(2022) Binuclear platinum(ii) complexes bearing various bridging 1,1′-diphosphinoferrocene ligands as potential anticancer agents: synthesis and biological evaluation. New Journal of Chemistry. pp. 931-940. ISSN 11440546 (ISSN)
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Abstract
Novel binuclear platinum(ii) complexes driven by CN cyclometalated ligands with the general formula Pt2(C^N)2Cl2(μ-L), where C^N = 2-phenylpyridine (ppyH) or 2-(2,4-difluorophenyl)pyridine (dfppyH) and L = 1,1′-bis(diphenylphosphino)ferrocene (dppf), 1,1′-bis(diisopropylphosphino)ferrocene (dippf), and 1,1′-bis(dicyclohexylphosphino)ferrocene (dcpf), have been designed, synthesized, and characterized. Single crystal X-ray analysis confirmed the molecular structures of complexes. The electronic absorption spectra of these Pt(ii) complexes are examined, and density functional theory (DFT) and time-dependent DFT (TD-DFT) were employed for geometry optimization and electronic structure computations, respectively. To evaluate the potential of these complexes as anticancer agents, the biological activities including cytotoxic activity, DNA interaction and molecular docking were accomplished. The cytotoxic activity of the prepared complexes was assessed against A549, HeLa, and MCF-7 tumor cell lines using the MTT assay. The results demonstrated that 2c and 3c had reasonable cytotoxic activities, while the other complexes revealed less cytotoxic activity. In comparison to cisplatin, 3c showed significantly higher cytotoxicity against A549 cells. Additionally, the SAR results established that the dfppy ligand, which contains fluorine atoms improved the cytotoxic activity of these complexes. To understand the antiproliferative mechanism of 3c, analyses of DNA damage (comet assay) and apoptosis were carried out. In addition to this, the detection of cellular reactive oxygen species (ROS) was evaluated. Moreover, molecular docking simulations suggested reasonable interactions between these complexes and DNA. This study suggests that metal-based drug design can be developed utilizing the scaffold of 3c as a valuable anticancer agent. © 2023 The Royal Society of Chemistry.
| Item Type: | Article |
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| Keywords: | Cell culture Cell death Chelation Cytotoxicity Density functional theory Design for testability DNA Electronic structure Iron compounds Molecular modeling Organometallics Platinum compounds Single crystals Structural optimization Synthesis (chemical) X ray diffraction analysis Agent synthesis Anti-cancer agents Biological evaluation Cyclometalated ligand Cytotoxic activities Ferrocenes General formulas Platinum complexes Potential anticancer agents Synthesis evaluation Ligands antineoplastic metal complex cisplatin ferrocene derivative fluorine ligand phenyl group phosphine derivative pyridine derivative reactive oxygen metabolite unclassified drug platinum complex (2 phenylpyridine) 2 mu 1,1' bis(dicyclohexylphosphino)ferrocene]] platinum complex (2 phenylpyridine) 2 mu 1,1' bis(diisopropylphosphino)ferrocene]] platinum complex (2 phenylpyridine) 2 mu 1,1' bis(diphenylphosphino)ferrocene]] platinum complex 2 (2,4 difluorophenyl)pyridine] 2 mu 1,1' bis(dicyclohexylphosphino)ferrocene platinum complex 2 (2,4 difluorophenyl)pyridine 2 mu 1,1' bis(diisopropylphosphino)ferrocene platinum complex 2 (2,4 difluorophenyl)pyridine 2 mu 1,1' bis(diphenylphosphino)ferrocene A-549 cell line antineoplastic activity antiproliferative activity apoptosis apoptotic cell percentage Article comet assay complex formation controlled study crystal structure DNA fragmentation drug binding site drug conformation drug cytotoxicity drug design drug DNA interaction drug structure drug synthesis electrospray mass spectrometry female fluorine nuclear magnetic resonance genotoxicity HeLa cell line human human cell IC50 in vitro study MCF-10A cell line MCF-7 cell line mitochondrial membrane potential molecular docking MTT assay proton nuclear magnetic resonance structure activity relation ultraviolet visible spectroscopy X ray crystallography |
| Page Range: | pp. 931-940 |
| Journal or Publication Title: | New Journal of Chemistry |
| Journal Index: | Scopus |
| Volume: | 47 |
| Number: | 2 |
| Identification Number: | https://doi.org/10.1039/d2nj05303a |
| ISSN: | 11440546 (ISSN) |
| Depositing User: | خانم ناهید ضیائی |
| URI: | http://eprints.mui.ac.ir/id/eprint/24327 |
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