Cyclopalladated and cycloplatinated benzophenone imines: Antitumor, antibacterial and antioxidant activities, DNA interaction and cathepsin B inhibition

Abstract

The antitumor, antibacterial and antioxidant activity, DNA interaction and cathepsin B inhibition of cyclo-ortho-palladated and -platinated compounds [Pd(C,N)]2(μ-X)2 [X=OAc (1), X=Cl (2)] and trans-N,P-[M(C,N)X(PPh3)] [M=Pd, X=OAc (3), M=Pd, X=Cl (4), M=Pt, X=Cl (5)] are discussed [(C,N)=cyclo-ortho-metallated benzophenone imine]. The cytotoxicity of compound 5 has been evaluated towards human breast (MDA-MB-231 and MCF-7) and colon (HCT-116) cancer cell lines and that of compounds 1-4 towards the HCT-116 human colon cancer cell line. These cytotoxicities have been compared with those previously reported for compounds 1-4 towards MDA-MB-231 and MCF-7 cancer cell lines. Compound 3 and 4 were approximately four times more active than cisplatin against the MDA-MB-231 and MCF-7 cancer cell lines, and compound 5, was approximately four times more potent than cisplatin against the HCT-116 cancer cell line. The antibacterial activity of compounds 1-5 was in between the ranges of activity of the commercial antibiotic compounds cefixime and roxithromycin. Complexes 1-2 and 4-5 presented also antioxidant activity. Compounds 1-5 alter the DNA tertiary structure in a similar way to cisplatin, but at higher concentration, and do not present a high efficiency as cathepsin B inhibitors. Compound 5 has not been previously described, and its preparation, characterization, and X-ray crystal structure are reported.

On the stability and biological behavior of cyclometallated Pt(IV) complexes with halido and aryl ligands in the axial positions

“…A notable potency for a highly cytotoxic coordination compound containing two non-cyclometallated amine ligands [58] has been observed in our research group. On the other hand, we have also reported that a series of cyclopalladated and cycloplatinated benzophenone imines were not efficient inhibitors of cathepsin B, although showing in vitro high cytotoxicity [59]. a The enzyme was preincubated for 2 h with each compound (from 5 to 100 µM).…”

Carboxymethyl Cellulose/Gelatin Hydrogel Films Loaded with Zinc Oxide Nanoparticles for Sustainable Food Packaging Applications

“…At T 660 nm and T 280 nm, the neat CMC and gelatin films had transmittance values of 87.2 ± 0.50, 90.7 ± 0.15, 58.3 ± 1.25, and 30.4 ± 1.50, respectively. When ZnO-Nps was added to CMC/gelatin blend, the percentage transmittance of films at 280 nm was drastically reduced, falling to just 0.3%, whereas the percentage transmittance values at 660 nm only slightly decreased as ZnO-Nps concentrations were increased [ 35 ]. The amount of ZnO-Nps present had a significant impact on the transmittance value of the nanocomposite films.…”

“…The incorporation of ZnO nanoparticles has increased the elongation at break, and tensile strength values for the CMC/GEL films to 44.6 MPa and 10%, respectively. The increased tensile strength of CMC/gelatin films may be attributed to the incorporation of the proper amount of nanoparticles as well as the bonding between hdroxy groups of gelatin and the hydrophilic groups of CMC, resulting in the formation of a mechanically stable nanocomposite between CMC, gelatin, and zinc oxide nanoparticles [ 35 ].…”

“…Synthesized composite films containing ZnO-Nps showed free radical scavenging activity with IC 50 in the range of 39 to 85 µg/mL while their respective matrix polymers (CMC/GEL) showed activity more than 100 µg/mL. On comparison of IC 50 values of CMC, GEL and their composite films with different wt ratio of ZnO-Nps, it was observed that such CMC/GEL/ZnO-nanocomposites are more active for DPPH activity than their parent polymers [ 35 , 36 ].…”

Synthesis and Evaluation of Promising Antibacterial, Antifungal, and Antioxidant Activities for New Imidazo[1,2‐A]Pyridine‐Derived Imines

“…[34,36,38,43,44] The synthesized Schiff bases exhibited comparable or lower MIC values compared to other heterocyclic imine families. [27,38,39,45,46] The results obtained against Gram-negative and Gram-positive bacteria demonstrate the broad-spectrum antibacterial activity of these newly synthesized compounds, which could be mediated through multiple mechanisms targeting essential bacterial growth steps. Previous publications suggest that these mechanisms include the inhibition of crucial metabolic enzymes in the target microorganism, interference with cell wall synthesis, destruction of specific microbial cellular proteins, and alteration of normal cellular processes.…”