An unusual iminoacylation of 2-amino pyridyl thiazole: Synthesis, X-ray crystallography and DFT study of copper(II) amidine complexes and their cytotoxicity, DNA binding and cleavage study

Brandão, Paula; Mondal, Gopinath; Santra, Ananyakumari; Jana, Arpita; Mokhamatam, Raveendra B.; Manna, Sunil K.; Mandal, Tarun K.; Bera, Pulakesh

doi:10.1016/j.poly.2018.11.069

Cited by 13 publications

(6 citation statements)

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“…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. Some of these works have reported the induction of apoptosis as a putative mechanism of action.…”

Section: ■ Introductionmentioning

confidence: 78%

“…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%

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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: 78%

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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“…A capability of binding to calf thymus DNA was reported for different thiazole derivatives (pyrazolo[3,4-d]pyrimidine-benzimidazoles) [23], as well as for iminoacylated 2-amino pyridylthiazole derivatives and copper-containing thiazolepyridine compounds [24]. Molecular docking and fluorescent spectroscopy (EtBr replacement) approaches were applied to confirm binding of studied compounds to the DNA molecule [23,24]. We have used the electrophoretic retardation of plasmid DNA and replacement of methyl green dye for confirmation of our suggestion that compounds 1 and 2 neither bind DNA directly nor intercalate into the DNA molecule.…”

Section: Resultsmentioning

confidence: 99%

Apoptosis induction in human leukemia cells by novel 2-amino-5-benzylthiazole derivatives

Finiuk¹,

Ivasechko²,

Klyuchivska³

et al. 2019

Ukr.Biochem.J

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“…The absorbance of the plate was recorded at 595 nm using BIO-RAD iMark Microplate Reader. 73 The percentage of cell death was calculated considering cell death in untreated cells as zero and cells treated with doxorubin as a positive control. The data obtained was transformed, normalized to calculate IC 50 values, using GraphPad Prism 8.…”

Section: Computational Studymentioning

confidence: 99%

Evaluation of the anticancer activities with various ligand substituents in Co(ii/iii)-picolyl phenolate derivatives: synthesis, characterization, DFT, DNA cleavage, and molecular docking studies

et al. 2022

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An unusual iminoacylation of 2-amino pyridyl thiazole: Synthesis, X-ray crystallography and DFT study of copper(II) amidine complexes and their cytotoxicity, DNA binding and cleavage study

Cited by 13 publications

References 58 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

Apoptosis induction in human leukemia cells by novel 2-amino-5-benzylthiazole derivatives

Evaluation of the anticancer activities with various ligand substituents in Co(ii/iii)-picolyl phenolate derivatives: synthesis, characterization, DFT, DNA cleavage, and molecular docking studies

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