Synthesis, crystal structure and Hirshfeld surface analysis of copper(II) complexes: DNA- and BSA-binding, molecular modeling, cell imaging and cytotoxicity

Anjomshoa, Marzieh; Torkzadeh‐Mahani, Masoud; Janczak, Jan; Rizzoli, Corrado; Sahihi, Mehdi; Ataei, Farangis; Dehkhodaei, Monireh

doi:10.1016/j.poly.2016.08.018

Cited by 24 publications

(6 citation statements)

References 63 publications

(78 reference statements)

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“…The bovine-variant BSA presents chemical properties similar to those of human serum albumin (HSA), with only a few differences . Thus, BSA has been largely used as a model in order to study the interactions with many compounds, including copper complexes. ,− These complexes are well-known by their BSA binding propensity, showing a strong affinity for the protein. − In recent studies, authors evaluated the interactions of both HSA and BSA with copper(II) complexes. The values found for the binding constants, as well as for the number of binding sites, are in agreement, − although exceptions, such as the work of Manna and co-workers, were identified.…”

Section: Resultssupporting

confidence: 56%

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: 56%

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

et al. 2019

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“…AutoDock 4.2 using Lamarckian genetic algorithm together with the AutoDock Tools was employed to set up and perform blind docking calculations of complex 1 binding to DNA and BSA. 40 According to the literature method, 41 the structure of DNA (PDB ID: 423D) with sequenced (ACCGACGTCGGT)2 and BSA (PDB ID: 4F5S) taken from the Protein Data Bank (http:// www.rcsb.org/pdb) with the resolution of 1.60 and 2.47Å, and the r-value of 0.206 and 0.259 for DNA and BSA, respectively, were employed to establish the docking mode, in which polar hydrogen atoms as well as Kollman charges were added to receptor molecules. The coordinate of the complex 1 was taken from the crystal structures as CIF les and converted to the PDB format using Mercury soware (http://www.ccdc.cam.ac.uk/) and missing hydrogen atoms and Gasteiger charges were added.…”

Section: Molecular Dockingmentioning

confidence: 99%

Synthesis and crystal structure of new monometallic Ni(ii) and Co(ii) complexes with an asymmetrical aroylhydrazone: effects of the complexes on DNA/protein binding property, molecular docking, and in vitro anticancer activity

Yang

Zhou

2017

RSC Adv.

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“…In continuation of our investigations to provide further insights into the therapeutic properties of metal-based compounds [108] , [109] , [110] , [111] , [112] , [113] , [114] , [115] , [116] , [117] , [118] , we herein highlight the recent progress conducted on the potential therapeutic applications of AMSs. This review begins with mechanistic concepts of AMS-catalyzed nucleic acids cleavage ( Section 2 ), followed by model substrates and instrumentations employed in cleavage studies ( Section 3 ).…”

Section: Introductionmentioning

confidence: 94%

Nuclease-like metalloscissors: Biomimetic candidates for cancer and bacterial and viral infections therapy

Anjomshoa

Amirheidari

2022

Coordination Chemistry Reviews

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Despite the extensive and rapid discovery of modern drugs for treatment of cancer, microbial infections, and viral illnesses; these diseases are still among major global health concerns. To take inspiration from natural nucleases and also the therapeutic potential of metallopeptide antibiotics such as the bleomycin family, artificial metallonucleases with the ability of promoting DNA/RNA cleavage and eventually affecting cellular biological processes can be introduced as a new class of therapeutic candidates. Metal complexes can be considered as one of the main categories of artificial metalloscissors, which can prompt nucleic acid strand scission. Accordingly, biologists, inorganic chemists, and medicinal inorganic chemists worldwide have been designing, synthesizing and evaluating the biological properties of metal complexes as artificial metalloscissors. In this review, we try to highlight the recent studies conducted on the nuclease-like metalloscissors and their potential therapeutic applications. Under the light of the concurrent Covid-19 pandemic, the human need for new therapeutics was highlighted much more than ever before. The nuclease-like metalloscissors with the potential of RNA cleavage of invading viral pathogens hence deserve prime attention.

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Synthesis, crystal structure and Hirshfeld surface analysis of copper(II) complexes: DNA- and BSA-binding, molecular modeling, cell imaging and cytotoxicity

Cited by 24 publications

References 63 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 and crystal structure of new monometallic Ni(ii) and Co(ii) complexes with an asymmetrical aroylhydrazone: effects of the complexes on DNA/protein binding property, molecular docking, and in vitro anticancer activity

Nuclease-like metalloscissors: Biomimetic candidates for cancer and bacterial and viral infections therapy

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