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Merck

T1443

TCPOBOP

≥98% (HPLC), CAR agonist, solid

Synonym(s):

1,4-Bis-[2-(3,5-dichloropyridyloxy)]benzene, 3,3′,5,5′-Tetrachloro-1,4-bis(pyridyloxy)benzene

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About This Item

Empirical Formula (Hill Notation):
C16H8N2O2Cl4
CAS Number:
76150-91-9
Molecular Weight:
402.06
UNSPSC Code:
12352200
PubChem Substance ID:
24278723
NACRES:
NA.77
MDL number:
MFCD00057368

Key Documents

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Product Name

TCPOBOP, ≥98% (HPLC), solid

SMILES string

Clc1cnc(Oc2ccc(Oc3ncc(Cl)cc3Cl)cc2)c(Cl)c1

InChI key

BAFKRPOFIYPKBQ-UHFFFAOYSA-N

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

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... NR1I3(9970)

Related Categories

Application

TCPOBOP has been used for enhancing Mcl-1-Italics promoter functions in mouse hepatoma cells. TCPOBOP has also been used to study constitutive androstane receptor(CAR)-induced gene expression in mouse hepatocytes.

Biochem/physiol Actions

TCPOBOP enhances the nuclear receptor CAR transactivation of cytochrome P450 (CYP), as dose-dependent direct agonist of CAR.
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.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

TCPOBOP is soluble in DMSO at a concentration that is greater than 10 mg/ml. It is insoluble in water.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000166349
0000142615
0000142615
0000166349
0000128888

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Christopher Reed et al.
The American journal of pathology, 184(6), 1853-1859 (2014-04-15)
Diverse etiologic events are associated with the development of hepatocellular carcinoma. During hepatocarcinogenesis, genetic events likely occur that subsequently cooperate with long-term exposures to further drive the progression of hepatocellular carcinoma. In this study, the frequent loss of the retinoblastoma
Nicholas J Lodato et al.
Toxicological sciences : an official journal of the Society of Toxicology, 164(1), 115-128 (2018-04-05)
Activation of the nuclear receptor and transcription factor CAR (Nr1i3) by its specific agonist ligand TCPOBOP (1, 4-bis[2-(3, 5-dichloropyridyloxy)]benzene) dysregulates hundreds of genes in mouse liver and is linked to male-biased hepatocarcinogenesis. To elucidate the genomic organization of CAR-induced gene
Andrei A Yarushkin et al.
European journal of pharmacology, 879, 173135-173135 (2020-04-28)
It is well known that activating the constitutive androstane receptor (CAR, NR1I3) leads to a significant proliferation of liver cells, which suggests that NR1I3 could be a therapeutic target for the partial resection of this organ. Studies describing NR1I3-mediated proliferative
Savvina Moustafa et al.
Journal of virology, 92(9) (2018-02-16)
Viruses often encompass overlapping reading frames and unconventional translation mechanisms in order to maximize the output from a minimum genome and to orchestrate their timely gene expression. Hepatitis C virus (HCV) possesses such an unconventional open reading frame (ORF) within
Sandra Mattu et al.
Journal of hepatology, 64(4), 891-898 (2015-12-15)
l-2-Hydroxy acid oxidases are flavin mononucleotide-dependent peroxisomal enzymes, responsible for the oxidation of l-2-hydroxy acids to ketoacids, resulting in the formation of hydrogen peroxide. We investigated the role of HAO2, a member of this family, in rat, mouse and human
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