Similarities and differences between two modes of antagonism of the thyroid hormone receptor

ACS Chemical Biology

Volumn 6, Issue 10, 2011, Pages 1096-1106

  Sadana, Prabodh ^c   Hwang, Jong Yeon ^a   Attia, Ramy R ^a   Arnold, Leggy A ^b   Neale, Geoffrey ^a   Guy, R Kiplin ^a  

^a ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^b UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^c NORTHEAST OHIO MEDICAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOKETONE; BETA AMINOKETONE; COMPLEMENTARY DNA; DNA; SJ 000311413; THYROID HORMONE; THYROID HORMONE RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HEK293; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG RECEPTOR BINDING; GENE EXPRESSION REGULATION; HORMONE RECEPTOR INTERACTION; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL; PROMOTER REGION; REAL TIME POLYMERASE CHAIN REACTION; TRANSCRIPTION REGULATION; WESTERN BLOTTING;

CELL LINE; GENE EXPRESSION REGULATION; HEP G2 CELLS; HUMANS; KETONES; RECEPTORS, THYROID HORMONE; SIGNAL TRANSDUCTION; SULFONES; TRIIODOTHYRONINE;

EID: 80054988658     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb200092v     Document Type: Article

References (48)

1. Rodriguez, A. L., Tamrazi, A., Collins, M. L., and Katzenellenbogen, J. A. (2004) Design, synthesis, and in vitro biological evaluation of small molecule inhibitors of estrogen receptor alpha coactivator binding J. Med. Chem. 47, 600-611 (Pubitemid 38129718)
2. Parent, A. A., Gunther, J. R., and Katzenellenbogen, J. A. (2008) Blocking estrogen signaling after the hormone: pyrimidine-core inhibitors of estrogen receptor-coactivator binding J. Med. Chem. 51, 6512-6530
3. Becerril, J. and Hamilton, A. D. (2007) Helix mimetics as inhibitors of the interaction of the estrogen receptor with coactivator peptides Angew. Chem., Int. Ed. 46, 4471-4473 (Pubitemid 46954597)
4. Gunther, J. R., Parent, A. A., and Katzenellenbogen, J. A. (2009) Alternative inhibition of androgen receptor signaling: peptidomimetic pyrimidines as direct androgen receptor/coactivator disruptors ACS Chem. Biol. 4, 435-440
5. Estebanez-Perpina, E., Arnold, L. A., Nguyen, P., Rodrigues, E. D., Mar, E., Bateman, R., Pallai, P., Shokat, K. M., Baxter, J. D., Guy, R. K., Webb, P., and Fletterick, R. J. (2007) A surface on the androgen receptor that allosterically regulates coactivator binding Proc. Natl. Acad. Sci. U.S.A. 104, 16074-16079 (Pubitemid 350099366)
6. Wang, H., Li, H., Moore, L. B., Johnson, M. D., Maglich, J. M., Goodwin, B., Ittoop, O. R., Wisely, B., Creech, K., Parks, D. J., Collins, J. L., Willson, T. M., Kalpana, G. V., Venkatesh, M., Xie, W., Cho, S. Y., Roboz, J., Redinbo, M., Moore, J. T., and Mani, S. (2008) The phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane X receptor Mol. Endocrinol. 22, 838-857 (Pubitemid 351482821)
7. Huang, H., Wang, H., Sinz, M., Zoeckler, M., Staudinger, J., Redinbo, M. R., Teotico, D. G., Locker, J., Kalpana, G. V., and Mani, S. (2007) Inhibition of drug metabolism by blocking the activation of nuclear receptors by ketoconazole Oncogene 26, 258-268 (Pubitemid 46095736)
8. Arnold, L. A., Estebanez-Perpina, E., Togashi, M., Jouravel, N., Shelat, A., McReynolds, A. C., Mar, E., Nguyen, P., Baxter, J. D., Fletterick, R. J., Webb, P., and Guy, R. K. (2005) Discovery of small molecule inhibitors of the interaction of the thyroid hormone receptor with transcriptional coregulators J. Biol. Chem. 280, 43048-43055 (Pubitemid 43049270)
9. Lazar, M. A. (2003) Thyroid hormone action: a binding contract J. Clin. Invest. 112, 497-499 (Pubitemid 38056333)
10. Cooper, D. S., Greenspan, F. S., and Ladenson, P. W. (2007) The Thyroid Gland, In Greenspan's Basic and Clinical Endocrinology (Shanahan, J., Ed.) 8 th ed., pp 209-280, McGraw Hill-Medical, New York.
11. Sadana, P., Zhang, Y., Song, S., Cook, G. A., Elam, M. B., and Park, E. A. (2007) Regulation of carnitine palmitoyltransferase I (CPT-Ialpha) gene expression by the peroxisome proliferator activated receptor gamma coactivator (PGC-1) isoforms Mol. Cell. Endocrinol. 267, 6-16
12. Govindan, M., Meng, X., Denis, C. L., Webb, P., Baxter, J. D., and Walfish, P. G. (2009) Identification of CCR4 and other essential thyroid hormone receptor co-activators by modified yeast synthetic genetic array analysis Proc. Natl. Acad. Sci. U.S.A. 106, 19854-19859
13. Chen, W., Yang, Q., and Roeder, R. G. (2009) Dynamic interactions and cooperative functions of PGC-1alpha and MED1 in TRalpha-mediated activation of the brown-fat-specific UCP-1 gene Mol. Cell 35, 755-768
14. Horwitz, K. B., Jackson, T. A., Bain, D. L., Richer, J. K., Takimoto, G. S., and Tung, L. (1996) Nuclear receptor coactivators and corepressors Mol. Endocrinol. 10, 1167-1177 (Pubitemid 26330950)
15. Glass, C. K. and Rosenfeld, M. G. (2000) The coregulator exchange in transcriptional functions of nuclear receptors Genes Dev. 14, 121-141 (Pubitemid 30070977)
16. Darimont, B. D., Wagner, R. L., Apriletti, J. W., Stallcup, M. R., Kushner, P. J., Baxter, J. D., Fletterick, R. J., and Yamamoto, K. R. (1998) Structure and specificity of nuclear receptor-coactivator interactions Genes Dev. 12, 3343-3356 (Pubitemid 28520983)
17. Moore, J. M. and Guy, R. K. (2005) Coregulator interactions with the thyroid hormone receptor Mol. Cell. Proteomics 4, 475-482 (Pubitemid 40590566)
18. Hur, E., Pfaff, S. J., Payne, E. S., Gron, H., Buehrer, B. M., and Fletterick, R. J. (2004) Recognition and accommodation at the androgen receptor coactivator binding interface PLoS Biol. 2, E274
19. Heery, D. M., Kalkhoven, E., Hoare, S., and Parker, M. G. (1997) A signature motif in transcriptional co-activators mediates binding to nuclear receptors Nature 387, 733-736 (Pubitemid 27270617)
20. Arnold, L. A., Estebanez-Perpina, E., Togashi, M., Shelat, A., Ocasio, C. A., McReynolds, A. C., Nguyen, P., Baxter, J. D., Fletterick, R. J., Webb, P., and Guy, R. K. (2006) A high-throughput screening method to identify small molecule inhibitors of thyroid hormone receptor coactivator binding Sci. STKE 2006, pl3
21. Arnold, L. A., Kosinski, A., Estebanez-Perpina, E., Fletterick, R. J., and Guy, R. K. (2007) Inhibitors of the interaction of a thyroid hormone receptor and coactivators: preliminary structure-activity relationships J. Med. Chem. 50, 5269-5280 (Pubitemid 350057839)
22. Hwang, J. Y., Arnold, L. A., Zhu, F., Kosinski, A., Mangano, T. J., Setola, V., Roth, B. L., and Guy, R. K. (2009) Improvement of pharmacological properties of irreversible thyroid receptor coactivator binding inhibitors J. Med. Chem. 52, 3892-3901
23. Estebanez-Perpina, E., Arnold, L. A., Jouravel, N., Togashi, M., Blethrow, J., Mar, E., Nguyen, P., Phillips, K. J., Baxter, J. D., Webb, P., Guy, R. K., and Fletterick, R. J. (2007) Structural insight into the mode of action of a direct inhibitor of coregulator binding to the thyroid hormone receptor Mol. Endocrinol. 21, 2919-2928 (Pubitemid 350223505)
24. Nguyen, N. H., Apriletti, J. W., Cunha Lima, S. T., Webb, P., Baxter, J. D., and Scanlan, T. S. (2002) Rational design and synthesis of a novel thyroid hormone antagonist that blocks coactivator recruitment J. Med. Chem. 45, 3310-3320 (Pubitemid 34774281)
25. Busch, S. J., Barnhart, R. L., Martin, G. A., Flanagan, M. A., and Jackson, R. L. (1990) Differential regulation of hepatic triglyceride lipase and 3-hydroxy-3-methylglutaryl-CoA reductase gene expression in a human hepatoma cell line, HepG2 J. Biol. Chem. 265, 22474-22479 (Pubitemid 120014325)
26. Knowles, B. B., Howe, C. C., and Aden, D. P. (1980) Human hepatocellular carcinoma cell lines secrete the major plasma proteins and hepatitis B surface antigen Science 209, 497-499
27. Darlington, G. J., Kelly, J. H., and Buffone, G. J. (1987) Growth and hepatospecific gene expression of human hepatoma cells in a defined medium In Vitro Cell. Dev. Biol. 23, 349-354
28. Ostlund, R. E., Jr., Seemayer, R., Gupta, S., Kimmel, R., Ostlund, E. L., and Sherman, W. R. (1996) A stereospecific myo-inositol/D-chiro-inositol transporter in HepG2 liver cells. Identification with D-chiro-[3-3H]inositol J. Biol. Chem. 271, 10073-10078
29. Wilkening, S., Stahl, F., and Bader, A. (2003) Comparison of primary human hepatocytes and hepatoma cell line Hepg2 with regard to their biotransformation properties Drug Metab. Dispos. 31, 1035-1042 (Pubitemid 36975674)
30. Yen, P. M., Feng, X., Flamant, F., Chen, Y., Walker, R. L., Weiss, R. E., Chassande, O., Samarut, J., Refetoff, S., and Meltzer, P. S. (2003) Effects of ligand and thyroid hormone receptor isoforms on hepatic gene expression profiles of thyroid hormone receptor knockout mice EMBO Rep. 4, 581-587 (Pubitemid 36939949)
31. Flores-Morales, A., Gullberg, H., Fernandez, L., Stahlberg, N., Lee, N. H., Vennstrom, B., and Norstedt, G. (2002) Patterns of liver gene expression governed by TRbeta Mol. Endocrinol. 16, 1257-1268 (Pubitemid 34621074)
32. Feng, X., Jiang, Y., Meltzer, P., and Yen, P. M. (2000) Thyroid hormone regulation of hepatic genes in vivo detected by complementary DNA microarray Mol. Endocrinol. 14, 947-955 (Pubitemid 32250513)
33. Chan, I. H. and Privalsky, M. L. (2009) Isoform-specific transcriptional activity of overlapping target genes that respond to thyroid hormone receptors alpha1 and beta1 Mol. Endocrinol. 23, 1758-1775
34. Loose, D. S., Cameron, D. K., Short, H. P., and Hanson, R. W. (1985) Thyroid hormone regulates transcription of the gene for cytosolic phosphoenolpyruvate carboxykinase (GTP) in rat liver Biochemistry 24, 4509-4512 (Pubitemid 15233701)
35. Ludwig, M. G., Basset, P., and Anglard, P. (2000) Multiple regulatory elements in the murine stromelysin-3 promoter. Evidence for direct control by CCAAT/enhancer-binding protein beta and thyroid and retinoid receptors J. Biol. Chem. 275, 39981-39990 (Pubitemid 32064620)
36. Grover, G. J., Dunn, C., Nguyen, N. H., Boulet, J., Dong, G., Domogauer, J., Barbounis, P., and Scanlan, T. S. (2007) Pharmacological profile of the thyroid hormone receptor antagonist NH3 in rats J. Pharmacol. Exp. Ther. 322, 385-390 (Pubitemid 46956356)
37. Oberste-Berghaus, C., Zanger, K., Hashimoto, K., Cohen, R. N., Hollenberg, A. N., and Wondisford, F. E. (2000) Thyroid hormone-independent interaction between the thyroid hormone receptor beta2 amino terminus and coactivators J. Biol. Chem. 275, 1787-1792 (Pubitemid 30060800)
38. Tang, H. Y., Lin, H. Y., Zhang, S., Davis, F. B., and Davis, P. J. (2004) Thyroid hormone causes mitogen-activated protein kinase-dependent phosphorylation of the nuclear estrogen receptor Endocrinology 145, 3265-3272 (Pubitemid 38829999)
39. Hiroi, Y., Kim, H. H., Ying, H., Furuya, F., Huang, Z., Simoncini, T., Noma, K., Ueki, K., Nguyen, N. H., Scanlan, T. S., Moskowitz, M. A., Cheng, S. Y., and Liao, J. K. (2006) Rapid nongenomic actions of thyroid hormone Proc. Natl. Acad. Sci. U.S.A. 103, 14104-14109 (Pubitemid 44452987)
40. Koenig, R. J., Brent, G. A., Warne, R. L., Larsen, P. R., and Moore, D. D. (1987) Thyroid hormone receptor binds to a site in the rat growth hormone promoter required for induction by thyroid hormone Proc. Natl. Acad. Sci. U.S.A. 84, 5670-5674
41. Shah, V., Nguyen, P., Nguyen, N. H., Togashi, M., Scanlan, T. S., Baxter, J. D., and Webb, P. (2008) Complex actions of thyroid hormone receptor antagonist NH-3 on gene promoters in different cell lines Mol. Cell. Endocrinol. 296, 69-77
42. Lapp, C. A., Stachura, M. E., Tyler, J. M., and Lee, Y. S. (1987) GH3 cell secretion of growth hormone and prolactin increases spontaneously during perifusion In Vitro Cell. Dev. Biol. 23, 686-690
43. Miller, M. J., Fels, E. C., Shapiro, L. E., and Surks, M. I. (1987) L-triiodothyronine stimulates growth by means of an autocrine factor in a cultured growth-hormone-producing cell line J. Clin. Invest. 79, 1773-1781 (Pubitemid 17117285)
44. Kitamura, S., Jinno, N., Ohta, S., Kuroki, H., and Fujimoto, N. (2002) Thyroid hormonal activity of the flame retardants tetrabromobisphenol A and tetrachlorobisphenol A Biochem. Biophys. Res. Commun. 293, 554-559 (Pubitemid 34694244)
45. Schriks, M., Vrabie, C. M., Gutleb, A. C., Faassen, E. J., Rietjens, I. M., and Murk, A. J. (2006) T-screen to quantify functional potentiating, antagonistic and thyroid hormone-like activities of poly halogenated aromatic hydrocarbons (PHAHs) Toxicol. in Vitro 20, 490-498
46. Davis, P. J., Davis, F. B., and Cody, V. (2005) Membrane receptors mediating thyroid hormone action Trends Endocrinol Metab 16, 429-435 (Pubitemid 41506950)
47. Durbin, B. P., Hardin, J. S., Hawkins, D. M., and Rocke, D. M. (2002) A variance-stabilizing transformation for gene-expression microarray data Bioinformatics 18 (Suppl 1) S105-110
48. Benjamini, Y. and Hochberg, Y. (1995) Controlling the false discovery rate - a practical and powerful approach to multiple testing J. R. Stat. Soc. Ser. B, Methodol. 57, 289-300