Bromopyruvic acid

Bromopyruvic acid

Names
Preferred IUPAC name 3-Bromo-2-oxopropanoic acid
Other names Bromopyruvate 3-Bromopyruvic acid 3-Bromopyruvate 3-BrPA 3BP 3-Br-Pyr
Identifiers
CAS Number	1113-59-3^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:131461^N
ChEMBL	ChEMBL177837^Y
ChemSpider	63850^Y
ECHA InfoCard	100.012.915
EC Number	214-206-5
PubChem CID	70684
UNII	63JMV04GRK^Y
CompTox Dashboard (EPA)	DTXSID7040940
InChI InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)^Y Key: PRRZDZJYSJLDBS-UHFFFAOYSA-N^Y InChI=1/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7) Key: PRRZDZJYSJLDBS-UHFFFAOYAU
SMILES C(C(=O)C(=O)O)Br BrCC(=O)C(=O)O
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H290, H314
Precautionary statements	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). N verify (what is ^YN ?) Infobox references

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.

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, 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]

References

1. Peter L. Pedersen (2012). "3-Bromopyruvate (3BP) A Fast Acting, Promising, Powerful, Specific, and Effective "Small Molecule" Anti-Cancer Agent Taken from Labside to Bedside: Introduction to a Special Issue". J. Bioenerg. Biomembr. 44 (1): 1–6. doi:10.1007/s10863-012-9425-4. PMID 22382780. S2CID 43773994.
2. Barnard, JP; Reynafarje, B; Pedersen, PL (1993). "Glucose catabolism in African trypanosomes. Evidence that the terminal step is catalyzed by a pyruvate transporter capable of facilitating uptake of toxic analogs". The Journal of Biological Chemistry. 268 (5): 3654–3661. doi:10.1016/S0021-9258(18)53743-1. PMID 8429041.
3. Liu, Zhe; Sun, Yiming; Hong, Haiyu; Zhao, Surong; Zou, Xue; Ma, Renqiang; Jiang, Chenchen; Wang, Zhiwei; Li, Huabin (2015-08-15). "3-bromopyruvate enhanced daunorubicin-induced cytotoxicity involved in monocarboxylate transporter 1 in breast cancer cells". American Journal of Cancer Research. 5 (9): 2673–2685. ISSN 2156-6976. PMC 4633897. PMID 26609475.

External links

• Mathupala, Saroj P.; Ko, Young H.; Pedersen, Peter L. (2010). "The pivotal roles of mitochondria in cancer: Warburg and beyond and encouraging prospects for effective therapies". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 1797 (6–7): 1225–1230. doi:10.1016/j.bbabio.2010.03.025. PMC 2890051. PMID 20381449.
• Mathupala, Saroj P.; Ko, Young H.; Pedersen, Peter L. (2009). "Hexokinase-2 bound to mitochondria: Cancer's stygian link to the "Warburg effect" and a pivotal target for effective therapy". Seminars in Cancer Biology. 19 (1): 17–24. doi:10.1016/j.semcancer.2008.11.006. PMC 2714668. PMID 19101634.
• Ko, Young H.; Smith, Barbara L.; Wang, Yuchuan; Pomper, Martin G.; Rini, David A.; Torbenson, Michael S.; Hullihen, Joanne; Pedersen, Peter L. (2004). "Advanced cancers: Eradication in all cases using 3-bromopyruvate therapy to deplete ATP". Biochemical and Biophysical Research Communications. 324 (1): 269–75. doi:10.1016/j.bbrc.2004.09.047. PMID 15465013.
• Mathupala, S P; Ko, Y H; Pedersen, P L (2006). "Hexokinase II: Cancer's double-edged sword acting as both facilitator and gatekeeper of malignancy when bound to mitochondria". Oncogene. 25 (34): 4777–86. doi:10.1038/sj.onc.1209603. PMC 3385868. PMID 16892090.
• The cancer cell's "power plants" as promising therapeutic targets: An overview, by Peter Pederson