Büyükgüngör, Orhan2022-12-222022-12-222017-05-24Yılmaz, V. T. vd. (2017). ''Synthesis, structures and biomolecular interactions of new silver(I) 5,5-diethylbarbiturate complexes of monophosphines targeting Gram-positive bacteria and breast cancer cells''. Dalton Transactions. 46(25), 8110-8124.1477-9226https://doi.org/10.1039/c7dt01286a1477-9234https://pubs.rsc.org/en/content/articlelanding/2017/DT/C7DT01286Ahttp://hdl.handle.net/11452/30043A 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.eninfo:eu-repo/semantics/closedAccessChemistryHeterocyclic carbene complexesBovine serum-albuminCrystal-structuresDna-binding2,2'-dipyridylamine synthesisAntimicrobial activityAntibacterial agentsAntioxidant activityPhosphorus ligandsMolecular dockingBacteriaBinding energyBinsCell cultureCell deathCellsComplexationCrystallographyCytologyCytotoxicityDiseases; EEscherichia coliHydrophobicityLigandsPhosphorus compoundsPlatinum compoundsSelf assemblySilverX ray crystallographySynthesis (chemical)5 ,5-diethylbarbiturateAnti-microbial activityBiomolecular interactionsGram-positive bacteriumGroove binding modesHydrophobic interactionsSilver sulfadiazinesTriphenyl phosphinesA549 cellsAnti-Bacterial agentsAntineoplastic agentsApoptosisBarbituratesCell survivalCoordination complexesGram-positive bacteriaHumansHydrophobic and hydrophilicInteractionsMCF-7 cellsMolecular docking simulationPhosphinesSilverHT29 cellsArticle0004044675000172-s2.0-8502174997881108124462528607988Chemistry, inorganic & nuclearThiobarbituric Acid; Crystal Structure; DMVAntiinfective agentAntineoplastic agentBarbituric acid derivativeCoordination compoundPhosphine derivativeSilverA-549 cell lineApoptosisCell survivalChemical phenomenaChemistryDrug effectGram positive bacteriumHT-29 cell lineHumanMCF-7 cell lineMolecular dockingSynthesis