Synthesis, Antimicrobial and Antiproliferative Activity of Novel Silver(I) Tris(pyrazolyl)methanesulfonate and 1,3,5-Triaza-7-phosphadamantane Complexes

Abstract

4), and [Ag(Tpms)(PTA)] (5) {Tpms = tris(pyrazol-1-yl)methanesulfonate, PPh3 = triphenylphosphane, PCy3 = tricyclohexylphosphane, PTA = 1,3,5-triaza-7-phosphaadamantane) have been synthesized and fully characterized by elemental analyses, H-1, C-13, and P-31 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 N2O-coordination is found, with the SO3 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 (UA1S9), 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 AgNO3, which has been used as a control, following the same order of activity inhibition on DNA, i.e., 3 > 2 > 1 > 5 > AgNO3 >> 4.

Anticancer activities and mechanism of action of 2 novel metal complexes, C16H34N8O5Ag2Cd and C11H16N7O2Ag3Ni

“…In addition, these complexes resulted in the DNA degradation of cancer cell DNA (data not shown), indicating their apoptotic potential. These results were somewhat similar to those of previous studies by Zachariadis et al (2004), El-Din et al (2011), Korany et al (2013), Pettinari et al (2011), and Banti and Hadjikakou (2013).…”

Neutral and ionic platinum compounds containing a cyclometallated chiral primary amine: synthesis, antitumor activity, DNA interaction and topoisomerase I–cathepsin B inhibition

“…Interest in fluorinated derivatives 3-R and 6-R is related to the fact that fluoro substituents have been proposed as an excellent choice to modify the electronic properties and hydrophobicity of related cycloplatinated complexes 34 while keeping stereochemical changes to a minimum. [36][37][38][39][40] Compounds 3-R, 4-R and 6-R were prepared from compound [PtCl{(R)-NH 2 CH(CH 3 )C 10 H 6 }(SOMe 2 )] (1-R) after stirring an equimolar mixture of this compound and the corresponding mono or diphosphine in acetone at room temperature. 35 On the other hand, the water-soluble monodentate phosphine 1,3,5-triaza-7-phosphaadamantane (PTA) in compound 4-R is a useful hydrophilic co-ligand, which may impart a pH-dependent behavior in biologically active transition metal compounds.…”

C-Homoscorpionate Oxidation Catalysts—Electrochemical and Catalytic Activity

“…However, in the last two decades, mainly driven by improved syntheses [9,10], coordination behavior and physicochemical properties of poly(pyrazol-1-yl)methanes have attracted considerable interest [5][6][7][8] in order to perform the precise tuning of target scorpionates towards a desired function [3,6,7]. Applications of this highly versatile class of metal compounds range from organic synthesis, analytical, bio-inorganic or catalytic chemistry to material sciences [3,[6][7][8][11][12][13][14][15][16][17][18]. The development of sustainable efficient catalytic processes for the activation of abundant and inexpensive raw-materials into high-added-value products remains a great challenge for both academic and industrial purposes.…”

“…A systematic investigation of the coordination behavior of new C-scorpionates, as well as some of the known ones, toward a variety of transition metals (e.g., V [44,[46][47][48][49], Mo [17,19,50], Re [51,52], Fe [44,46,49,53], Ru [54], Co [12,13], Ni [44,49,55], Pd [44], Cu [43,45,46,56,57], Ag [14], Au [58] or Zn [44,56]) followed, leading to new classes of complexes exhibiting different types of coordination modes (Figures 4 and 5). Like the pincer of a scorpion, these versatile tripodal ligands bind metal centers with nitrogen atoms from two pyrazolyl rings attached to the central carbon atom; the third pyrazolyl attached to carbon rotates forward like a scorpion's tail to "sting" the metal; hence the name of "scorpionates" (Figure 4).…”

“…In addition, the tripodal functionalized coordination flexibility (e.g., N 3 -or N 2 O-coordination modes for sulfonated derivatives, Figure 5d) involving the functionalized methine carbon [7,8,14,45,49,50] is also tailored by such co-ligands, an important pre-requisite for their catalytic activity.…”