Synthesis and Biological Evaluation of Zeise's Salt Derivatives with Acetylsalicylic Acid Substructure

International Journal of Molecular Sciences
Alexander WeningerRonald Gust

Abstract

The development of novel biologically active organometallic compounds bearing an acetylsalicylic acid (ASA) substructure led to the synthesis of analogical Zeise-type salts that accordingly inhibit cyclooxygenase (COX) enzymes. In order to determine the influence of the length of the alkyl chain between the platinum(II) center and the ASA moiety, compounds with varying methylene groups (n = 1⁻4) were synthesized and characterized. For the propene derivative structural elucidation by X-ray crystallography was possible. Prior to evaluation of biological activity, the complexes were investigated regarding their stability in different media, such as water, physiological sodium chloride, and phosphate buffered saline. Therefore, an analytical method based on capillary electrophoresis was established. All of the compounds were tested for their COX inhibitory potential. In general, complexes with longer alkyl chains caused higher inhibition of COX enzymes and the inhibitory potential towards COX enzymes was enhanced when compared to Zeise's salt. The growth inhibitory effects of the synthesized substances were investigated in vitro against colon carcinoma (HT-29) and breast cancer (MCF-7) cells. The IC50 values of the new derivatives ...Continue Reading

References

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Oct 9, 2002·The American Journal of Pathology·Glen KristiansenSteffen Hauptmann
Feb 23, 2007·Archiv der Pharmazie·Ingo Ott, Ronald Gust
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Sep 11, 2010·European Journal of Medicinal Chemistry·Gerhard RubnerRonald Gust
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Jan 22, 2015·Angewandte Chemie·Sandra MeieranzRonald Gust
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Nov 25, 2017·Chemical Society Reviews·Samuel M Meier-MenchesBernhard K Keppler

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Citations

Jul 1, 2020·Chemistry : a European Journal·Gilian T ThomasJason Scott McIndoe
Feb 16, 2020·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Monika Cziferszky, Ronald Gust

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Methods Mentioned

BETA
NMR
X-ray
electrophoresis
column chromatography

Software Mentioned

Prism
SADABS
SHELXS
GraphPad

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