Mono-, Di- and Tetra-iron Complexes with Selenium or Sulphur Functionalized Vinyliminium Ligands: Synthesis, Structural Characterization and Antiproliferative Activity
by
Gabriele Agonigi 1, Lucinda K. Batchelor 2, Eleonora Ferretti 3, Silvia Schoch 1, Marco Bortoluzzi 4
, Simona Braccini 1, Federica Chiellini 1, Lorenzo Biancalana 1, Stefano Zacchini 5, Guido Pampaloni 1, Biprajit Sarkar 3, Paul J. Dyson 2 and Fabio Marchetti 1,*
Gabriele Agonigi 1, Lucinda K. Batchelor 2, Eleonora Ferretti 3, Silvia Schoch 1, Marco Bortoluzzi 4, Simona Braccini 1, Federica Chiellini 1, Lorenzo Biancalana 1, Stefano Zacchini 5, Guido Pampaloni 1, Biprajit Sarkar 3, Paul J. Dyson 2 and Fabio Marchetti 1,*
1
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, I-56124 Pisa, Italy
2
Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland
3
Institut für Chemie und Biochemie, Fabeckstr 34-36, 14195 Berlin, Germany
4
Dipartimento di Scienze Molecolari e Nanosistemi, Ca’ Foscari Università di Venezia, Via Torino 155, I-30170 Mestre (VE), Italy
5
Dipartimento di Chimica Industriale “Toso Montanari”, Università di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(7), 1656; https://doi.org/10.3390/molecules25071656
Received: 25 March 2020 / Revised: 1 April 2020 / Accepted: 2 April 2020 / Published: 3 April 2020
(This article belongs to the Special Issue Exclusive Feature Papers in Inorganic Chemistry)
A series of diiron/tetrairon compounds containing a S- or a Se-function (2a–d, 4a–d, 5a–b, 6), and the monoiron [FeCp(CO){SeC1(NMe2)C2HC3(Me)}] (3) were prepared from the diiron μ-vinyliminium precursors [Fe2Cp2(CO)( μ-CO){μ-η1: η3-C3(R’)C2HC1N(Me)(R)}]CF3SO3 (R = R’ = Me, 1a; R = 2,6-C6H3Me2 = Xyl, R’ = Ph, 1b; R = Xyl, R’ = CH2OH, 1c), via treatment with S8 or gray selenium. The new compounds were characterized by elemental analysis, IR and multinuclear NMR spectroscopy, and structural aspects were further elucidated by DFT calculations. The unprecedented metallacyclic structure of 3 was ascertained by single crystal X-ray diffraction. The air-stable compounds (3, 4a–d, 5a–b, 6) display fair to good stability in aqueous media, and thus were assessed for their cytotoxic activity towards A2780, A2780cisR, and HEK-293 cell lines. Cyclic voltammetry, ROS production and NADH oxidation studies were carried out on selected compounds to give insights into their mode of action.
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Keywords:
bioorganometallic chemistry; metal-based drugs; diiron complexes; vinyliminium ligand; sulphur; selenium
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MDPI and ACS Style
Agonigi, G.; Batchelor, L.K.; Ferretti, E.; Schoch, S.; Bortoluzzi, M.; Braccini, S.; Chiellini, F.; Biancalana, L.; Zacchini, S.; Pampaloni, G.; Sarkar, B.; Dyson, P.J.; Marchetti, F. Mono-, Di- and Tetra-iron Complexes with Selenium or Sulphur Functionalized Vinyliminium Ligands: Synthesis, Structural Characterization and Antiproliferative Activity. Molecules 2020, 25, 1656.
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