Jump to main content
Jump to site search


Synthesis, structures and biomolecular interactions of new silver(I) 5,5-diethylbarbiturate complexes of monophosphines targeting Gram-positive bacteria and breast cancer cells

Author affiliations

Abstract

A series of new silver(I) 5,5-diethylbarbiturate (barb) complexes with the formulas [Ag2(μ-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 = tricyclohexylphosphine) 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.

Graphical abstract: Synthesis, structures and biomolecular interactions of new silver(i) 5,5-diethylbarbiturate complexes of monophosphines targeting Gram-positive bacteria and breast cancer cells

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Apr 2017, accepted on 24 May 2017 and first published on 25 May 2017


Article type: Paper
DOI: 10.1039/C7DT01286A
Citation: Dalton Trans., 2017, Advance Article
  •   Request permissions

    Synthesis, structures and biomolecular interactions of new silver(I) 5,5-diethylbarbiturate complexes of monophosphines targeting Gram-positive bacteria and breast cancer cells

    V. T. Yilmaz, C. Icsel, J. Batur, S. Aydinlik, M. Cengiz and O. Buyukgungor, Dalton Trans., 2017, Advance Article , DOI: 10.1039/C7DT01286A

Search articles by author

Spotlight

Advertisements