TCPOBOP

Product NameTCPOBOP
CAS76150-91-9
MFC16H8Cl4N2O2
MW402.06
EINECS
MOL File76150-91-9.mol

Chemical Properties

Boiling point	444.8±45.0 °C(Predicted)
Density	1.518±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: >10 mg/mL
pka	-0.52±0.10(Predicted)
form	solid
color	white
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 week.
InChI	1S/C16H8Cl4N2O2/c17-9-5-13(19)15(21-7-9)23-11-1-2-12(4-3-11)24-16-14(20)6-10(18)8-22-16/h1-8H
InChIKey	BAFKRPOFIYPKBQ-UHFFFAOYSA-N
SMILES	Clc1cnc(Oc2ccc(Oc3ncc(Cl)cc3Cl)cc2)c(Cl)c1

Safety Information

Safety Statements	22-24/25
WGK Germany	3
RTECS	UT7145000
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

TCPOBOP (76150-91-9) is an activator of the mouse constitutive androstane receptor (mCAR) and human Preganane X receptor.1 Tumor promoter of mouse hepatocarcinogenesis.

Uses

TCPOBOP is an agonist for mCAR, inducing cytochrome P450 monooxygenases and multidrug resistance and cenobiotic efflux proteins.

General Description

A highly potent inducer of phenobarbital-like class of cytochrome P450 (CYP) enzymes. A tumor promoter that induces hepatocyte proliferation, independent of the presence of cytokines or transcription factors. Activates orphan nuclear receptors mCAR (mouse constitutive androstane receptor) and hPXR (human pregane X receptor), but has little or no effect on hCAR and mPXR. Also suppresses the expression of multi-drug resistance genes mdr2 and mdr3 in mouse liver.

Biochem/physiol Actions

TCPOBOP enhances the nuclear receptor CAR transactivation of cytochrome P450 (CYP), as dose-dependent direct agonist of CAR. The most potent known member of the phenobarbital-like class of CYP-inducing agents.

in vivo

TCPOBOP (oral; 3 mg/kg; 1-5 days) remarkable increases Liver weight to body weight in LW/BW ratio at 48 hours^[1].

Animal Model:	MET^fl/fl: Tam-Cre^+/+ mice with a targeted deletion for exon 16 with MET KO^[1]
Dosage:	3 mg/kg
Administration:	Oral; 1, 2, 5 days
Result:	Increased Liver weight to body weight.

IC 50

Bcl-2

References

[1] I TZAMELI. The xenobiotic compound 1,4-bis[2-(3,5-dichloropyridyloxy)]benzene is an agonist ligand for the nuclear receptor CAR.[J]. Molecular and Cellular Biology, 2000, 20 9: 2951-2958. DOI:10.1128/mcb.20.9.2951-2958.2000
[2] B A DIWAN. Tumor-promoting and hepatocarcinogenic effects of 1,4-bis[2-(3,5-dichloropyridyloxy)]benzene (TCPOBOP) in DBA/2NCr and C57BL/6NCr mice and an apparent promoting effect on nasal cavity tumors but not on hepatocellular tumors in F344/NCr rats initiated with N-nitrosodiethylamine.[J]. Carcinogenesis, 1992, 13 10: 1893-1901. DOI:10.1093/carcin/13.10.1893

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