Synthesis and structure of new tetracopper(II) complexes with N-benzoate-N′-[3-(diethylamino)propyl]oxamide as a bridging ligand: The influence of hydrophobicity on enhanced DNA/BSA-binding and anticancer activity

Fu, Hong-Lei; Zheng, Kang; Zhang, Mei-Jiao; Li, Yan‐Tuan; Wu, Zhi‐Yong; Yan, Cui‐Wei

doi:10.1016/j.jphotobiol.2016.04.032

Cited by 11 publications

(7 citation statements)

References 45 publications

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“…The calculated binding constants for complexes 1 and 2 are (3.50 ± 0.08) × 10 3 and (4.38 ± 0.08) × 10 4 M –1 , respectively. These values are comparable to those obtained for other reported copper(II) complexes . However, they are lower than the values usually found for representative DNA intercalators, such as ethidium bromide (which is around 10 5 –10 6 M –1 ) .…”

Section: Resultssupporting

confidence: 83%

“…Scattering techniques have recently been used as an alternative tool to other spectroscopic methods for characterizing the structures formed due to the interaction between different compounds and BSA. − Figure presents the size distributions of BSA before and after the addition of different concentrations of 1 and 2 . The corresponding autocorrelation functions are presented in Figure S20.…”

Section: Resultsmentioning

confidence: 99%

“…Upon the addition of increasing amounts ctDNA to solutions containing 1 and 2 , a clear hypochromic effect is observed in the complexes’ absorption bands, which suggests an interaction with the biopolymer (Figure A,B). Hypochromism is commonly associated with intercalative binding . The free ligands H 3 L1 and H 3 L2 present a similar behavior in the presence of ctDNA (Figure C,D).…”

Section: Resultsmentioning

confidence: 99%

“…Hypochromism is commonly associated with intercalative binding. 98 The free ligands H 3 L1 and H 3 L2 present a similar behavior in the presence of ctDNA (Figure 7C,D).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…These values are comparable to those obtained for other reported copper(II) complexes. 98 However, they are lower than the values usually found for representative DNA intercalators, such as ethidium bromide (which is around 10 5 −10 6 M −1 ). 109 This outcome could indicate that intercalation between the base pairs is not the main mode of interaction of the synthesized dicopper(II) complexes with DNA.…”

Section: ■ Results and Discussionmentioning

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: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Hypochromism is commonly associated with intercalative binding. 98 The free ligands H 3 L1 and H 3 L2 present a similar behavior in the presence of ctDNA (Figure 7C,D).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

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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Synthesis, structure, and biological active evaluation of a new cyclic tetranuclear copper(II) complex bridged both by oxamido and carboxylate groups

Zhang

Liu

et al. 2017

J Biochem & Molecular Tox

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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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Synthesis and structure of new tetracopper(II) complexes with N-benzoate-N′-[3-(diethylamino)propyl]oxamide as a bridging ligand: The influence of hydrophobicity on enhanced DNA/BSA-binding and anticancer activity

Cited by 11 publications

References 45 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

Synthesis, structure, and biological active evaluation of a new cyclic tetranuclear copper(II) complex bridged both by oxamido and carboxylate groups

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

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