Abstract
A series of 16 novel diiron complexes of general formula [Fe2Cp2(CO)(μ-CO){μ-η1:η3-C(R′)C(R″)CN(R)(Y)}]CF3SO3 (2–7), bearing different substituents on the bridging vinyliminium ligand, was synthesized in 69–95% yields from the reactions of diiron μ-aminocarbyne precursors with various alkynes. The products were characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy; moreover the X-ray structures of 2c (R = Y = CH2Ph, R′ = R″ = Me) and 3a (R = CH2CH=CH2, Y = R′ = Me, R″ = H) were ascertained by single-crystal X-ray diffraction studies. NMR and UV–Vis methods were used to assess the D2O solubility, the stability in aqueous solution at 37 °C and the octanol–water partition coefficients of the complexes. A screening study evidenced a potent cytotoxicity of 2–7 against the A2780 cancer cell line, with a remarkable selectivity compared to the nontumoral Balb/3T3 cell line; complex 4c (R = Cy, Y = R′ = R″ = Me) revealed as the most performant of the series. The antiproliferative activity of a selection of complexes was also assessed on the cisplatin-resistant A2780cisR cancer cell line, and these complexes were capable of inducing a significant ROS production. Moreover, ESI-MS experiments indicated the absence of interaction of selected complexes with cytochrome c and the potentiality to inhibit the thioredoxin reductase enzyme (TrxR).
Highlights
There is an urgent demand for the development of new, effective and targeted anticancer drugs, and in this regard transition metal complexes are at the forefront of research [1–6]
A series of diiron complexes with novel vinyliminium ligands, 2–7, was synthesized from the respective aminocarbyne precursors, 1a–f, by means of a two-step procedure
Diiron complexes based on the {Fe2 Cp2 (CO)2 } scaffold and containing a bridging vinyliminium ligand display some notable properties for a potential drug, i.e., the presence of a biocompatible metal element, straightforward synthesis from inexpensive precursors, appreciable water solubility and/or amphiphilicity, and remarkable stability in aqueous media
Summary
There is an urgent demand for the development of new, effective and targeted anticancer drugs, and in this regard transition metal complexes are at the forefront of research [1–6] This category of compounds offers peculiar properties associated with the presence of one or more transition elements, i.e., the availability of a variety of oxidation states, coordination environments and geometries, and the possibility of replacement and/or activation of ligands under suitable conditions [7–9]. Such arsenal of tools may provide an increased added pharmaceutical value with respect to common organic molecules, and in this light few platinum complexes have been successfully employed worldwide in clinical treatments against several types of tumors, in combination with other drugs [10,11].
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