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  • Synthesis, Modification, and Biological Evaluation of a Library of Novel Water-Soluble Thiopyridone-Based Organometallic Complexes and Their Unexpected (Biological) Behavior.

Synthesis, Modification, and Biological Evaluation of a Library of Novel Water-Soluble Thiopyridone-Based Organometallic Complexes and Their Unexpected (Biological) Behavior.

Chemistry (Weinheim an der Bergstrasse, Germany) (2020-01-21)
Sophia Harringer, Barbara Happl, Marius Ozenil, Caroline Kast, Michaela Hejl, Debora Wernitznig, Anton A Legin, Andreas Schweikert, Natalie Gajic, Alexander Roller, Gunda Koellensperger, Michael A Jakupec, Wolfgang Kandioller, Bernhard K Keppler
ABSTRACT

A series of 16 dinuclear thiopyridone-based organometallics with excellent water solubility, increased stability and remarkable cytotoxicity were synthesized and characterized. The complexes of this work formed dimeric species featuring a double positive charge in polar protic solvents, accounting for their outstanding solubility in aqueous solution. Most of them displayed higher antiproliferative activity than their parental thiomaltol complex, with unexpected cytotoxicity trends depending on the employed metal center, ligand modification, and cell line. Insights into their behavior in biological systems were gathered by means of amino-acid interaction studies, cytotoxicity tests in 3D spheroid models, laser ablation, cellular accumulation measurements, as well as cell cycle experiments.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Lawesson reagent, 97%
Sigma-Aldrich
Ruthenium(III) chloride, Ru content 45-55%
Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Sigma-Aldrich
Maltol, ≥99.0%, FCC, FG
Sigma-Aldrich
Rhodium(III) chloride, 98%