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.

Synthesis, Crystal Structure and Thermal Stability of 1D Linear Silver(I) Coordination Polymers with 1,1,2,2-Tetra(pyrazol-1-yl)ethane

“…Silver coordination polymers are receiving much attention because of their antimicrobial [6][7][8][9], anti-tumor [10] and luminescent properties [11]. Bitopic bis-and tris(pyrazol-1-yl)methane ligands have been used for the preparation of coordination polymers of various topologies [12][13][14][15][16][17][18][19][20].…”

Crystal structure, DNA-binding properties and antioxidative activities of a novel silver(I) inorganic polymer

“…Silver(I) complexes have attracted considerable interest due to their structural features and biological and pharmacological properties which provide them with antifungal and antibacterial activities and, consequently, their potential applications & Huilu Wu wuhuilu@163.com [1][2][3][4][5]. Silver has been, since antiquity, used as an antimicrobial agent; it was earlier employed in the purification of drinking water, wine and vinegar, and also Hippocrates remarked on its therapeutic properties [6].…”

Antiproliferative Activity of Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N’-Diacetate

“…The two major problems associated with the use of cisplatin derivatives are the severe toxic side effects (11)(12)(13)(14)(15) and the intrinsic or acquired resistance manifested in various types of cancers (16). Therefore, in recent decades, a large number of new metal-based complexes have been developed and tested (17)(18)(19).…”