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Anticancer Potential of Diiron Vinyliminium Complexes
Author(s) -
Rocco Dalila,
Batchelor Lucinda K.,
Agonigi Gabriele,
Braccini Simona,
Chiellini Federica,
Schoch Silvia,
Biver Tarita,
Funaioli Tiziana,
Zacchini Stefano,
Biancalana Lorenzo,
Ruggeri Marina,
Pampaloni Guido,
Dyson Paul J.,
Marchetti Fabio
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902885
Subject(s) - chemistry , cyclopentadienyl complex , hek 293 cells , reactive oxygen species , cell culture , combinatorial chemistry , fragmentation (computing) , ferrocene , stereochemistry , biochemistry , receptor , biology , electrode , electrochemistry , genetics , catalysis , ecology
Abstract Although ferrocene derivatives have attracted considerable attention as possible anticancer agents, the medicinal potential of diiron complexes has remained largely unexplored. Herein, we describe the straightforward multigram‐scale synthesis and the antiproliferative activity of a series of diiron cyclopentadienyl complexes containing bridging vinyliminium ligands. IC 50 values in the low‐to‐mid micromolar range were determined against cisplatin sensitive and resistant human ovarian carcinoma (A2780 and A2780cisR) cell lines. Notable selectivity towards the cancerous cells lines compared to the non‐tumoral human embryonic kidney (HEK‐293) cell line was observed for selected compounds. The activity seems to be multimodal, involving reactive oxygen species (ROS) generation and, in some cases, a fragmentation process to afford monoiron derivatives. The large structural variability, amphiphilic character and good stability in aqueous media of the diiron vinyliminium complexes provide favorable properties compared to other widely studied classes of iron‐based anticancer candidates.