Naphthoquinones of natural origin: Aqueous chemistry and coordination to half-sandwich organometallic cations

• Published in: Journal of organometallic chemistry Vol. 907; pp. 121070 - 121079
• Main Authors: Mészáros, János P., Geisler, Heiko, Poljarević, Jelena M., Roller, Alexander, Legina, Maria S., Hejl, Michaela, Jakupec, Michael A., Keppler, Bernhard K., Kandioller, Wolfgang, Enyedy, Éva A.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.02.2020; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Cytotoxicity; Half-sandwich complexes; Natural ligands; Physical Sciences; Science & Technology; Solution stability; X-ray crystal structures; X-ray crystal structures; Solution stability; Cytotoxicity; Natural ligands; Half-sandwich complexes; 1,4-NAPHTHOQUINONE; CONSTANTS; CANCER; RUTHENIUM(II)-ARENE COMPLEXES; ANTICANCER; DRUGS; BIOLOGICAL EVALUATION; AGENTS; DERIVATIVES
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2019.121070

Half-sandwich organometallic complexes featuring Ru(II), Os(II) and Rh(III) metal centers and naturally occurring bidentate 2-hydroxy-[1,4]-naphthoquinone ligands (lawsone and phthiocol) have been synthesized and characterized in both solid state and solution phase by analytical, spectroscopic, electrochemical and single crystal X-ray diffraction techniques. Comparative studies revealed the influence of the respective metal center (Ru, Os, Rh), leaving group (Cl, Br, I) and arene (p-cymene, toluene, pentamethylcyclopentadienyl), as well as the naphthoquinone ligand on the structural properties and solution speciation. Additionally, cytotoxicity was tested in SW480, CH1/PA-1 and A549 human cancer cell lines showing a broad range of IC50 values. [Display omitted] •Single crystal X-ray structure of five half-sandwich phthiocol complexes.•Anticancer activity in three human cancer cell lines.•Solution stability of Ru(II) and Rh(III) complexes of 2-hydroxy-[1,4]-naphthoquinones.•Comparison with other bidentate (O,O) ligands.