title: Selenoquinones stabilized by ruthenium(II) arene complexes: synthesis, structure, and cytotoxicity.
abstract: A new series of monoselenoquinone and diselenoquinone π complexes, [(η(6) -p-cymene)Ru(η(4) -C6 R4 SeE)] (R=H, E=Se (6); R=CH3 , E=Se (7); R=H, E=O (8)), as well as selenolate π complexes [(η(6) -p-cymene)Ru(η(5) -C6 H3 R2 Se)][SbF6 ] (R=H (9); R=CH3 (10)), stabilized by arene ruthenium moieties were prepared in good yields through nucleophilic substitution reactions from dichlorinated-arene and hydroxymonochlorinated-arene ruthenium complexes [(η(6) -p-cymene)Ru(C6 R4 XCl)][SbF6 ]2 (R=H, X=Cl (1); R=CH3 , X=Cl (2); R=H, X=OH (3)) as well as the monochlorinated π complexes [(η(6) -p-cymene)Ru(η(5) -C6 H3 R2 Cl)][SbF6 ]2 (R=H (4); R=CH3 (5)). The X-ray crystallographic structures of two of the compounds, [(η(6) -p-cymene)Ru(η(4) -C6 Me4 Se2 )] (7) and [(η(6) -p-cymene)Ru(η(4) -C6 H4 SeO)] (8), were determined. The structures confirm the identity of the target compounds and ascertain the coordination mode of these unprecedented ruthenium π complexes of selenoquinones. Furthermore, these new compounds display relevant cytotoxic properties towards human ovarian cancer cells.
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, Université Pierre et Marie Curie, Institut Parisien de Chimie Moléculaire (IPCM) UMR 8232, 4 place Jussieu, 75252 Paris cedex 05, France, Fax: (+33) 1-44-27-38-41; CNRS, Centre National de la Recherche Scientifique, Institut Parisien de Chimie Moléculaire (IPCM) UMR 8232, 4 place Jussieu, 75252 Paris cedex 05, France, Fax: (+33) 1-44-27-38-41.
authors.forename: Julien
authors.initials: J
authors.lastname: Dubarle-Offner
authors.forename: Catherine M
authors.initials: CM
authors.lastname: Clavel
authors.forename: Geoffrey
authors.initials: G
authors.lastname: Gontard
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Dyson
authors.forename: Hani
authors.initials: H
authors.lastname: Amouri
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D045744:Cell Line, Tumor; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003603:Cytotoxins / Q000737:chemistry*; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010051:Ovarian Neoplasms / Q000188:drug therapy; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D056831:Coordination Complexes; D003603:Cytotoxins; D011809:Quinones; D012428:Ruthenium
keywords: cytotoxicity; pi interactions; ruthenium; sandwich complexes; selenoquinones