Chlorpyrifos Oxon
Names
Biological Activity
[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].
[Related Catalog]:
[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].
[References]
Chemical & Physical Properties
[ Density]:
1.461g/cm3
[ Boiling Point ]:
357.8ºC at 760mmHg
[ Molecular Formula ]:
C9H11Cl3NO4P
[ Molecular Weight ]:
334.52100
[ Flash Point ]:
170.2ºC
[ Exact Mass ]:
332.94900
[ PSA ]:
67.46000
[ LogP ]:
4.60170
[ Index of Refraction ]:
1.523
[ Storage condition ]:
0-6°C
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- TC2370100
- CHEMICAL NAME :
- Phosphoric acid, diethyl 3,5,6-trichloro-2-pyridyl ester
- CAS REGISTRY NUMBER :
- 5598-15-2
- LAST UPDATED :
- 199612
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C9-H11-Cl3-N-O4-P
- MOLECULAR WEIGHT :
- 334.53
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 135 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB85-143766
Safety Information
[ Hazard Codes ]:
T+
[ RIDADR ]:
UN 2783
[ Packaging Group ]:
III
[ Hazard Class ]:
6.1(b)