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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:131461 ;
ChEMBL	ChEMBL177837 ;
ChemSpider	63850 ;
ECHA InfoCard	100.012.915
EC Number	214-206-5;
PubChem CID	70684;
UNII	63JMV04GRK ;
CompTox Dashboard (EPA)	DTXSID7040940 ;
	InChI InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7) Key: PRRZDZJYSJLDBS-UHFFFAOYSA-N ; 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). verify (what is ?) 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

Bromopyruvic acid attracts attention in the biomedical research capacity through its potential to inhibit tyrosine phosphatases. Activity of such phosphatases is required for the activation of platelets, especially in a process called venous thromboembolism, a major cause of mortality during gastrointestinal cancer. Bromopyruvic-mediated inhibition of tyrosine phosphases can counteract such thromboembolism and is investigated as novel angel to combat cancer-associated mortality. ^[2] 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.^[3] 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.^[4]

References

^ 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.
^ Faria AV, Andrade SS, Reijm AN, Spaander MC, de Maat MP, Peppelenbosch MP, Ferreira-Halder CV, Fuhler GM (June 2019). "Targeting Tyrosine Phosphatases by 3-Bromopyruvate Overcomes Hyperactivation of Platelets from Gastrointestinal Cancer Patients". J Clin Med. 8 (7): 936. doi:10.3390/jcm8070936. PMC 6678874. PMID 31261776.
^ 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.
^ 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

[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] Faria AV, Andrade SS, Reijm AN, Spaander MC, de Maat MP, Peppelenbosch MP, Ferreira-Halder CV, Fuhler GM (June 2019). "Targeting Tyrosine Phosphatases by 3-Bromopyruvate Overcomes Hyperactivation of Platelets from Gastrointestinal Cancer Patients". J Clin Med. 8 (7): 936. doi:10.3390/jcm8070936. PMC 6678874. PMID 31261776.

[3] 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.

[4] 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.

[1]

[2]

[3]

[4]