Ch223191 is a ligand-selective antagonist of the Ah (dioxin) receptor

Toxicological Sciences

Volumn 117, Issue 2, 2010, Pages 393-403

  Zhao, Bin ^a,b   DeGroot, Danica E ^a   Hayashi, Ai ^a   He, Guochun ^a   Denison, Michael S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

2,3,7,8 tetrachlorodibenzo p dioxin; Ah receptor; Beta naphthoflavone; CH223191; TCDD

Indexed keywords

AROMATIC HYDROCARBON; AROMATIC HYDROCARBON RECEPTOR; AROMATIC HYDROCARBON RECEPTOR BLOCKING AGENT; CH 223191; FLAVONE; FLAVONOID; INDIRUBIN; POLYCYCLIC AROMATIC HYDROCARBON; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DNA BINDING; GENE EXPRESSION; HUMAN; HUMAN CELL; LIGAND BINDING; MOUSE; NONHUMAN; RAT; REPORTER GENE; SIGNAL TRANSDUCTION;

ANIMALS; AZO COMPOUNDS; BETA-NAPHTHOFLAVONE; CELL LINE; ENVIRONMENTAL POLLUTANTS; ENZYME INHIBITORS; GENE EXPRESSION; GUINEA PIGS; HUMANS; LIGANDS; MALE; MICE; PROTEIN BINDING; PYRAZOLES; RATS; RECEPTORS, ARYL HYDROCARBON; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TETRACHLORODIBENZODIOXIN;

CAVIA; RATTUS;

EID: 77956911339     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfq217     Document Type: Article

References (50)

1. Backlund, M., and Ingelman-Sundberg, M. (2004). Different structural requirements of the ligand binding domain of the aryl hydrocarbon receptor for high- and low-affinity ligand binding and receptor activation. Mol. Pharmacol. 65, 416-425.
2. Beischlag, T. V., Luis Morales, J., Hollingshead, B. D., and Perdew, G. H. (2008). The aryl hydrocarbon receptor complex and the control of gene expression. Crit. Rev. Eukaryot. Gene Expr. 18, 207-250.
3. Bradshaw, T. D., and Bell, D. R. (2009). Relevance of the aryl hydrocarbon receptor (AhR) for clinical toxicology. Clin. Toxicol. 47, 632-642.
4. Connor, C. E., Norris, J. D., Broadwater, G., Willson, T. M., Gottardis, M. M., Dewhirst, M. W., and McDonnell, D. P. (2001). Circumventing tamoxifen resistance in breast cancer cells using antiestrogens that induce unique conformational changes in the estrogen receptor. Cancer Res. 61, 2917-2922.
5. De Bosscher, K. (2010). Selective glucocorticoid receptor modulators. J. Steroid Biochem. Mol. Biol. 120, 96-104.
6. Denison, M. S., and Heath-Pagliuso, S. (1998). The Ah receptor: a regulator of the biochemical and toxicological actions of structurally diverse chemicals. Bull. Environ. Contam. Toxicol. 61, 557-568.
7. Denison, M. S., and Nagy, S. R. (2003). Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 43, 309-334.
8. Denison, M. S., Pandini, A., Nagy, S. R., Baldwin, E. P., and Bonati, L. (2002). Ligand binding and activation of the Ah receptor. Chem. Biol. Int. 141, 3-24.
9. Denison, M. S., Rogers, J. M., Rushing, S. R., Jones, C. L., Tetangco, S. C., and Heath-Pagliuso, S. (2002). Analysis of the Ah receptor signal transduction pathway. In Current Protocols in Toxicology (M. Maines, L. G. Costa, D. J. Reed, S. Sassa, and I. G. Sipes, Eds.), pp. 4.8.1-4.8.45. John Wiley and Sons, New York, NY.
10. Denison, M. S., Seidel, S. D., Rogers, W. J., Ziccardi, M., Winter, G. M., and Heath-Pagliuso, S. (1998). Natural and synthetic ligands for the Ah receptor. In Molecular Biology Approaches to Toxicology (A. Puga and K. B. Wallace, Eds.), pp. 393-410. Taylor & Francis, Philadelphia, PA.
11. DuSell, C. D., Nelson, E. R., Wittmann, B. M., Fretz, J. A., Thomas, R. S., Pike, J. W., and McDonnell, D. P. (2010). Regulation of aryl hydrocarbon receptor function by selective estrogen receptor modulators. Mol. Endocrinol. 24, 33-46.
12. DuSell, C. D., Umetani, M., Shaul, P. W., Manglesdorf, D. J., and McDonnell, D. P. (2008). 27-Hydroxycholesterol is an endogenous selective estrogen receptor modulator. Mol. Endocrinol. 22, 65-77.
13. Ellmann, S., Sticht, H., Thiel, F., Beckmann, M. W., Strick, R., and Strissel, P. L. (2009). Estrogen and progesterone receptor: from molecular structures to clinical targets. Cell Mol. Life Sci. 66, 2405-2426.
14. Esser, C., Rannug, A., and Stockinger, B. (2009). The aryl hydrocarbon receptor in immunity. Trends Immunol. 30, 447-454.
15. Furness, S. G., and Whelan, F. (2009). The pleiotropy of dioxin toxicityxenobiotic misappropriation of the aryl hydrocarbon receptor's alternative physiological roles. Pharmacol. Ther. 124, 336-354.
16. Garrison, P. M., Tullis, K., Aarts, J. M., Brouwer, A., Giesy, J. P., and Denison, M. S. (1996). Species-specific recombinant cell lines as bioassay systems for the detection of 2,3,7,8-tetrachlorodibenzo-p-dioxin-like chemicals. Fundam. Appl. Toxicol. 30, 194-203.
17. Ghosh, U., Ganessunker, D., Sattigeri, V. J., Carlson, K. E., Mortensen, D. J., Katzenellenbogen, B. S., and Katzenellenbogen, J. A. (2003). Estrogenic diazenes: heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes. Bioorg. Med. Chem. 11, 629-657.
18. Goergens, A., Frericks, M., and Esser, C. (2009). The aryl hydrocarbon receptor is only marginally involved in the antileukemic effects of its ligand curcumin. Anticancer Res. 29, 4657-4664.
19. Goryo, K., Suzuki, A., Del Carpio, C. A., Siizaki, K., Kuriyama, E., Mikami, Y., Kinoshita, K., Yasumoto, K., Rannug, A., Miyamoto, A., et al. (2007). Identification of amino aid residues in the Ah receptor involved in ligand binding. Biochem. Biophys. Res. Comm. 354, 396-402.
20. Gouédard, C., Barouki, R., and Morel, Y. (2004). Dietary polyphenols increase paraoxonase 1 gene expression by an aryl hydrocarbon receptor-dependent mechanism. Mol. Cell. Biol. 24, 5209-5222.
21. Hall, J., Barhoover, M. A., Kazmin, D., McDonnell, D. P., Greenlee, W. F., and Thomas, R. S. (2010). Activation of the aryl hydrocarbon receptor inhibits invasive and metastatic feature of human breast cancer cells and promotes breast cancer cell differentiation. Mol. Endocrinol. 24, 359-369.
22. Han, D., Nagy, S. R., and Denison, M. S. (2004). Comparison of recombinant cell bioassays for the detection of Ah receptor agonists. Biofactors 20, 11-22.
23. Han, E. H., Kim, H. G., Im, J. H., Jeong, T. C., and Jeong, H. G. (2009). Up-regulation of CYP1A1 by rutaecarpine is dependent on aryl hydrocarbon receptor and calcium. Toxicology 266, 38-47.
24. Henry, E. C., and Gasiewicz, T. A. (2008). Molecular determinants of speciesspecific agonist and antagonist activity of a substituted flavone towards the aryl hydrocarbon receptor. Arch. Biochem. Biophys. 472, 77-88.
25. Kazmin, D., Prytkova, T., Cook, C. E., Wolfinger, R., Chu, T. M., Beratan, D., Norris, J. D., Chang, C. Y., and McDonnell, D. P. (2006). Linking ligand-induced alterations in androgen receptor structure to differential gene expression: a first step in the rational design of selective androgen receptor modulators. Mol. Endocrinol. 20, 1201-1207.
26. Kewley, R. J., Whitelaw, M. L., and Chapman-Smith, A. (2004). The mammalian basic helix-loop-helix/PAS family of transcriptional regulators. Int. J. Biochem. Cell. Biol. 36, 189-204.
27. Kim, S. H., Henry, E. C., Kim, D. K., Kim, Y. H., Shin, K. J., Han, M. S., Lee, T. G., Kang, J. K., Gasiewicz, T. A., Ryu, S. H., et al. (2006). Novel compound 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-4-o-tolylazo- phenyl)amide (CH-223191) prevents 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor. Mol. Pharmacol. 69, 1871-1878.
28. Knockaert, M., Blondel, M., Bach, S., Leost, M., Elbi, C., Hager, G. L., Nagy, S. R., Han, D., Denison, M., French, M., et al. (2004). Independent actions on cyclin-dependent kinases and aryl hydrocarbon receptor mediate the antiproliferative effects of indirubins. Oncogene 23, 4400-4412.
29. Lu, Y. F., Santostefano, M., Cunningham, B. D., Threadgill, M. D., and Safe, S. (1995). Identification of 3'-methoxy-4'-nitroflavone as a pure aryl hydrocarbon (Ah) receptor antagonist and evidence for more than one form of the nuclear Ah receptor in MCF-7 human breast cancer cells. Arch. Biochem. Biophys. 316, 470-477.
30. Ma, Q. (2001). Induction of CYP1A1. The AhR/DRE paradigm: transcription, receptor regulation, and expanding biological roles. Curr. Drug Metabol. 2, 149-164.
31. Marshall, N. B., and Kerkvliet, N. I. (2010). Dioxin and immune regulation: emerging role of aryl hydrocarbon receptor in the generation of regulatory T cells. Ann. N. Y. Acad. Sci. 1183, 25-37.
32. Matikainen, T., Perez, G. I., Jurisicova, A., Pru, J. K., Schlezinger, J. J., Ryu, H. Y., Laine, J., Sakai, T., Korsmeyer, S. J., Casper, R. F., et al. (2001). Aromatic hydrocarbon receptor-driven Bax gene expression is required for premature ovarian failure caused by biohazardous environmental chemicals. Nat. Genet. 28, 355-360.
33. Murray, I. A., Flaveny, C. A., DiNatale, B. C., Chairo, C. R., Schroeder, J. C., Kusnadi, A., and Perdew, G. H. (2010a). Antagonism of aryl hydrocarbon receptor signalling by 6,2',4'-trimethoxyflavone. J. Pharmacol. Exp. Ther. 332, 135-144.
34. Murray, I. A., Morales, J. L., Flaveny, C. A., Dinatale, B. C., Chiaro, C., Gowdahalli, K., Amin, S., and Perdew, G. H. (2010b). Evidence for ligandmediated selective modulation of aryl hydrocarbon receptor activity. Mol. Pharmacol. 77, 247-254.
35. Ngan, C. H., Beglov, D., Rudnitskaya, A. N., Kozakov, D., Waxman, D. J., and Vajda, S. (2009). The structural basis of pregnane X receptor binding promiscuity. Biochemistry 48, 11572-11581.
36. Nguyen, L. P., and Bradfield, C. A. (2008). The search for endogenous activators of the aryl hydrocarbon receptor. Chem. Res. Toxicol. 21, 102-106.
37. Noy, N. (2007). Ligand specificity of nuclear hormone receptors: sifting through promiscuity. Biochemistry 46, 13461-13467.
38. Pandini, A., Denison, M. S., Song, Y., Soshilov, A. A., and Bonati, L. (2007). Structural and functional characterization of the Aryl hydrocarbon receptor ligand binding domain by homology modeling and mutational analysis. Biochemistry 46, 696-708.
39. Pandini, A., Soshilov, A. A., Song, Y., Zhao, J., Bonati, L., and Denison, M. S. (2009). Detection of the TCDD binding fingerprint within the Ah receptor ligand binding domain by structurally driven mutagenesis and functional analysis. Biochemistry 48, 5972-5983.
40. Petko, P. I., Rowlands, J. C., Budinsky, R., Zhao, B., Denison, M. S., and Mekenyan, O. (2010). Mechanism-based common reactivity pattern (COREPA) modelling of aryl hydrocarbon receptor binding affinity. SAR QSAR Environ. Res. 21, 187-214.
41. Poland, A., and Glover, E. (1980). 2,3,7,8-Tetrachlorodibenzo-p-dioxin: segregation of toxicity with the Ah locus. Mol. Pharmacol. 17, 86-94.
42. Poland, A., and Knutson, J. C. (1982). 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu. Rev. Pharmacol. Toxicol. 22, 517-554.
43. Safe, S. (1990). Polychlorinated biphenyls (PCBs), dibenzo-pdioxins (PCDDs), dibenzofurans (PCDFs), and related compounds: environmental and mechanistic considerations which support the development of toxic equivalency factors (TEFs). Crit. Rev. Toxicol. 21, 51-88.
44. Springsteel, M. F., Galietta, L. J., Ma, T., By, K., Berger, G. O., Yang, H., Dicus, C. W., Choung, W., Quan, C., Shelat, A. A., et al. (2003). Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: towards a pharmacophore model for the nucleotide-binding domain. Bioorg. Med. Chem. 11, 4113-4120.
45. van Grevenynghe, J., Bernard, M., Langouet, S., Le Berre, C., Fest, T., and Fardel, O. (2005). Human CD34-positive hematopoietic stem cells constitute targets for carcinogenic polycyclic aromatic hydrocarbons. J. Pharmacol. Exp. Ther. 314, 693-702.
46. Veldhoen, M., Hirota, K., Christensen, J., O'Garra, A., and Stockinger, B. (2009). Natural agonists for aryl hydrocarbon receptor in culture media are essential for optimal differentiation of Th17 T cells. J. Exp. Med. 206, 43-49.
47. Whelan, F., Hao, N., Furness, S. G., Whitelaw, M. L., and Chapman-Smith, A. (2010). Amino acid substitutions in the aryl hydrocarbon receptor (AhR) ligand binding domain reveal YH439 as a atypical AhR activator. Mol. Pharmacol. 77, 1037-1046.
48. Zhang, S., Lei, P., Liu, X., Li, X., Walker, K., Kotha, L., Rowlands, C., and Safe, S. (2009). The aryl hydrocarbon receptor as a target for estrogen receptor-negative breast cancer chemotherapy. Endocr. Relat. Cancer 16, 835-844.
49. Zhang, S., Rowlands, C., and Safe, S. (2008). Ligand-dependent interactions of the Ah receptor with coactivators in a mammalian two-hybrid assay. Toxicol. Appl. Pharmacol. 227, 196-206.
50. Zhou, J., and Gasiewicz, T. A. (2003). 3'-Methyl-4'-nitroflavone, a reported aryl hydrocarbon receptor antagonist, enhances Cyp1a1 transcription by a dioxin response element-dependent mechanism. Arch. Biochem. Biophys. 416, 68-80.