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Chlorpyrifos-oxon

Catalog No. T40642 CAS 5598-15-2

Chlorpyrifos-oxon, an active metabolite of Chlorpyrifos, is a powerful phosphorylating agent with potent inhibition of AChE activity. It induces cross-linking between tubulin subunits and disrupts microtubule function[4].

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Chlorpyrifos-oxon, CAS 5598-15-2

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Biological Description

Chemical Properties

Storage & Solubility Information

Description	Chlorpyrifos-oxon, an active metabolite of Chlorpyrifos, is a powerful phosphorylating agent with potent inhibition of AChE activity. It induces cross-linking between tubulin subunits and disrupts microtubule function[4].
In vitro	Treatment with 1.5 mM Chlorpyrifos-oxon (CPO) induces aggregation in tubulin proteins. Remarkably, at a concentration as low as 1.5 μM, Chlorpyrifos-oxon still facilitates the formation of cross-linked trimers. This compound enhances the cross-linking of tubulin monomers through isopeptide bonds, resulting in the formation of multimers[2]. In the context of cultured PC12 cells, exposure to Chlorpyrifos at a concentration 10 times lower than that required to inhibit acetylcholinesterase (AChE) activity (3.0 μM) adversely affects neurite outgrowth. Conversely, Chlorpyrifos-oxon exhibits its inhibitory effect on neurite extension at an even lower concentration of 1.0 nM[3].
In vivo	Chlorpyrifos-oxon (CPO) undergoes rapid detoxification in human liver microsomes through CYP-dependent deethylation and dearylation, as well as glutathione-S-transferase activity. Additionally, it is efficiently degraded or scavenged by liver enzymes, including A-esterases like paraoxonase 1 (PON 1) and B-esterases such as carboxylesterase and butyrylcholinesterase (BChE). Moreover, when wild-type mice are treated with Chlorpyrifos-oxon (3 mg/kg, ip; once), it significantly affects microtubule integrity, reducing their size to approximately 60% compared to those in control mice, indicating altered amino acid covalency and compromised microtubule structure, which suggests a disruption of their function[1][4].

Molecular Weight	334.52
Formula	C9H11Cl3NO4P
CAS No.	5598-15-2

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

References and Literature

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. Toxicol Sci. 2010 May;115(1):183-93.

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Keywords

Chlorpyrifos-oxon 5598-15-2 Chlorpyrifos oxon Chlorpyrifosoxon inhibitor inhibit

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