Bromopyruvic Acid - CAS 1113-59-3
Catalog number:
1113-59-3
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C₃H₃BrO₃
Molecular Weight:
166.96
COA:
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Targets:
Hexokinase
Description:
This active molecular is a synthetic brominated derivative of pyruvic acid which is a hexokinase II inhibitor and an effective antitumor agent because it is a highly reactive alkylating agent. The acute toxicity study provided an LD50 of 191.7 mg/kg for 3-BrPA in vivo. In 2010, Preclinical trials in Cancer in USA (Intra-arterial) for bromopyruvate was approved. In 2013, US FDA approved IND application for bromopyruvate in Liver cancer .
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Purity:
98%
Appearance:
Orange Low Melting Solid
Synonyms:
3-Bromo-2-oxopropanoic Acid; 3-Bromopyruvate; 3-Bromopyruvic Acid; NSC 11731; NSC 62343; β-Bromopyruvic Acid;
Solubility:
DMSO, Ethyl Acetate, H2O: ≥ 32 mg/mL
Storage:
Hygroscopic, -20°C Freezer, Under inert atmosphere
MSDS:
Inquire
Application:
eliminating aggressive liver tumors
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
InChIKey:
PRRZDZJYSJLDBS-UHFFFAOYSA-N
InChI:
InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
Canonical SMILES:
C(C(=O)C(=O)O)Br
Current Developer:
PreScience Labs
1.Mitochondrial dysfunction and effect of antiglycolytic bromopyruvic acid in GL15 glioblastoma cells.
Macchioni L1, Davidescu M, Sciaccaluga M, Marchetti C, Migliorati G, Coaccioli S, Roberti R, Corazzi L, Castigli E. J Bioenerg Biomembr. 2011 Oct;43(5):507-18. doi: 10.1007/s10863-011-9375-2. Epub 2011 Jul 21.
Most cancer cells, including GL15 glioblastoma cells, rely on glycolysis for energy supply. The effect of antiglycolytic bromopyruvate on respiratory parameters and viability of GL15 cells was investigated. Bromopyruvate caused Δψ(m) and MTT collapse, ATP decrease, and cell viability loss without involving apoptotic or necrotic pathways. The autophagy marker LC3-II was increased. Δψ(m) decrease was accompanied by reactive oxygen species (ROS) increase and cytochrome c (cyt c) disappearance, suggesting a link between free radical generation and intramitochondrial cyt c degradation. Indeed, the free radical inducer menadione caused a decrease in cyt c that was reversed by N-acetylcysteine. Cyt c is tightly bound to the inner mitochondrial membrane in GL15 cells, which may confer protein peroxidase activity, resulting in auto-oxidation and protein targeting to degradation in the presence of ROS. This process is directed towards impairment of the apoptotic cyt c cascade, although cells are committed to die.
2.2-(3'-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities.
Tantak MP1, Wang J2, Singh RP3, Kumar A1, Shah K4, Kumar D5. Bioorg Med Chem Lett. 2015 Oct 1;25(19):4225-31. doi: 10.1016/j.bmcl.2015.07.105. Epub 2015 Aug 6.
A new series of 2-(3'-indolyl)-N-arylthiazole-4-carboxamides 17a-p has been designed and synthesized. Initial reaction of readily available thioamides 15 with bromopyruvic acid under refluxing conditions produced different thiazole carboxylic acids 16 which upon coupling with arylamines by using EDCI·HCl and HOBt afforded diverse arylthiazole-4-carboxamides 17a-p in 78-87% yields. Antibacterial activity evaluation against Gram-positive and Gram-negative bacterial strains led to compounds 17i-k and 17o as potent and selectively (Gram-negative) antibacterial agents. The cytotoxicity of thiazole carboxamides 17a-p was also evaluated on a panel of human cancer cell lines. Among the tested derivatives, compounds 17i (IC50=8.64μM; HEK293T) and 17l (IC50=3.41μM; HeLa) were identified as the most potent analogues of the series. Preliminary mechanism of action studies of thiazole carboxamide 17i suggested that its cytotoxicity against HeLa cells involves the induction of cell death by apoptosis.
3.Effect of 3-bromopyruvic acid on human erythrocyte antioxidant defense system.
Sadowska-Bartosz I1, Bartosz G. Cell Biol Int. 2013 Dec;37(12):1285-90. doi: 10.1002/cbin.10160. Epub 2013 Aug 19.
3-Bromopyruvate (3-BP) is a promising compound for anticancer therapy, its main mode of action being the inhibition of glycolytic enzymes, but this compound also induces oxidative stress. This study aimed at characterisation of the effect of 3-BP on the antioxidant defense system of erythrocytes. Suspensions of erythrocytes in PBS containing 5 mM glucose were treated with different concentration of 3-BP at 37°C for 1 h. Activities of antioxidant enzymes were estimated by standard colorimetric methods. The antioxidant capacity of erythrocytes was estimated using the 2,2'-azinobis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS(•+)) decolorisation assay and ferricyanide reduction. The content of reduced and oxidized glutathione was estimated fluorimetrically with o-phtalaldehyde. 3-BP did not affect the integrity of the erythrocyte membrane (lack of changes in the osmotic fragility). However, it induced oxidative stress in erythrocytes, as evidenced by the decrease in the content of acid-soluble thiols and reduced glutathione (GSH).
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, Wei Y, Yu X, Peng J, Leng X1. Anticancer Agents Med Chem. 2014 Jun;14(5):771-6.
Over-expressed in cancer cells, hexokinase II (HK II) forms a mitochondrial complex, which promotes cancer survival. 3- Bromopyruvic acid (3-BrPA) dissociates HK II from this complex, causing cell death, and thus, having an anti-tumor effect. The design of this study was to first analyze the expression of HK II in the hepatoma cell line, BEL-7402, then investigate the effects of 3-Br-PA on these cells, and finally, discuss its potential for clinical usage. HK II expression was detected in BEL-7402 cells by immunocytochemistry and reverse transcriptase polymerase chain reaction (RT-PCR). In vitro treatment of cells with 3-BrPA significantly inhibited their growth, as evaluated by MTT assay and adenosine triphosphate-tumor chemosensitivity assay (ATP-TCA). To analyze the in vivo function and safety of this drug, a tumor model was established by subcutaneously implanting hepatic cancer cells into nude mice. 3-BrPA treatment (50 mg/kg ip. daily, 6 days/week for three weeks) was effective in the animal model by attenuating tumor growth and causing tumor necrosis.
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CAS 1113-59-3 Bromopyruvic Acid

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