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3-Bromopyruvic acid (CAS 1113-59-3)

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Alternate Names:
3-Bromopyruvic acid is also known as 3-Bromo-2-oxopropionic acid.
Application:
3-Bromopyruvic acid is a cross-linker between nucleic acids and proteins, and is also an affinity label for cysteine residues.
CAS Number:
1113-59-3
Purity:
≥97%
Molecular Weight:
166.96
Molecular Formula:
C3H3BrO3
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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3-Bromopyruvic acid is a brominated derivative derived from pyruvic acid (sc-208191). This compound presents as a colorless solid with a distinct pungent odor and exhibits solubility in water and alcohol. Widely employed in organic synthesis, medicinal chemistry, and biochemistry, 3-Bromopyruvic acid holds significant versatility. It serves as a catalyst for synthesizing diverse organic compounds and acts as a reagent for producing biologically active substances. Furthermore, the compound finds extensive utilization in scientific research applications. In vitro studies have extensively employed 3-Bromopyruvic acid to explore the effects of various compounds on cells and their ensuing biochemical and physiological impacts. Additionally, it has facilitated investigations into the mechanisms of action of diverse drugs and the identification of potential drug targets. Notably, 3-Bromopyruvic acid has been observed to inhibit HXK II (hexokinase II) in cancer cells, impairing their ability to metabolize glucose into ATP directly. Studies on MCF-7 (sc-2206) breast cancer cells have demonstrated that 3-Bromopyruvic acid reduces the expression of Bcl-2, c-Myc, and mutant p53, which are components of the cell death signal transduction pathway. Furthermore, alternative studies have indicated that 3-Bromopyruvic acid exhibits notable selectivity as an antibiotic, inhibiting the growth of specific yeast strains. While the precise mechanism of action of 3-Bromopyruvic acid remains incompletely understood, it is believed to function as a proton-ionophore. This characteristic allows the compound to transport protons across cell membranes, thereby modulating the activity of enzymes and proteins within cells and inducing a wide array of biochemical and physiological effects.


3-Bromopyruvic acid (CAS 1113-59-3) References

  1. 3-BROMOPYRUVIC ACID, A HIGHLY SELECTIVE ANTIMICROBIAL AGENT AGAINST CERTAIN YEASTS.  |  ZYGMUNT, WA. and MARTIN, TA. 1964. J Pharm Sci. 53: 1420-1. PMID: 14253613
  2. Inhibitive effect of 3-bromopyruvic acid on human breast cancer MCF-7 cells involves cell cycle arrest and apoptotic induction.  |  Liu, XH., et al. 2009. Chin Med J (Engl). 122: 1681-5. PMID: 19719971
  3. Effect of 3-bromopyruvic acid on human erythrocyte antioxidant defense system.  |  Sadowska-Bartosz, I. and Bartosz, G. 2013. Cell Biol Int. 37: 1285-90. PMID: 23881849
  4. 3-Bromopyruvic acid, a hexokinase II inhibitor, is an effective antitumor agent on the hepatoma cells : in vitro and in vivo findings.  |  Gong, L., et al. 2014. Anticancer Agents Med Chem. 14: 771-6. PMID: 24738957
  5. Limitations of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay when compared to three commonly used cell enumeration assays.  |  van Tonder, A., et al. 2015. BMC Res Notes. 8: 47. PMID: 25884200
  6. Critical Role of Glucose Metabolism in Rheumatoid Arthritis Fibroblast-like Synoviocytes.  |  Garcia-Carbonell, R., et al. 2016. Arthritis Rheumatol. 68: 1614-26. PMID: 26815411
  7. Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione.  |  Sadowska-Bartosz, I., et al. 2016. Pharmacol Rep. 68: 502-5. PMID: 26922560
  8. 3-Bromopyruvic Acid Inhibits Tricarboxylic Acid Cycle and Glutaminolysis in HepG2 Cells.  |  Jardim-Messeder, D. and Moreira-Pacheco, F. 2016. Anticancer Res. 36: 2233-41. PMID: 27127128
  9. ABCB1-overexpressing MDCK-II cells are hypersensitive to 3-bromopyruvic acid.  |  Sadowska-Bartosz, I., et al. 2016. Life Sci. 162: 138-44. PMID: 27534909
  10. 3-Bromopyruvate induces expression of antioxidant genes.  |  Pulaski, L., et al. 2019. Free Radic Res. 53: 170-178. PMID: 30362385
  11. Electron-Induced Reactions in 3-Bromopyruvic Acid.  |  Ferreira da Silva, F., et al. 2019. Chemistry. 25: 5498-5506. PMID: 30706547
  12. Upregulated hexokinase 2 expression induces the apoptosis of dopaminergic neurons by promoting lactate production in Parkinson's disease.  |  Li, J., et al. 2022. Neurobiol Dis. 163: 105605. PMID: 34973450
  13. Novel insights into the anti-cancer effects of 3-bromopyruvic acid against castration-resistant prostate cancer.  |  Yeh, HC., et al. 2022. Eur J Pharmacol. 923: 174929. PMID: 35364071
  14. 3-Bromopyruvic acid regulates glucose metabolism by targeting the c-Myc/TXNIP axis and induces mitochondria-mediated apoptosis in TNBC cells.  |  Li, J., et al. 2022. Exp Ther Med. 24: 520. PMID: 35837063
  15. Data on the combined effect of atovaquone, mefloquine, and 3-bromopyruvic acid against Echinococcus multilocularis protoscoleces.  |  Kouguchi, H., et al. 2022. Data Brief. 45: 108707. PMID: 36426011

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

3-Bromopyruvic acid, 1 g

sc-260854
1 g
$46.00

3-Bromopyruvic acid, 5 g

sc-260854A
5 g
$82.00

3-Bromopyruvic acid, 10 g

sc-260854B
10 g
$117.00

3-Bromopyruvic acid, 50 g

sc-260854D
50 g
$378.00

3-Bromopyruvic acid, 100 g

sc-260854C
100 g
$802.00

3-Bromopyruvic acid, 500 g

sc-260854E
500 g
$2404.00