Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione

Izabela Sadowska-Bartosz*, Rafal Szewczyk, Lukasz Jaremko, Mariusz Jaremko, Grzegorz Bartosz

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Background 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. Methods GSH was incubated with various amounts of 3-BP and the extent of reaction was titrated with 1H NMR and 1H-1H 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(13C) and analyzed using the targeted LC-MS/MS method in negative ionization MRM mode. Results 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. Conclusions 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.

Original languageEnglish (US)
Pages (from-to)502-505
Number of pages4
JournalPharmacological Reports
Volume68
Issue number2
DOIs
StatePublished - Apr 1 2016
Externally publishedYes

Keywords

  • 3-Bromopyruvate
  • Erythrocyte
  • Glutathione
  • Mass spectrometry

ASJC Scopus subject areas

  • Pharmacology

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