Conoidin A

Names

[ Name ]:
Conoidin A

[Synonym ]:
2,3-bis(bromomethyl)quinoxaline-1,4-dioxide
quinoxaline, 2,3-bis(bromomethyl)-, 1,4-dioxide
Quinoxalinium, 2,3-bis(bromomethyl)-1,4-dihydro-4-hydroxy-1-oxo-, inner salt
2,3-Bis-bromomethyl-quinoxaline 1,4-dioxide
2,3-Bis(bromomethyl)-1-oxoquinoxalin-1-ium-4(1H)-olate
2,3-Bis-brommethyl-chinoxalin-1,4-dioxid

Biological Activity

[Description]:

Conoidin A is a cell permeable inhibitor of T. gondii enzyme peroxiredoxin II (TgPrxII) with nematicidal properties. Conoidin A covalently binds to the peroxidatic Cys47 of TgPrxII, irreversibly inhibiting its hyperperoxidation activity with an IC50 of 23 µM. Conoidin A also inhibits hyperoxidation of mammalian PrxI and PrxII (but not PrxIII)[1][2]. Conoidin A has antioxidant, neuroprotective effects and can be used for the research of ischaemic heart disease[3].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Research Areas >> Infection

Research Areas >> Neurological Disease

[Target]

IC50: 23 µM (T. gondii enzyme peroxiredoxin II (TgPrxII))[1]

[In Vitro]

Peroxiredoxins are a widely conserved family of enzymes that function in antioxidant defense and signal transduction. And the changes in PrxII expression are associated with a variety of human diseases, including cancer[1]. Conoidin A binds to the peroxidatic cysteine of TgPrxII, inhibiting its enzymatic activity in vitro. Conoidin A also shown to alkylate or crosslink catalytic cysteines of wild type AcePrx-1 in Ancylostoma ceylanicum and human PrxII and PrxIV with similar efficiency. But it is ineffective to mitochondrial hPrxIII[2]. Conoidin A (5 µM) can inhibit the glucose oxidase-mediated hyperoxidation of mammalian peroxiredoxin I and II[2].

[In Vivo]

Conoidin A (intraperitoneal injection; 5 mg/kg; for three successive days before MI/R injury) blocks the effect of Luteolin (HY-N0162) on the ST‐segment elevation. Furthermore, an increase in the infarct size presented of the MI/R group can be reduced by Luteolin. But pre‐treatment with conoidin A abolishs the effect of Luteolin. Pre‐treatment with conoidin A also prevents Luteolin-reduced activities of CK‐MB, AST and LDH in vivo[3]. Animal Model: Rat myocardial I/R model[3] Dosage: 5 mg/kg Administration: Intraperitoneal injection; 5 mg/kg; for three successive days before MI/R injury Result: Significantly reversed the antioxidative effect of Luteolin. Impaired the protective effects of luteolin.

[References]

[1]. Jeralyn D Haraldsen, et al. IDENTIFICATION OF CONOIDIN A AS A COVALENT INHIBITOR OF PEROXIREDOXIN II. Org Biomol Chem. 2009;7:3040-3048.

[2]. Gu Liu, et al. Optimisation of conoidin A, a peroxiredoxin inhibitor. ChemMedChem. 2010 Jan;5(1):41-5.

[3]. Bo Wei, et al. Luteolin ameliorates rat myocardial ischaemia-reperfusion injury through activation of peroxiredoxin II. Br J Pharmacol

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₀H₈Br₂N₂O₂

[ Molecular Weight ]:
347.991

[ Exact Mass ]:
345.895233

[ PSA ]:
50.92000

[ LogP ]:
3.48660

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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