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:
Molecular Weight:
402.06
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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
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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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
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
Edina Bugyik et al.
International journal of experimental pathology, 93(2), 125-129 (2012-01-17)
The proliferative response of hepatocytes in vivo can be induced by two mechanisms: severe damage to hepatic tissue results in regenerative growth and so-called primary hepatocyte mitogens can initiate liver cell proliferation without preceding loss of parenchyma. The regulation of
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
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