3-Bromopyruvic acid

Names

[ Name ]:
3-Bromopyruvic acid

[Synonym ]:
Propanoic acid, 3-bromo-2-oxo-
3-Bromo-2-oxopropanoic acid
3-BROMOPYRUVIC ACID HYDRATE
EINECS 214-206-5
3-Bromo-2-oxopropionic Acid
3-BROMOPYRUVICACID(3-BROMOPYRUVATE)
3-BROMO-2-OXOPROPANOICACID
3-BromopYHuvic acid
3-Bromopyruvicacid
BROMOPYRUVIC ACID/3-BROMO-2-OXOPROPIONIC ACID
BROMOPYRUVICACID
MFCD00002587
PROPANOIC ACID,3-BROMO-2-OXO-
3-Bromopyruvic acid
3-BROMO-2-OXO-PROPIONIC ACID

Biological Activity

[Description]:

3-Bromopyruvic acid is a hexokinase II inhibitor, is an effective antitumor agent on the hepatoma cells.Target: hexokinase II in vitro: 3-BrPA dissociates HK II from this complex, causing cell death, and thus, having an anti-tumor effect. 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). [1] 3-Bromopyruvic acid (3-BP) is a glycolytic inhibitor and a promising anticancer compound, induces oxidative stress and depletes cells of glutathione (GSH). [2]in vivo: 3-BrPA treatment (50 mg/kg ip. daily, 6 days/week for three weeks) is effective in the animal model by attenuating tumor growth and causing tumor necrosis. Toxic signs were not observed. The acute toxicity study provided an LD50 of 191.7 mg/kg for 3-BrPA. [1]

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Hexokinase

Research Areas >> Cancer

[References]

[1]. Gong L, 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. 2014 Jun;14(5):771-6.

[2]. Sadowska-Bartosz I, et al. Anticancer agent 3-bromopyruvic acid forms a conjugate with glutathione. Pharmacol Rep. 2016 Apr;68(2):502-5.

[Related Small Molecules]

2-Deoxy-D-glucose | Lonidamine

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
223.4±23.0 °C at 760 mmHg

[ Melting Point ]:
77-82 °C

[ Molecular Formula ]:
C₃H₃BrO₃

[ Molecular Weight ]:
166.958

[ Flash Point ]:
88.9±22.6 °C

[ Exact Mass ]:
165.926544

[ PSA ]:
54.37000

[ LogP ]:
-0.54

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.521

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UZ0840000

CHEMICAL NAME :: Pyruvic acid, bromo-

CAS REGISTRY NUMBER :: 1113-59-3

BEILSTEIN REFERENCE NO. :: 1746786

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C3-H3-Br-O3

MOLECULAR WEIGHT :: 166.97

WISWESSER LINE NOTATION :: QVV1E

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 72 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 123,48,1958

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H314

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
C:Corrosive;

[ Risk Phrases ]:
R20/21/22;R34

[ Safety Phrases ]:
S26-S36/37/39-S45-S27

[ RIDADR ]:
UN 3261 8/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
UZ0840000

[ Packaging Group ]:
II

[ Hazard Class ]:
8

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

3-Bromopyruvate: A novel antifungal agent against the human pathogen Cryptococcus neoformans

Biochem. Biophys. Res. Commun. 434(2) , 322-7, (2013)

Highlights • We examined the antifungal activity of 3-bromopyruvic acid (3-BP). • 3-BP could be a novel antifungal agent against Cryptococcus neoformans. • 3-BP acts on C. neoformans through fast depl...

Inhibition of glucose turnover by 3-bromopyruvate counteracts pancreatic cancer stem cell features and sensitizes cells to gemcitabine.

Oncotarget 5(13) , 5177-89, (2014)

According to the cancer stem cell (CSC) hypothesis, the aggressive growth and early metastasis of pancreatic ductal adenocarcinoma (PDA) is due to the activity of CSCs, which are not targeted by curre...

Insights into the carboxyltransferase reaction of pyruvate carboxylase from the structures of bound product and intermediate analogs.

Biochem. Biophys. Res. Commun. 441(2) , 377-82, (2013)

Pyruvate carboxylase (PC) is a biotin-dependent enzyme that catalyzes the MgATP- and bicarbonate-dependent carboxylation of pyruvate to oxaloacetate, an important anaplerotic reaction in central metab...