3-Bromopyruvic acid
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MedKoo CAT#: 407106

CAS#: 113-59-3

Description: Bromopyruvic acid is a hexokinase II inhibitor and an effective antitumor agent. The characteristics of 3-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 at Johns Hopkins has suggested that 3-bromopyruvate could be used to selectively kill cancer cells, while leaving normal cells intact. Recently, the FDA accepted an IND application for the use of 3-bromopyruvate for a Phase I clinical trial in liver cancer. IMPORTANT NOTE: this product we are offering is a pure chemical solid powder, which is for research use only, not for human or therapeutic use. Buyer must be a professional and understands how to use and handle the chemical properly.

Chemical Structure

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3-Bromopyruvic acid
CAS# 113-59-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407106
Name: 3-Bromopyruvic acid
CAS#: 113-59-3
Chemical Formula: C3H3BrO3
Exact Mass: 165.93
Molecular Weight: 166.960
Elemental Analysis: C, 21.58; H, 1.81; Br, 47.86; O, 28.75

Price and Availability

Size Price Availability Quantity
5g USD 150 Ready to ship
10g USD 250 Ready to ship
25g USD 450 Ready to ship
50g USD 750 Ready to ship
100g USD 1250 Ready to ship
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Synonym: 3-BrPA; 3-BP; BPV; NSC 11731; NSC-11731; NSC11731; NSC 62343; NSC62343; NSC-62343; SBB053571; BRN 1746786; Bromopyruvic acid; 3-Bromopyruvic acid, bromopyruvic acid; 3-bromo-2-oxopropanoic acid; bromopyruvate; 3-bromopyruvate; beta.-Bromopyruvic acid; bromo-2-oxopropanoic acid; 3-bromo-2-oxo-propanoic acid; c-bromoacetylformate

IUPAC/Chemical Name: 3-bromo-2-oxopropanoic acid

InChi Key: PRRZDZJYSJLDBS-UHFFFAOYSA-N

InChi Code: InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)

SMILES Code: O=C(CBr)C(O)=O

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >10 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: N/A
In vitro activity: At higher concentrations > 60 μM 3-BrPA (3-Bromopyruvic acid), a reduction of ROS was seen in B8у fibroblasts (Fig. 3a). B8vc fibroblasts which should have a controlled rate of ROS production displayed a much higher reduction of ROS levels at increasing 3-BrPA concentrations compared to PA28у overexpressing cells (Fig. 3a). The p values were ≤ 0.036 in the concentration range of 80 to 120 μM. The decrease of ∆FUnorm under 3-BrPA therapy indicates a decrease of ROS production presumably due to mitochondrial complex I and III dysfunctions, and PA28у overexpression seems to temper the effect of 3-BrPA while normal fibroblasts seem to be more sensitive. Reference: BMC Cancer. 2020; 20: 896. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7501688/
In vivo activity: The effects of 3-BrPA (3-Bromopyruvic acid) on apoptosis in MCT rats were further examined by measuring the changes in the expression of apoptosis-associated proteins. The amount of cleaved Casp 3 protein expression was increased in the 3-BrPA treatment MCT rats [Figure 7A]. Furthermore, this study observed decreased Cyto C in mitochondria [Figure 7B] and increased the release of Cyto C into the cytoplasm in the 3-BrPA-treated MCT rats compared to those of PBS-treated MCT rats [Figure 7C]. These results show that 3-BrPA leads to the activation of the mitochondrial apoptotic signaling pathway. Reference: Chin Med J (Engl). 2020 Jan 5; 133(1): 49–60. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7028200/

Preparing Stock Solutions

The following data is based on the product molecular weight 166.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Linke C, Wösle M, Harder A. Anti-cancer agent 3-bromopyruvate reduces growth of MPNST and inhibits metabolic pathways in a representative in-vitro model. BMC Cancer. 2020 Sep 18;20(1):896. doi: 10.1186/s12885-020-07397-w. PMID: 32948135; PMCID: PMC7501688. 2. Szczuka I, Wiśniewski J, Kustrzeba-Wójcicka I, Terlecki G. The effect of 3-bromopyruvate on the properties of cathepsin B in the aspect of metastatic potential of colon cancer cells. Adv Clin Exp Med. 2020 Aug;29(8):949-957. doi: 10.17219/acem/123622. PMID: 32820873. 3. Liu J, Wang W, Wang L, Qi XM, Sha YH, Yang T. 3-Bromopyruvate alleviates the development of monocrotaline-induced rat pulmonary arterial hypertension by decreasing aerobic glycolysis, inducing apoptosis, and suppressing inflammation. Chin Med J (Engl). 2020 Jan 5;133(1):49-60. doi: 10.1097/CM9.0000000000000577. PMID: 31923104; PMCID: PMC7028200. 4. Xin Q, Yuan M, Li H, Song X, Lu J, Jing T. In vitro and in vivo effects of 3-bromopyruvate against Echinococcus metacestodes. Vet Res. 2019 Nov 19;50(1):96. doi: 10.1186/s13567-019-0710-7. PMID: 31744550; PMCID: PMC6862786.
In vitro protocol: 1. Linke C, Wösle M, Harder A. Anti-cancer agent 3-bromopyruvate reduces growth of MPNST and inhibits metabolic pathways in a representative in-vitro model. BMC Cancer. 2020 Sep 18;20(1):896. doi: 10.1186/s12885-020-07397-w. PMID: 32948135; PMCID: PMC7501688. 2. Szczuka I, Wiśniewski J, Kustrzeba-Wójcicka I, Terlecki G. The effect of 3-bromopyruvate on the properties of cathepsin B in the aspect of metastatic potential of colon cancer cells. Adv Clin Exp Med. 2020 Aug;29(8):949-957. doi: 10.17219/acem/123622. PMID: 32820873.
In vivo protocol: 1. Liu J, Wang W, Wang L, Qi XM, Sha YH, Yang T. 3-Bromopyruvate alleviates the development of monocrotaline-induced rat pulmonary arterial hypertension by decreasing aerobic glycolysis, inducing apoptosis, and suppressing inflammation. Chin Med J (Engl). 2020 Jan 5;133(1):49-60. doi: 10.1097/CM9.0000000000000577. PMID: 31923104; PMCID: PMC7028200. 2. Xin Q, Yuan M, Li H, Song X, Lu J, Jing T. In vitro and in vivo effects of 3-bromopyruvate against Echinococcus metacestodes. Vet Res. 2019 Nov 19;50(1):96. doi: 10.1186/s13567-019-0710-7. PMID: 31744550; PMCID: PMC6862786.

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1: Gong L, Wei Y, Yu X, Peng J, Leng X. 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. 2014 Jun;14(5):771-6. PubMed PMID: 24738957.

2: Sadowska-Bartosz I, Soszyński M, Ułaszewski S, Ko Y, Bartosz G. Transport of 3-bromopyruvate across the human erythrocyte membrane. Cell Mol Biol Lett. 2014 Jun;19(2):201-14. doi: 10.2478/s11658-014-0189-1. Epub 2014 Apr 9. PubMed PMID: 24715475.

3: Sadowska-Bartosz I, Bartosz G. Effect of 3-bromopyruvic acid on human erythrocyte antioxidant defense system. Cell Biol Int. 2013 Dec;37(12):1285-90. doi: 10.1002/cbin.10160. Epub 2013 Aug 19. PubMed PMID: 23881849.

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6: Macchioni L, Davidescu M, Sciaccaluga M, Marchetti C, Migliorati G, Coaccioli S, Roberti R, Corazzi L, Castigli E. Mitochondrial dysfunction and effect of antiglycolytic bromopyruvic acid in GL15 glioblastoma cells. J Bioenerg Biomembr. 2011 Oct;43(5):507-18. doi: 10.1007/s10863-011-9375-2. Epub 2011 Jul 21. PubMed PMID: 21833601.

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8: Liu XH, Zheng XF, Wang YL. Inhibitive effect of 3-bromopyruvic acid on human breast cancer MCF-7 cells involves cell cycle arrest and apoptotic induction. Chin Med J (Engl). 2009 Jul 20;122(14):1681-5. PubMed PMID: 19719971.

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11: Wang MH, Wang ZX, Zhao KY. Kinetics of inactivation of bovine pancreatic ribonuclease A by bromopyruvic acid. Biochem J. 1996 Nov 15;320 ( Pt 1):187-92. PubMed PMID: 8947485; PubMed Central PMCID: PMC1217915.

12: Ouchi Y, Fukuyama H, Ogawa M, Yamauchi H, Kimura J, Magata Y, Yonekura Y, Konishi J. Cholinergic projection from the basal forebrain and cerebral glucose metabolism in rats: a dynamic PET study. J Cereb Blood Flow Metab. 1996 Jan;16(1):34-41. PubMed PMID: 8530553.

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20: Johne H, Seifert K, Johne S, Bulka E. [The reaction of bromopyruvic acid ethyl ester with thiosemicarbazides and the synthesis of derivatives of 4-carbethoxy- and 4-carboxythiazolyl-(2)-hydrazines]. Pharmazie. 1978 May;33(5):259-63. German. PubMed PMID: 27825.