Synthesis and characterization of novel heterocyclic diazenyl pyridinone copper(II) complexes with antimicrobial, antioxidant, and anticancer properties

Abstract

The novel diazenyl pyridinone heterocyclic ligands and their Cu(II) complexes have been prepared and characterized utilizing miscellaneous analytical tools, thermogravimetric analysis (TGA), and nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), electron paramagnetic resonance (EPR), and ultraviolet-visible spectroscopies. The investigated ligands are coordinated in a bidentate fashion through the azo nitrogen atom and the hydroxyl oxygen atom to the Cu(II) center. The EPR spectra indicated that the obtained complexes were monomeric, and density functional theory (DFT) calculations confirmed that the Cu(II) atom adopted a six-coordinated octahedral geometry.The ligands and their complexes were investigated for their in vitro antimicrobial activity against some types of bacteria and fungi. The antioxidant and anticancer activities of the complexes were also assessed. The results show that these complexes exhibit higher antitumor efficiency and selectivity index against the models of human breast adenocarcinoma cells MCF-7 and human primary hepatocytes THLE-2 than the reference standard material doxorubicin. The results were supported by DFT calculations, molecular docking, and Hirshfeld surface analysis.

Facile synthesis of novel NNO-tethered copper(ii) complexes: characterization details, theoretical studies, promising enzyme-like activities, and biomolecular interactions

“…These complexes find their applications in a wide spectrum of biological processes such as electron transfer, oxidation, dioxygen transport, 40 catalysis, 41,42 magnetism, 43,44 and DNA damage, and they also exhibit anticancer, protein binding, antioxidative, and cytotoxic activity. 45–49 They possess a long history of medicinal use. 45–49 The complexes can covalently or non-covalently interact with DNA, a key target in cancer therapy, or they can trigger DNA hydrolysis or oxidative cleavage.…”

“…45–49 They possess a long history of medicinal use. 45–49 The complexes can covalently or non-covalently interact with DNA, a key target in cancer therapy, or they can trigger DNA hydrolysis or oxidative cleavage. 50–53 As a result, they interfere with DNA replication to ensure the death of the most rapidly proliferating cells.…”

Synthesis of a new benzoate bridged NNO tethered copper(ii) complex: exploration of its bio, catalytic and anticancer activities

“…These complexes are used in redox activities, O 2 transport, 29 catalysis, 30–32 magnetism 33,34 DNA damage, protein binding, anticancer, antioxidative and cytotoxic actions. 35–42 They've been used medicinally for a very long time. The complexes have the ability to engage covalently or non-covalently with DNA, a crucial target in cancer therapy, or they can cause DNA hydrolysis or oxidative cleavage.…”

New copper (II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies

“…[16][17][18][19][20][23][24][25] On the other hand, complexes composed of pyridone-based azo dyes find their application in optical recording layers with improved light stability 26 and are characterized by good thermal and light stability. [23][24][25][26] The most recent study has proven that azo pyridone dyes-based complexes exhibit antimicrobial, antioxidant, 22 antitubercular, and antiinflammatory activities. 21 Furthermore, these complexes are proven to have higher antitumor efficiency against human breast adenocarcinoma cells MCF-7 and human primary hepatocytes THLE-2 than the reference standard drug doxorubicin.…”

“…21 Furthermore, these complexes are proven to have higher antitumor efficiency against human breast adenocarcinoma cells MCF-7 and human primary hepatocytes THLE-2 than the reference standard drug doxorubicin. 22 On the other hand, Cu(II) complexes are rapidly gaining credit as metallodrugs in the field of modern medicine, as a replacement for platinum-based drugs in chemotherapeutic treatment. 27 Cu(II) complexes derived from the different hydrazone-based ligands possess cytotoxic activity against various cancer cell lines [28][29][30][31][32] as well as excellent antimicrobial 29,31 and antioxidant 32 activity and are recognized as potential modulators of autoimmune and inflammatory responses.…”