New opportunities for pregnane X receptor (PXR) targeting in drug development. Lessons from enantio- and species-specific PXR ligands identified from a discovery library of amino acid analogues

Mini-Reviews in Medicinal Chemistry

Volumn 7, Issue 6, 2007, Pages 617-625

  Wipf, Peter ^a   Gong, Haibiao ^a   Janjic, Jelena M ^a   Li, Song ^a   Day, Billy W ^a   Xie, Wen ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Discovery library screening; Enantiospecific binding; Gene expression; Nuclear hormone receptors; Peptide mimetics; Pregnane X receptor; PXR; Small molecule modulators; Species specificity

Indexed keywords

4 HYDROXYTAMOXIFEN; 4,4' ISOPROPYLIDENEDIPHENOL; ALPHA TOCOPHEROL; BILE ACID; CAROTENOID; CLOTRIMAZOLE; FARNOQUINONE; GLUTETHIMIDE; GLYCYRRHIZA URALENSIS EXTRACT; HYPERICUM PERFORATUM EXTRACT; HYPOCHOLESTEROLEMIC AGENT; INDINAVIR; METYRAPONE; MEVINOLIN; NIFEDIPINE; NONACHLOR; NONYLPHENOL; ORAL CONTRACEPTIVE AGENT; PACLITAXEL; PHENOBARBITAL; PREGNANE X RECEPTOR; RITONAVIR; SCHISANDRA CHINENSIS EXTRACT; SPIRONOLACTONE; SR 12812; SR 12813; TAMOXIFEN; TRANSCRIPTION FACTOR; TROGLITAZONE; UNCLASSIFIED DRUG; UNINDEXED DRUG; WARFARIN; AMIDE; AMINO ACID; CELL RECEPTOR; LIGAND; STEROID RECEPTOR;

DRUG ANTAGONISM; DRUG DESIGN; DRUG MECHANISM; DRUG METABOLISM; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; ENANTIOMER; ENANTIOSELECTIVITY; GENE EXPRESSION REGULATION; HUMAN; LIPOPHILICITY; NONHUMAN; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN EXPRESSION; PROTEIN FUNCTION; REVIEW; SIGNAL TRANSDUCTION; SPECIES DIFFERENCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; CONFORMATION; DRUG EFFECT; DRUG POTENTIATION; PHYSIOLOGY; STEREOISOMERISM; SYNTHESIS;

AMIDES; AMINO ACIDS; ANIMALS; HUMANS; LIGANDS; MOLECULAR CONFORMATION; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, STEROID; STEREOISOMERISM;

EID: 34447133457     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955707780859404     Document Type: Review

References (48)

1. Mangelsdorf, D.J.; Thummel, C.; Beato, M.; Herrlich, P.; Schutz, G.; Umesono, K.; Blumberg, B.; Kastner, P.; Mark, M.; Chambon, P.; Evans R.M. Cell, 1995, 83, 835.
2. Glass, C.K.; Rosenfeld, M.G. Genes Dev., 2000, 14, 121.
3. Mangelsdorf, D.J.; Evans, R.M. Cell, 1995, 83, 841.
4. Blumberg, B.; Evans, R.M. Genes Dev., 1998, 12, 3149.
5. Wipf, P.; Kendall, C.; Stephenson, C.R. J. Am. Chem. Soc., 2001, 123, 5122.
6. Wipf, P.; Kendall, C.; Stephenson, C.R. J. Am. Chem. Soc., 2003, 125, 761.
7. Janjic, J.M.; Mu, Y.; Kendall, C.; Stephenson, C.R.; Balachandran, R.; Raccor, B.S.; Lu, Y.; Zhu, G.; Xie, W.; Wipf, P.; Day, B.W. Bioorg. Med. Chem., 2005, 13, 157.
8. Mu, Y.; Stephenson, C.R.; Kendall, C.; Saini, S.P.; Toma, D.; Ren, S.; Cai, H.; Strom, S.C.; Day, B.W.; Wipf, P.; Xie, W. Mol. Pharmacol., 2005, 68, 403.
9. Kliewer, S.A.; Goodwin, B.; Willson, T.M. Endocr. Rev., 2002, 23, 687.
10. Xie, W.; Evans, R.M. J. Biol. Chem., 2001, 276, 37739.
11. Gong, H.; Xie, W. Expert Opin. Ther. Targets, 2004, 8, 49.
12. Ekins, S.; Schuetz, E. Trends Pharmacol. Sci., 2002, 23, 49.
13. Watkins, R.E.; Noble, S.M.; Redinbo, M.R. Curr. Opin. Drug. Discov. Devel., 2002, 5, 150.
14. Watkins, R.E.; Wisely, G.B.; Moore, L.B.; Collins, J.L.; Lambert, M.H.; Williams, S.P.; Willson, T.M.; Kliewer, S.A.; Redinbo, M.R. Science, 2001, 292, 2329.
15. Blumberg, B.; Sabbagh, W., Jr.; Juguilon, H.; Bolado, J., Jr.; van Meter, C.M.; Ong, E.S.; Evans, R.M. Genes Dev., 1998, 12, 3195.
16. Kliewer, S.A.; Moore, J.T.; Wade, L.; Staudinger, J.L.; Watson, M.A.; Jones, S.A.; McKee, D.D.; Oliver, B.B.; Willson, T.M.; Zetterstrom, R.H.; Perlmann, T.; Lehmann, J.M. Cell, 1998, 92, 73.
17. Gong, H.; Singh, S.V.; Singh, S.P.; Mu, Y.; Lee, J.H.; Saini, S.P.; Toma, D.; Ren, S.; Kagan, V.E.; Day, B.W.; Zimniak, P.; Xie, W. Mol. Endocrinol., 2006, 20, 279.
18. Xie, W.; Yeuh, M.F.; Radominska-Pandya, A.; Saini, S.P.; Negishi, Y.; Bottroff, B.S.; Cabrera, G.Y.; Tukey, R.H.; Evans, R.M. Proc. Natl. Acad. Sci. USA, 2003, 100, 4150.
19. Bauer, B.; Hartz, A.M.; Fricker, G.; Miller, D.S. Mol. Pharmacol., 2004, 66, 413.
20. Synold, T.W.; Dussault, I.; Forman, B.M. Nat. Med., 2001, 7, 584.
21. Bertilsson, G.; Heidrich, J.; Svensson, K.; Asman, M.; Jendeberg, L.; Sydow-Backman, M.; Ohlsson, R.; Postlind, H.; Blomquist, P.; Berkenstam, A. Proc. Natl. Acad. Sci. USA, 1998, 95, 12208.
22. Lehmann, J.M.; McKee, D.D.; Watson, M.A.; Willson, T.M.; Moore, J.T.; Kliewer, S.A. J. Clin. Invest., 1998, 102, 1016.
23. Gerbal-Chaloin, S.; Daujat, M.; Pascussi, J.M.; Pichard-Garcia, L.; Vilarem, M.J.; Maurel, P. J. Biol. Chem., 2002, 277, 209.
24. Gerbal-Chaloin, S.; Pascussi, J.M.; Pichard-Garcia, L.; Daujat, M.; Waechter, F.; Fabre, J.M.; Carrere, N.; Maurel, P. Drug Metab. Dispos., 2001, 29, 242.
25. Goodwin, B.; Moore, L.B.; Stoltz, C.M.; McKee, D.D.; Kliewer, S.A. Mol. Pharmacol., 2001, 60, 427.
26. Xie, W.; Barwick, J.L.; Simon, C.M.; Pierce, A.M.; Safe, S.; Blumberg, B.; Guzelian, P.S.; Evans, R.M. Genes Dev., 2000, 14, 3014.
27. Sonoda, J.; Xie, W.; Rosenfeld, J.M.; Barwick, J.L.; Guzelian, P.S.; Evans, R.M. Proc. Natl. Acad. Sci. USA, 2002, 99, 13801.
28. Dussault, I.; Lin, M.; Hollister, K.; Wang, E.H.; Synold, T.W.; Forman, B.M. J. Biol. Chem., 2001, 276, 33309.
29. Tabb, M.M.; Sun, A.; Zhou, C.; Grun, F.; Errandi, J.; Romero, K.; Pham, H.; Inoue, S.; Mallick, S.; Lin, M.; Forman, B.M.; Blumberg, B. J. Biol. Chem., 2003, 278, 43919.
30. Zhou, C.; Tabb, M.M.; Sadatrafiei, A.; Grun, F.; Blumberg, B. Drug Metab. Dispos., 2004, 32, 1075.
31. Ruhl, R.; Sczech, R.; Landes, N.; Pfluger, P.; Kluth, D.; Schweigert, F.J. Eur. J. Nutr., 2004, 43, 336.
32. Moore, L.B.; Goodwin, B.; Jones, S.A.; Wisely, G.B.; Serabjit-Singh, C.J.; Willson, T.M.; Collins, J.L.; Kliewer, S.A. Proc. Natl. Acad. Sci. USA, 2000, 97, 7500.
33. Mu, Y.; Zhang, J.; Zhang, S.; Zhou, H.H.; Toma, D.; Ren, S.; Huang, L.; Yaramus, M.; Baum, A.; Venkataramanan, R.; Xie, W. J. Pharmacol. Exp. Ther., 2006, 316, 1369.
34. Desai, P.B.; Nallani, S.C.; Sane, R.S.; Moore, L.B.; Goodwin, B.J.; Buckley, D.J.; Buckley, A.R. Drug Metab. Dispos., 2002, 30, 608.
35. Jones, S.A.; Moore, L.B.; Shenk, J.L.; Wisely, G.B.; Hamilton, G.A.; McKee, D.D.; Tomkinson, N.C.; LeCluyse, E.L.; Lambert, M.H.; Willson, T.M.; Kliewer, S.A.; Moore, J.T. Mol. Endocrinol., 2000, 14, 27.
36. Staudinger, J.L.; Goodwin, B.; Jones, S.A.; Hawkins-Brown, D.; MacKenzie, K.I.; LaTour, A.; Liu, Y.; Klaassen, C.D.; Brown, K.K.; Reinhard, J.; Willson, T.M.; Koller, B.H.; Kliewer, S.A. Proc. Natl. Acad. Sci. USA, 2001, 98, 3369.
37. Xie, W.; Radominska-Pandya, A.; Shi, Y.; Simon, C.M.; Nelson, M.C.; Ong, E.S.; Waxman, D.J.; Evans, R.M. Proc. Natl. Acad. Sci. USA, 2001, 98, 3375.
38. Dussault, I.; Yoo, H.D.; Lin, M.; Wang, E.; Fan, M.; Batta, A.K.; Salen, G.; Erickson, S.K.; Forman, B.M. Proc. Natl. Acad Sci. USA, 2003, 100, 833.
39. Goodwin, B.; Gauthier, K.C.; Umetani, M.; Watson, M.A.; Lochansky, M.I.; Collins, J.L.; Leitersdorf, E.; Mangelsdorf, D.J.; Kliewer, S.A.; Repa, J.J. Proc. Natl. Acad. Sci. USA, 2003, 100, 223.
40. Xie, W.; Barwick, J.L.; Downes, M.; Blumberg, B.; Simon, C.M.; Nelson, M.C.; Neuschwander-Tetri, B.A.; Brunt, E.M.; Guzelian, P.S.; Evans, R.M. Nature, 2000, 406, 435.
41. Tirona, R.G.; Leake, B.F.; Podust, L.M.; Kim, R.B. Mol. Pharmacol., 2004, 65, 36.
42. Zhou, J.; Zhai, Y.; Mu, Y.; Gong, H.; Uppal, H.; Toma, D.; Ren, S.; Evans, R.M.; Xie, W. J. Biol. Chem., 2006, 281, 15013.
43. Saini, S.P.; Mu, Y.; Gong, H.; Toma, D.; Uppal, H.; Ren, S.; Li, S.; Poloyac, S.M.; Xie, W. Hepatology, 2005, 41, 497.
44. Maurel, P. Cytochrome P450: Metabolic and Toxicological Aspects, CRC Press: Boca Raton, 1996; pp. 241-270.
45. Gong, H.; Sinz, M.W.; Feng, Y.; Chen, T.; Venkataramanan, R.; Xie, W. Methods Enzymol., 2005, 400, 598.
46. Sonoda, J.; Rosenfeld, J.M.; Xu, L.; Evans, R.M.; Xie, W. Curr. Drug. Metab., 2003, 4, 59.
47. Xie, W.; Uppal, H.; Saini, S.P.; Mu, Y.; Little, J.M.; Radominska-Pandya, A.; Zemaitis, M.A. Drug Discov. Today, 2004, 9, 442.
48. Zhou, J.; Zhang, J.; Xie, W. Curr. Drug Metab., 2005, 6, 289.