Square-Planar vs. Trigonal Bipyramidal Geometry in Pt(II) Complexes Containing Triazole-Based Glucose Ligands as Potential Anticancer Agents

Abstract

This article describes the synthesis, characterization, and biological activity of novel square-planar cationic platinum(II) complexes containing glucoconjugated triazole ligands and a comparison with the results obtained from the corresponding five-coordinate complexes bearing the same triazole ligands. Stability in solution, reactivity with DNA and small molecules of the new compounds were evaluated by NMR, fluorescence, and UV–vis absorption spectroscopy, together with their cytotoxic action against pairs of immortalized and tumorigenic cell lines. The results show that the square-planar species exhibit greater stability than the corresponding five-coordinate ones. Furthermore, although the square-planar complexes are less cytotoxic than the latter ones, they exhibit a certain selectivity. These results simultaneously demonstrate that overall stability is a fundamental prerequisite for preserving the performance of the agents and that coordinative saturation constitutes a point in favor of their biological action.

Glucosyl Platinum(II) Complexes Inhibit Aggregation of the C-Terminal Region of the Aβ Peptide

“…Some of us also designed new pentacoordinate glycoconjugate platinum­(II) complexes that can act as anticancer compounds . Sugar ligands were introduced aiming to enhance their biocompatibility, aqueous solubility, and recognition by cancer cells through the “Warburg effect”. , The coordinative saturation is also an important stereoelectronic requisite that improves their general stability. In particular, the peracetylated NHC complex 1Pt in Figure , prepared along with its deprotected counterpart 1Pt dep , showed high activity and selectivity toward a panel of cell lines …”

Halo complexes of gold(i) containing glycoconjugate carbene ligands: synthesis, characterization, cytotoxicity and interaction with proteins and DNA model systems

“…The pro-carbene ligand Im-Me was obtained by reacting the glycoconjugate imidazole Im, reported in previous works, 52,55 with an excess of iodomethane in chloroform for 24 h. The alkylated product was isolated by removing the volatiles under vacuum (Scheme 2).…”

“…48 Our research group successfully applied glycoconjugation to organometallic platinum complexes with NHC [49][50][51] and N-heterocyclic ligands. [52][53][54][55] The concept was also extended to gold(I) NHC complexes. In 2017, D'Amora et al described the synthesis, characterization and anticancer activity of a series of neutral and cationic Au(I) complexes with a glycoconjugate NHC ligand derived from methylimidazole.…”

Metallodrugs: Mechanisms of Action, Molecular Targets and Biological Activity

“…Four manuscripts submitted for this Special Issue report new data on the cytotoxic and potential antitumor actions of Pt(II), Fe(III), Cu(II), Zn(II) and Ir(III) compounds [ 10 , 11 , 12 , 13 ].…”

“…Annunziata et al describe the synthesis, characterization and cytotoxic activity of square-planar cationic Pt(II) complexes containing glucoconjugated triazole ligands [ 10 ]. The results obtained with the newly synthetized compounds were compared to those found using parent five-coordinate (5C) complexes bearing the same triazole ligands [ 14 ].…”