1. Neuronal Signaling
  2. AChE
  3. Chlorpyrifos-oxon

Chlorpyrifos-oxon 

Cat. No.: HY-136610
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Chlorpyrifos-oxon, an active metabolite of Chlorpyrifos, is a potent phosphorylating agent that potently inhibits AChE. Chlorpyrifos-oxon can induce cross-linking between subunits of tubulin and disrupt microtubule function.

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Chlorpyrifos-oxon Chemical Structure

Chlorpyrifos-oxon Chemical Structure

CAS No. : 5598-15-2

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Description

Chlorpyrifos-oxon, an active metabolite of Chlorpyrifos, is a potent phosphorylating agent that potently inhibits AChE. Chlorpyrifos-oxon can induce cross-linking between subunits of tubulin and disrupt microtubule function[1][2][3][4].

In Vitro

Treatment of tubulin with 1.5 mM Chlorpyrifos-oxon (CPO) leads to protein aggregation. However, even at 1.5 μM Chlorpyrifos-oxon cross-linked trimers are apparent. Chlorpyrifos-oxon promotes isopeptide bond cross-linking of tubulin monomers to make multimers[2].
In PC12 cells in culture, 24 hours of exposure to Chlorpyrifos at a concentration 10-fold below the concentration that inhibits AChE activity (3.0 μM) impaired neurite outgrowth while Chlorpyrifos-oxon inhibits neurite outgrowth at 1.0 nM[3].

In Vivo

Chlorpyrifos-oxon (CPO) is rapidly detoxified by human liver microsomes via CYP-dependent deethylation and dearylation, and by glutathione-S-transferase. In addition, reactions with A-esterases such as paraoxonase 1 (PON 1) or B-esterases such as carboxylesterase and butyrylcholinesterase (BChE) in the liver may rapidly degrade or scavenge Chlorpyrifos-oxon[1].
Chlorpyrifos-oxon (3 mg/kg, ip; once; wild-type mice) treatment shows the dimensions of microtubules from Chlorpyrifos-oxon-treated mice are about 60% of those from control mice. The microtubules from mice exposed to Chlorpyrifos-oxon have covalently modified amino acids and abnormal structure, suggesting disruption of microtubule function[4].

Molecular Weight

334.52

Formula

C₉H₁₁Cl₃NO₄P

CAS No.

5598-15-2

SMILES

O=P(OCC)(OC1=NC(Cl)=C(Cl)C=C1Cl)OCC

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Keywords:

Chlorpyrifos-oxonAChEAcetylcholinesteraseChlorpyrifosphosphorylatingmetaboliteacetylcholinesteraseCYP2B6pesticidetubulinaggregationcross-linkingInhibitorinhibitorinhibit

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