Palladium(II) complexes with thiosemicarbazones: syntheses, characterization and cytotoxicity against breast cancer cells and Anti-Mycobacterium tuberculosis activity

Abstract

= triphenylphosphine; Haptsc = 2-acetylpyridine-thiosemicarbazone; Hapmtsc = 2-acetylpyridine-N(4)-methyl-thiosemicarbazone and Happtsc = 2-acetylpyridine-N(4)-phenylthiosemicarbazone. All complexes were characterized by elemental analysis, IR, UV-Vis, 1 H and 31 P{ 1 H} NMR spectroscopies, and had their crystalline structures determined by X-ray diffractometry from single crystals. The monoanionic thiosemicarbazonate ligands act in a tridentate mode, binding to the metal through the pyridine nitrogen, the azomethine nitrogen and the sulfur atoms. The cytotoxic activity against the breast cancer cell line MDA-MB231 and the anti-Mycobacterium tuberculosis H 37 Rv ATCC 27294 activity were evaluated for the compounds. All Pd II complexes were highly active against the studied cell line, presenting similar values of IC 50 , around 5 μmol L -1 , while the clinically applied antitumor agent cisplatin was inactive. The compounds show remarkable anti-M. tuberculosis activities, presenting MIC values comparable or better than some commercial anti-M tuberculosis drugs.

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

“…The absorptions at 815-878 cm −1 in the spectra of free bases, N,N-disubstituted-N′-acyl thioureas, attributed to the ν(C_S) stretching vibrations, shift to the 752-799 cm −1 range in the complexes spectra. This substantial change suggests deprotonation of the ligands, indicating coordination through the sulfur atom with a formally C\S single bond [34][35][36][37]. The absorptions at about 470 cm − 1 in the IR spectra of the complexes can be assigned to the M\O vibration mode [38,39] and the assignment of the Pd\S stretching vibration bands at about 330 cm −1 are in accordance to the reported by Orysyk et al for palladium(II) complexes with 1-allyl-3-(2-pyridyl)thioureas [40].…”

Manganese(II) complexes with thiosemicarbazones as potential anti-Mycobacterium tuberculosis agents

“…Thiosemicarbazones (TSCs) are of great interest both in chemistry and biology, especially due to their antiparasital [11], antitumor [12][13][14] and antibacterial activities [15]. Moreover, the biological properties of the TSCs are often referred to their complex formation since it can increase the biological activity by forming chelates with metal ions [12,16,17].…”

“…Moreover, the biological properties of the TSCs are often referred to their complex formation since it can increase the biological activity by forming chelates with metal ions [12,16,17]. Previous studies showed that V(IV,V) complexes [18] and octahedral Ni(II) complexes [19] derived from 2-acetylpyridine thiosemicarbazones possess anti-MTB activity that can be increased by structural modifications on the thiosemicarbazone moiety.…”

Unusual saccharin-N,O (carbonyl) coordination in mixed-ligand copper(II) complexes: Synthesis, X-ray crystallography and biological activity

“…Both MT2APH and ET2APH also had similar fragmentation patterns with a base peak at m/z 105 but displayed fragmentation corresponding to C 2 H 2 N 3 S .+ and C 6 H 5 N2 + . 16 …”

“…Thiosemicarbazones derived from 2-acetylpyridine have also been reported to have anti-tuberculosis activity [16]. A series of related 2-acetylpyridinethiosemicarbazone, Haptsc ligands and their vanadium complexes 4 were tested against Mycobacterium tuberculosis H 37 Rv ATCC 27294 and their biological properties varied correspondingly with variation of substituents on the N4 atom of the thiosemicarbazones moiety.…”