Bromopyruvic acid is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula BrCH₂COCO₂H. This colorless solid is the

brominated Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...

derivative of

pyruvic acid Pyruvic acid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the cell. Pyruvic aci ...

. It bears

structural similarity The structural similarity index measure (SSIM) is a method for predicting the perceived quality of digital television and cinematic pictures, as well as other kinds of digital images and videos. SSIM is used for measuring the similarity between tw ...

lactic acid Lactic acid is an organic acid. It has a molecular formula . It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natu ...

and

. It has been investigated as a metabolic poison and an anticancer agent. Like other α-bromoketones, it is a strong

alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

Research

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 Glyceraldehyde 3-phosphate dehydrogenase (abbreviated GAPDH) () is an enzyme of about 37kDa that catalyzes the sixth step of glycolysis and thus serves to break down glucose for energy and carbon molecules. In addition to this long establishe ...

, which is highly sensitive to

inhibition Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...

by bromopyruvate. The pyruvate transporter system, which is known to be overexpressed in cancer cells, was later identified to be a

monocarboxylate transporter The monocarboxylate transporters, or MCTs, are a family of proton-linked plasma membrane transporters that carry molecules having one carboxylate group (monocarboxylates), such as lactate, pyruvate, and ketones across biological membranes. MCTs ...

called

monocarboxylate transporter 1 Monocarboxylate transporter 1 is a ubiquitous protein that in humans is encoded by the ''SLC16A1'' gene (also known as MCT1). It is a proton coupled monocarboxylate transporter. Biochemistry Detailed kinetic analysis of monocarboxylate transport i ...

References

External links

* * * * {{cite journal, doi=10.1038/sj.onc.1209603, title=Hexokinase II: Cancer's double-edged sword acting as both facilitator and gatekeeper of malignancy when bound to mitochondria, year=2006, last1=Mathupala, first1=S P, last2=Ko, first2=Y H, last3=Pedersen, first3=P L, journal=Oncogene, volume=25, issue=34, pages=4777–86, pmid=16892090, pmc=3385868
The cancer cell's "power plants" as promising therapeutic targets: An overview
by Peter Pederson Alkylating agents Propionic acids Organobromides Alpha-keto acids