TCPOBOP is an agonist of the constitutive androstane receptor (CAR) (EC50 = 20 nM). 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. 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.
| Catalog Number | R015088 |
| CAS Number | 76150-91-9 |
| Synonyms | 1,4-Bis(3,5-dichloro-2-pyridyloxy)benzene; 1,4-Bis[2-(3,5-dichloropyridyloxy)]benzene; |
| Molecular Formula | C16H8Cl4N2O2 |
| Purity | ≥95% |
| Target | Androgen Receptor |
| Solubility | Soluble in DMSO > 10 mM |
| Storage | Store at +4C |
| IUPAC Name | 3,5-dichloro-2-[4-(3,5-dichloropyridin-2-yl)oxyphenoxy]pyridine |
| InChI | 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 | C1=CC(=CC=C1OC2=C(C=C(C=N2)Cl)Cl)OC3=C(C=C(C=N3)Cl)Cl |
| Reference | </br>1:Identification of Candidate Target Cyp Genes for microRNAs Whose Expression Is Altered by PCN and TCPOBOP, Representative Ligands of PXR and CAR. Moriya N, Kataoka H, Nishikawa J, Kugawa F.Biol Pharm Bull. 2016 Aug 1;39(8):1381-6. doi: 10.1248/bpb.b16-00279. Epub 2016 May 24. PMID: 27237601 Free Article</br>2:Expression of c-jun is not mandatory for mouse hepatocyte proliferation induced by two nuclear receptor ligands: TCPOBOP and T3. Leoni VP, Ledda-Columbano GM, Pibiri M, Saliba C, Perra A, Kowalik MA, Grober OM, Ravo M, Weisz A, Locker J, Ghiso E, Giordano S, Columbano A.J Hepatol. 2011 Nov;55(5):1069-78. doi: 10.1016/j.jhep.2011.02.016. Epub 2011 Feb 25. PMID: 21354444 </br>3:The primary mitogen (TCPOBOP)-induced hepatocyte proliferation is resistant to transforming growth factor- β-1 inhibition. Turányi E, Dezso K, Bugyik E, Szurián K, Paku S, Nagy P.Liver Int. 2010 Nov;30(10):1505-10. doi: 10.1111/j.1478-3231.2010.02324.x. Epub 2010 Sep 8. PMID: 21040405 </br>4:Constitutive androstane receptor agonist, TCPOBOP, attenuates steatohepatitis in the methionine choline-deficient diet-fed mouse. Baskin-Bey ES, Anan A, Isomoto H, Bronk SF, Gores GJ.World J Gastroenterol. 2007 Nov 14;13(42):5635-41. PMID: 17948939 Free PMC Article</br>5:Constitutive androstane receptor (CAR) ligand, TCPOBOP, attenuates Fas-induced murine liver injury by altering Bcl-2 proteins. Baskin-Bey ES, Huang W, Ishimura N, Isomoto H, Bronk SF, Braley K, Craig RW, Moore DD, Gores GJ.Hepatology. 2006 Jul;44(1):252-62. PMID: 16799968 </br>6:Aging does not reduce the hepatocyte proliferative response of mice to the primary mitogen TCPOBOP. Ledda-Columbano GM, Pibiri M, Cossu C, Molotzu F, Locker J, Columbano A.Hepatology. 2004 Oct;40(4):981-8. PMID: 15382178 </br>7:Sex difference in the proliferative response of mouse hepatocytes to treatment with the CAR ligand, TCPOBOP. Ledda-Columbano GM, Pibiri M, Concas D, Molotzu F, Simbula G, Cossu C, Columbano A.Carcinogenesis. 2003 Jun;24(6):1059-65. Epub 2003 Apr 24. PMID: 12807759 </br>8:Increased expression of c-fos, c-jun and LRF-1 is not required for in vivo priming of hepatocytes by the mitogen TCPOBOP. Columbano A, Ledda-Columbano GM, Pibiri M, Piga R, Shinozuka H, De Luca V, Cerignoli F, Tripodi M.Oncogene. 1997 Feb 20;14(7):857-63. PMID: 9047393 Free Article</br>9:Dose-response relationships for the induction of P450 2B by 1,4-bis[2-(3,5-dichloropyridyloxy)]benzne (TCPOBOP) in rat and cultured rat hepatocytes. Nims RW, Sinclair PR, Sinclair JF, Dragnev KH, Jones CR, Mellini DW, Thomas PE, Lubet RA.Xenobiotica. 1993 Dec;23(12):1411-26. Erratum in: Xenobiotica 1994 Mar;24(3):292. PMID: 7510916 </br>10: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. Diwan BA, Lubet RA, Ward JM, Hrabie JA, Rice JM.Carcinogenesis. 1992 Oct;13(10):1893-901. PMID: 1330346 |
