Journal Article

DZNE-2020-04753

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione.

Sadowska-Bartosz, I. (Corresponding author) ; Szewczyk, R. ; Jaremko, L.DZNE* ; Jaremko, M. ; Bartosz, G.

2016
Elsevier Amsterdam [u.a.]

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Please use a persistent id in citations: doi:10.1016/j.pharep.2015.11.007

Abstract: 3-Bromopyruvic acid (3-BP), a glycolytic inhibitor and a promising anticancer compound, induces oxidative stress and depletes cells of glutathione (GSH). The causes of GSH loss remain unclear. The aim of this study was to ascertain whether 3-BP forms a conjugate with glutathione.GSH was incubated with various amounts of 3-BP and the extent of reaction was titrated with (1)H NMR and (1)H-(1)H NMR. The reaction outcome was identified by MS/MS. Intracellular formation of the conjugate was assessed in cells treated with 3-BP and 3-BP((13)C) and analyzed using the targeted LC-MS/MS method in negative ionization MRM mode.3-BP was found to react with GSH in a 1:1 ratio forming an S-conjugate. The same conjugate was formed intracellularly in erythrocytes and MCF-7 cells.3-BP reacts with GSH in the absence of cells and intracellularly. This reaction appears to be the main cause of GSH loss in 3-BP treated cells.

Keyword(s): Antineoplastic Agents: pharmacology (MeSH) ; Cell Line, Tumor (MeSH) ; Chromatography, Liquid: methods (MeSH) ; Erythrocytes: drug effects (MeSH) ; Erythrocytes: metabolism (MeSH) ; Glutathione: metabolism (MeSH) ; Humans (MeSH) ; MCF-7 Cells (MeSH) ; Magnetic Resonance Spectroscopy: methods (MeSH) ; Oxidative Stress: drug effects (MeSH) ; Pyruvates: pharmacology (MeSH) ; Tandem Mass Spectrometry: methods (MeSH) ; Antineoplastic Agents ; Pyruvates ; bromopyruvate ; Glutathione

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Contributing Institute(s):

1. Translational Structural Biology (AG Zweckstetter)

Research Program(s):

1. 342 - Disease Mechanisms and Model Systems (POF3-342) (POF3-342)

Appears in the scientific report 2016

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Database coverage:
; BIOSIS Previews ; Clarivate Analytics Master Journal List ; IF < 5 ; JCR ; NCBI Molecular Biology Database ; SCOPUS ; Science Citation Index Expanded ; Web of Science Core Collection

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