Names | |
---|---|
Preferred IUPAC name
3-Bromo-2-oxopropanoic acid | |
Other names
Bromopyruvate
3-Bromopyruvic acid 3-Bromopyruvate 3-BrPA 3BP 3-Br-Pyr | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.012.915 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C3H3BrO3 | |
Molar mass | 166.958 g·mol−1 |
Appearance | white solid |
Melting point | 79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate) |
Hazards | |
GHS labelling: | |
Danger | |
H290, H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Bromopyruvic acid is the organic compound with the formula BrCH2COCO2H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural similarity to lactic acid and pyruvic acid. It has been investigated as a metabolic poison and an anticancer agent. [1] Like other α-bromoketones, it is a strong alkylating agent.
The pyruvate transporter system can be used to deliver bromopyruvate inside trypanosomal cells. Once intracellular, the primary target of 3BP is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by bromopyruvate. [2] The pyruvate transporter system, which is known to be overexpressed in cancer cells, was later identified to be a monocarboxylate transporter called monocarboxylate transporter 1. [3]
Names | |
---|---|
Preferred IUPAC name
3-Bromo-2-oxopropanoic acid | |
Other names
Bromopyruvate
3-Bromopyruvic acid 3-Bromopyruvate 3-BrPA 3BP 3-Br-Pyr | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.012.915 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C3H3BrO3 | |
Molar mass | 166.958 g·mol−1 |
Appearance | white solid |
Melting point | 79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate) |
Hazards | |
GHS labelling: | |
Danger | |
H290, H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Bromopyruvic acid is the organic compound with the formula BrCH2COCO2H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural similarity to lactic acid and pyruvic acid. It has been investigated as a metabolic poison and an anticancer agent. [1] Like other α-bromoketones, it is a strong alkylating agent.
The pyruvate transporter system can be used to deliver bromopyruvate inside trypanosomal cells. Once intracellular, the primary target of 3BP is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by bromopyruvate. [2] The pyruvate transporter system, which is known to be overexpressed in cancer cells, was later identified to be a monocarboxylate transporter called monocarboxylate transporter 1. [3]