Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity

Abstract

From the well-known 1,3,5-triaza-phosphaadamantane (PTA, 1a), the novel N-allyl and N-benzyl tetrafuoroborate salts 1-allyl-1-azonia-3,5-diaza-7-phosphaadamantane (APTA(BF4), 1b) and 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantane (BzPTA(BF4), 1c) were obtained. These phosphines were then allowed to react with (Pt(μ-Cl)(C6F5)(tht))2 (tht = tetrahydrothiophene) affording the water soluble Pt(II) complexes trans-(PtCl(C6F5)(PTA)2) (2a) and its bis-cationic congeners trans-(PtCl(C6F5)(APTA)2)(BF4)2 (2b) and trans-(PtCl(C6F5)(BzPTA)2)(BF4)2 (2c). The compounds were fully characterized by multinuclear NMR, ESI-MS, elemental analysis and (for 2a) also by single crystal X-ray diffraction, which proved the trans configuration of the phosphine ligands. Furthermore, in order to evaluate the cytotoxic activities of all complexes the normal human dermal fibroblast (NHDF) cell culture were used. The antineoplastic activity of the investigated compounds was checked against the human lung carcinoma (A549), epithelioid cervix carcinoma (HeLa) and breast adenocarcinoma (MCF-7) cell cultures. Interactions between the complexes and human serum albumin (HSA) using fluorescence spectroscopy and circular dichroism spectroscopy (CD) were also investigated.

Self-Assembly and Multifaceted Bioactivity of a Silver(I) Quinolinate Coordination Polymer

“…This is also in agreement with prior data for PTA (MIC > 600 μg mL –1 ) and H 2 quin (MIC > 1024 μg mL –1 ) established for the same species of bacteria. The MIC values shown by 1 are comparable to those reported for other Ag-based CPs. − On the basis of the aforementioned findings, we can hypothesize that the antimicrobial properties of 1 are mainly associated with the action of Ag + ions, which might be strongly influenced by the type of coordination environment present and binding affinity of O-, N-, and P-donor ligands. However, further studies are required to shed light on the actual mechanism of antimicrobial action of compound 1 .…”

“…In contrast to discrete metal complexes, some silver­(I)-based coordination polymers represent improved stability and release properties, thus also gaining an impetus for applications in anticancer and antimicrobial treatment. − In particular, water-soluble cagelike aminophosphine ligands such as PTA (1,3,5-triaza-7-phospha­adamantane) and its various derivatives constitute an appealing class of linkers for designing bioactive coordination polymers. − Notable examples of such silver­(I)-based compounds with potent and diverse bioactivity were reported in our previous studies. − Within this context and following our major goal in exploring the chemistry and biofunctional applications of silver–PTA coordination polymers, herein we report the self-assembly synthesis, characterization, spectroscopic and structural features, and antiviral, antimicrobial, and antiproliferative properties of a new silver­(I) coordination polymer derived from PTA and quinolinic acid, [Ag­(Hquin)­(μ-PTA)] n ·H 2 O ( 1 ).…”

Synthesis, Spectroscopic, and Biological Assessments on Some New Rare Earth Metal Adrenaline Adducts

“…Of this, 100 µL of the microbial suspension were distributed on agar plates that corresponded to the broth in which they were kept. Isolated colonies of each organism that might be detrimental were chosen from the main agar plates and their vulnerability was evaluated using the disc dispersion technique [18][19][20][21][22][23][24][25][26][27][28]. There are many research papers that deal with the disc dispersion technique in conducting the biological evaluation of the prepared chemical compounds, and the findings of these can be listed as follows: the use of Ruthenium complexes with 2-pyridin-2-yl-1H-benzimidazole as potential antimicrobial agents has been discussed according to the correlation between chemical properties and anti-biofilm effects [18].…”

“…Providing insight into their analytical applications and biological activity, the quinolone complexes with lanthanide ions [22], Cu(II), Zn(II) complexes with theophylline [23], Mn(II), Co(II), Ni(II), Cr(III) and Fe(III) melatonin drug complexes [24] were discussed. The antimicrobial and antifungal screening of the 3-benzenedicarbonyl-bis-(amino acid) and dipeptide candidates [25], as well as the pentafluorophenyl platinum(II) complexes of N-allyl and N-benzyl derivatives, were reported [26].…”

Synthesis and Characterization of Novel [2 + 1] Tricarbonyl Rhenium Complexes with the Hydrophilic Phosphine Ligands PTA and CAP

“…The coordination chemistry of PTA with transition metals has been extensively reported [ 9 , 13 , 14 ]. In relation to their use as medicinal compounds, ruthenium and platinum have attracted the main focus of relevant research since PTA complexes with these metals exhibit potent anticancer action [ 15 – 17 ]. However, the chemistry of PTA with rhenium is being increasingly investigated thanks to rhenium's promising medical and catalytical applications.…”