3-Bromopyruvic acid
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    WARNING: This product is for research use only, not for human or veterinary use.

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.


Price and Availability

Size
Price

5g
USD 150
500g
USD 2950
Size
Price

20g
USD 450
1kg
USD 4250
Size
Price

100g
USD 1250

Bromopyruvic acid, purity > 98%, is in stock. Order of less than 1kg can be shipped in the same day after PO is received. Lead time for order > 1kg is about 1 month.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407106
Name: 3-Bromopyruvic acid
CAS#: 113-59-3
Chemical Formula: C3H3BrO3
Exact Mass: 165.92656
Molecular Weight: 166.96
Elemental Analysis: C, 21.58; H, 1.81; Br, 47.86; O, 28.75


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


Technical Data

Appearance:
Solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


References

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.

4: Schaefer NG, Geschwind JF, Engles J, Buchanan JW, Wahl RL. Systemic administration of 3-bromopyruvate in treating disseminated aggressive lymphoma. Transl Res. 2012 Jan;159(1):51-7. doi: 10.1016/j.trsl.2011.08.008. Epub 2011 Sep 22. PubMed PMID: 22153810.

5: Saigusa S, Toiyama Y, Tanaka K, Okugawa Y, Fujikawa H, Matsushita K, Uchida K, Inoue Y, Kusunoki M. Prognostic significance of glucose transporter-1 (GLUT1) gene expression in rectal cancer after preoperative chemoradiotherapy. Surg Today. 2012 May;42(5):460-9. doi: 10.1007/s00595-011-0027-2. Epub 2011 Nov 11. PubMed PMID: 22072148.

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.

7: Herath A, Dahl R, Cosford ND. Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles. Org Lett. 2010 Feb 5;12(3):412-5. doi: 10.1021/ol902433a. PubMed PMID: 20038130; PubMed Central PMCID: PMC2814065.

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.

9: Wong DJ, Nuyten DS, Regev A, Lin M, Adler AS, Segal E, van de Vijver MJ, Chang HY. Revealing targeted therapy for human cancer by gene module maps. Cancer Res. 2008 Jan 15;68(2):369-78. doi: 10.1158/0008-5472.CAN-07-0382. PubMed PMID: 18199530.

10: Peng QP, Liang HJ, Zhou Q, Zhou JM, Fu XL, Zhong DP. [Expression of hexokinase-II gene in human colon cancer cells and the therapeutic significance of inhibition thereof]. Zhonghua Yi Xue Za Zhi. 2007 Apr 17;87(15):1058-62. Chinese. PubMed PMID: 17672972.

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.

13: Conroy CW, Buck RH, Maren TH. The microchemical detection of carbonic anhydrase in corneal epithelia. Exp Eye Res. 1992 Oct;55(4):637-40. PubMed PMID: 1483509.

14: Phillips RS, Gollnick PD. Evidence that cysteine 298 is in the active site of tryptophan indole-lyase. J Biol Chem. 1989 Jun 25;264(18):10627-32. PubMed PMID: 2659590.

15: Murakami H, Sly WS. Purification and characterization of human salivary carbonic anhydrase. J Biol Chem. 1987 Jan 25;262(3):1382-8. PubMed PMID: 2433278.

16: Weinstein CL, Griffith OW. beta-Sulfopyruvate: chemical and enzymatic syntheses and enzymatic assay. Anal Biochem. 1986 Jul;156(1):154-60. PubMed PMID: 3740406.

17: Sundaram V, Rumbolo P, Grubb J, Strisciuglio P, Sly WS. Carbonic anhydrase II deficiency: diagnosis and carrier detection using differential enzyme inhibition and inactivation. Am J Hum Genet. 1986 Feb;38(2):125-36. PubMed PMID: 3080873; PubMed Central PMCID: PMC1684750.

18: Conroy CW, Maren TH. The determination of osteopetrotic phenotypes by selective inactivation of red cell carbonic anhydrase isoenzymes. Clin Chim Acta. 1985 Nov 15;152(3):347-54. PubMed PMID: 3933860.

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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.