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
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
Masayoshi Onuki et al.
International immunology, 31(4), 251-262 (2018-12-28)
Inflammatory bowel disease (IBD), including ulcerative colitis and Crohn's disease, is an intractable disease of the gastrointestinal tract. Multiple environmental factors, including food ingredients, have been implicated in the development of these diseases. For example, animal fat-rich diets are predisposing
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
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