New pyridazine-based binuclear nickel(<scp>ii</scp>), copper(<scp>ii</scp>) and zinc(<scp>ii</scp>) complexes as prospective anticancer agents

Rafi, Ummer Muhammed; Mahendiran, Dharmasivam; Haleel, Azees Khan; Nankar, Rakesh P.; Doble, Mukesh; Rahiman, A. Kalilur

doi:10.1039/c5nj02739j

Cited by 63 publications

(39 citation statements)

References 54 publications

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“…Copper(II) perchlorate hexahydrate was prepared by the reaction of 70% perchloric acid with copper(II) carbonate. The ligands 3‐chloro‐6‐(salicylidenehydrazinyl)pyridazine (HL 1 ), 3‐chloro‐6‐(4‐diethylaminosalicylidenehydrazinyl)pyridazine (HL 2 ) and 3‐chloro‐6‐(5‐bromosalicylidenehydrazinyl)pyridazine (HL 3 ) were synthesized according to the procedure reported in our earlier publication . Solvents used in the synthesis were dried and purified before being used according to standard procedures…”

Section: Methodsmentioning

confidence: 99%

“…MTT assay and cell death determination by the Hoechst dye staining method were performed for the synthesized heteroleptic copper(II) complexes ( 1–3 ) as described previously …”

Section: Methodsmentioning

confidence: 99%

“…A docking investigation was performed to locate the exact binding site for the copper(II) complexes using AutoDock Tools version 1.5.6 and AutoDock version 4.2.5.1 docking programs employing a procedure as reported by us previously . The structures of complexes 1 – 3 were converted into PDB format from mol format using OPENBABEL.…”

Section: Methodsmentioning

confidence: 99%

“…Pyridazolato‐bridged copper(II) complexes also exhibited anti‐proliferative and apoptosis‐inducing effects against oestrogen‐independent breast (BT‐20) and androgen‐independent prostate (PC‐3) cancer cells . More recently, our group has reported the anticancer activity of metal(II) complexes of pyridazine‐based tridentate N‐donor ligands against breast cancer (MDA‐MB‐231) cell line . In the study presented here, we chose pyridazine‐based ligands and ciprofloxacin to synthesize heteroleptic copper(II) complexes in order to investigate their in vitro anti‐proliferative activity against three human cancer cell lines and one non‐cancer cell line.…”

Section: Introductionmentioning

confidence: 99%

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In vitro anti‐proliferative and in silico docking studies of heteroleptic copper(II) complexes of pyridazine‐based ligands and ciprofloxacin

Rafi¹,

Mahendiran

Rahiman³

2019

Applied Organom Chemis

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Three heteroleptic copper(II) complexes of the type [Cu(L1–3)(cf)(ClO4)] (1–3), where cf = ciprofloxacin, have been synthesized using pyridazine‐based ligands 3‐chloro‐6‐(salicylidenehydrazinyl)pyridazine (HL1), 3‐chloro‐6‐(4‐diethylaminosalicylidenehydrazinyl)pyridazine (HL2) and 3‐chloro‐6‐(5‐bromosalicylidenehydrazinyl)pyridazine (HL3). Electronic spectral data and magnetic moment values suggest octahedral geometry for the synthesized copper(II) complexes. Electrochemical data of the copper(II) complexes present an irreversible one‐electron reduction wave in the cathodic potential region (Epc) between −0.631 and −0.670 V. Frontier molecular orbital calculations were carried out, and the obtained low‐energy gap supports the bio‐efficacy of the complexes. All the complexes were screened for their in vitro cytotoxicity activity against three human cancerous (breast adenocarcinoma (MCF‐7), hepatoma (HepG‐2) and cervical (HeLa)) and one non‐cancerous (non‐tumorigenic human dermal fibroblast (NHDF)) cell lines using MTT assay, in which complex 2 exhibited higher activity. The apoptosis induction by the complexes was analysed using the Hoechst dye staining method with MCF‐7 cell line, which indicates higher apoptotic activity of complex 2. A molecular docking study was carried out to ascertain the binding affinity of the synthesized heteroleptic copper(II) complexes with phosphoinositide 3‐kinase gamma (PI3Kγ) receptor.

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Section: Methodsmentioning

confidence: 99%

“…MTT assay and cell death determination by the Hoechst dye staining method were performed for the synthesized heteroleptic copper(II) complexes ( 1–3 ) as described previously …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

In vitro anti‐proliferative and in silico docking studies of heteroleptic copper(II) complexes of pyridazine‐based ligands and ciprofloxacin

Rafi¹,

Mahendiran

Rahiman³

2019

Applied Organom Chemis

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“…1). The antimicrobial activity of metal ligand complex by disc method were analyzed as referred (Rafi et al, 2016). The sterile disc with metal and ligand was prepared with the minimum inhibitory concentration.…”

Section: Antibiotic Sensitivity Assay:-mentioning

confidence: 99%

Antimicrobial Analysis of Schiff Base Ligands Pyrazole and Diketone Metal Complex Against Pathogenic Organisms.

Sivaprakash¹,

Tharmaraj²,

Jothibasu³

et al. 2017

IJAR

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Biocatalysis, DNA–protein interactions, cytotoxicity and molecular docking of Cu(II), Ni(II), Zn(II) and V(IV) Schiff base complexes

Balakrishnan

Theetharappan

Kowsalya

et al. 2017

Applied Organom Chemis

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Four mononuclear metal complexes (Cu(II) (1), Ni(II) (2), Zn(II) (3) and V(IV) (4)) were synthesized using the Schiff base ligand 2,2′‐{cyclohexane‐1,2‐diylbis[nitrilo(1E)eth‐1‐yl‐1‐ylidine]}bis[5‐(prop‐2‐yn‐1‐yloxy)phenol] and structurally characterized by various spectral techniques. The catecholase‐mimicking activities of 1–4 were investigated and the results reveal that all the complexes have ability to oxidize 3,5‐di‐tert‐butylcatechol (3,5‐DTBC) to 3,5‐di‐tert‐butylquinone in aerobic conditions. Electrospray ionization mass spectrometry studies were performed for 1–4 in the presence of 3,5‐DTBC to determine the possible complex–substrate intermediates. X‐band electron paramagnetic resonance spectroscopy results indicate that the metal centres are involved in the catecholase activity. Ligand‐centred radical generation was further confirmed by density functional theory calculation. The phosphatase‐like activity of 1–4 was investigated using 4‐nitrophenylphosphate as a model substrate. All the complexes exhibit excellent phosphatase activity in acetonitrile medium. The interactions of 1–4 with calf thymus DNA (CT‐DNA) and bovine serum albumin (BSA) protein were investigated using absorption and fluorescence titration methods. All the complexes strongly interact with CT‐DNA and BSA protein. The complexes exhibit significant hydrolytic cleavage of supercoiled pUC19 DNA. Complexes 1–4 exhibit significant in vitro cytotoxicity against MCF7 (human breast cancer) and MIA‐PA‐CA‐2 (human pancreatic cancer) cell lines. Moreover, the molecular docking technique was employed to determine the binding affinity with DNA and protein molecules.

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New pyridazine-based binuclear nickel(ii), copper(ii) and zinc(ii) complexes as prospective anticancer agents

Abstract: The complexes containing diethylamino substituents exhibit promising cytotoxicity against the estrogen receptor (ER) negative MDA-MB-231 breast cancer cell line.

Cited by 63 publications

References 54 publications

In vitro anti‐proliferative and in silico docking studies of heteroleptic copper(II) complexes of pyridazine‐based ligands and ciprofloxacin

In vitro anti‐proliferative and in silico docking studies of heteroleptic copper(II) complexes of pyridazine‐based ligands and ciprofloxacin

Antimicrobial Analysis of Schiff Base Ligands Pyrazole and Diketone Metal Complex Against Pathogenic Organisms.

Biocatalysis, DNA–protein interactions, cytotoxicity and molecular docking of Cu(II), Ni(II), Zn(II) and V(IV) Schiff base complexes

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