Impact of the carbon chain length of novel platinum complexes derived from N-alkyl-propanediamines on their cytotoxic activity and cellular uptake

Platinum(II) complexes containing long-chain hydrophobic N-alkyl-diamine ligands: Synthesis, characterization, molecular modeling, and cytotoxic activity

“…A relationship between cytotoxicity and carbon chain length in platinum compounds was previously reported by our group for complexes with different 1,3-propanediamine derivatives [15]. A similar relationship was also found by Kelland et al in a study of a series of alkylamine ammine dicarboxylatodichloroplatinum(IV) complexes [26].…”

“…In a previous work [15], we were able to correlate the cytotoxic activity of platinum complexes containing diamine ligands having different carbon chains lengths with the lipophilicity of the compounds. We have found that the cytotoxic activity of the compounds increases proportionally as a function of carbon chain length, within the studied parameters.…”

A synthetic dinuclear copper(II) hydrolase and its potential as antitumoral: Cytotoxicity, cellular uptake, and DNA cleavage

“…It indicates that the complex is being concentrated within cells by some mechanism of transport, possibly the main copper influx transporter in human cells, the 190 amino acid Cu transporter 1 (hCtr1) [33]. For the sake of comparison, similar experiments were reported with antitumoral platinum compounds: for cisplatin and carboplatin, at IC 50 the intracellular platinum concentration was about 1.0 Â 10 À16 mol/cell [34] and for four complexes derived from N-alkylpropanediamines at IC 50 doses the intracellular platinum concentration was about 4.0 Â 10 À16 mol/cell [35]. Interestingly, the uptake of cisplatin is reported to be mediated by the copper transporter Ctr1 in yeast and mammals [36,37].…”

Vibrational and conformational studies of 1,3-diaminopropane and its N-deuterated and N-ionised derivatives

“…18,24,25 1,3-dap is also quite relevant at an industrial level, namely in food and pharmaceutic industries. Regarding the latter, it may be used for the design of new diuretic 26 and anticancer [27][28][29][30] drugs.…”

“…In fact, these types of Pt(II) and Pd(II)-polyamine chelates were shown to display promising cytotoxic properties via an unconventional interaction with DNA. [27][28][29][30]33,[37][38][39][40][41][42][43][44] With a view to understand both the antitumor activity of these compounds and the structural dependence of such activity, it is crucial to have deep knowledge of their aliphatic ligands. Hence, the present work aimed at a conformational study of 1,3-dap, one of the smallest diamines, as well as its N-ionised derivative, using DFT methods and vibrational spectroscopy (both optical -Raman and FTIR -and neutron scattering techniques).…”