title: New water-soluble polypyridine silver(I) derivatives of 1,3,5-triaza-7-phosphaadamantane (PTA) with significant antimicrobial and antiproliferative activities.
abstract: The new series of silver(I) coordination polymers [Ag(N-N)(μ-PTA)]n(X)n (1, 2, 4-8, 10, 11) and discrete monomers [Ag(N-N)(PTA)2](X) (3, 9) {N-N = bpy (1-3), dtbpy (4), neocup (5, 6), phen (7-9), dione (10, 11); X = NO3 (1, 3, 5, 7, 9, 10), PF6 (2, 4, 6, 8, 11)} were generated by self-assembly reactions, in MeOH at ~25 °C, of AgNO3 or AgPF6 with 1,3,5-triaza-7-phosphaadamantane (PTA) and the corresponding polypyridines, namely 2,2'-bipyridine (bpy), 4,4'-di-tert-butyl-2,2'-bipyridine (dtbpy), 1,10-phenanthroline (phen), 2,9-dimethyl-1,10-phenanthroline (neocup) and 1,10-phenanthroline-5,6-dione (dione). The compounds were obtained as air and light stable solids and characterized by IR, (1)H and (31)P{(1)H} NMR spectroscopy, ESI(+)-MS and elemental analyses. The crystal structure of 1 was determined by single crystal X-ray diffraction analysis, revealing infinite one-dimensional (1D) linear chains driven by μ-PTA N,P-linkers. Apart from representing the first examples of the metal-PTA derivatives bearing polypyridine ligands, 1-11 also feature solubility in water (S(25°C) ≈ 4-18 mg mL(-1)). Selected compounds (1, 3, 5, 7, 9 and 10) were thus tested for their biological properties and found to exhibit significant antibacterial and antifungal activities, screened in vitro against the standard strains of Staphylococcus aureus, Staphylococcus pyogenes, Staphylococcus pneumoniae, Staphylococcus sanguinis, Staphylococcus mutans, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli and Candida albicans. Furthermore, the compounds 5, 7, 9 and 10 show a pronounced antiproliferative activity against human malignant melanoma (A375), and the effects on the inhibition of tumor cells in vitro are in agreement with the DNA-binding studies.
authors.affiliation: Faculty of Chemistry, University of Wrocław, Wrocław, Poland. piotr.smolenski@chem.uni.wroc.pl
authors.forename: Piotr
authors.initials: P
authors.lastname: Smoleński
authors.forename: Sabina W
authors.initials: SW
authors.lastname: Jaros
authors.forename: Claudio
authors.initials: C
authors.lastname: Pettinari
authors.forename: Giulio
authors.initials: G
authors.lastname: Lupidi
authors.forename: Luana
authors.initials: L
authors.lastname: Quassinti
authors.forename: Massimo
authors.initials: M
authors.lastname: Bramucci
authors.forename: Luca A
authors.initials: LA
authors.lastname: Vitali
authors.forename: Dezemona
authors.initials: D
authors.lastname: Petrelli
authors.forename: Andrzej
authors.initials: A
authors.lastname: Kochel
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Kirillov
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004247:DNA / Q000378:metabolism; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D012995:Solubility; D014867:Water / Q000737:chemistry*
chemical_list: C501763:1,3,5-triaza-7-phosphaadamantane; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D011725:Pyridines; D014867:Water; D012834:Silver; D004247:DNA; C023666:pyridine; D000218:Adamantane