Inhibitors of the interaction of a thyroid hormone receptor and coactivators: Preliminary structure-activity relationships

Journal of Medicinal Chemistry

Volumn 50, Issue 22, 2007, Pages 5269-5280

  Arnold, Leggy A ^a   Kosinski, Aaron ^a   Estébanez Perpiñá, Eva ^b   Fletterick, Robert J ^b   Guy, R Kiplin ^a  

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

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (DIMETHYLAMINO) 1 (4 HEXYLPHENYL)PROPAN 1 ONE; BETA AMINOPHENYLKETONE DERIVATIVE; MOLECULAR INTERACTION INHIBITOR; THYROID HORMONE RECEPTOR; THYROID HORMONE RECEPTOR COACTIVATOR INTERACTION INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; CELL MEMBRANE PERMEABILITY; CELL VIABILITY; CONTROLLED STUDY; CORRELATION ANALYSIS; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; GENE CONTROL; HUMAN; HUMAN CELL; MOLECULAR INTERACTION; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

ACRYLAMIDES; ACRYLATES; BINDING, COMPETITIVE; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; KETONES; MEMBRANES, ARTIFICIAL; MODELS, MOLECULAR; NUCLEAR RECEPTOR COACTIVATOR 2; PEPTIDES; PERMEABILITY; PROTEIN ISOFORMS; SOLUBILITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THYROID HORMONE RECEPTORS ALPHA; THYROID HORMONE RECEPTORS BETA;

EID: 35848969820     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070556y     Document Type: Article

References (36)

1. Yen, P. M. Physiological and molecular basis of thyroid hormone action. Physiol. Rev. 2001, 81 (3), 1097-1142.
2. Malm, J. Thyroid hormone ligands and metabolic diseases. Curr. Pharm. Des. 2004, 10, (28), 3525-3532.
3. Aranda, A.; Pascual, A. Nuclear hormone receptors and gene expression. Physiol. Rev. 2001, 81 (3), 1269-1304.
4. Harvey, C. B.; Williams, G. R. Mechanism of thyroid hormone action. Thyroid 2002, 12 (6), 441-446.
5. Williams, G. R. Cloning and characterization of two novel thyroid hormone receptor beta isoforms. Mol. Cell Biol. 2000, 20 (22), 8329-8342.
6. Mangelsdorf, D. J.; Thummel, C.; Beato, M.; Herrlich, P.; Schutz, G.; Umesono, K.; Blumberg, B.; Kastner, P.; Mark, M.; Chambon, P.; Evans, R. M. The nuclear receptor superfamily - the 2nd decade. Cell 1995, 83 (6), 835-839.
7. Xu, J. M.; Li, Q. T. Review of the in vivo functions of the p160 steroid receptor coactivator family. Mol. Endocrinol. 2003, 17 (9), 1681-1692.
8. Hu, X.; Lazar, M. A. Transcriptional repression by nuclear hormone receptors. Trends Endorinol. Metab. 2000, 11 (1), 6-10.
9. Onate, S. A.; Tsai, S. Y.; Tsai, M. J.; Omalley, B. W. Sequence and characterization of a coactivator for the steroid-hormone receptor superfamily. Science 1995, 270 (5240), 1354-1357.
10. Voegel, J. J.; Heine, M. J. S.; Zechel, C.; Chambon, P.; Gronemeyer, H. TIF2, a 160 kDa transcriptional mediator for the ligand-dependent activation function AF-2 of nuclear receptors. EMBO J. 1996, 15 (14), 3667-3675.
11. Hong, H.; Kohli, K.; Garabedian, M. J.; Stallcup, M. R. GRIP1, a transcriptional coactivator for the AF-2 transactivation domain of steroid, thyroid, retinoid, and vitamin D receptors. Mol. Cell Biol. 1997, 17 (5), 2735-2744.
12. Suen, C. S.; Berrodin, T. J.; Mastroeni, R.; Cheskis, B. J.; Lyttle, C. R.; Frail, D. E. A transcriptional coactivator, steroid receptor coactivator-3, selectively augments steroid receptor transcriptional activity. J. Biol. Chem. 1998, 273 (42), 27645-27653.
13. Darimont, B. D.; Wagner, R. L.; Apriletti, J. W.; Stallcup, M. R.; Kushner, P. J.; Baxter, J. D.; Fletterick, R. J.; Yamamoto, K. R. Structure and specificity of nuclear receptor-coactivator interactions. Genes Dev. 1998, 12 (21), 3343-3356.
14. Feng, W. J.; Ribeiro, R. C. J.; Wagner, R. L.; Nguyen, H.; Apriletti, J. W.; Fletterick, R. J.; Baxter, J. D.; Kushner, P. J.; West, B. L. Hormone-dependent coactivator binding to a hydrophobic cleft on nuclear receptors. Science 1998, 280 (5370), 1747-1749.
15. Moore, J. M. R.; Galicia, S. J.; McReynolds, A. C.; Nguyen, N. H.; Scanlan, T. S.; Guy, R. K. Quantitative proteomics of the thyroid hormone receptor-coregulator interactions. J. Biol. Chem. 2004, 279 (26), 27584-27590.
16. Moore, J. M. R.; Guy, R. K. Coregulator interactions with the thyroid hormone receptor. Mol. Cell. Proteomics 2005, 4 (4), 475-482.
17. Geistlinger, T. R.; Guy, R. K. An inhibitor of the interaction of thyroid hormone receptor beta and glucocorticoid interacting protein 1. J. Am. Chem. Soc. 2001, 123 (7), 1525-1526.
18. Geistlinger, T. R.; Guy, R. K. Novel selective inhibitors of the interaction of individual nuclear hormone receptors with a mutually shared steroid receptor coactivator 2. J. Am. Chem. Soc. 2003, 125 (23), 6852-6853.
19. Arnold, L. A.; Estébanez-Perpiñá, E.; Togashi, M.; Jouravel, N.; Shelat, A.; McReynolds, A. C.; Mar, E.; Nguyen, P.; Baxter, J. D.; Fletterick, R. J.; Webb, P.; Guy, R. K. Discovery of small molecule inhibitors of the interaction of the thyroid hormone receptor with transcriptional coregulators. J. Biol. Chem. 2005, 280 (52), 43048-43055.
20. Arend, M.; Westermann, B.; Risch, N. Modern variants of the Mannich reaction. Angew. Chem., Int. Ed. 1998, 37 (8), 1045-1070.
21. Karpati, E.; Domok, L.; Szporny, L. 1-Piperidino-3-(4′-octylphenyl) propane-3-one-hydrochloride, a new peripheral and coronary vasodilator. Arzneimittelforschung 1969, 19 (6), 1011-1015.
22. Kudrin, A. N.; Aslaniants, Z. K.; Polevoi, L. G. Combined administration of quinidine with the beta-adrenolytic agent inderal and the local anaesthetic of the beta-aminoketone group, hexacaine, in various experimental models of arrhythmias. Cor Vasa 1975, 17 (2), 133-144.
23. Profit, E. The production of new, highly effective anesthetics with great latitude of efficacy. Chem. Tech. (Leibzig, Ger.) 1951, 3, 210-213.
24. Shelmire, B.; Gastineau, F. M.; Shields, T. L. Evaluation of a new topical anesthetic, dyclonine hydrochloride. AMA Arch. Dermatol. 1955, 71 (6), 728-730.
25. Armstrong, C. M.; Hille, B. Voltage-gated ion channels and electrical excitability. Neuron 1998, 20 (3), 371-380.
26. Gul, M.; Gul, H. I.; Das, U.; Hanninen, O. Biological evaluation and structure-activity relationships of bis-(3-aryl-3-oxo-propyl)methylamine hydrochlorides and 4-aryl-3-arylcarbonyl-1-methyl-4-piperidinol hydrochlorides as potential cytotoxic agents and their alkylating ability towards cellular glutathione in human leukemic T cells. Arzneimittelforschung 2005, 55 (6), 332-337.
27. Davioud-Charvet, E.; McLeish, M. J.; Veine, D. M.; Giegel, D.; Arscott, L. D.; Andricopulo, A. D.; Becker, K.; Muller, S.; Schirmer, R. H.; Williams, C. H.; Kenyon, G. L. Mechanism-based inactivation of thioredoxin reductase from Plasmodium falciparum by Mannich bases. Implication for cytotoxicity. Biochemistry 2003, 42 (45), 13319-13330.
28. Ward, R. S.; Davies, J.; Hodges, G.; Roberts, D. W. Synthesis of quaternary alkylammonium sulfobetaines. Synthesis 2002, (16), 2431-2439.
29. Arnold, L. A.; Estébanez-Perpiñá, E.; Togashi, M.; Shelat, A.; Ocasio, C. A.; McReynolds, A. C.; Nguyen, P.; Baxter, J. D.; Fletterick, R. J.; Webb, P.; Guy, R. K. A high-throughput screening method to identify small molecule inhibitors of thyroid hormone receptor coactivator binding. Sci. STKE 2006, (341), p13.
30. Chen, S. T.; Shieh, H. Y.; Lin, J. D.; Chang, K. S.; Lin, K. H. Overexpression of thyroid hormone receptor beta1 is associated with thyrotropin receptor gene expression and proliferation in a human thyroid carcinoma cell line. J. Endocrinol. 2000, 165 (2), 379-389.
31. Bookout, A. L.; Jeong, Y.; Downes, M.; Yu, R. T.; Evans, R. M.; Mangelsdorf, D. J. Anatomical profiling of nuclear receptor expression reveals a hierarchical transcriptional network. Cell 2006, 126 (4), 789-799.
32. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Tetrapropylammonium perruthenate, Pr4N+Ruo4-, Tpap - a catalytic oxidant for organic-synthesis. Synthesis 1994, (7), 639-666.
33. Truce, W. E. The preparation of fluoroacetyl chloride. J. Am. Chem. Soc. 1948, 70 (8), 2828-2828.
34. Molecular Operating Environment (MOE), version 2003.02; Chemical Computing Group: Quebec, Canada, 2003.
35. Ruell, J. A.; Tsinman, K. L.; Avdeef, A. PAMPA - a drug absorption in vitro model 5. Unstirred water layer in iso-pH mapping assays and pK(a)(flux)-optimized design (pOD-PAMPA). Eur. J. Pharm. Sci. 2003, 20 (4-5), 393-402.
36. Yu, S.; Konstantin, T.; Zhu, Z.; Graham, T. Automation of a double-sink PAMPA permeability assay on the Biomek FX Laboratory Automation Workstation Pharm. Discovery 2005, online www.pharmadd.com.