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T1443

Sigma-Aldrich

TCPOBOP

≥98% (HPLC), 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
MDL number:
MFCD00057368
UNSPSC Code:
12352200
PubChem Substance ID:
24278723
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

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

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

InChI key

BAFKRPOFIYPKBQ-UHFFFAOYSA-N

Gene Information

human ... NR1I3(9970)

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. 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Albert Braeuning et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(5), 1138-1145 (2009-02-25)
Basal as well as xenobiotic-induced expression of the main enzymes from phase I and phase II of drug metabolism is confined to the perivenous areas of the mammalian liver lobule. Whereas signal transduction pathways that govern xenobiotic-induced expression of these
Edwina S Baskin-Bey et al.
Hepatology (Baltimore, Md.), 44(1), 252-262 (2006-06-27)
The constitutive androstane receptor (CAR) modulates xeno- and endobiotic hepatotoxicity by regulating detoxification pathways. Whether activation of CAR may also protect against liver injury by directly blocking apoptosis is unknown. To address this question, CAR wild-type (CAR+/+) and CAR knockout
Yong Chun Chong et al.
Hepatology communications, 4(9), 1362-1381 (2020-09-15)
Tumor-specific metabolic rewiring, acquired to confer a proliferative and survival advantage over nontransformed cells, represents a renewed focus in cancer therapy development. Hepatocellular carcinoma (HCC), a malignancy that has hitherto been resistant to compounds targeting oncogenic signaling pathways, represents a
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