Home Other Building Blocks Bromopyruvic acid

Bromopyruvic acid

CAS No.:
1113-59-3
Catalog Number:
AG0035V2
Molecular Formula:
C3H3BrO3
Molecular Weight:
166.9581
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
96%
In Stock USA
United States
$19
- +
5g
96%
In Stock USA
United States
$38
- +
25g
96%
In Stock USA
United States
$138
- +
100g
96%
In Stock USA
United States
$369
- +
Product Description
Catalog Number:
AG0035V2
Chemical Name:
Bromopyruvic acid
CAS Number:
1113-59-3
Molecular Formula:
C3H3BrO3
Molecular Weight:
166.9581
MDL Number:
MFCD00149107
IUPAC Name:
3-bromo-2-oxopropanoic acid
InChI:
InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
InChI Key:
PRRZDZJYSJLDBS-UHFFFAOYSA-N
SMILES:
OC(=O)C(=O)CBr
EC Number:
214-206-5
UNII:
63JMV04GRK
Properties
Complexity:
98.4  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
165.927g/mol
Formal Charge:
0
Heavy Atom Count:
7  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
166.958g/mol
Monoisotopic Mass:
165.927g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
54.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.5  
Literature
Title Journal
Antitumor and chemosensitizing action of 3-bromopyruvate: Implication of deregulated metabolism. Chemico-biological interactions 20170525
Mechanisms underlying 3-bromopyruvate-induced cell death in colon cancer. Journal of bioenergetics and biomembranes 20150101
Regulation of death induction and chemosensitizing action of 3-bromopyruvate in myeloid leukemia cells: energy depletion, oxidative stress, and protein kinase activity modulation. The Journal of pharmacology and experimental therapeutics 20140201
MCT1-mediated transport of a toxic molecule is an effective strategy for targeting glycolytic tumors. Nature genetics 20130101
D-Amino acid oxidase-induced oxidative stress, 3-bromopyruvate and citrate inhibit angiogenesis, exhibiting potent anticancer effects. Journal of bioenergetics and biomembranes 20121001
Glutamine deprivation enhances antitumor activity of 3-bromopyruvate through the stabilization of monocarboxylate transporter-1. Cancer research 20120901
Glycolysis inhibitors as a potential therapeutic option to treat aggressive neuroblastoma expressing GLUT1. Journal of pediatric surgery 20120701
Prognostic significance of glucose transporter-1 (GLUT1) gene expression in rectal cancer after preoperative chemoradiotherapy. Surgery today 20120501
3-Bromopyruvate inhibits calcium uptake by sarcoplasmic reticulum vesicles but not SERCA ATP hydrolysis activity. The international journal of biochemistry & cell biology 20120501
Casiopeina II-gly and bromo-pyruvate inhibition of tumor hexokinase, glycolysis, and oxidative phosphorylation. Archives of toxicology 20120501
Aerosolized 3-bromopyruvate inhibits lung tumorigenesis without causing liver toxicity. Cancer prevention research (Philadelphia, Pa.) 20120501
Mefloquine interferes with glycolysis in schistosomula of Schistosoma mansoni via inhibition of enolase. Parasitology 20120401
Mitochondrial genome-knockout cells demonstrate a dual mechanism of action for the electron transport complex I inhibitor mycothiazole. Marine drugs 20120401
Science to practice: what do molecular biologic studies in rodent models add to our understanding of interventional oncologic procedures including percutaneous ablation by using glyceraldehyde-3-phosphate dehydrogenase antagonists? Radiology 20120301
Human hepatocellular carcinoma in a mouse model: assessment of tumor response to percutaneous ablation by using glyceraldehyde-3-phosphate dehydrogenase antagonists. Radiology 20120301
Effect of glucose availability on glucose transport in bovine mammary epithelial cells. Animal : an international journal of animal bioscience 20120301
PPARγ contributes to PKM2 and HK2 expression in fatty liver. Nature communications 20120214
Rab25 increases cellular ATP and glycogen stores protecting cancer cells from bioenergetic stress. EMBO molecular medicine 20120201
Up-regulation of hexokinaseII in myeloma cells: targeting myeloma cells with 3-bromopyruvate. Journal of bioenergetics and biomembranes 20120201
3-Bromopyruvate: targets and outcomes. Journal of bioenergetics and biomembranes 20120201
3-Bromopyruvate antagonizes effects of lactate and pyruvate, synergizes with citrate and exerts novel anti-glioma effects. Journal of bioenergetics and biomembranes 20120201
Bromopyruvate mediates autophagy and cardiolipin degradation to monolyso-cardiolipin in GL15 glioblastoma cells. Journal of bioenergetics and biomembranes 20120201
Flow cytometric evaluation of the effects of 3-bromopyruvate (3BP) and dichloracetate (DCA) on THP-1 cells: a multiparameter analysis. Journal of bioenergetics and biomembranes 20120201
Effect of the antitumoral alkylating agent 3-bromopyruvate on mitochondrial respiration: role of mitochondrially bound hexokinase. Journal of bioenergetics and biomembranes 20120201
Experimental results using 3-bromopyruvate in mesothelioma: in vitro and in vivo studies. Journal of bioenergetics and biomembranes 20120201
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 20120201
Targeting aerobic glycolysis: 3-bromopyruvate as a promising anticancer drug. Journal of bioenergetics and biomembranes 20120201
Enhancement of hexokinase II inhibitor-induced apoptosis in hepatocellular carcinoma cells via augmenting ER stress and anti-angiogenesis by protein disulfide isomerase inhibition. Journal of bioenergetics and biomembranes 20120201
Butyrate activates the monocarboxylate transporter MCT4 expression in breast cancer cells and enhances the antitumor activity of 3-bromopyruvate. Journal of bioenergetics and biomembranes 20120201
Over-expression of GAPDH in human colorectal carcinoma as a preferred target of 3-bromopyruvate propyl ester. Journal of bioenergetics and biomembranes 20120201
Transport and cytotoxicity of the anticancer drug 3-bromopyruvate in the yeast Saccharomyces cerevisiae. Journal of bioenergetics and biomembranes 20120201
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 20120201
D-amino acid oxidase gene therapy sensitizes glioma cells to the antiglycolytic effect of 3-bromopyruvate. Cancer gene therapy 20120101
Intracellular ATP levels are a pivotal determinant of chemoresistance in colon cancer cells. Cancer research 20120101
Systemic administration of 3-bromopyruvate in treating disseminated aggressive lymphoma. Translational research : the journal of laboratory and clinical medicine 20120101
Cancer metabolism: current perspectives and future directions. Cell death & disease 20120101
Clotrimazole preferentially inhibits human breast cancer cell proliferation, viability and glycolysis. PloS one 20120101
Thyrocyte-specific inactivation of p53 and Pten results in anaplastic thyroid carcinomas faithfully recapitulating human tumors. Oncotarget 20111201
MondoA senses non-glucose sugars: regulation of thioredoxin-interacting protein (TXNIP) and the hexose transport curb. The Journal of biological chemistry 20111104
Mitochondrial dysfunction and effect of antiglycolytic bromopyruvic acid in GL15 glioblastoma cells. Journal of bioenergetics and biomembranes 20111001
Role of SLC5A8, a plasma membrane transporter and a tumor suppressor, in the antitumor activity of dichloroacetate. Oncogene 20110922
Metabolic oxidative stress elicited by the copper(II) complex [Cu(isaepy)2] triggers apoptosis in SH-SY5Y cells through the induction of the AMP-activated protein kinase/p38MAPK/p53 signalling axis: evidence for a combined use with 3-bromopyruvate in neuroblastoma treatment. The Biochemical journal 20110801
Inhibition of hypoxia-inducible carbonic anhydrase-IX enhances hexokinase II inhibitor-induced hepatocellular carcinoma cell apoptosis. Acta pharmacologica Sinica 20110701
Metabolism and brain cancer. Clinics (Sao Paulo, Brazil) 20110601
Novel intraarterial therapy for liver cancer using ethylbromopyruvate dissolved in an iodized oil. Academic radiology 20110401
Assessment of tumoricidal efficacy and response to treatment with 18F-FDG PET/CT after intraarterial infusion with the antiglycolytic agent 3-bromopyruvate in the VX2 model of liver tumor. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20110201
Cellular ATP synthesis mediated by type III sodium-dependent phosphate transporter Pit-1 is critical to chondrogenesis. The Journal of biological chemistry 20110128
Inhibition of hexokinase leads to neuroprotection against excitotoxicity in organotypic hippocampal slice culture. Journal of neuroscience research 20110101
The bioenergetic signature of isogenic colon cancer cells predicts the cell death response to treatment with 3-bromopyruvate, iodoacetate or 5-fluorouracil. Journal of translational medicine 20110101
The dynamics of glutathione species and ophthalmate concentrations in plasma from the VX2 rabbit model of secondary liver tumors. HPB surgery : a world journal of hepatic, pancreatic and biliary surgery 20110101
Stereocomplexes Formed From Select Oligomers of Polymer d-lactic Acid (PDLA) and l-lactate May Inhibit Growth of Cancer Cells and Help Diagnose Aggressive Cancers-Applications of the Warburg Effect. Perspectives in medicinal chemistry 20110101
Mitochondrial approaches to protect against cardiac ischemia and reperfusion injury. Frontiers in physiology 20110101
The metabolic advantage of tumor cells. Molecular cancer 20110101
Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review. International journal of molecular sciences 20110101
Differential utilization of ketone bodies by neurons and glioma cell lines: a rationale for ketogenic diet as experimental glioma therapy. BMC cancer 20110101
Anticancer targets in the glycolytic metabolism of tumors: a comprehensive review. Frontiers in pharmacology 20110101
Efficient elimination of cancer cells by deoxyglucose-ABT-263/737 combination therapy. PloS one 20110101
Mitochondrial NAD+-dependent malic enzyme from Anopheles stephensi: a possible novel target for malaria mosquito control. Malaria journal 20110101
Systematic exploration of synergistic drug pairs. Molecular systems biology 20110101
Glycolysis inhibition inactivates ABC transporters to restore drug sensitivity in malignant cells. PloS one 20110101
Lactate produced by glycogenolysis in astrocytes regulates memory processing. PloS one 20110101
3-bromopyruvate: a new targeted antiglycolytic agent and a promise for cancer therapy. Current pharmaceutical biotechnology 20100801
Interventional oncology: new options for interstitial treatments and intravascular approaches: targeting tumor metabolism via a loco-regional approach: a new therapy against liver cancer. Journal of hepato-biliary-pancreatic sciences 20100701
Interleukin-7 mediates glucose utilization in lymphocytes through transcriptional regulation of the hexokinase II gene. American journal of physiology. Cell physiology 20100601
3-Bromopyruvate induces necrotic cell death in sensitive melanoma cell lines. Biochemical and biophysical research communications 20100528
The pyruvic acid analog 3-bromopyruvate interferes with the tetrazolium reagent MTS in the evaluation of cytotoxicity. Assay and drug development technologies 20100401
Glycolytic enzyme inhibitors affect pancreatic cancer survival by modulating its signaling and energetics. Anticancer research 20100301
3-Bromopyruvate induces endoplasmic reticulum stress, overcomes autophagy and causes apoptosis in human HCC cell lines. Anticancer research 20100301
Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles. Organic letters 20100205
Cancer as a metabolic disease. Nutrition & metabolism 20100101
Quantitative proteomics identification of phosphoglycerate mutase 1 as a novel therapeutic target in hepatocellular carcinoma. Molecular cancer 20100101
Analyzing the regulation of metabolic pathways in human breast cancer. BMC medical genomics 20100101
Role of the mitochondrion in programmed necrosis. Frontiers in physiology 20100101
Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) is pyruvylated during 3-bromopyruvate mediated cancer cell death. Anticancer research 20091201
Targets of 3-bromopyruvate, a new, energy depleting, anticancer agent. Medicinal chemistry (Shariqah (United Arab Emirates)) 20091101
Transport by SLC5A8 with subsequent inhibition of histone deacetylase 1 (HDAC1) and HDAC3 underlies the antitumor activity of 3-bromopyruvate. Cancer 20091015
Metabolic control analysis in a cellular model of elevated MAO-B: relevance to Parkinson's disease. Neurotoxicity research 20091001
Glucose deprivation contributes to the development of KRAS pathway mutations in tumor cells. Science (New York, N.Y.) 20090918
A one-pot synthesis of functionalized thiazoles from acid chlorides, secondary amines, ethyl bromopyruvate, and ammonium thiocyanate. Molecular diversity 20090801
Inhibitive effect of 3-bromopyruvic acid on human breast cancer MCF-7 cells involves cell cycle arrest and apoptotic induction. Chinese medical journal 20090720
Role of mitochondria-associated hexokinase II in cancer cell death induced by 3-bromopyruvate. Biochimica et biophysica acta 20090501
Mitochondria and energetic depression in cell pathophysiology. International journal of molecular sciences 20090501
Specificity of the anti-glycolytic activity of 3-bromopyruvate confirmed by FDG uptake in a rat model of breast cancer. Investigational new drugs 20090401
Hexokinase inhibitor screening based on adenosine 5'-diphosphate determination by electrophoretically mediated microanalysis. Electrophoresis 20090401
Novel therapy for malignant pleural mesothelioma based on anti-energetic effect: an experimental study using 3-Bromopyruvate on nude mice. Anticancer research 20090401
Inhibition of glycolysis modulates prednisolone resistance in acute lymphoblastic leukemia cells. Blood 20090226
Inhibition of energy-producing pathways of HepG2 cells by 3-bromopyruvate. The Biochemical journal 20090201
Hexokinase-2 bound to mitochondria: cancer's stygian link to the 'Warburg Effect' and a pivotal target for effective therapy. Seminars in cancer biology 20090201
Senescence induction; a possible cancer therapy. Molecular cancer 20090101
The antitumor effect and hepatotoxicity of a hexokinase II inhibitor 3-bromopyruvate: in vivo investigation of intraarterial administration in a rabbit VX2 hepatoma model. Korean journal of radiology 20090101
Role of reactive oxygen species-mediated mitochondrial dysregulation in 3-bromopyruvate induced cell death in hepatoma cells : ROS-mediated cell death by 3-BrPA. Journal of bioenergetics and biomembranes 20081201
Non-invasive MRI tumor imaging and synergistic anticancer effect of HSP90 inhibitor and glycolysis inhibitor in RIP1-Tag2 transgenic pancreatic tumor model. Cancer chemotherapy and pharmacology 20081101
Targeting of VX2 rabbit liver tumor by selective delivery of 3-bromopyruvate: a biodistribution and survival study. The Journal of pharmacology and experimental therapeutics 20081001
Hamster sperm capacitation: role of pyruvate dehydrogenase A and dihydrolipoamide dehydrogenase. Biology of reproduction 20080801
Strategies for molecular imaging dementia and neurodegenerative diseases. Neuropsychiatric disease and treatment 20080601
3-Bromopyruvate as inhibitor of tumour cell energy metabolism and chemopotentiator of platinum drugs. Molecular oncology 20080601
Synergistic antipancreatic tumor effect by simultaneously targeting hypoxic cancer cells with HSP90 inhibitor and glycolysis inhibitor. Clinical cancer research : an official journal of the American Association for Cancer Research 20080315
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A novel strategy involved in [corrected] anti-oxidative defense: the conversion of NADH into NADPH by a metabolic network. PloS one 20080101
Development of a new orthotopic animal model of metastatic liver cancer in the rabbit VX2 model: effect on metastases after partial hepatectomy, intra-arterial treatment with 3-bromopyruvate and chemoembolization. Clinical & experimental metastasis 20080101
Systems biology approach to identification of biomarkers for metastatic progression in cancer. BMC bioinformatics 20080101
Cytometric assessment of DNA damage by exogenous and endogenous oxidants reports aging-related processes. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20071101
Apoptosis-inducing antitumor efficacy of hexokinase II inhibitor in hepatocellular carcinoma. Molecular cancer therapeutics 20070901
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Local toxicity of hepatic arterial infusion of hexokinase II inhibitor, 3-bromopyruvate: In vivo investigation in normal rabbit model. Academic radiology 20070101
Intraarterial therapy with a new potent inhibitor of tumor metabolism (3-bromopyruvate): identification of therapeutic dose and method of injection in an animal model of liver cancer. Journal of vascular and interventional radiology : JVIR 20070101
FDG-PET for evaluating the antitumor effect of intraarterial 3-bromopyruvate administration in a rabbit VX2 liver tumor model. Korean journal of radiology 20070101
The oncoprotein H-RasV12 increases mitochondrial metabolism. Molecular cancer 20070101
The role of glucose metabolism and glucose-associated signalling in cancer. Perspectives in medicinal chemistry 20070101
Hepatic intra-arterial injection of 3-bromopyruvate in rabbit VX2 tumor. Acta radiologica (Stockholm, Sweden : 1987) 20061201
Colony-stimulating factor-1 requires PI3-kinase-mediated metabolism for proliferation and survival in myeloid cells. Cell death and differentiation 20061101
Inactivation of H+-vacuolar ATPase by the energy blocker 3-bromopyruvate, a new antitumour agent. Life sciences 20061019
Hexokinase II: cancer's double-edged sword acting as both facilitator and gatekeeper of malignancy when bound to mitochondria. Oncogene 20060807
Synthesis of functionalized 5-imino-2,5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate. Molecular diversity 20060801
Hypoxia stimulates proliferation of human hepatoma cells through the induction of hexokinase II expression. Journal of hepatology 20050301
Inhibition of glycolysis in cancer cells: a novel strategy to overcome drug resistance associated with mitochondrial respiratory defect and hypoxia. Cancer research 20050115
Targeting energy metabolism in brain cancer: review and hypothesis. Nutrition & metabolism 20050101
Advanced cancers: eradication in all cases using 3-bromopyruvate therapy to deplete ATP. Biochemical and biophysical research communications 20041105
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Carbonic anhydrase in mammalian vascular smooth muscle. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20040801
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Biochemical and structural studies of malate synthase from Mycobacterium tuberculosis. The Journal of biological chemistry 20030117
Energy blocker to treat liver cancer. Drug discovery today 20020915
3-Bromopyruvate kills cancer cells in animals. The Lancet. Oncology 20020901
Novel therapy for liver cancer: direct intraarterial injection of a potent inhibitor of ATP production. Cancer research 20020715
Lack of antifertility properties of novel halogenated glycolytic inhibitors and the urinary excretion and metabolism of 1,6-dichloro-1,6-dideoxy-D-fructofuranose in the male rat. International journal of andrology 20020601
An absolute requirement of fructose 1,6-bisphosphate for the Lactobacillus casei L-lactate dehydrogenase activity induced by a single amino acid substitution. Protein engineering 20020101
Investigation of red blood cell carbonic anhydrase, glucose 6-phosphate dehydrogenase, hexokinase enzyme activities, and zinc concentration in patients with hyperthyroid diseases. Endocrine research 20020101
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Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. Journal of enzyme inhibition 20011101
2-Methylisocitrate lyases from the bacterium Escherichia coli and the filamentous fungus Aspergillus nidulans: characterization and comparison of both enzymes. European journal of biochemistry 20010601
Alkylation of isocitrate lyase from Escherichia coli by 3-bromopyruvate. Archives of biochemistry and biophysics 19900501
Chemical modifications of Serratia marcescens anthranilate synthase component I. The Journal of biological chemistry 19811010
Equilibrium substrate binding studies of the malic enzyme of pigeon liver. Equivalence of nucleotide sites and anticooperativity associated with the binding of L-malate to the enzyme-manganese(II)-reduced nicotinamide adenine dinucleotide phosphate ternary complex. Biochemistry 19800304
Properties