Glycogen phosphorylase a inhibitors with a phenethylphenylphthalimide skeleton derived from thalidomide-related α-glucosidase inhibitors and liver X receptor antagonists

Biological and Pharmaceutical Bulletin

Volumn 32, Issue 9, 2009, Pages 1618-1620

  Motoshima, Kazunori ^a   Ishikawa, Minoru ^a   Sugita, Kazuyuki ^a   Hashimoto, Yuichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Enzyme inhibitor; Glycogen phosphorylase; Phthalimide; Structure activity relationship

Indexed keywords

1,4 DIDEOXY 1,4 IMINO DEXTRO ARABINITOL; ALPHA GLUCOSIDASE INHIBITOR; GLYCOGEN PHOSPHORYLASE; GLYCOGEN PHOSPHORYLASE A INHIBITOR; GLYCOSYLTRANSFERASE INHIBITOR; LIVER X RECEPTOR ANTAGONIST; PHENETHYLPHENYLPHTHALIMIDE DERIVATIVE; PHTHALIMIDE DERIVATIVE; THALIDOMIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG ACTIVITY; DRUG EFFICACY; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; RABBIT; STRUCTURE ACTIVITY RELATION;

ALPHA-GLUCOSIDASES; ANIMALS; ENZYME INHIBITORS; GLYCOGEN PHOSPHORYLASE, LIVER FORM; GLYCOGEN PHOSPHORYLASE, MUSCLE FORM; ORPHAN NUCLEAR RECEPTORS; PHTHALIMIDES; RABBITS; THALIDOMIDE;

EID: 69949145117     PISSN: 09186158     EISSN: 13475215     Source Type: Journal    
DOI: 10.1248/bpb.32.1618     Document Type: Article

References (36)

1. Oikonomakos N. G., Curr. Protein Pept. Sci., 3, 561-586 (2002).
2. Henke B. R., Sparks S. M., Mini-Rev. Med. Chem., 6, 845-857 (2006).
3. Treadway J. L., Mendys P., Hoover D. J., Expert Opin. Invest. Drugs, 10, 439-454 (2001).
4. Johnson L. N., FASEB J., 6, 2274-2282 (1992).
5. Oikonomakos N. G., Acharya K. R., Johnson, L. N., "Posttranslational Modification of Proteins," ed. by Harding J. J., Crabbe M. J. C, CRC Press, Inc., Boca Raton, Florida, 1992, pp. 81-151.
6. Oikonomakos N. G., Somsák L., Curr. Opin. Investig. Drugs, 9, 379-395 (2008).
7. Bichard C. J. F., Mitchell E. P., Wormald M. R., Watson K. A., Johnson L. N., Zographos S. E., Koutra D. D., Oikonomakos N. G., Fleet G. W. J., Tetrahedron Lett., 34, 2145-2148 (1995).
8. Martin J. L., Veluraja K., Ross K., Johnson L. N., Fleet G. W. J., Ramsden N. G., Bruce I., Orchard M. G., Oikonomakos N. G., Papageorgiou A. C., Leonidas D. D., Tsitoura H. S., Biochemistry, 30, 10101-10116 (1991).
9. Board M., Hadwen M., Johnson L. N., Eur. J. Biochem., 228, 753-761 (1995).
10. Oikonomakos N. G., Kosmopoulou M., Zographos S. E., Leonidas D. D., Chrysina E. D., Somsák L., Nagy V., Praly J.-P., Docsa T., Tóth B., Gergely P., Eur. J. Biochem., 269, 1684-1696 (2002).
11. Jakobsen P., Lundbeck J. M., Kristiansen M., Breinholt J., Demuth H., Pawlas J., Candela M. P. T., Andersen B., Westergaard N., Lundgren K., Asano N., Bioorg. Med. Chem., 9, 733-744 (2001).
12. Fosgerau K., Westergaard N., Quistorff B., Grunnet N., Kristiansen M., Lundgren K., Arch. Biochem., 380, 274-284 (2000).
13. Andersen B., Westergaard N., Biochem. J., 367, 443-450 (2002).
14. Oikonomakos N. G., Tiraidis C., Leonidas D. D., Zographos S. E., Kristiansen M., Jessen C. U., Nørskov-Lauritsen L., Agius L., J. Med. Chem., 49, 5687-5701 (2006).
15. Koonin E., V., Wolf Y. I., Karev G. P., Nature (London), 420, 218-223 (2002).
16. Grishin N. V., J. Struct. Biol., 134, 167-185 (2001).
17. Koch M. A., Wittenberg L.-O., Basu S., Jeyaraj D. A., Gourzoulidou E., Reinecke K., Odermatt A., Waldmann H., Proc. Natl. Acad. Sci. U.S.A., 101, 16721-16726 (2004).
18. Hosoda S., Matsuda D., Tomoda H., Hashimoto Y., Mini-Rev. Med. Chem., 9, 572-580 (2009).
19. Hashimoto Y., Arch. Pharm. Chem. Life Sci., 341, 536-547 (2008).
20. Hashimoto Y., Tanatani A., Nagasawa K., Miyachi H., Drugs Future, 29, 383-391 (2004).
21. Hashimoto Y., Bioorg. Med. Chem., 10, 461-479 (2002).
22. Bartlett J. B., Dredge K., Dalgleish A. G., Nat. Rev. Cancer, 4, 314-322 (2004).
23. Hashimoto Y., Curr. Med. Chem., 5, 163-178 (1998).
24. Hashimoto Y., Mini-Rev. Med. Chem., 2, 543-551 (2002).
25. Takahashi H., Sou S., Yamasaki R., Sodeoka M., Hashimoto Y., Chem. Pharm. Bull., 48, 1494-1499 (2000).
26. Noguchi-Yachide T., Aoyama A., Makishima M., Miyachi H., Hashimoto Y., Bioorg. Med. Chem. Lett., 17, 3957-3961 (2007).
27. Yu C., Lee A. M., Bassler B. L., Roseman S., J. Biol. Chem., 266, 24260-24267 (1991).
28. Legler G., Adv. Carbohydr. Chem. Biochem., 48, 319-384 (1990).
29. Yoshikawa M., Shimada H., Nishida N., Li Y., Toguchida I., Yamahara J., Matsuda H., Chem. Pharm. Bull., 46, 113-119 (1998).
30. Repa J. J., Mangelsdolf D. J., Annu. Rev. Cell Dev. Biol., 16, 459-481 (2000).
31. Repa J. J., Turley S. D., Lobaccaro J.-M. A., Medina J., Li L., Lustig K., Shan B., Heyman R. A., Dietschy J. M., Mangelsdorf D. J., Science, 289, 1524-1529 (2000).
32. Peet D. J., Turley S. D., Ma W., Janowski B. A., Lobaccaro J.-M. A., Hammer R. E., Mangelsdorf D. J., Cell, 93, 693-704 (1998).
33. Mitro N., Mak P. A., Vargas L., Godio C., Hampton E., Molteni V., Kreusch A., Saez E., Nature (London), 445, 219-223 (2007).
34. Kase E. T., Thoresen G. H., Westerlund S., Højlund K., Rustan A. C., Gaster M., Diabetologia, 50, 2171-2180 (2007).
35. Motoshima K., Noguchi-Yachide T., Sugita K., Hashimoto Y., Ishikawa M., Bioorg. Med. Chem., 17, 5001-5014 (2009).
36. Martin W. H., Hoover D. J., Armento S. J., Stock I. A., McPherson R. K., Danley D. E., Stevenson R. W., Barrett E. J., Treadway J. L., Proc. Natl. Acad. Sci. U.S.A., 95, 1776-1781 (1998).