3-Bromopyruvic acid
Catalog No.: GC15523Purity:>97.00%Synonyms: Bromopyruvic acid; Hexokinase II Inhibitor II, 3-BP
3-Bromopyruvic acid is an antitumor agent able to inhibit aerobic glycolysis and oxidative phosphorylation, with IC50 values of 15 and 35μM for pyruvate dehydrogenase (PDH) and isocitrate dehydrogenase (IDH), respectively.
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Cas No.: 1113-59-3
1gIn Stock
$38.00
1
5gIn Stock
$42.00
1
10gIn Stock
$56.00
1
25gIn Stock
$118.00
1
| Pack Size | Price | Availability | Quantity | Action |
|---|---|---|---|---|
| 1g | $38.00 | In Stock | 1 | |
| 5g | $42.00 | In Stock | 1 | |
| 10g | $56.00 | In Stock | 1 | |
| 25g | $118.00 | In Stock | 1 |
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Citations
1 publicationsPublications from researchers using this productDescription
3-Bromopyruvic acid is an antitumor agent able to inhibit aerobic glycolysis and oxidative phosphorylation, with IC50 values of 15 and 35μM for pyruvate dehydrogenase (PDH) and isocitrate dehydrogenase (IDH), respectively[1]. 3-Bromopyruvic acid covalently modifies hexokinase II (HEK II) and the dissociation of HEK II from mitochondria [2]. In the model of malignant tumor cells, 3-Bromopyruvic acid is used as an inhibitor of ATPase activity, which reduces ATP levels and counteracts drug efflux by acting on ATP-binding cassette transporters to reverse chemotherapy resistance[3].
In vitro, 3-Bromopyruvic acid treatment at a concentration of 25μg/ml for 48 hours led to the appearance of typical apoptotic morphological features in MCF-7 cells, including nuclear shrinkage, excessive cytoplasmic granules, and significant reductions in the expression of Bcl-2, c-Myc, and mutant p53[4]. Treatment with 3-Bromopyruvic acid (40μM) for 2 hours led to a significant decrease in the viability of U118 glioblastoma cells, and an increase in reactive oxygen species (ROS) produced in the mitochondria[5]. Treatment with 100μM 3-Bromopyruvic acid for 12 hours induced DNA breaks in THP-1 cells, thereby triggering phosphorylation of H2A.X[6].
In vivo, 3-Bromopyruvic acid treatment via intraperitoneal injection (20mg/kg; every other day for 30 days) significantly reduced tumor growth in the pancreatic cancer model of mice, prolonged the survival time of mice, led to a significant decrease in the number of myeloid suppressor cells in tumor tissues, and increased the infiltration of CD8+ T cells[7]. Intraperitoneal injection of 3-Bromopyruvic acid (8mg/kg), every 4 days, for 28 consecutive days, significantly inhibited tumor progression in the SW480 cell-xenograft mouse model, resulting in disordered vascular distribution in the tumor tissue, shrinkage of cell nuclei, and infiltration of inflammatory cells[8].
References:
[1] Jardim-Messeder D, Moreira-Pacheco F. 3-Bromopyruvic acid inhibits tricarboxylic acid cycle and glutaminolysis in HepG2 cells[J]. Anticancer research, 2016, 36(5): 2233-2241.
[2] Chen Z, Zhang H, Lu W, et al. Role of mitochondria-associated hexokinase II in cancer cell death induced by 3-bromopyruvate[J]. Biochimica et Biophysica Acta (BBA)-Bioenergetics, 2009, 1787(5): 553-560.
[3] Shoshan M C. 3-Bromopyruvate: targets and outcomes[J]. Journal of bioenergetics and biomembranes, 2012, 44(1): 7-15.
[4] Liu X, Zheng X, Wang Y. Inhibitive effect of 3-bromopyruvic acid on human breast cancer MCF-7 cells involves cell cycle arrest and apoptotic induction[J]. Chinese medical journal, 2009, 122(14): 1681-1685.
[5] Petricciuolo M, Davidescu M, Fettucciari K, et al. The efficacy of the anticancer 3-bromopyruvate is potentiated by antimycin and menadione by unbalancing mitochondrial ROS production and disposal in U118 glioblastoma cells[J]. Heliyon, 2020, 6(12).
[6] Cal M, Matyjaszczyk I, Litwin I, et al. The anticancer drug 3-bromopyruvate induces DNA damage potentially through reactive oxygen species in yeast and in human cancer cells[J]. Cells, 2020, 9(5): 1161.
[7] Roy S, Dukic T, Bhandary B, et al. 3-Bromopyruvate inhibits pancreatic tumor growth by stalling glycolysis, and dismantling mitochondria in a syngeneic mouse model[J]. American Journal of Cancer Research, 2022, 12(11): 4977.
[8] Sun Y, Liu Z, Zou X, et al. Mechanisms underlying 3-bromopyruvate-induced cell death in colon cancer[J]. Journal of bioenergetics and biomembranes, 2015, 47(4): 319-329.
Protocol
| Cell experiment [1]: | |
Cell lines | SW480 cells |
Preparation Method | SW480 cells were cultured in high glucose Dames Modified Eagle's Medium (DMEM) medium. The medium was supplemented with 10% fetal bovine serum, 100U/ml penicillin and 100μg/ml streptomycin. The culture temperature was 37°C and the air concentration was 95%, with a carbon dioxide concentration of 5%. The SW480 cells were seeded at a density of 6×103 cells per well in a 96-well plate and treated with different concentrations of 3-Bromopyruvic acid (0, 40, 80, 160, and 320μM). At 24, 48 and 72 hours, MTT (5mg/ml phosphate-buffered saline, PBS) was added and incubated at 37°C for 4 hours. After 4 hours, the solution was replaced with 150μl dimethyl sulfoxide (DMSO), and 30 minutes later, the absorbance was measured at 490nm using an enzyme reader to determine cell viability. |
Reaction Conditions | 0, 40, 80, 160, and 320μM; 24h |
Applications | 3-Bromopyruvic acid treatment significantly inhibited the cell viability of SW480 cells in dose-dependent manner. |
| Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | Panc-2 cells were subcutaneously injected into the right abdomen of 8-week-old female C57BL/6 mice. During anesthesia of the mice, 3.5-4% isoflurane and 100% oxygen were used. For tumor implantation, the uncombined Panc-2 cells were digested with trypsin, washed with cold 1 × PBS, and then mixed 1 × 106 cells with Matrigel at a 1:1 ratio (50µl + 50µl), and injected into a 0.5ml cold syringe equipped with a 27-1/2-gauge needle. The cell mixture (100µl) was carefully injected subcutaneously into the right abdomen of the mice. One week later, the tumor volume (approximately 100mm3) was measured, and the mice were randomly divided into 4 groups (n = 8 mice per group). The mice received vehicle control (only saline and buffer) and 20mg/kg 3-Bromopyruvic acid treatment via intraperitoneal (IP) injection every other day for 30 days. After the treatment period, the mice were euthanized, the tumors were imaged and processed for further analysis. The tumor volume was measured every day using a digital caliper, using the formula: volume = (L×W2)/2, where L = larger length, W = smaller length. The body weight was measured once a week. |
Dosage form | 20mg/kg every other day for 30 days; i.p. |
Applications | 3-Bromopyruvic acid treatment reduced the growth of pancreatic tumors and prolonged the survival period of the mice. |
References: | |
Product Documents
Purity:>97.00%Appearance:A solid
Chemical Properties
CAS No.
1113-59-3
Synonyms
Bromopyruvic acid; Hexokinase II Inhibitor II, 3-BP
Chemical Name
3-bromo-2-oxopropanoic acid
SMILES
BrCC(C(O)=O)=O
Molecular Formula
C3H3BrO3
Molecular Weight
166.96
Solubility
≥ 16.7mg/mL in Water
Storage
Store at 2-8°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.
CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility
g/mol
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