Bromopyruvic acid

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Bromopyruvic acid
Skeletal formula of bromopyruvic acid
Ball-and-stick model of the bromopyruvic acid molecule
Names
Preferred IUPAC name
3-Bromo-2-oxopropanoic acid
Other names
Bromopyruvate
3-Bromopyruvic acid
3-Bromopyruvate
3-BrPA
3BP
3-Br-Pyr
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.915
Properties
C3H3BrO3
Molar mass 166.96 g·mol−1
Appearance white solid
Melting point 79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate)
Hazards
R-phrases (outdated) R34
S-phrases (outdated) S25 S36/37/39 S45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 is the organic compound with the formula BrCH2COCO2H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural similarity to lactic acid and pyruvic acid. It has been investigated as a metabolic poison and an anticancer agent.[1] Like other α-bromoketones, it is a strong alkylating agent.

Research[edit]

The pyruvate transporter system can be used to deliver bromopyruvate inside trypanosomal cells. Once intracellular, the primary target of 3BP is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by bromopyruvate.[2] 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.[3]

References[edit]

  1. ^ Peter L. Pedersen (2012). "3-Bromopyruvate (3BP) A Fast Acting, Promising, Powerful, Specific, and Effective "Small Molecule" Anti-Cancer Agent Taken from Labside to Bedside: Introduction to a Special Issue". J. Bioenerg. Biomembr. 44: 1–6. doi:10.1007/s10863-012-9425-4.
  2. ^ 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.
  3. ^ 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 4633897. PMID 26609475.

External links[edit]