title: Synthesis, antimicrobial and antiproliferative activity of novel silver(I) tris(pyrazolyl)methanesulfonate and 1,3,5-triaza-7-phosphadamantane complexes.
abstract: Five new silver(I) complexes of formulas [Ag(Tpms)] (1), [Ag(Tpms)(PPh(3))] (2), [Ag(Tpms)(PCy(3))] (3), [Ag(PTA)][BF(4)] (4), and [Ag(Tpms)(PTA)] (5) {Tpms = tris(pyrazol-1-yl)methanesulfonate, PPh(3) = triphenylphosphane, PCy(3) = tricyclohexylphosphane, PTA = 1,3,5-triaza-7-phosphaadamantane} have been synthesized and fully characterized by elemental analyses, (1)H, (13)C, and (31)P NMR, electrospray ionization mass spectrometry (ESI-MS), and IR spectroscopic techniques. The single crystal X-ray diffraction study of 3 shows the Tpms ligand acting in the N(3)-facially coordinating mode, while in 2 and 5 a N(2)O-coordination is found, with the SO(3) group bonded to silver and a pendant free pyrazolyl ring. Features of the tilting in the coordinated pyrazolyl rings in these cases suggest that this inequivalence is related with the cone angles of the phosphanes. A detailed study of antimycobacterial and antiproliferative properties of all compounds has been carried out. They were screened for their in vitro antimicrobial activities against the standard strains Enterococcus faecalis (ATCC 29922), Staphylococcus aureus (ATCC 25923), Streptococcus pneumoniae (ATCC 49619), Streptococcus pyogenes (SF37), Streptococcus sanguinis (SK36), Streptococcus mutans (UA159), Escherichia coli (ATCC 25922), and the fungus Candida albicans (ATCC 24443). Complexes 1-5 have been found to display effective antimicrobial activity against the series of bacteria and fungi, and some of them are potential candidates for antiseptic or disinfectant drugs. Interaction of Ag complexes with deoxyribonucleic acid (DNA) has been studied by fluorescence spectroscopic techniques, using ethidium bromide (EB) as a fluorescence probe of DNA. The decrease in the fluorescence of DNA-EB system on addition of Ag complexes shows that the fluorescence quenching of DNA-EB complex occurs and compound 3 is particularly active. Complexes 1-5 exhibit pronounced antiproliferative activity against human malignant melanoma (A375) with an activity often higher than that of AgNO(3), which has been used as a control, following the same order of activity inhibition on DNA, i.e., 3 > 2 > 1 > 5 > AgNO(3)≫ 4.
authors: School of Pharmacy, Università degli Studi di Camerino, via S Agostino 1, 62032 Camerino MC, Italy. claudio.pettinari@unicam.it
authors: Claudio
authors: C
authors: Pettinari
authors: Fabio
authors: F
authors: Marchetti
authors: Giulio
authors: G
authors: Lupidi
authors: Luana
authors: L
authors: Quassinti
authors: Massimo
authors: M
authors: Bramucci
authors: Dezemona
authors: D
authors: Petrelli
authors: Luca A
authors: LA
authors: Vitali
authors: M Fátima C Guedes
authors: MF
authors: da Silva
authors: Luísa M D R S
authors: LM
authors: Martins
authors: Piotr
authors: P
authors: Smoleński
authors: Armando J L
authors: AJ
authors: Pombeiro
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001424:Bacterial Infections / Q000188:drug therapy / Q000382:microbiology; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D002177:Candidiasis / Q000188:drug therapy / Q000382:microbiology; D002417:Cattle; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D018360:Crystallography, X-Ray; D004247:DNA / Q000037:antagonists & inhibitors / Q000737:chemistry; D004202:Disinfectants / Q000138:chemical synthesis* / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000254:growth & development; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008545:Melanoma / Q000188:drug therapy / Q000473:pathology; D008698:Mesylates / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D009943:Organophosphorus Compounds / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: C501763:1,3,5-triaza-7-phosphaadamantane; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004202:Disinfectants; D008698:Mesylates; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D018030:Silver Compounds; C045880:methanesulfonic acid; D004247:DNA; C427203:calf thymus DNA; D000218:Adamantane