Separation of α-glucosidase-inhibitory and liver X receptor-antagonistic activities of phenethylphenyl phthalimide analogs and generation of LXRα-selective antagonists

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 14, 2009, Pages 5001-5014

  Motoshima, Kazunori ^a   Noguchi Yachide, Tomomi ^a   Sugita, Kazuyuki ^a   Hashimoto, Yuichi ^a   Ishikawa, Minoru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Glucosidase inhibitor; LXR antagonist; Thalidomide analog

Indexed keywords

ALPHA GLUCOSIDASE; CHOLESTEROL; LIVER X RECEPTOR ALPHA; N [4 [2 (4 METHOXYPHENYL)ETHYL]PHENYL]PHTHALIMIDE; PHTHALIMIDE DERIVATIVE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; METABOLIC SYNDROME X; RECEPTOR BLOCKING;

ALPHA-GLUCOSIDASES; CELL LINE; DNA-BINDING PROTEINS; HUMANS; KIDNEY; MOLECULAR STRUCTURE; PHTHALIMIDES; RECEPTORS, CYTOPLASMIC AND NUCLEAR; SACCHAROMYCES; STRUCTURE-ACTIVITY RELATIONSHIP; THALIDOMIDE;

EID: 67650077280     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.066     Document Type: Article

References (44)

1. Repa J.J., and Mangelsdolf D.J. Annu. Rev. Cell Dev. Biol. 16 (2000) 459
2. Willy P.J., Umesono K., Ong E.S., Evans R.M., Heyman R.A., and Mangelsdorf D.J. Genes Dev. 9 (1995) 1033
3. Teboul M., Enmark E., Li Q., Wikström A.C., Pelto-Huikko M., and Gustafsson J.-A. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 2096
4. Glass C.K., and Rosenfeld M.G. Genes Dev. 14 (2000) 121
5. McKenna N.J., and O'Malley B.W. Cell 108 (2002) 465
6. Zelcer N., and Tontonoz P. J. Clin. Invest. 116 (2006) 607
7. Peet D.J., Turley S.D., Ma W., Janowski B.A., Lobaccaro J.-M.A., Hammer R.E., and Mangelsdorf D.J. Cell 93 (1998) 693
8. Costet P., Luo Y., Wang N., and Tall A.R. J. Biol. Chem. 275 (2000) 28240
9. Repa J.J., Turley S.D., Lobaccaro J.A., Medina J., Li L., Lustig K., Shan B., Heyman R.A., Dietschy J.M., and Mangelsdorf D.J. Science 289 (2000) 1524
10. Repa J.J., Berge K.E., Pomajzl C., Richardson J.A., Hobbs H., and Mangelsdorf D.J. J. Biol. Chem. 277 (2002) 18793
11. Kennedy M.A., Venkateswaran A., Tarr P.T., Xenarious I., Kudoh J., Shimizu N., and Edwards P.A. J. Biol. Chem. 276 (2001) 39438
12. Sabol S.L., Brewer Jr. H.B., and Santamarina-Fojo S. J. Lipid Res. 46 (2005) 2151
13. Terasaka N., Hiroshima A., Koieyama T., Ubukata N., Morikawa Y., Nakai D., and Inaba T. FEBS Lett. 536 (2003) 6
14. Joseph S.B., McKilligin E., Pei L., Watson M.A., Collins A.R., Laffitte B.A., Chen M., Noh G., Goodman J., Hagger G.N., Tran J., Tippin T.K., Wang X., Lusis A.J., Hsueh W.A., Law R.E., Collins J.L., Willson T.M., and Tontonoz P. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 7604
15. Schultz J.R., Tu H., Luk A., Repa J.J., Medina J.C., Li L., Schwendner S., Wang S., Thoolen M., Mangelsdorf D.J., Lustig K.D., and Shan B. Genes Dev. 14 (2000) 2831
16. Collins J.L., Fivush A.M., Watson M.A., Galardi C.M., Lewis M.C., Moore L.B., Parks D.J., Wilson J.G., Tippin T.K., Binz J.G., Plunket K.D., Morgan D.G., Beaudet E.J., Whitney K.D., Kliewer S.A., and Willson T.M. J. Med. Chem. 45 (2002) 1963
17. Joseph S.B., Laffitte B.A., Patel P.H., Watson M.A., Matsukuma K.E., Walczak R., Collins J.L., Osborne T.F., and Tontonoz P. J. Biol. Chem. 277 (2002) 11019
18. Lund E.G., Peterson L.B., Adams A.D., Lam M.-H.N., Burton C.A., Chin J., Guo Q., Huang S., Latham M., Lopez J.C., Menke J.G., Milot D.P., Mitnaul L.J., Rex-Rabe S.E., Rosa R.L., Tian J.Y., Wright S.D., and Sparrow C.P. Biochem. Pharmacol. 71 (2006) 453
19. Walczak R., Joseph S.B., Laffitte B.A., Castrillo A., Pei L., and Tontonoz P. J. Biol. Chem. 279 (2004) 9905
20. Hu B., Quinet E., Unwalla R., Collini M., Jetter J., Dooley R., Andraka D., Nogle L., Savio D., Halpern A., Goos-Nilsson A., Wihelmsson A., Nambi P., and Wrobel J. Bioorg. Med. Chem. Lett. 18 (2008) 54
21. Kim K.H., Choi S.H., Lee T.S., Oh W.K., Kim D.S., and Kim J.B. Biochem. Biophys. Res. Commun. 349 (2006) 513
22. Thomas J., Bramlett K.S., Montrose C., Foxworthy P., Eacho P.I., McCann D., Cao G., Kiefer A., McCowan J., Yu K., Grese T., Chin W.W., Burris T.P., and Michael L.F. J. Biol. Chem. 278 (2003) 2403
23. Tamehiro N., Sato Y., Suzuki T., Hashimoto T., Asakawa Y., Yokoyama S., Kawanishi T., Ohno Y., Inoue K., Nagano T., and Nishimaki-Mogami T. FEBS Lett. 579 (2005) 5299
24. Dodo K., Aoyama A., Noguchi-Yachide T., Makishima M., Miyachi H., and Hashimoto Y. Bioorg. Med. Chem. 16 (2008) 4272
25. Janowski B.A., Grogan M.J., Jones S.A., Wisely G.B., Kliewer S.A., Corey E.J., and Mangelsdorf D.J. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 266
26. Koonin E.V., Wolf Y.I., and Karev G.P. Nature 420 (2002) 218
27. Grishin N.V. J. Struct. Biol. 134 (2001) 167
28. Koch M.A., Wittenberg L.-O., Basu S., Jeyaraj D.A., Gourzoulidou E., Reinecke K., Odermatt A., and Waldmann H. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 16721
29. Hosoda, S.; Matsuda, D.; Tomoda, H.; Hashimoto, Y. Mini-Rev. Med. Chem. 2009, 9, 572.
30. Hashimoto Y. Arch. Pharm. Chem. Life. Sci. 341 (2008) 536
31. Hashimoto Y. Bioorg. Med. Chem. 10 (2002) 461
32. Hashimoto Y. Cancer Chemother. Pharmacol. 52 (2003) S16
33. Hashimoto Y., Tanatani A., Nagasawa K., and Miyachi H. Drugs Future 29 (2004) 383
34. Noguchi-Yachide T., Aoyama A., Makishima M., Miyachi H., and Hashimoto Y. Bioorg. Med. Chem. Lett. 17 (2007) 3957
35. Noguchi-Yachide T., Miyachi H., Aoyama H., Aoyama A., Makishima M., and Hashimoto Y. Chem. Pharm. Bull. 55 (2007) 1750
36. Takahashi H., Sou S., Yamasaki R., Sodeoka M., and Hashimoto Y. Chem. Pharm. Bull. 48 (2000) 1494
37. Sou S., Mayumi S., Takahashi H., Yamasaki R., Kadoya S., Sodeoka M., and Hashimoto Y. Bioorg. Med. Chem. Lett. 10 (2000) 1081
38. Sou S., Takahashi H., Yamasaki R., Kagechika H., Endo Y., and Hashimoto Y. Chem. Pharm. Bull. 49 (2001) 791
39. Makishima M., Okamoto A.Y., Repa J.J., Tu H., Learned R.M., Luk A., Hull M.V., Lustig K.D., Mangelsdolf D.J., and Shan B. Science 284 (1999) 1362
40. Makishima M., Lu T.T., Xie W., Whitfield G.K., Domoto H., Evans R.M., Haussler M.R., and Mangelsdolf D.J. Science 296 (2002) 1313
41. Kasuga J., Makishima M., Hashimoto Y., and Miyachi H. Bioorg. Med. Chem. Lett. 16 (2006) 554
42. Breitmeier D., Günther S., and Heymann H. Arch. Biochem. Biophys. 346 (1997) 7
43. Alberti S., Steffensen K.R., and Gustafsson J.-A. Gene 243 (2000) 93
44. Williams S., Bledsoe R.K., Collins J.L., Boggs S., Lambert M.H., Miller A.B., Moore J., McKee D.D., Moore L., Nichols J., Parks D., Watson M., Wisely B., and Willson T.M. J. Biol. Chem. 278 (2003) 27138