Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione.

Sadowska-Bartosz, I.; Szewczyk, R.; Jaremko, L.; Jaremko, M.; Bartosz, G.

doi:10.1016/j.pharep.2015.11.007

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione.

MPS-Authors

/persons/resource/persons84653

Jaremko, L.
Research Group of Protein Structure Determination using NMR, MPI for biophysical chemistry, Max Planck Society;

/persons/resource/persons84648

Jaremko, M.
Research Group of Protein Structure Determination using NMR, MPI for biophysical chemistry, Max Planck Society;

External Resource

http://www.sciencedirect.com/science/article/pii/S1734114015003552/pdfft?md5=5984943c72f05c823a0e84a1594a0826&pid=1-s2.0-S1734114015003552-main.pdf
(Publisher version)

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Sadowska-Bartosz, I., Szewczyk, R., Jaremko, L., Jaremko, M., & Bartosz, G. (2016). Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione. Pharmacological Reports, 68(2), 502-505. doi:10.1016/j.pharep.2015.11.007.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002A-1C0D-2

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 H-1 NMR and H-1-H-1 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(C-13) 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.