Synthesis, chemical characterization and cancer cell growth-inhibitory activities of Cu(ii) and Ru(iii) aliphatic and aromatic dithiocarbamato complexes

Abstract

The effects mediated by different cyclic dithiocarbamic ligands on three classes of antiproliferative coordination compounds were studied.

CuII and AuIII Complexes with Glycoconjugated Dithiocarbamato Ligands for Potential Applications in Targeted Chemotherapy

“…During the dithiocarbamate synthesis (Scheme (iv), Figure ), we observed that the nucleophilic attack of the glycosyl‐conjugated secondary amine toward CS 2 in water is slower (6 h) than the same process involving less sterically hindered alkyl amines as starting material (usually 1–2 h, for example, piperidine) …”

“…Two main IR regions are taken into account when characterizing DTC derivatives, both ligand salts and metal–DTC complexes. First is the spectral region 1100–1550 cm −1 , in which the ν (N−CSS) band can be found and its position depends strongly on the extent of double bond character of the N−C bond . In the case of a single‐bond form, the band is located at 1250–1350 cm −1 , whereas it is found at higher wavenumbers (1640–1690 cm −1 ) if the DTC ligand contains a basically double C=N bond (thioureidic form) …”

“…Moving to far FTIR, for the Au III compounds the absorption in the range 370–440 cm −1 is ascribed to the Au−S asymmetric stretching associated with a bidentate symmetric coordination …”

“…During the dithiocarbamate synthesis (Scheme 1( iv), Figure1), we observedt hat the nucleophilic attack of the glycosyl-conjugated secondary amine toward CS 2 in water is slower (6 h) than the same process involving less sterically hindered alkyl amines as startingm aterial( usually 1-2 h, for example,piperidine). [24,33] All the NMR spectra of the ligands were acquired in [D 6 ]DMSO and are provided in the Supporting Information. This aprotic solventa llows the detection of resonances related to the alcoholicf unctions of the monosaccharides.…”

“…In this work, we combine some Au III and Cu II dithiocarbamates (DTCs) with various carbohydrates. The metal centers Au III and Cu II were chosen owing to their well‐known low‐micromolar cytotoxic effects, when complexed with DTCs or other appropriate ligands, against a wide panel of human tumor cell lines. In this regard, different mechanisms of action have been recognized in the literature over the last years: for example, while reactivity toward the selenoenzyme thioredoxin reductase, aquaporins, proteasome, or PARP‐1 has been detected for Au III compounds, induced oxidative DNA or mitochondrial damage has been observed for Cu II counterparts …”