Bromopyruvic acid - 10mM in DMSO , CAS No.1113-59-3

CAS: 1113-59-3 Cat. No.: B420621 Formula: C₃H₃BrO₃ Peso molecolare: 166.96 Beilstein Registry Number: 1746786 Numero EC: 214-206-5

GRADE & PURITY 10mM in DMSO

Synonyms

AS-16146 | B1153 | 3-bromopyruvic acid | bromo-2-oxopropanoic acid | bromopyruvic acid | Bromopyruvic acid, >=97.0% (T) | J-650255 | 3-bromopyruvate | BPV | J-511892 | 3-bromo-2-oxopropanoic acid | AKOS015892643 | AM84337 | EINECS 214-206-5 | 3-BP | 3-BrP

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

3-Bromopyruvic acid is a brominated derivative of pyruvic acid , which inhibits HXK II (hexokinase II) in cancer cells. As a result of this inhibition the cells are unable to metabolize glucose into ATP directly. Studies conducted on MCF-7 breast cancer cells show that 3-Bromopyruvic acid hydrate reduces the expression of Bcl-2, c-Myc and mutant p53, which are involved in the cell death signal transduction pathway. Alternate studies indicate that 3-Bromopyruvic acid hydrate is a very selective antibiotic, inhibiting the growth of certain yeasts.
Affinity label for cysteine residues; Cross-linker between nucleic acids and proteins

Specifications

Sinonimi

AS-16146 | B1153 | 3-bromopyruvic acid | bromo-2-oxopropanoic acid | bromopyruvic acid | Bromopyruvic acid, >=97.0% (T) | J-650255 | 3-bromopyruvate | BPV | J-511892 | 3-bromo-2-oxopropanoic acid | AKOS015892643 | AM84337 | EINECS 214-206-5 | 3-BP | 3-BrP

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Hexokinase II inhibitor. Antitumor agent. Inhibits glutathione S-transferase and SOD. Pyruvic acid derivative. Induces oxidative stress. Induces S and G2/M cell cycle arrest. Shows antiproliferative effects. Shows antitumor and antimicrobial

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Tipo di azione

INHIBITOR

Nomi e identificatori

• Pubchem Sid: 528772984
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/528772984
• Sorrisi canonici: C(C(=O)C(=O)O)Br
• IUPAC Name: 3-bromo-2-oxopropanoic acid
• InChIKey: PRRZDZJYSJLDBS-UHFFFAOYSA-N
• INCHI: 1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
• Isomeri SMILES: C(C(=O)C(=O)O)Br
• WGK Germania: 3
• RTECS: UZ0840000
• Peso molecolare: 166.96
• Beilstein: 1746786
• Reaxy-Rn: 1746786
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1746786&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Keto acids and derivatives
      • Subclass Alpha-keto acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Keto acids and derivatives
• Subclass: Alpha-keto acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Alpha-keto acids and derivatives
• Alternative Parents: Alpha-hydroxy ketones Alpha-haloketones Monocarboxylic acids and derivatives Carboxylic acids Organobromides Organic oxides Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-keto acid - Alpha-haloketone - Alpha-hydroxy ketone - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organobromide - Organohalogen compound - Carbonyl group - Organic oxide - Organic oxygen compound - Alkyl halide - Alkyl bromide - Hydrocarbon derivative - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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rep Replicase polyprotein 1ab (378 Activities)

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icl1 Isocitrate lyase 1 (45 Activities)

Discover Target: icl1

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Sensibilità: Air Sensitive,Hygroscopic,Heat Sensitive
• Punto di fusione (°C): 77°C
• Peso molecolare: 166.960 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.927 Da
• Monoisotopic Mass: 165.927 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 98.400
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Riferimenti

1. Xuan Meng, Lin Wang, Ning Zhao, Delong Zhao, Yongli Shen, Yuan Yao, Wenjie Jing, Shuli Man, Yujie Dai, Yanjun Zhao.  (2023)  Stimuli-responsive cancer nanomedicines inhibit glycolysis and impair redox homeostasis.  Acta Biomaterialia,      [PMID:37343908] [10.1016/j.actbio.2023.06.016]

2. Yongli Shen, Lin Wang, Binglong Ji, Xinlei Lu, Delong Zhao, Yujie Dai, Xuan Meng.  (2024)  Stimulus-responsive nanomedicine mediated by metabolic intervention mechanisms to amplify redox anticancer therapy.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.150130]

3. Gongyuan Zhang, Tom Albrow-Owen, Wenjun Peng, Xin Liang, Xianming Zhang, Pan Wang, Dawei Di, Shurong Dong, Jikui Luo, Guo Wang, Hongfeng Mu, Qian Zhao, Xuhan Guo, Qi Jie Wang, Tawfique Hasan, Zongyin Yang.  (2025)  Stress-engineered ultra-broadband spectrometers.  Science Advances,  11  (20):   [PMID:40367181] [10.1126/sciadv.adu4225]

4. Chao Liu, Yanqiao Ren, Can Hong, Xuyu Li, Mengqing Guo, Le Zhao, Yan Liu, Chuansheng Zheng, Xiangliang Yang, Yanbing Zhao.  (2026)  Radiofrequency-responsive liposomal hydrogels loaded 3-bromopyruvate energizes artery embolization on liver cancer.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2026.174632]

5. Tu Maopu, Deng Xiaoyu, Zhou Zhiyong, Li Xiaodong, Mao Shengxun, Lai Bin, Pang Lisong, Zhong Qilin, Cao Jiaqing, Liu Haipeng, Ouyang Xi.  (2026)  Multifunctional copper-based nanoparticles potentiate colorectal cancer immunotherapy via synergistic metabolic remodeling and cGAS-STING pathway activation.  JOURNAL OF NANOBIOTECHNOLOGY,      [PMID:41796309] [10.1186/s12951-026-04267-8]