Thiomaltol-Based Organometallic Complexes with 1-Methylimidazole as Leaving Group: Synthesis, Stability, and Biological Behavior

Author(s)

Carmen M. Hackl, Maria S. Legina, Verena Pichler, Melanie Schmidlehner, Alexander Roller, Orsolya Domotor, Eva A. Enyedy, Michael A. Jakupec, Wolfgang Kandioller, Bernhard K. Keppler

Abstract

Thiomaltol, a potential S,O-coordinating molecule, has been utilized for the complexation of four different organometallic fragments, yielding the desired Ru

^II, Os

^II, Rh

^III, and Ir

^IIIcomplexes having a “piano-stool” configuration. In addition to the synthesis of these compounds with a chlorido leaving group, the analogous 1-methylimidazole derivatives have been prepared, giving rise to thiomaltol-based organometallics with enhanced stability under physiological conditions. The organometallic compounds have been characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction analysis. Their behavior in aqueous solution and their interactions with certain amino acids have been studied by ESI mass spectrometry. Their pH-dependent stability has been investigated by

¹H NMR in aqueous solution, and their cytotoxicity against three different cancer cell lines has been investigated. Furthermore, their capacity as topoisomerase IIα inhibitors as well as their effect on the cell cycle distribution and reactive oxygen species (ROS) generation have been elucidated.

Organisation(s)

Department of Inorganic Chemistry, Core Facility Crystal Structure Analysis

External organisation(s)

University of Szeged, University of Vienna

Journal

Chemistry: A European Journal

Volume

22

Pages

17269-17281

No. of pages

13

ISSN

0947-6539

DOI

https://doi.org/10.1002/chem.201603206

Publication date

11-2016

Peer reviewed

Yes

Austrian Fields of Science 2012

104003 Inorganic chemistry, 104004 Chemical biology

Keywords

ASJC Scopus subject areas

Catalysis, Organic Chemistry

Sustainable Development Goals

SDG 3 - Good Health and Well-being

Portal url

https://ucrisportal.univie.ac.at/en/publications/ad692847-9ea3-4ad2-bb07-4d11f5935693