A high-affinity subtype-selective agonist ligand for the thyroid hormone receptor

Chemistry and Biology

Volumn 5, Issue 6, 1998, Pages 299-306

  Chiellini, Grazia ^a   Apriletti, James W ^a   Yoshihara, Hikari Al ^a   Baxter, John D ^a   Ribeiro, Ralff C J ^a   Scanlan, Thomas S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biaryl alcohol; Selective alkylation; Subtype selectivity; Thyroid hormone receptor; Thyromimetic

Indexed keywords

ANIMALIA; VERTEBRATA;

EID: 0032101890     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90168-5     Document Type: Article

References (26)

1. Greenspan, F.S. (1994). The Thyroid Gland. In Basic and Clinical Endocrinology. (Greenspan F.S., and Baxter, J.D., eds), pp. 160-223, Appleton & Lange, Norwalk.
2. Mangelsdorf, D.J., et al., & Evans, R.M. (1996). The nuclear receptor superfamily: the second decade. Cell 83, 835-839.
3. Mangelsdorf, D.J. & Evans, R.M. (1996). The RXR heterodimers and orphan receptors. Cell 83, 841-850.
4. Katzenellenbogen, J.A. & Katzenellenbogen, B.S. (1996). Nuclear hormone receptors: ligand-activated regulators of transcription and diverse cell responses. Chem. Biol. 3, 529-536.
5. Tsai, M. & O'Malley, B. (1994). Molecular mechanisms of action of steroid/thyroid receptor superfamily members. Ann. Rev. Biochem. 86, 451-486.
6. Horlein, A.J., et al., & Rosenfeld, M.G. (1995). Ligand-independent repression by the thyroid hormone receptor mediated by a nuclear receptor co-repressor. Nature 377, 397-404.
7. Wagner, R.L., Apriletti, J.W., McGrath, M.E., West, B.L., Baxter, J.D. & Fletterick, R.J. (1995). A structural role for hormone in the thyroid hormone receptor. Nature 378, 690-697.
8. Renaud, J.P., et al., & Moras, D. (1995). Crystal structure of the RAR-γ ligand-binding domain bound to all-trans retinoic acid. Nature 378, 681-689.
9. Brzozowski, A.M., et al., & Carlquist, M. (1997). Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389, 753-758.
10. Oppenheimer, J.H., Schwartz, H.L. & Strait, K.A. (1994). Thyroid hormone action 1994: the plot thickens. Eur. J. Endocrinol. 130, 15-24.
11. Lazar, M.A. (1993). Thyroid hormone receptors: multiple forms, multiple possibilities. Endocrine Rev. 14, 184-193.
12. Underwood, A.H., et al., & Shah, V.P. (1986). A thyromimetic that decreases plasma cholesterol levels without increasing cardiac activity. Nature 324, 425-429.
13. Leeson, P.D., Ellis, D., Emmett, J.C., Shah, V.P., Showell, G.A. & Underwood, A.M. (1988). Thyroid hormone analogues. Synthesis of 3′-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart. J. Med. Chem. 31, 37-54.
14. Leeson, P.D., et al., & Underwood, A.M. (1989). Selective thyromimetics. Cardiac-sparing thyroid hormone analogues containing 3′-arylmethyl substituents. J. Med. Chem. 32, 320-336.
15. Yokoyama, N., et al., & Steele, R.E. (1995). Synthesis and structure-activity relationships of oxamic acid and acetic acid derivatives related to L-thyronine. J. Med. Chem. 38, 695-707.
16. Taylor, A.H., Stephan, Z.F., Steele, R.E. & Wong, N.C.W. (1997). Beneficial effects of a novel thyromimetic on lipoprotein metabolism. Mol. Pharmacol. 52, 542-547.
17. Jorgenson, E.C. (1978). Thyroid hormones. In Hormonal Proteins and Peptides. (Li, C.H., éd.), pp. 108-204, Academic Press, New York.
18. Dietrich, S.W., Bolger, M.B., Kollman, P.A. & Jorgensen, E.C. (1977). Thyroxine analogues. 23. Quantitative structure-activity correlation studies of in vivo and in vitro thyromimetic activities. J. Med. Chem. 20, 863-880.
19. Olson, W.T., et al., & Gibbons, L.C. (1947). The synthesis and purification of ethers. J. Am. Chem. Soc. 69, 2451-2452.
20. Ribeiro, R.C.J., et al., & Baxter, J.D. (1995). The molecular biology of thyroid hormone action. Ann. N.Y. Acad. Sci. 758, 366-389.
21. Apriletti, J.W., Baxter, J.D., Lau, K.H. & West, B.L (1995). Expression of the rat alpha 1 thyroid hormone receptor ligand binding domain in Escherichia coli and the use of a ligand-induced conformational change as a method for its purification to homogeneity. Protein Express. Purif. 6, 363-370.
22. Swillens, S. (1995). Interpretation of binding curves obtained with high receptor concentrations: practical aid for computer analysis. Mol. Pharmacol. 47, 1197-1203.
23. Leitman, D.C., Ribeiro, R.C., Mackow, E.R., Baxter, J.D. & West, B.L. (1991). Identification of a tumor necrosis factor-responsive element in the tumor necrosis factor alpha gene. J. Biol. Chem. 266, 9343-9346.
24. Ribeiro, R.C.J., Cavalieri, R.R., Lomri, N., Rahmaouhi, C.M., Baxter, J.D. & Scharschmidt, B.F. (1996). Thyroid hormone export regulates cellular hormone content and response. J. Biol. Chem. 271, 17147-17151.
25. Neumann, J.R., Morency, C.A. & Russian, K.O. (1987). A novel rapid assay for chloramphenicol acetyltransferase gene expression. BioTechniques 5, 444-447.
26. Brasier, A.R., Tate, J.E. & Habener, J.F. (1989). Optimized use of the firefly luciferase assay as reporter gene in mammalian cell lines. BioTechniques 7, 1116-1122.