Bromopyruvic acid

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Bromopyruvic acid
Bromopyruvic acid.png
Names
IUPAC name
3-bromo-2-oxopropanoic acid
Other names
bromopyruvate
3-bromopyruvic acid
3-bromopyruvate
3-BrPA
3BP
3-Br-Pyr
Identifiers
1113-59-3 YesY
ChEMBL ChEMBL177837 YesY
ChemSpider 63850 YesY
Jmol-3D images Image
Image
PubChem 70684
Properties
C3H3BrO3
Molar mass 166.95812
Melting point 79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate)
Hazards
R-phrases R34
S-phrases S25 S36/37/39 S45
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references
3-bromopyruvate molecule

3-bromopyruvic acid, or its alkaline form, 3-bromopyruvate, are synthetic brominated derivatives of pyruvic acid. They are lactic acid and pyruvate analogs.

The characteristics of 3-bromopyruvate in vitro and in vivo have been reported in the scientific literature since the 1940s. Because it is a highly reactive alkylating agent and it is inherently unstable, it had been described as a metabolic poison.

Research activity[edit]

In 1993 researchees at the Johns Hopkins School of Medicine reported that a pyruvate transporter system could be used to deliver 3-bromopyruvate inside trypanosomal cells where its primary target is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by 3-bromopyruvate.[1] A 2002 study suggested that intra-arterial delivery of bromopyruvic acid directly to the site of tumors in rabbits could represent a strategy for stopping the growth of liver cancer while minimizing toxic side-effects.[2] An application for patent has been submitted.[3]

Research at Johns Hopkins has suggested that 3-bromopyruvate could be used to selectively kill cancer cells, while leaving normal cells intact.[4][5] A Johns Hopkins press release dated October 14, 2004 stated that, "Building on their earlier work, Johns Hopkins researchers have discovered that an apparently nontoxic cellular "energy blocker" can eradicate large liver tumors grown in rats. Recently, the FDA accepted an IND application for the use of 3-bromopyruvate for a Phase I clinical trial in liver cancer.[6]

References[edit]

  1. ^ 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. PMID 8429041. 
  2. ^ Geschwind, JF; Ko, YH; Torbenson, MS; Magee, C; Pedersen, PL (2002). "Novel therapy for liver cancer: Direct intraarterial injection of a potent inhibitor of ATP production". Cancer research 62 (14): 3909–13. PMID 12124317. 
  3. ^ Therapeutics for cancer using 3-bromopyruvate and other selective inhibitors of ATP production
  4. ^ Pedersen, Peter L. (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". Journal of Bioenergetics and Biomembranes 44 (1): 1–6. doi:10.1007/s10863-012-9425-4. PMID 22382780. 
  5. ^ Ko, Y. H.; Verhoeven, H. A.; Lee, M. J.; Corbin, D. J.; Vogl, T. J.; Pedersen, P. L. (2012). "A translational study "case report" on the small molecule "energy blocker" 3-bromopyruvate (3BP) as a potent anticancer agent: From bench side to bedside". Journal of Bioenergetics and Biomembranes 44 (1): 163–70. doi:10.1007/s10863-012-9417-4. PMID 22328020. 
  6. ^ "PreScience Labs Announced that the FDA Accepts IND Application for Novel Oncology Drug" (Press release). Reuters. 24 July 2013. 

External links[edit]