[CAS NO. 5598-15-2] Chlorpyrifos-oxon
PRODUCTS SPECIFICATIONS [5598-15-2]
DESCRIPTION [5598-15-2]
Overview
| MDL | - |
|---|---|
| Molecular Weight | 334.52 |
| Molecular Formula | C9H11Cl3NO4P |
| SMILES | O=P(OCC)(OC1=NC(Cl)=C(Cl)C=C1Cl)OCC |
Summary
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]
.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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]
.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Appearance
<43°C Solid,>53°C Liquid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
-20°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Solvent & Solubility
DMSO : 100 mg/mL ( 298.94 mM ; Need ultrasonic)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 2.9894 mL | 14.9468 mL | 29.8936 mL |
| 5 mM | 0.5979 mL | 2.9894 mL | 5.9787 mL |
| 10 mM | 0.2989 mL | 1.4947 mL | 2.9894 mL |
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References
- [1] Florian Eyer, et al. Extreme variability in the formation of chlorpyrifos oxon (CPO) in patients poisoned by chlorpyrifos (CPF). Biochem Pharmacol. 2009 Sep 1;78(5):531-7.
- [2] Lawrence M Schopfer, et al. Chlorpyrifos oxon promotes tubulin aggregation via isopeptide cross-linking between diethoxyphospho-Lys and Glu or Asp: Implications for neurotoxicity. J Biol Chem. 2018 Aug 31;293(35):13566-13577.
- [3] Jie Gao, et al. Chlorpyrifos and chlorpyrifos oxon impair the transport of membrane bound organelles in rat cortical axons. Neurotoxicology. 2017 Sep;62:111-123.
- [4] Wei Jiang, et al. Mice treated with chlorpyrifos or chlorpyrifos oxon have organophosphorylated tubulin in the brain and disrupted microtubule structures, suggesting a role for tubulin in neurotoxicity associated with exposure to organophosphorus agents.
