5α-Bile alcohols function as farnesoid X receptor antagonists

Biochemical and Biophysical Research Communications

Volumn 339, Issue 1, 2006, Pages 386-391

  Nishimaki Mogami, Tomoko ^a   Kawahara, Yosuke ^b   Tamehiro, Norimasa ^a   Yoshida, Takemi ^b   Inoue, Kazuhide ^a   Ohno, Yasuo ^a   Nagao, Taku ^a   Une, Mizuho ^c  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^b SHOWA UNIVERSITY   (Japan)

^c HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

Agonist; Antagonist; Bile acid; Bile alcohol; Coactivator; Farnesoid X receptor; Nuclear receptor

Indexed keywords

5ALPHA BUFOL; 5ALPHA CYPRINOL; ALCOHOL DERIVATIVE; BILE ACID; BILE SALT; FARNESOID X RECEPTOR ANTAGONIST; HORMONE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; CELL RECEPTOR; CHOLESTANOL; DNA BINDING PROTEIN; FARNESOID X RECEPTOR; FARNESOID X-ACTIVATED RECEPTOR; MESSENGER RNA; TRANSCRIPTION FACTOR;

ARTICLE; CIS TRANS ISOMERISM; CONTROLLED STUDY; GENE EXPRESSION; GENE TARGETING; HUMAN; HUMAN CELL; PRIORITY JOURNAL; TRANSACTIVATION; BIOSYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; DRUG POTENTIATION; METABOLISM; REPORTER GENE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

CELL LINE, TUMOR; CHOLESTANOLS; DNA-BINDING PROTEINS; GENES, REPORTER; HUMANS; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RNA, MESSENGER; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANS-ACTIVATION (GENETICS); TRANSCRIPTION FACTORS;

EID: 28144454959     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.11.027     Document Type: Article

References (37)

1. M. Makishima, A.Y. Okamoto, J.J. Repa, H. Tu, R.M. Learned, A. Luk, M.V. Hull, K.D. Lustig, D.J. Mangelsdorf, and B. Shan Identification of a nuclear receptor for bile acids Science 284 1999 1362 1365
2. D.J. Parks, S.G. Blanchard, R.K. Bledsoe, G. Chandra, T.G. Consler, S.A. Kliewer, J.B. Stimmel, T.M. Willson, A.M. Zavacki, D.D. Moore, and J.M. Lehmann Bile acids: natural ligands for an orphan nuclear receptor Science 284 1999 1365 1368
3. T. Fujino, M. Une, T. Imanaka, K. Inoue, and T. Nishimaki-Mogami Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation J. Lipid Res. 45 2004 132 138
4. T. Nishimaki-Mogami, M. Une, T. Fujino, Y. Sato, N. Tamehiro, Y. Kawahara, K. Shudo, and K. Inoue Identification of intermediates in the bile acid synthetic pathway as ligands for the farnesoid X receptor J. Lipid Res. 45 2004 1538 1545
5. R.A. Davis, J.H. Miyake, T.Y. Hui, and N.J. Spann Regulation of cholesterol-7α-hydroxylase: BAREly missing a SHP J. Lipid Res. 43 2002 533 543
6. P.A. Edwards, H.R. Kast, and A.M. Anisfeld BAREing it all: the adoption of LXR and FXR and their roles in lipid homeostasis J. Lipid Res. 43 2002 2 12
7. R.K. Bledsoe, V.G. Montana, T.B. Stanley, C.J. Delves, C.J. Apolito, D.D. McKee, T.G. Consler, D.J. Parks, E.L. Stewart, T.M. Willson, M.H. Lambert, J.T. Moore, K.H. Pearce, and H.E. Xu Crystal structure of the glucocorticoid receptor ligand binding domain reveals a novel mode of receptor dimerization and coactivator recognition Cell 110 2002 93 105
8. A.M. Brzozowski, A.C. Pike, Z. Dauter, R.E. Hubbard, T. Bonn, O. Engstrom, L. Ohman, G.L. Greene, J.A. Gustafsson, and M. Carlquist Molecular basis of agonism and antagonism in the oestrogen receptor Nature 389 1997 753 758
9. J.S. Sack, K.F. Kish, C. Wang, R.M. Attar, S.E. Kiefer, Y. An, G.Y. Wu, J.E. Scheffler, M.E. Salvati, S.R. Krystek Jr., R. Weinmann, and H.M. Einspahr Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone Proc. Natl. Acad. Sci. USA 98 2001 4904 4909
10. M. Downes, M.A. Verdecia, A.J. Roecker, R. Hughes, J.B. Hogenesch, H.R. Kast-Woelbern, M.E. Bowman, J.L. Ferrer, A.M. Anisfeld, P.A. Edwards, J.M. Rosenfeld, J.G. Alvarez, J.P. Noel, K.C. Nicolaou, and R.M. Evans A chemical, genetic, and structural analysis of the nuclear bile acid receptor FXR Mol. Cell 11 2003 1079 1092
11. L.Z. Mi, S. Devarakonda, J.M. Harp, Q. Han, R. Pellicciari, T.M. Willson, S. Khorasanizadeh, and F. Rastinejad Structural basis for bile acid binding and activation of the nuclear receptor FXR Mol. Cell 11 2003 1093 1100
12. C.K. Glass, D.W. Rose, and M.G. Rosenfeld Nuclear receptor coactivators Curr. Opin. Cell Biol. 9 1997 222 232
13. K.W. Nettles, and G.L. Greene Nuclear receptor ligands and cofactor recruitment: is there a coactivator "on deck"? Mol. Cell 11 2003 850 851
14. A.K. Shiau, D. Barstad, J.T. Radek, M.J. Meyers, K.W. Nettles, B.S. Katzenellenbogen, J.A. Katzenellenbogen, D.A. Agard, and G.L. Greene Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism Nat. Struct. Biol. 9 2002 359 364
15. T. Hoshita Bile alcohols and primitive bile acids H. Danielsson J. Sjovall Sterols and Bile Acids, New Comprehensive Biochemistry vol. 12 1985 Elsevier Science Amsterdam 279 302
16. T. Hoshita, S. Nagayoshi, and T. Kazuno Stereo-bile acids and bile sterols. LIV. Studies on the bile of carp J. Biochem. (Tokyo) 54 1963 369 374
17. B. Amos, I.G. Anderson, G.A. Haslewood, and L. Tokes Bile salts of the lungfishes Lepidosiren, Neoceratodus and Protopterus and those of the coelacanth Latimeria chalumnae Smith Biochem. J. 161 1977 201 204
18. M. Une, N. Matsumoto, K. Kihira, M. Yasuhara, T. Kuramoto, and T. Hoshita Bile salts of frogs: a new higher bile acid, 3 alpha, 7 alpha, 12 alpha, 26-tetrahydroxy-5-beta-cholestanoic acid from the bile Rana plancyi J. Lipid Res. 21 1980 269 276
19. B. Goodwin, S.A. Jones, R.R. Price, M.A. Watson, D.D. McKee, L.B. Moore, C. Galardi, J.G. Wilson, M.C. Lewis, M.E. Roth, P.R. Maloney, T.M. Willson, and S.A. Kliewer A regulatory cascade of the nuclear receptors FXR, SHP-1, and LRH-1 represses bile acid biosynthesis Mol. Cell 6 2000 517 526
20. T.T. Lu, M. Makishima, J.J. Repa, K. Schoonjans, T.A. Kerr, J. Auwerx, and D.J. Mangelsdorf Molecular basis for feedback regulation of bile acid synthesis by nuclear receptors Mol. Cell 6 2000 507 515
21. M. Ananthanarayanan, N. Balasubramanian, M. Makishima, D.J. Mangelsdorf, and F.J. Suchy Human bile salt export pump promoter is transactivated by the farnesoid X receptor/bile acid receptor J. Biol. Chem. 276 2001 28857 28865
22. T. Hoshita, T. Sasaki, Y. Tanaka, S. Betsuki, and T. Kazuno Stero-bile acids and bile sterols. LXXIV. Biosynthesis of bile acids and bile alcohols in toad J. Biochem. (Tokyo) 57 1965 751 757
23. P.R. Maloney, D.J. Parks, C.D. Haffner, A.M. Fivush, G. Chandra, K.D. Plunket, K.L. Creech, L.B. Moore, J.G. Wilson, M.C. Lewis, S.A. Jones, and T.M. Willson Identification of a chemical tool for the orphan nuclear receptor FXR J. Med. Chem. 43 2000 2971 2974
24. J. Yu, J.L. Lo, L. Huang, A. Zhao, E. Metzger, A. Adams, P.T. Meinke, S.D. Wright, and J. Cui Lithocholic acid decreases expression of bile salt export pump through farnesoid X receptor antagonist activity J. Biol. Chem. 277 2002 31441 31447
25. T. Goto, F. Holzinger, L.R. Hagey, C. Cerre, H.T. Ton-Nu, C.D. Schteingart, J.H. Steinbach, B.L. Shneider, and A.F. Hofmann Physicochemical and physiological properties of 5alpha-cyprinol sulfate, the toxic bile salt of cyprinid fish J. Lipid Res. 44 2003 1643 1651
26. M. Axelson, E. Ellis, B. Mork, K. Garmark, A. Abrahamsson, I. Bjorkhem, B.G. Ericzon, and C. Einarsson Bile acid synthesis in cultured human hepatocytes: support for an alternative biosynthetic pathway to cholic acid Hepatology 31 2000 1305 1312
27. Y.H. Yeh, D.Y. Wang, J.F. Deng, S.K. Chen, and D.F. Hwang Short-term toxicity of grass carp bile powder, 5alpha-cyprinol and 5alpha-cyprinol sulfate in rats Comp. Biochem. Physiol. C. Toxicol. Pharmacol. 131 2002 1 8
28. B.H. Xuan, T.X. Thi, S.T. Nguyen, D.S. Goldfarb, M.B. Stokes, and R.A. Rabenou Ichthyotoxic ARF after fish gallbladder ingestion: a large case series from Viet Nam Am. J. Kidney Dis. 41 2003 220 224
29. T. Gerloff, B. Stieger, B. Hagenbuch, J. Madon, L. Landmann, J. Roth, A.F. Hofmann, and P.J. Meier The sister of P-glycoprotein represents the canalicular bile salt export pump of mammalian liver J. Biol. Chem. 273 1998 10046 10050
30. S.S. Strautnieks, L.N. Bull, A.S. Knisely, S.A. Kocoshis, N. Dahl, H. Arnell, E. Sokal, K. Dahan, S. Childs, V. Ling, M.S. Tanner, A.F. Kagalwalla, A. Nemeth, J. Pawlowska, A. Baker, G. Mieli-Vergani, N.B. Freimer, R.M. Gardiner, and R.J. Thompson A gene encoding a liver-specific ABC transporter is mutated in progressive familial intrahepatic cholestasis Nat. Genet. 20 1998 233 238
31. J.L. Lew, A. Zhao, J. Yu, L. Huang, N. De Pedro, F. Pelaez, S.D. Wright, and J. Cui The farnesoid X receptor controls gene expression in a ligand- and promoter-selective fashion J. Biol. Chem. 279 2004 8856 8861
32. J.A. Holt, G. Luo, A.N. Billin, J. Bisi, Y.Y. McNeill, K.F. Kozarsky, M. Donahee, d.Y. Wang, T.A. Mansfield, S.A. Kliewer, B. Goodwin, and S.A. Jones Definition of a novel growth factor-dependent signal cascade for the suppression of bile acid biosynthesis Genes Dev. 17 2003 1581 1591
33. T.A. Kerr, S. Saeki, M. Schneider, K. Schaefer, S. Berdy, T. Redder, B. Shan, D.W. Russell, and M. Schwarz Loss of nuclear receptor SHP impairs but does not eliminate negative feedback regulation of bile acid synthesis Dev. Cell 2 2002 713 720
34. L. Wang, Y.K. Lee, D. Bundman, Y. Han, S. Thevananther, C.S. Kim, S.S. Chua, P. Wei, R.A. Heyman, M. Karin, and D.D. Moore Redundant pathways for negative feedback regulation of bile acid production Dev. Cell 2 2002 721 731
35. M.D. Krasowski, K. Yasuda, L.R. Hagey, and E.G. Schuetz Evolution of the pregnane X receptor: adaptation to cross-species differences in biliary bile salts Mol. Endocrinol. 19 2005 1720 1739
36. N.L. Urizar, A.B. Liverman, D.T. Dodds, F.V. Silva, P. Ordentlich, Y. Yan, F.J. Gonzalez, R.A. Heyman, D.J. Mangelsdorf, and D.D. Moore A natural product that lowers cholesterol as an antagonist ligand for FXR Science 296 2002 1703 1706
37. A. Moschetta, A.L. Bookout, and D.J. Mangelsdorf Prevention of cholesterol gallstone disease by FXR agonists in a mouse model Nat. Med. 10 2004 1352 1358