Molecules (Basel, Switzerland), 2021-10, Vol.26 (21), p.6466
2021
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- Autor(en) / Beteiligte
- Titel
- Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
- Ist Teil von
- Molecules (Basel, Switzerland), 2021-10, Vol.26 (21), p.6466
- Ort / Verlag
- Switzerland: MDPI AG
- Erscheinungsjahr
- 2021
- Quelle
- EZB-FREE-00999 freely available EZB journals
- Beschreibungen/Notizen
- Copper(II) complexes with 1,1,1-trifluoro-4-(4-methoxyphenyl)butan-2,4-dione (H ) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, and single crystal X-ray diffraction. The biological properties of H and -[Cu( ) (DMSO)] ( ) were examined against Gram-positive and Gram-negative bacteria and opportunistic unicellular fungi. The cytotoxicity was estimated towards the HeLa and Vero cell lines. Complex demonstrated antibacterial activity towards comparable to that of streptomycin, lower antifungal activity than the ligand H and moderate cytotoxicity. The bioactivity was compared with the activity of compounds of similar structures. The effect of changing the position of the methoxy group at the aromatic ring in the ligand moiety of the complexes on their antimicrobial and cytotoxic activity was explored. We propose that complex has lower bioavailability and reduced bioactivity than expected due to strong intermolecular contacts. In addition, molecular docking studies provided theoretical information on the interactions of tested compounds with ribonucleotide reductase subunit R2, as well as the chaperones Hsp70 and Hsp90, which are important biomolecular targets for antitumor and antimicrobial drug search and design. The obtained results revealed that the complexes displayed enhanced affinity over organic ligands. Taken together, the copper(II) complexes with the trifluoromethyl methoxyphenyl-substituted β-diketones could be considered as promising anticancer agents with antibacterial properties.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 1420-3049eISSN: 1420-3049DOI: 10.3390/molecules26216466Titel-ID: cdi_doaj_primary_oai_doaj_org_article_af26447aeb60433a929bcb5b78c9029e
- Format
- –
- Schlagworte
- Animals, Anti-Bacterial Agents - chemical synthesis, Anti-Bacterial Agents - chemistry, Anti-Bacterial Agents - pharmacology, Antibacterial activity, Antibiotics, anticancer agents, Antifungal activity, antimicrobial activity, Antimicrobial agents, Antineoplastic Agents - chemical synthesis, Antineoplastic Agents - chemistry, Antineoplastic Agents - pharmacology, Aromatic compounds, Bacteria, Bacterial infections, Bioavailability, Biocompatibility, Biological activity, Biological properties, Cancer therapies, Cell lines, Cell Proliferation - drug effects, Cell Survival - drug effects, Chemotherapy, Chlorocebus aethiops, Coordination Complexes - chemical synthesis, Coordination Complexes - chemistry, Coordination Complexes - pharmacology, Copper, Copper - chemistry, Copper - pharmacology, copper(II), cytotoxic activity, Cytotoxicity, diketonates, Diketones, Dose-Response Relationship, Drug, Drug development, Drug Screening Assays, Antitumor, Drugs, Escherichia coli - drug effects, Fungicides, Gram-negative bacteria, Gram-positive bacteria, HeLa Cells, Hospitals, Hsp70 protein, Hsp90 protein, Humans, Hydrogen bonds, Infrared analysis, Infrared spectroscopy, Ketones - chemistry, Ketones - pharmacology, Ligands, Microbial Sensitivity Tests, Molecular docking, Molecular Docking Simulation, Molecular Structure, Neutropenia, Nosocomial infections, Pathogens, Reductases, Single crystals, Staphylococcus aureus - drug effects, Streptomycin, Structure-Activity Relationship, Vero Cells, X-ray diffraction