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A series of 16 novel diiron complexes of general formula [Fe 2 Cp 2 (CO)(μ-CO){μ-η 1 :η 3 -C(R')C(R″)CN(R)(Y)}]CF 3 SO 3 ( 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, 1 H and 13 C NMR spectroscopy; moreover the X-ray structures of 2c (R = Y = CH 2 Ph, R' = R″ = Me) and 3a (R = CH 2 CH=CH 2 , Y = R' = Me, R″ = H) were ascertained by single-crystal X-ray diffraction studies. NMR and UV-Vis methods were used to assess the D 2 O 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).

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study