Bromopyruvic acid

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Bromopyruvic acid
Skeletal formula of bromopyruvic acid
Ball-and-stick model of the bromopyruvic acid molecule
Names
IUPAC name
3-Bromo-2-oxopropanoic acid
Other names
Bromopyruvate
3-Bromopyruvic acid
3-Bromopyruvate
3-BrPA
3BP
3-Br-Pyr
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.915
Properties
C3H3BrO3
Molar mass 166.96 g·mol−1
Melting point 79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate)
Hazards
R-phrases R34
S-phrases S25 S36/37/39 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bromopyruvic acid and its alkaline form, bromopyruvate, are synthetic brominated derivatives of pyruvic acid. They are lactic acid and pyruvate analogs.

The characteristics of bromopyruvate in vitro and in vivo have been reported in the scientific literature since the 1940s. Because it is a highly reactive alkylating agent and it is inherently unstable, it had been described as a metabolic poison.

Research activity[edit]

In 1993, researchers at the Johns Hopkins School of Medicine reported that a pyruvate transporter system could be used to deliver bromopyruvate inside trypanosomal cells where its primary target is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by bromopyruvate.[1] The pyruvate transporter system, which is known to be overexpressed in cancer cells, was later identified to be a monocarboxylate transporter called monocarboxylate transporter 1.[2]

References[edit]

  1. ^ Barnard, JP; Reynafarje, B; Pedersen, PL (1993). "Glucose catabolism in African trypanosomes. Evidence that the terminal step is catalyzed by a pyruvate transporter capable of facilitating uptake of toxic analogs". The Journal of Biological Chemistry. 268 (5): 3654–3661. PMID 8429041. 
  2. ^ Liu, Zhe; Sun, Yiming; Hong, Haiyu; Zhao, Surong; Zou, Xue; Ma, Renqiang; Jiang, Chenchen; Wang, Zhiwei; Li, Huabin (2015-08-15). "3-bromopyruvate enhanced daunorubicin-induced cytotoxicity involved in monocarboxylate transporter 1 in breast cancer cells". American Journal of Cancer Research. 5 (9): 2673–2685. ISSN 2156-6976. PMC 4633897Freely accessible. PMID 26609475. 

External links[edit]