Synthesis, structures and biomolecular interactions of new silver(I) 5,5-diethylbarbiturate complexes of monophosphines targeting Gram-positive bacteria and breast cancer cells
| Autor: | Murat Cengiz, Jenaidullah Batur, Seyma Aydinlik, Veysel T. Yilmaz, Ceyda Icsel, Orhan Büyükgüngör |
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| Přispěvatelé: | Ondokuz Mayıs Üniversitesi, Uludağ Üniversitesi/Fen-Edebiyet Fakültesi/Kimya Bölümü., Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Biyoloji Bölümü., Uludağ Üniversitesi/Veteriner Fakültesi/Farmakoloji ve Toksikoloji Anabilim Dalı., Yılmaz, Veysel T., İçsel, Ceyda, Batur, Jenaidullah, Aydınlık, Seyma, Cengiz, Murat, L-7238-2018, AAI-3342-2021, ABI-2909-2020, ABE-5935-2020 |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Cytotoxicity
Hydrophobicity Coordination complexes Interactions Apoptosis Antimicrobial activity MCF-7 cell line Ligands 01 natural sciences Cell survival Thiobarbituric Acid Crystal Structure DMV Chemical phenomena chemistry.chemical_compound Barbituric acid derivative Synthesis Gram positive bacterium Dna-binding Antineoplastic agents Cytotoxic T cell A549 cells MCF-7 cells Molecular docking simulation Phosphorus compounds Antiinfective agent Platinum compounds HT-29 cell line Crystal-structures Crystallography biology Chemistry Diseases E Heterocyclic carbene complexes Anti-Bacterial agents 2 2'-dipyridylamine synthesis Self assembly Gram-positive bacteria Chemistry inorganic & nuclear Phosphine derivative Bovine serum-albumin Antineoplastic agent Synthesis (chemical) A-549 cell line Lipophilicity Molecular docking Complexation Hydrophobic interactions Biomolecular interactions Hydrophobic and Hydrophilic Interactions Coordination compound medicine.drug Human Cell death Silver Stereochemistry Phosphorus ligands Bins Phosphines Cells Gram-positive bacterium 5 5-diethylbarbiturate Binding energy 010402 general chemistry Inorganic Chemistry Anti-microbial activity Groove binding modes Antioxidant activity medicine Escherichia coli Humans Hydrophobic and hydrophilic HT29 cells Cisplatin Bacteria 010405 organic chemistry Tricyclohexylphosphine X ray crystallography Triphenyl phosphines biology.organism_classification Molecular biology In vitro 0104 chemical sciences Drug effect Antibacterial agents Cell culture Barbiturates Silver sulfadiazines Cytology DNA |
| Popis: | Yilmaz, Veysel/0000-0002-2849-3332 WOS: 000404467500017 PubMed: 28607988 A series of new silver(I) 5,5-diethylbarbiturate (barb) complexes with the formulas [Ag-2(mu-barb)(2)(PPh3)(2)] (1), [Ag(barb)(PPh2Cy)] (2), [Ag(barb)(PPhCy2)] (3) and [Ag(barb)(PCy3)] (4) (PPh3 = triphenylphosphine, PPh2Cy = diphenylcyclohexylphosphine, PPhCy2 = dicyclohexylphenylphosphine and PCy3 = tricyclo-hexylphosphine) were synthesized and fully characterized by elemental analysis, IR, NMR, ESI-MS and X-ray crystallography. All the complexes display a significant affinity towards DNA with a groove binding mode and also strongly bind to BSA via hydrophobic interactions. Lipophilicity increases from 1 to 4 with an increasing number of Cy groups in the phosphine ligands. Screening of the in vitro antimicrobial activity of 1-4 against the strains of Gram-negative (S. typhimurium ATCC 14028, E. coli ATCC 25922 and O157:H7) and Gram-positive (L. garvieae 40456, S. aureus ATCC 25923, and ATCC 33591) bacteria demonstrated that all the complexes exhibit very high activity and specific selectivity against the Gram-positive bacteria, compared to AgNO3 and silver sulfadiazine. Furthermore, the growth inhibitory effects of 1-4 on four human cancer cell lines (MCF-7, PC-3, A549 and HT-29) showed that 4 has a potent cytotoxic activity against MCF-7 cells, significantly higher than cisplatin and carboplatin. The effects of the complexes on the inhibition of the cells are closely related to their lipophilicity as well as DNA/protein binding. The induction of apoptosis of MCF-7 cells treated with 4 was probed through Hoechst 33342 staining, Annexin V positivity and caspase 3/7 activity. In addition, increased ROS levels in the presence of 4 are most likely responsible for damage to both mitochondria and genomic DNA. Uludag UniversityUludag University; OUAP [F-2016/9] This work is a part of a research project, OUAP (F-2016/9). The authors are thankful to Uludag University for the financial support given to the project. |
| Databáze: | OpenAIRE |
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