5.30746

Peroxiredoxin Inhibitor, Conoidin A

• Synonym(s): Peroxiredoxin Inhibitor, Conoidin A, 2,3- bis(Bromomethyl)quinoxaline-1,4-dioxide, Prx Inhibitor, 2,3-bis(Bromomethyl)quinoxaline-1,4-dioxide, Prx Inhibitor
• Empirical Formula (Hill Notation): C₁₀H₈Br₂N₂O₂
• CAS Number: 18080-67-6
• Molecular Weight: 347.99
• MDL number: MFCD00186742
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥95% (NMR)
• Form: solid
• Storage condition: OK to freeze, desiccated, protect from light

Properties

• assay: ≥95% (NMR)
• Quality Segment: 100
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, desiccated, protect from light
• color: yellow-brown
• solubility: DMSO: 50 mg/mL
• storage temp.: −20°C
• SMILES string: BrCC1=C(N(c2c(cccc2)[N+]1=O)[O-])CBr
• InChI: 1S/C10H8Br2N2O2/c11-5-9-10(6-12)14(16)8-4-2-1-3-7(8)13(9)15/h1-4H,5-6H2
• InChI key: DQKNFTLRMZOAMG-UHFFFAOYSA-N

Description

General description

A cell-permeable dibromomethylquinoxaline-dioxide compound with nematicidal properties that covalently binds to the peroxidatic cysteine of peroxiredoxin II in Toxoplasma gondii (TgPrxII) and irreversibly blocks its hyperperoxidation activity (IC₅₀ = 23 µM). Also shown to alkylate or crosslink catalytic cysteines of wild type AcePrx-1 in Ancylostoma ceylanicum and human PrxII and PrxIV to inhibit their catalytic activity with similar efficiency. Ineffective towards mitochondrial hPrxIII.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Peroxiredoxin

Reversible: no

Target IC₅₀: 23 µM for blocking TgPrxII hyperperoxidation activity

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-70°C). Stock solutions are stable for up to 2 weeks at -70°C.

Use only fresh DMSO for reconstitution.

Other Notes

Nguyen, J.B., et al. 2013. Chem. Biol.20, 991.
Haraldsen, J. D., et al. 2009. Org. Biomol. Chem.7, 3040.
Carey, K.L., et al. 2004. Proc. Natl. Acad. Sci. USA101, 7433.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• hcodes: H413
• pcodes: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable