An alkylating agent and antimetabolite of pyruvate
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3-Bromopyruvic Acid

Item No. 19068

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-bromo-2-oxo-propanoic acid
CAS Number
1113-59-3
Synonyms
  • 3-BP
  • β-Bromopyruvic acid
  • NSC 11731
  • NSC 62343
Molecular Formula
C3H3BrO3
Formula Weight
167.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 16 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
OC(C(CBr)=O)=O
InChi Code
InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
InChi Key
PRRZDZJYSJLDBS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $49

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    5 g

    $96

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    Cayman Chemical
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    Product Description

    3-Bromopyruvic Acid (3-BP) is an alkylating agent and an antimetabolite of pyruvate that is metabolized through glutathione conjugation.1,2 It decreases proliferation of hepatocellular carcinoma BEL-7402 cells that express hexokinase II, an isoform of hexokinase overexpressed in many cancers.3,4 3-BP reduces tumor growth and induces tumor necrosis in a hepatocellular carcinoma mouse xenograft model when administered at a dose of 50 mg/kg per day, six days per week, for three weeks.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sadowska-Bartosz, I., Szewczyk, R., Jaremko, L., et al. Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione. Pharmacol. Rep. 68(2), 502-505 (2016).

    2. El Sayed, S.M., Baghdadi, H., Zolaly, M., et al. The promising anticancer drug 3-bromopyruvate is metabolized through glutathione conjugation which affects chemoresistance and clinical practice: An evidence-based view. Med. Hypotheses 100, 67-77 (2017).

    3. Gong, L., Wei, Y., Yu, X., et al. 3-Bromopyruvic acid, a hexokinase II inhibitor, is an effective antitumor agent on the hepatoma cells: In vitro and in vivo findings. Anticancer Agents Med. Chem. 14(5), 771-776 (2014).

    4. Lis, P., Dylag, M., Niedźwiecka, K., et al. The HK2 dependent "Warburg Effect" and mitochondrial oxidative phosphorylation in cancer: Targets for effective therapy with 3-bromopyruvate. Molecules 21(12), E1730 (2016).