Pyrazine arotinoids with inverse agonist activities on the retinoid and rexinoid receptors

ChemBioChem

Volumn 10, Issue 7, 2009, Pages 1252-1259

  García, José ^a   Khanwalkar, Harshal ^b   Pereira, Raquel ^a   Erb, Cathie ^b   Voegel, Johannes J ^c   Collette, Pascal ^c   Mauvais, Pascale ^c   Bourguet, William ^d   Gronemeyer, Hinrich ^b   de Lera, Ángel R ^a  

^a UNIVERSITY OF VIGO   (Spain)

^b INSTITUT DE GÉNÉTIQUE ET DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^c Galderma R and D   (France)

^d INSERM   (France)

Author keywords

Arotinoids; Heterocycles; Nuclear hormone receptors; Retinoid receptors; Structure activity relationships

Indexed keywords

4 [2 [5,6 DIHYDRO 5,5 DIMETHYL 8 (4 METHYLPHENYL) 2 NAPHTHYL]ETHYNYL]BENZOIC ACID; AROTINOID; BMS 204493; BMS 493; CD 3254; PYRAZINE AROTINOID DERIVATIVE; PYRAZINE DERIVATIVE; RETINOIC ACID RECEPTOR; RETINOID X RECEPTOR; UNCLASSIFIED DRUG; UVI 3003; LIGAND; RETINOID; RETINOID X RECEPTOR ALPHA;

ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; CHEMISTRY; DRUG POTENTIATION; INVERSE AGONISM; METABOLISM; SYNTHESIS; TWO HYBRID SYSTEM;

DRUG INVERSE AGONISM; LIGANDS; PYRAZINES; RECEPTORS, RETINOIC ACID; RETINOID X RECEPTOR ALPHA; RETINOIDS; TWO-HYBRID SYSTEM TECHNIQUES;

EID: 67650486116     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900030     Document Type: Article

References (54)

1. P. Germain, P. Chambon, G. Eichele, R. M. Evans, M. A. Lazar, M. Leid, A. R. de Lera, R. Lotan, D. J. Mangelsdorf, H. Gronemeyer, Pharmacol. Rev. 2006, 58, 712-725.
2. P. Germain, P. Chambon, G. Eichele, R. M. Evans, M. A. Lazar, M. Leid, A. R. de Lera, R. Lotan, D. J. Mangelsdorf, H. Gronemeyer, Pharmacol. Rev. 2006, 58, 760-772.
3. V. Laudet, H. Gronemeyer, The Nuclear Receptor Facts Book; Academic Press, San Diego, 2002.
4. M. Mark, N. Ghyselinck, P. Chambon, Annu. Rev. Pharmacol. Toxicol. 2006, 46, 451-480.
5. L. Altucci, H. Gronemeyer, Nat. Rev. Cancer 2001, 1, 181-193.
6. L. Altucci, M. D. Leibowitz, K. M. Ogilvie, A. R. de Lera, H. Gronemeyer, Nat. Rev. Drug Discovery 2007, 6, 793-810.
7. A. I. Shulman, D. J. Mangelsdorf, N. Engl. J. Med. 2005, 353, 604-615.
8. A. Chawla, Y. J. Repa, R. M. Evans, D. J. Mangelsdorf, Science 2001, 294, 1866-1870.
9. J. J. Repa, D. J. Mangelsdorf, Nat. Med. 2002, 8, 1243-1248.
10. B. P. Klaholz, J.-P. Renaud, A. Mitschler, C. Zusi, P. Chambon, H. Gronemeyer, D. Moras, Nat. Struct. Biol. 1998, 5, 199-202.
11. W. Bourguet, M. Ruff, P. Chambon, H. Gronemeyer, D. Moras, Nature 1995, 375, 377-382.
12. A. R. de Lera, W. Bourguet, L. Altucci, H. Gronemeyer, Nat. Rev. Drug. Discovery 2007, 6, 811-820.
13. P. Loeliger, W. Bollag, H. Mayer, Eur. J. Med. Chem. 1980, 15, 9-15.
14. M. I. Dawson, L. Jong, P. D. Hobbs, D. Xiao, K.-C. Feng, W.-R. Chao, C. Pan, J. A. Fontana, X.-k. Zhang, Bioorg. Med. Chem. Lett. 2000, 10, 1311-1313.
15. A. Dhar, S. Liu, J. Klucik, K. D. Berlin, M. M. Madler, S. Lu, R. T. Ivey, D. Zacheis, C. W. Brown, E. C. Nelson, P. J. Birkbichler, D. M. Benbrook, J. Med. Chem. 1999, 42, 3602-3614.
16. D. Simoni, M. Roberti, F. P. Invidiata, R. Rondanin, R. Baruchello, C. Malagutti, A. Mazzali, M. Rossi, S. Grimaudo, F. Capone, L. Dusonchet, M. V. Raimondi, M. Landino, N. D'Alessandro, M. Tolomeo, D. Arindam, S. Lu, D. M. Benbrook, J. Med. Chem. 2001, 44, 2308-2318.
17. D. L. Gernert, D. A. Neel, M. F. Boehm, M. D. Leibowitz, D. E. Mais, P. Y. Michellys, D. Rungta, A. Reifer-Miller, T. A. Grese, Bioorg. Med. Chem. Lett. 2004, 14, 2759-2763.
18. C. D. Haffner, J. M. Lenhard, A. B. Miller, D. L. McDougald, K. Dwornik, O. R. Ittoop, R. T. Gampe, H. E. Xu, S. Blanchard, V. G. Montana, T. G. Consler, R. K. Bledsoe, A. Ayscue, D. Croom, J. Med. Chem. 2004, 47, 2010-2029.
19. J. Sakaki, M. Kishida, K. Konishi, H. Gunji, A. Toyao, Y. Matsumoto, T. Kanazawa, H. Uchiyama, H. Fukaya, H. Mitani, Y. Arai, M. Kimura, Bioorg. Med. Chem. Lett. 2007, 17, 4804-4807.
20. Metal-Catalyzed Cross-Coupling Reactions, 2nd. ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
21. E. L. Ghisalberti, C. H. Hocart, P. R. Jefferies, G. M. Proudfoot, B. W. Skelton, A. H. White, Aust. J. Chem. 1983, 36, 993-1000.
22. N. K. Garg, R. Sarpong, B. M. Stoltz, J. Am. Chem. Soc. 2002, 124, 13179-13184.
23. K. Pieterse, A. Lauritsen, A. P. H. J. Schenning, J. A. J. M. Vekemans, E. W. Meijer, Chem. Eur. J. 2003, 9, 5597-5604.
24. N. K. Garg, B. M. Stoltz, Tetrahedron Lett. 2005, 46, 2423-2426.
25. R. J. Huntley, R. L. Funk, Org. Lett. 2006, 8, 4775-4778.
26. H. Nakamura, D. Takeuchi, A. Murai, Synlett 1995, 1227-1228.
27. T. Jeffery, Tetrahedron 1996, 52, 10113-10130.
28. N. E. Leadbeater, M. Marco, Org. Lett. 2002, 4, 2973-2976.
29. N. E. Leadbeater, M. Marco, J. Org. Chem. 2003, 68, 888-892.
30. H. Nakamura, M. Aizawa, D. Takeuchi, A. Murai, O. Shimoura, Tetrahedron Lett. 2000, 41, 2185-2188.
31. B. Jiang, C.-G. Yang, W.-N. Xiong, J. Wang, Bioorg. Med. Chem. 2001, 9, 1149-1154.
32. M. J. Reyes, R. Castillo, M. L. Izquierdo, J. Alvarez-Builla, Tetrahedron Lett. 2006, 47, 6457-6460.
33. J. Y. Chen, S. Penco, J. Ostrowski, P. Balaguer, M. Pons, J. E. Starrett, P. Reczek, P. Chambon, H. Gronemeyer, EMBO J. 1995, 14, 1187-1197.
34. J. Monod, J. Wyman, J. P. Changeux, J. Mol. Biol. 1965, 12, 88-118.
35. T. P. Kenakin, Recept. Channels 2001, 7, 371-385.
36. P. Germain, J. Iyer, C. Zechel, H. Gronemeyer, Nature 2002, 415, 187-192.
37. V. Nahoum, E. Pérez, P. Germain, F. Rodríguez-Barrios, F. Manzo, S. Kammerer, G. Lemaire, O. Hirsch, C. A. Royer, H. Gronemeyer, A. R. de Lera, W. Bourguet, Proc. Natl. Acad. Sci. USA 2007, 104, 17323-17328.
38. V. Pogenberg, J.-F. Guichou, V. Vivat-Hannah, S. Kammerer, E. Pérez, P. Germain, A. R. de Lera, H. Gronemeyer, C. A. Royer, W. Bourguet, J. Biol. Chem. 2005, 280, 1625-1633.
39. E. S. Klein, M. E. Pino, A. T. Johnson, P. J. A. Davies, S. Nagpal, S. M. Thacher, G. Krasinski, R. A. S. Chandraratna, J. Biol. Chem. 1996, 271, 22692-22696.
40. H. Gronemeyer, J.-A. Gustafsson, V. Laudet, Nat. Rev. Drug Discovery 2004, 3, 950-964.
41. L. Nagy, H. Y. Kao, J. D. Love, C. Li, E. Banayo, J. T. Gooch, V. Krishna, K. Chatterjee, R. M. Evans, J. W. Schwabe, Genes Dev. 1999, 13, 3209-3216.
42. V. Perissi, L. M. Staszewski, E. M. McInerney, R. Kurokawa, A. Krones, D. W. Rose, M. H. Lambert, M. V. Milburn, C. K. Glass, M. G. Rosenfeld, Genes Dev. 1999, 13, 3198-3208.
43. O. Hermanson, C. K. Glass, M. G. Rosenfeld, Trends Endocrinol. Metab. 2002, 13, 55-60.
44. K. Jepsen, O. Hermanson, T. M. Onami, A. S. Gleiberman, V. Lunyak, R. J. McEvilly, R. Kurokawa, V. Kumar, F. Liu, E. Seto, S. M. Hedrick, G. Mandel, C. K. Glass, D. W. Rose, M. G. Rosenfeld, Cell 2000, 102, 753-763.
45. N. J. McKenna, B. W. O'Malley, Cell 2002, 108, 465-474.
46. C. L. Smith, B. W. O'Malley, Endocr. Rev. 2004, 25, 45-71.
47. X. Hu, M. A. Lazar, Nature 1999, 402, 93-96.
48. M. I. Dawson, Curr. Med. Chem. Anti-Cancer Agents 2004, 4, 199-230.
49. M. Gèhin, V. Vivat, J.-M. Wurtz, R. Losson, P. Chambon, D. Moras, H. Gronemeyer, Chem. Biol. 1999, 6, 519-529.
50. W. Bourguet, V. Vivat, J.-M. Wurtz, P. Chambon, H. Gronemeyer, D. Moras, Mol. Cell 2000, 5, 289-298.
51. W. Bourguet, P. Germain, H. Gronemeyer, Trends Pharmacol. Sci. 2000, 21, 381-388.
52. J. Zhang, X. Hu, M. A. Lazar, Mol. Cell. Biol. 1999, 19, 6448-6457.
53. Arotinoids with pyrazine rings in the hydrophobic terminus and a pyrrole as central unit have been described: K. Kikuchi, S. Hibi, H. Yoshimura, K. Tai, T. Hida, N. Tokuhara, T. Yamauchi, M. Nagai, Bioorg. Med. Chem. Lett. 2000, 10, 619-622.
54. V. Vivat, C. Zechel, J.-M. Wurtz, W. Bourguet, H. Kagechika, H. Umemiya, K. Shudo, D. Moras, H. Gronemeyer, P. Chabon, EMBO J. 1997, 16, 5697-5709.