Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity

Journal of Medicinal Chemistry

Volumn 38, Issue 17, 1995, Pages 3368-3383

  Dawson, Marcia I ^a   Jong, Ling ^a   Hobbs, Peter D ^a   Cameron, James F ^a   Chao, Wan ru ^a   Pfahl, Michaela ^b   Lee, Mi Ock ^b   Pfahl, Magnus ^b   Shroot, Braham ^c  

^a SRI INTERNATIONAL   (United States)

^b BURNHAM INSTITUTE   (United States)

^c Galderma R and D   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 [1 (5,6,7,8 TETRAHYDRO 5,5,8,8 TETRAMETHYL 2 NAPHTHALENYL)PROPEN 1 YL]BENZOIC ACID; 4 [1 (5,6,7,8 TETRAHYDRO 5,5,8,8 TETRAMETHYL 2 NAPHTHYL)CYCLOPROPYL]BENZOIC ACID; ALITRETINOIN; RETINOIC ACID; RETINOIC ACID DERIVATIVE; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG CONFORMATION; GENETIC TRANSCRIPTION; HORMONE RECEPTOR INTERACTION; MOLECULAR INTERACTION; RECEPTOR AFFINITY; STEREOISOMERISM; TRANSCRIPTION INITIATION;

BETA-GALACTOSIDASE; CELL LINE; CHLORAMPHENICOL O-ACETYLTRANSFERASE; ISOTRETINOIN; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; RECEPTORS, RETINOIC ACID; SUPPORT, U.S. GOV'T, P.H.S.; TRANSCRIPTION FACTORS; TRANSCRIPTION, GENETIC;

EID: 0029102106     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00017a021     Document Type: Article

References (31)

1. Leid, M.; Kastner, P.; Chambon, P. Multiplicity generates diversity in the retinoic acid signalling pathways. Trends Biochem. Sci. 1992, 17, 427-433.
2. Mangelsdorf, D. J.; Umesono, K.; Evans, R. M. The retinoid receptors. In The Retinoids, 2nd ed.; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Academic Press: Orlando, FL, 1994; pp 319-349.
3. Pfahl, M. The retinoid response: A molecular dissection. Ann. Oncol. 1994, 5, S11-S15.
4. Zhang, X.-K.; Pfahl, M. Regulation of retinoid and thyroid action through homo- and heterodimeric receptors. Trends Endocrinol. Metab. 1993, 4, 156-162.
5. Pfahl, M. Vertebrate receptors: Molecular biology, dimerization and response elements. Semin. Cell Biol. 1994, 5, 95-103.
6. Pfahl, M.; Apfel, R.; Bendik, I. Nuclear retinoid receptors and their mechanism of action. In Vitamins and Hormones; Litwack, G., Ed.; Academic Press: San Diego, CA, 1994; pp 327-382.
7. Leid, M.; Kastner, P.; Lyons, R.; Nakshatri, H.; Saunders, M.; Zacharewski, T.; Chen, J. Y.; Staub, A.; Garnier, J.-M.; Mader, S.; Chambon, P. Cell 1992, 68, 377-395.
8. Fanjul, A.; Dawson, M. I.; Hobbs, P. D.; Jong, L.; Cameron, J. F.; Harlev, E.; Graupner, G.; Lu, X.-P.; Pfahl, M. A new class of retinoids with selective inhibition of AP-1 inhibits proliferation. Nature 1994, 372, 107-111.
9. Pfahl, M. Nuclear receptor/AP-1 interaction. Endocrinol. Rev. 1993, 14, 651-658.
10. Saatcioglu, F.; Helmberg, A.; Karin, M. Modulation of immune function through interference between nuclear receptors and AP-1, Fundam. Clin. Immunol. 1994, 2, 27-36.
11. Lehmann, J. M.; Dawson, M. I.; Hobbs, P. D.; Husmann, M.; Pfahl, M. Identification of retinoids with nuclear receptor subtype-selective activities. Cancer Res. 1991, 61, 4804-4809.
12. Jong, L; Lehmann, J. M.; Hobbs, P. D.; Harlev, E.; Huffman, J. C.; Pfahl, M.; Dawson, M. I. Conformational effects on retinoid receptor selectivity. 1. Effect of 9-double bond geometry on retinoid X receptor activity. J. Med. Chem. 1993, 36, 2605-2613.
13. Lehmann, J. M.; Jong, L.; Fanjul, A.; Cameron, J. F.; Lu, X. P.; Haefner, P.; Dawson, M. I.; Pfahl, M. Retinoids selective for retinoid X receptor response pathways. Science 1992, 258, 1944-1946.
14. Graupner, G.; Malle, G.; Maignan, J.; Lang, G.; Prunieras; Pfahl, M. 6′-Substituted naphthalene-2-carboxylic acid analogs, a new class of retinoic acid receptor subtype-specific ligands. Biochem. Biophys. Res. Commun. 1991, 179, 1554-1561.
15. Reichert, U.; Bemardon, J. M.; Charpentier, B.; Nedoncelle, P.; Martin, B.; Bernard, B. A.; Asselineau, D.; Michel, S.; Lenoir, M. C.; Delescluse, C.; Pilgrim, W. R.; Darmon, Y. M.; Shroot, B. Synthetic retinoids: Receptor selectivity and biological activity. In From Molecular Biology to Therapeutics. Pharmacology of the Skin; Bernard, B. A., Shroot, B., Eds.; Karger: Basel, Switzerland, 1993; Vol. 5, pp 117-127.
16. Davies, P. J. A.; Nagy, L.; Thomazy, V.; Gil, D.; Chandraratna, R. Studies on the role of retinoid receptors in the induction of gene expression, differentiation and cell death in human promyelocytic leukemia cells. Mechanism of Action of Retinoids, Vitamin D, and Steroid Hormones. Presented at the American Association of Cancer Research Conference, Banff, Alberta, Canada, March 15-20, 1993; Abstract B-28.
17. Beard, R. L.; Gil, D. W.; Marler, D. K.; Henry, E.; Colon, D. F.; Gillett, S. J.; Arefieg, T.; Breen, T. S.; Krauss, H.; Davis, P. J. A.; Chandraratna, R. A. S. Structural basis for the differential RXR & RAR activity of stilbene retinoid analogs. Bioorg. Med. Chem. Lett. 1994, 4, 1447-1452.
18. Boehm, M. F.; Zhang, L.; Badea, B. A.; White, S. K.; Mais, D. E.; Berger, E.; Suto, C. M.; Goldman, M. E.; Heyman, R. A. Synthesis and structure-activity relationships of novel retinoid X receptor-selective retinoids. J. Med. Chem. 1994, 37, 2930-2941.
19. Dawson, M. I.; Hobbs, P. D.; Stein, R. B.; Berger, T. S.; Heyman, R. A. Interaction of retinoids with retinoic acid nuclear receptor isoforms. In Retinoids: New Trends in Research and Clinical Applications; Livrea, M. A., Packer, L., Eds.; Marcel Dekker: New York, New York, 1992; pp 205-221.
20. Loeliger, P.; Bollag, W.; Mayer, H. Arotinoids, a new class of highly active retinoids. Eur. J. Med. Chem. 1980, 15, 9-15.
21. Dawson, M. I.; Chan, R. L.; Derdzinski, K.; Hobbs, P. D.; Chao, W.; Schiff, L. Synthesis and pharmacological activity of 6-(E)-2-(2, 6, 6-trimethyl-1-cyclohexen-1-yl) ethen-1-yl]- and 6-(1, 2, 3, 4-tetrahydro-1, 1, 4, 4-tetramethyl-6-naphthyl)-2-naphthalenecarboxylic acids. J. Med. Chem. 1983, 26, 1653-1656.
22. Dawson, M. I.; Hobbs, P. D.; Derdzinski, K. A.; Chao, W.; Frenking, G.; Loew, G. H.; Jetten, A. M.; Napoli, J. L.; Williams, J. B.; Sani, B. P.; Wille, J. J., Jr. Effect of structural modifications in the C7-C11 region of the retinoid skeleton on biological activity in a series of aromatic retinoids. J. Med. Chem. 1989, 32, 1504-1517.
23. Zhang, X.-K.; Hoffmann, B.; Tran, P. B.-V.; Graupner, G.; Pfahl, M. Retinoid X receptor is an auxiliary protein for thyroid hormone and retinoid acid receptors. Nature 1992, 355, 441-446.
24. Maignan, J.; Lang, G.; Malle, G.; Restle, S.; Shroot, B. Antiproliferative benzoyl-substituted indanes and tetralins and their derivatives, their pharmaceutical and cosmetic formulations, and processes for their preparation. Fr. Demande FR 2, 601, 670, Jan. 22, 1988.
25. Brewster, R. Q.; Strain, F. lodo derivatives of diphenyl ether. I. The mono and certain diiodo-derivatives of diphenyl ether and of 2- and 4-carboxy diphenyl ethers. J. Am. Chem. Soc. 1934, 56, 117-120.
26. Strickland, S.; Breitman, T. R.; Frickel, F.; Nürrenbach, A.; Hadicke, E.; Sporn, M. B. Structure-activity relationships of a new series of retinoidal benzoic acid derivatives as measured by induction of differentiation of murine F9 teratocarcinoma cells and human HL-60 promyelocytic leukemia cells. Cancer Res. 1983, 43, 2568-2572.
27. Dawson, M. I.; Chan, R.; Hobbs, P. D.; Chao, W.; Schiff, L. J. Aromatic retinoic acid analogues. II. Synthesis and pharmacological activity. J. Med. Chem. 1983, 26, 1282-1293.
28. Allenby, G.; Bocquel, M.-T.; Saunders, M.; Kazmer, S.; Speck, J.; Rosenberger, M.; Lovey, A.; Kastner, P.; Grippo, J. F.; Chambon, P.; Levin, A. A. Retinoic acid receptors and retinoid X receptors: Interactions with endogenous retinoic acids. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 30-34.
29. Olah, G. A.; Porter, R. D. Stable carbocations. CXXI. Carbon-13 magnetic resonance spectroscopy study of ethylenarenium ions (spiro[2. 5]octadienyl cations). J. Am. Chem. Soc. 1971, 93, 6877-6887.
30. Pfahl, M.; Zhang, X.-K.; Lehmann, J. M.; Dawson, M. I.; Cameron, J. F.; Hobbs, P. D.; Jong, L. RXR receptor homodimer formation and bridged bicyclic aromatic compounds and their use in modulating gene expression and screening modulating compounds. PCT Int. pl. WO 9412880 A2, June 6, 1994.
31. Pfahl, M.; Tzukerman, M.; Zhang, X.-K.; Lehmann, J. M.; Hermann, T.; Wills, K. N.; Graupner, G. Nuclear retinoic acid receptors: Cloning, analysis, and function. In Methods in Enzymology; Packer, L., Ed., Academic Press: San Diego, CA, 1991; Vol. 189, pp 256-270.