniques [dynamic light scattering (DLS) and small-angle X-ray scattering] suggest that the complexes and their free ligands interact with bovine serum albumin (BSA) in a reversible manner. The binding constants to BSA were determined for the complexes through fluorescence spectroscopy. Moreover, to gain insight into the mechanism of action of the compounds, calf thymus DNA binding studies by UV−visible and DLS measurements using plasmid pBR322 DNA were also performed. For the complexes, DLS data seem to point to the occurrence of DNA cleavage to Form III (linear). Both ligands and their dicopper(II) complexes display potent antiproliferative activity in a panel of four cancer cell lines, occasionally even in the submicromolar range, with the complexes being more potent than the free ligands. Our data on cellular models correlate quite well with the DNA interaction experiments. The results presented herein show that aroylhydrazone-derived binucleating ligands, as well as their dinuclear μ-hydroxodicopper(II) complexes, may represent a promising structural starting point for the development of a new generation of highly active potential antitumor agents.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Binucleating Hydrazonic Ligands and Their μ-Hydroxodicopper(II) Complexes as Promising Structural Motifs for Enhanced Antitumor Activity

et al. 2019

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“…[35] A significant shift was observed within 1610-1705 cm À 1 in the IR spectra of all complexes referring to the coordination of carbonyl oxygen with the metal in the synthesized complexes. [36] The low intensity band in the region of 405-559 cm À 1 are attributed to CuÀ N and CuÀ O vibration. [37] Peaks in a similar range were observed in all the synthesized complexes.…”

Section: Ftir Spectroscopymentioning

confidence: 97%

“…[14][15][16][17] Furthermore, oxamides are also documented as active biological agents known to hold anti-inflammatory, anti-bacterial activities, antimicrobial, [18] and anticancer activities. [19][20][21][22][23] The majority of oxamides have biological significance, including HIVÀ I protease inhibitors, [19] cephalosporin bactericides, aldose reductase inhibitors, tumor necrosis factor inhibitors, DNA-, and BSA-Binding Studies, [24] Cytotoxic Activities. [22,25] Kifunensine, a cyclic oxamide has been reported as a potent inhibitor of the glucosidase family.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In vitro and In silico Alpha Glucosidase and Lipoxygenase Inhibition Studies of Copper(II) Oxamide Complexes

Malik,

Ashiq,

Jamal

et al. 2024

ChemistrySelect

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Metal complexes have pivotal applications in catalysis, photochemistry, and biological systems. Due to their unique chemical properties, metal complexes occupy a coveted place in the field of drug design. The present study includes the synthesis of symmetrical oxamides (O1–O11) and their copper complexes (C1–C11) that have potential to inhibit α‐glucosidase and lipoxygenase enzymes. To elucidate the structures of these compounds, spectroscopic investigations including mass spectrometry, 1H‐NMR spectroscopy, UV‐Visible spectroscopy and IR spectroscopy were adapted along with CHN elemental analysis. The spectroscopic investigations suggested that the synthesized complexes to be square planar with metal to ligand ratio 1 : 2. All compounds were scanned for potential inhibitory studies against α‐glucosidase and lipoxygenase enzyme. Their structure activity relationships (SAR) were also established. It was found that all synthesized compounds are strong inhibitors of α‐glucosidase when compared to standard 1‐deoxynojirimycin. It was noteworthy that presence of substituent played a significant role for the enhancing potential inhibitory skills of the compounds. The results obtained were also compared with molecular docking studies. A similar inhibition trend was observed between experimental inhibitory activity and docking energies. The current work presents a special class of Cu(II) coordination complexes from the perspective of their biological as well as structural features.

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“…Dinuclear copper( ii ) species have been shown to possess antiproliferative activity as well, 31–38 especially those derived from binucleating hydrazonic ligands. 24,39,40…”

Section: Introductionmentioning

confidence: 99%

Copper(ii) complexes of a furan-containing aroylhydrazonic ligand: syntheses, structural studies, solution chemistry and interaction with HSA

Moura,

Sobrinho,

Stellet

et al. 2023

Dalton Trans.

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Synthesis and structure of new dicopper(II) complexes bridged by N-(2-hydroxy-5-methylphenyl)-N′-[3-(dimethylamino)propyl]oxamide with in vitro anticancer activity: A comparative study of reactivities towards DNA/protein by molecular docking and experimental assays

Cited by 20 publications

References 56 publications

Binucleating Hydrazonic Ligands and Their μ-Hydroxodicopper(II) Complexes as Promising Structural Motifs for Enhanced Antitumor Activity

Binucleating Hydrazonic Ligands and Their μ-Hydroxodicopper(II) Complexes as Promising Structural Motifs for Enhanced Antitumor Activity

Design, Synthesis, In vitro and In silico Alpha Glucosidase and Lipoxygenase Inhibition Studies of Copper(II) Oxamide Complexes

Copper(ii) complexes of a furan-containing aroylhydrazonic ligand: syntheses, structural studies, solution chemistry and interaction with HSA

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