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Chemical Structure| 1113-59-3 Chemical Structure| 1113-59-3

Structure of 3-Bromopyruvic acid
CAS No.: 1113-59-3

Chemical Structure| 1113-59-3

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3-Bromopyruvic acid is an inhibitor of hexokinase II with effective antitumor acitvity.

Synonyms: Bromopyruvic acid; Hexokinase II Inhibitor II, 3-BP; NSC 62343

4.5 *For Research Use Only !

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Product Citations

Product Citations

Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan ; Caljon, Guy ; Legoabe, Lesetja J. ;

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; ; drug likeliness properties ; ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

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Product Details of 3-Bromopyruvic acid

CAS No. :1113-59-3
Formula : C3H3BrO3
M.W : 166.96
SMILES Code : O=C(O)C(CBr)=O
Synonyms :
Bromopyruvic acid; Hexokinase II Inhibitor II, 3-BP; NSC 62343
MDL No. :MFCD00002587
InChI Key :PRRZDZJYSJLDBS-UHFFFAOYSA-N
Pubchem ID :70684

Safety of 3-Bromopyruvic acid

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Primary microglial cells 100 µM 24 hours Inhibited LPS-induced NO production J Neuroinflammation. 2021 Jun 9;18(1):129.
BV-2 microglial cells 100 µM 24 hours Inhibited LPS-induced NO production J Neuroinflammation. 2021 Jun 9;18(1):129.
Human erythrocytes 3.3 µM – 2 mM 1 minute To study the kinetics of 3-BP transport in human erythrocytes. Results showed that 3-BP transport was linear during the initial 3-5 minutes and pH-dependent. The Km and Vm values were 0.89 mM and 0.94 mmol/(l cells x min), respectively. Transport was competitively inhibited by pyruvate and significantly inhibited by DIDS, SITS, CHC, and various polyphenols such as luteolin and quercetin. Cell Mol Biol Lett. 2014 Jun;19(2):201-14.
MDA-MB-231 100 µM 1 or 24 hours 3BP was not toxic to MDA-MB-231 cells (>90% metabolic activity retained). Cancer Metab. 2021 Oct 14;9(1):37.
BT20 100 µM 1 or 24 hours 3BP significantly reduced metabolic activity in BT20 cells (to 61% after 24-hour exposure). Cancer Metab. 2021 Oct 14;9(1):37.
Pancreatic tumor organoids 100 µM 12 hours To evaluate the effect of 3-BP on the metabolism of pancreatic tumor organoids, results showed significant inhibition of organoid growth and metabolic activity Cell Death Discov. 2024 Mar 1;10(1):106.
THP-1 cells 25-100 µM 12 hours Assessed the impact of 3-BP on THP-1 cell viability, found 25 μM 3-BP has no impact, 50 μM leads to 40% viability loss Cells. 2020 May 8;9(5):1161.
Yeast cells 1-4 mM 1-4 hours Assessed the impact of 3-BP on wild type cell viability, found 3 h incubation with 3 mM 3-BP is not toxic for the cells Cells. 2020 May 8;9(5):1161.
Osteoarthritis fibroblast-like synoviocytes (OA FLS) 25 µM 24 hours To evaluate the effect of 3-bromopyruvic acid on OA FLS proliferation, migration, and cytokine secretion. Results showed that 3-bromopyruvic acid significantly inhibited OA FLS proliferation, migration, and secretion of IL-6. Arthritis Rheumatol. 2016 Jul;68(7):1614-26.
Rheumatoid arthritis fibroblast-like synoviocytes (RA FLS) 25 µM 24 hours To evaluate the effect of 3-bromopyruvic acid on RA FLS proliferation, migration, and cytokine secretion. Results showed that 3-bromopyruvic acid significantly inhibited RA FLS proliferation, migration, and secretion of IL-6 and MMP-3. Arthritis Rheumatol. 2016 Jul;68(7):1614-26.
Suit-2 cells 50–75 µM (normoxic conditions), 12.5–25 µM (hypoxic conditions) 24 hours To evaluate the cytotoxicity of β-CD-3-BrPA and free 3-BrPA under normoxic and hypoxic conditions. Results showed that both drugs were more effective under hypoxic conditions in Suit-2 cells, though the difference was less pronounced compared to MiaPaCa-2 cells. Clin Cancer Res. 2014 Dec 15;20(24):6406-17.
MiaPaCa-2 cells 50–75 µM (normoxic conditions), 12.5–25 µM (hypoxic conditions) 24 hours To evaluate the cytotoxicity of β-CD-3-BrPA and free 3-BrPA under normoxic and hypoxic conditions. Results showed that both drugs were more effective under hypoxic conditions in MiaPaCa-2 cells. Clin Cancer Res. 2014 Dec 15;20(24):6406-17.
SiMCT1-BT20 200 µM 24 hours SiMCT1-BT20 cells showed resistance to 3BP (72% viability vs 12% in wild type). Cancer Metab. 2021 Oct 14;9(1):37.
BT549 100 µM 24 hours 3BP rendered BT549 cells completely metabolically inactive. Cancer Metab. 2021 Oct 14;9(1):37.
SKOV3 ovarian cancer cells 40.5 µM (IC50) 24 hours Evaluate the cytotoxicity of 3-BP on SKOV3 cells, results showed IC50 of 40.5 μM Int J Mol Sci. 2021 Jan 12;22(2):709.
PEO1 ovarian cancer cells 18.7 µM (IC50) 24 hours Evaluate the cytotoxicity of 3-BP on PEO1 cells, results showed IC50 of 18.7 μM Int J Mol Sci. 2021 Jan 12;22(2):709.
KBM7 cells 50 µM 3 days To determine the effect of MCT1 loss on 3-BrPA sensitivity, results showed MCT1-null cells were completely resistant to 3-BrPA. Nat Genet. 2013 Jan;45(1):104-8.
SKOV-3 cells 10 µM–100 µM 3, 6, 24 hours Evaluate the cytotoxicity and HK2 inhibition effect of 3-BPA on SKOV-3 cells. Results showed that liposomal formulations exhibited stronger inhibitory effects and cytotoxicity at 3, 6, and 24 hours post-administration. Int J Nanomedicine. 2015 Jul 8;10:4405-23.
Breast cancer stem cells 5–40 μg/ml 4 hours Evaluate the metabolic inhibition and photothermal therapy effect of 3BP on breast cancer stem cells, showing significant reduction in cell viability Adv Healthc Mater. 2022 Apr;11(8):e2102272.
F98 rodent glioma cells 0.0001 mM–0.3 mM 48 and 72 hours 3-BrPA inhibited the growth and proliferation of F98 cells with IC50 values of 15.8–25.5 μM (48 hours) and 22.3–25.0 μM (72 hours). Neuro Oncol. 2015 Jan;17(1):70-80.
9L rodent gliosarcoma cells 0.0001 mM–0.3 mM 48 and 72 hours 3-BrPA inhibited the growth and proliferation of 9L cells with IC50 values of 15.8–25.5 μM (48 hours) and 22.3–25.0 μM (72 hours). Neuro Oncol. 2015 Jan;17(1):70-80.
U87 human glioblastoma cells 0.0001 mM–0.3 mM 48 and 72 hours 3-BrPA inhibited the growth and proliferation of U87 cells with IC50 values of 15.8–25.5 μM (48 hours) and 22.3–25.0 μM (72 hours). Neuro Oncol. 2015 Jan;17(1):70-80.
RAW264.7 macrophages 200 μg/mL 48 hours Evaluate the effect of MPB-3BP@CM NPs on macrophage polarization, results showed that MPB-3BP@CM NPs promoted macrophage polarization towards M1 phenotype Signal Transduct Target Ther. 2024 Jun 12;9(1):158.
Panc-2 cells 20 µM and 40 µM Significant decrease in HK2 expression level Adv Healthc Mater. 2023 Dec;12(31):e2301815.
HT29 cells 200 μg/mL 6 hours Evaluate the antitumor efficacy of MPB-3BP@CM NPs on HT29 cells, results showed that MPB-3BP@CM NPs significantly inhibited tumor cell proliferation and induced apoptosis Signal Transduct Target Ther. 2024 Jun 12;9(1):158.
HCT116 cells 200 μg/mL 6 hours Evaluate the antitumor efficacy of MPB-3BP@CM NPs on HCT116 cells, results showed that MPB-3BP@CM NPs significantly inhibited tumor cell proliferation and induced apoptosis Signal Transduct Target Ther. 2024 Jun 12;9(1):158.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
F344 rats 9L gliosarcoma allograft model Intracranial implantation 1%, 5%, 10%, 25%, or 50% Single implantation To evaluate the efficacy of 5% 3-BrPA polymer wafer in the 9L gliosarcoma model. Results showed that 5% 3-BrPA wafer significantly increased survival (median survival 18 days, P=0.0027). Neuro Oncol. 2015 Jan;17(1):70-80.
C57BL/6 female mice Subcutaneous pancreatic cancer model Injection 10 mg/kg Three times per week for 30 days Tumor volume reduced by 60-80%, decreased HK2 expression, increased Caspase3 expression Adv Healthc Mater. 2023 Dec;12(31):e2301815.
Balb/c nude mice 4T1 and MDA-MB-231 tumor models Intravenous injection 10 mg/kg Single injection followed by photothermal therapy after 24 hours Evaluate the metabolic inhibition and photothermal therapy effect of 3BP in vivo, showing significant tumor growth inhibition and reduced expression of CSC markers Adv Healthc Mater. 2022 Apr;11(8):e2102272.
Balb/c nude mice 4T1 tumor model Intravenous injection 10 mg/mL Single injection, observed for 48 hours Evaluate the in vivo distribution and therapeutic effects of 3BP@PLGA-IR780, showing effective accumulation in tumor sites and inhibition of tumor growth. J Nanobiotechnology. 2021 Dec 20;19(1):440
BALB/c nude mice HCT116 subcutaneous tumor model Intravenous injection 30.0 mg/kg Every other day for a total of three doses Evaluate the antitumor efficacy of MPB-3BP@CM NPs in vivo, results showed that MPB-3BP@CM NPs significantly inhibited tumor growth and prolonged survival time Signal Transduct Target Ther. 2024 Jun 12;9(1):158.
Mice K/BxN serum transfer arthritis model Intraperitoneal injection 5 mg/kg Once daily for 6 days To evaluate the effect of 3-bromopyruvic acid on arthritis severity. Results showed that 3-bromopyruvic acid significantly reduced clinical and histopathological scores of arthritis, decreased joint inflammation and cartilage damage. Arthritis Rheumatol. 2016 Jul;68(7):1614-26.
Male athymic nude mice Orthotopic xenograft model of human pancreatic ductal adenocarcinoma (PDAC) Intraperitoneal injection 5 mg/kg Daily for 4 weeks To evaluate the antitumor efficacy and toxicity of β-CD-3-BrPA in vivo. Results showed that β-CD-3-BrPA significantly inhibited tumor growth without toxicity, while free 3-BrPA exhibited high toxicity. Clin Cancer Res. 2014 Dec 15;20(24):6406-17.
Nude mice Subcutaneous xenograft model 8 mg/kg 3 weeks To evaluate the effect of MCT1 expression on tumor sensitivity to 3-BrPA, results showed MCT1 expression enhanced tumor sensitivity to 3-BrPA. Nat Genet. 2013 Jan;45(1):104-8.

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