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Arene Variation of Highly Cytotoxic Tridentate Naphthoquinone-Based Ruthenium(II) Complexes and In-Depth In Vitro Studies

ORCID
0000-0001-7511-5206
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Cseh, Klaudia;
ORCID
0000-0002-2536-5861
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Geisler, Heiko;
Affiliation
Institute of Theoretical Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 17, 1090 Vienna, Austria
Stanojkovska, Kristina;
ORCID
0000-0002-6531-0742
Affiliation
Wilhelm-Ostwald-Institute for Physical and Theoretical Chemistry, Faculty of Chemistry and Mineralogy, University of Leipzig, Linnéstr. 2, 04103 Leipzig, Germany
Westermayr, Julia;
ORCID
0000-0001-6919-0744
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Brunmayr, Philipp;
ORCID
0000-0001-5305-2048
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Wenisch, Dominik;
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Gajic, Natalie;
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Hejl, Michaela;
ORCID
0000-0003-4907-218X
Affiliation
Institute of Analytical Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 38, 1090 Vienna, Austria
Schaier, Martin;
ORCID
0000-0002-1460-4919
Affiliation
Institute of Analytical Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 38, 1090 Vienna, Austria
Koellensperger, Gunda;
ORCID
0000-0001-7945-1426
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Jakupec, Michael A.;
ORCID
0000-0002-8711-1533
Affiliation
Institute of Theoretical Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 17, 1090 Vienna, Austria
Marquetand, Philipp;
ORCID
0000-0002-5630-712X
Affiliation
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Str. 42, 1090 Vienna, Austria
Kandioller, Wolfgang

The main purpose of this study was to synthesize a new set of naphthoquinone-based ruthenium(II) arene complexes and to develop an understanding of their mode of action. This study systematically reviews the steps of synthesis, aiming to provide a simplified approach using microwave irradiation. The chemical structures and the physicochemical properties of this novel group of compounds were examined by 1 H-NMR and 13 C-NMR spectroscopy, X-ray diffractometry, HPLC-MS and supporting DFT calculations. Several aspects of the biological activity were investigated in vitro, including short- and long-term cytotoxicity tests, cellular accumulation studies, detection of reactive oxygen species generation, apoptosis induction and NAD(P)H:quinone oxidoreductase 1 (NQO1) activity as well as cell cycle analysis in A549, CH1/PA-1, and SW480 cancer cells. Furthermore, the DNA interaction ability was studied in a cell-free assay. A positive correlation was found between cytotoxicity, lipophilicity and cellular accumulation of the tested complexes, and the results offer some important insights into the effects of the arene. The most obvious finding to emerge from this study is that the usually very chemosensitive CH1/PA-1 teratocarcinoma cells showed resistance to these phthiocol-based organometallics in comparison to the usually less chemosensitive SW480 colon carcinoma cells, which pilot experiments suggest as being related to NQO1 activity.

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