Glucose analog inhibitors of glycogen phosphorylases as potential antidiabetic agents: Recent developments

Current Pharmaceutical Design

Volumn 9, Issue 15, 2003, Pages 1177-1189

  Somsák, László ^a   Nagy, Veronika ^a   Hadady, Zsuzsa ^a   Docsa, Tibor ^b   Gergely, Pál ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 4 DIMETHYLAMINOAZOBENZENE; ANTIDIABETIC AGENT; AZAFAGOMINE; AZOLOPERHYDROPYRIDINE DERIVATIVE; BAY W 1807; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; CARBAMIC ACID DERIVATIVE; CP 320626; CP 526423; ENZYME INHIBITOR; GLUCOPYRANOSYLIDENE SPIRO HYDANTOIN; GLUCOSE; GLUCOSE DERIVATIVE; GLYCOGEN PHOSPHORYLASE; GLYCOGEN PHOSPHORYLASE INHIBITOR; HYDANTOIN DERIVATIVE; ISOFAGOMINE; METHYL N (1 CARBOXAMIDOGLUCOPYRANOSYL)CARBAMATE; N (2 NAPHTHOYL) N' (BETA GLUCOPYRANOSYL)UREA; N ACETYL BETA GLUCOPYRANOSYLAMINE; NITROGEN; NOEUROMYCIN; NOJIRITETRAZOLE; PYRIDINE DERIVATIVE; SPIROTHIOHYDANTOIN; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; UREA DERIVATIVE;

BINDING SITE; BIOASSAY; CATALYSIS; COMPUTER AIDED DESIGN; CONTROLLED STUDY; CRYSTALLOGRAPHY; DRUG DESIGN; DRUG POTENCY; DRUG RESEARCH; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME REGULATION; GLUCOSE BLOOD LEVEL; HUMAN; IC 50; MORTALITY; NON INSULIN DEPENDENT DIABETES MELLITUS; PRIORITY JOURNAL; PROTEIN ANALYSIS; REVIEW; SYNTHESIS;

ANIMALS; DIABETES MELLITUS, TYPE 2; ENZYME INHIBITORS; GLUCOSE; GLYCOGEN PHOSPHORYLASE; HUMANS; HYPOGLYCEMIC AGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 0037648878     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612033454919     Document Type: Review

References (84)

1. Moller D E. Nature 2001; 414: 821-827.
2. Zimmet P, Alberti K G M M, Shaw J. Nature 2001; 414: 782-861.
3. Hengesh E J. In Principles of Medicinal Chemistry. Foye W O, Lemke T L, Williams D A, eds Williams & Wilkins: Baltimore 1995; pp 581-600.
4. Martin J L, Veluraja K, Ross K, Johnson L N, Fleet G W J, Ramsden N G, et al. Biochemistry 1991; 30: 10101-10116.
5. Cobb J, Dukes I. In Annual Reports in Medicinal Chemistry J A Bristol ed Academic Press: San Diego 1998; Vol 33: pp 213-222.
6. Perfetti R, Barnett P S, Mathur R, Egan J M. Diabetes/Metabolism Reviews 1998; 14: 207-225.
7. Rose M L, Paulik M A, Lenhard J M. Expert Opinion on Therapeutical Patents 1999; 9: 1-14.
8. Zhang B B, Moller D E. Current Opinion in Chemical Biology 2000; 4: 461-467.
9. Wagman A S, Nuss J M. Current Pharmaceutical Design 2001; 7: 417-450.
10. Cohen P. Philosophical Transactions of the Royal Society London B 1999; 354: 485-495.
11. Treadway J L, Mendys P, Hoover D J. Expert Opinion on Investigational Drugs 2001; 10: 439-454.
12. Saltiel A R, Kahn C R. Nature 2001; 414: 799-806.
13. Staehr P, Hother-Nielsen O, Beck-Nielsen H. Diabetes Obesity & Metabolism 2002; 4: 215-223.
14. Chu-Moyer M Y. Expert Opinion on Therapeutic Patents 2000; 10: 787-801.
15. McCarty M F. Medical Hypotheses 2000; 54: 483-487.
16. Oikonomakos N G, Kontou M, Zographos S E, Tsitoura H S, Johnson L N, Watson K A, et al. European Journal of Drug Metabolism and Pharmakokinetics 1994; 185-192.
17. Watson K A, Mitchell E P, Johnson L N, Son J C, Bichard C J F, Orchard M G, et al. Biochemistry 1994; 33: 5745-5758.
18. Watson K A, Mitchell E P, Johnson L N, Cruciani G, Son J C, Bichard C J F, et al. Acta Crystallographica 1995; D51: 458-472.
19. McCormack J G, Westergaard N, Kristiansen M, Brand C L, Lau J. Current Pharmaceutical Design 2001; 7: 1451-1474.
20. Oikonomakos N G. Current Protein & Peptide Science 2002; 3: 561-586.
21. Bollen M, Keppens S, Stalmans W. Biochemical Journal 1998; 336: 19-31.
22. Radziuk J, Pye S. Diabetes/Metabolism Research and Reviews 2001; 17: 250-272.
23. Andersen B, Rassov A, Westergaard N, Lundgren K. Biochemical Journal 1999; 342: 545-550.
24. Fosgerau K, Westergaard N, Quistorff B, Grunnet N, Kristiansen M, Lundgren K. Archives of Biochemistry and Biophysics 2000; 380: 274-284.
25. Waagepetersen H S, Westergaard N, Schousboe A. Neurochemistry International 2000; 36: 435-440.
26. Goldsmith E J, Sprang S R, Hamlin R, Xuong N H, Fletterick R. J Science 1989; 245: 528-532.
27. Johnson L N. The FASEB Journal 1992; 6: 2274-2282.
28. Oikonomakos N G, Skamnaki V T, Tsitsanou K E, Gavalas N G, Johnson L N. Structure 2000; 8: 575-584.
29. Rath V L, Ammirati M, LeMotte P K, Fennell K F, Mansour M N, Danley D E, et al. Molecular Cell 2000; 6: 139-148.
30. Coats W S, Browner M F, Fletterick R J, Newgard C B. Journal of Biological Chemistry 1991; 266: 16113-16119.
31. Zographos S E, Oikonomakos N G, Tsitsanou K E, Leonidas D D, Chrysina E D, Skamnaki V T, et al. Structure 1997; 5: 1413-1425.
32. Oikonomakos N G, Tsitsanou K E, Zographos S E, Skamnaki V T, Goldmann S, Bischoff H. Protein Science 1999; 8: 1930-1945.
33. Hoover D J, Lefkowitz-Snow S, Burgess-Henry J L, Martin W H, Armento S J, Stock I A, et al. Journal of Medicinal Chemistry 1998; 41: 2934-2938.
34. Rath V L, Ammirati M, Danley D E, Ekstrom J L, Gibbs E M, Hynes T R, et al. Chemistry & Biology 2000; 7: 677-682.
35. Board M, Hadwen M, Johnson L N. European Journal of Biochemistry 1995; 228: 753-761.
36. Gregoriou M, Noble M E M, Watson K A, Garman E F, Krulle T M, Fuente C, et al. Johnson L N. Protein Science 1998; 7: 915-927.
37. Somsák L, Kovács L, Tóth M, Osz E, Szilágyi L, Györgydeák Z, et al Journal of Medicinal Chemistry 2001; 44: 2843-2848.
38. Johnson L N, Acharya K R, Jordan M D, McLaughlin P J. Journal of Molecular Biology 1990; 211: 645-661.
39. Mitchell E P, Withers S G, Ermert P, Vasella A T, Garman E F, Oikonomakos N G, et al. Biochemistry 1996; 35: 7341-7355.
40. Bichard C J F, Mitchell E P, Wormald M R, Watson K A, Johnson L N, Zographos S E, et al. Tetrahedron Letters 1995; 36: 2145-2148.
41. Krülle T M, Fuente C, Watson K A, Gregoriou M, Johnson L N, Tsitsanou K E, et al. Synlett 1997; 211-213.
42. Osz E, Somsák L, Szilágyi L, Kovács L, Docsa T, Tóth B, et al. Bioorganic and Medicinal Chemistry Letters 1999; 9: 1385-1390.
43. Krülle T M, Watson K A, Gregoriou M, Johnson L N, Crook S, Watkin D J, et al. Tetrahedron Letters 1995; 36: 8291-8294.
44. So S -S, Karplus M. Journal of Medicinal Chemistry 1997; 40: 4360-4371.
45. Pastor M, Cruciani G, Clementi S. Journal of Medicinal Chemistry 1997; 40: 1455-1464.
46. Cruciani G, Clementi S, Pastor M. Perspectives in Drug Discovery and Design 1998; 12/13/14: 71-86.
47. Venkatarangan P, Hopfinger A J. Journal of Medicinal Chemistry 1999; 42: 2169-2179.
48. Venkatarangan P, Hopfinger A J. Journal of Chemical Information and Computer Sciences 1999; 39: 1141-1150.
49. So S -S, Karplus M. Journal of Computer-Aided Molecular Design 1999; 13: 243-258.
50. Marchand-Geneste N, Watson K A, Alsberg B K, King R D. Journal of Medicinal Chemistry 2002; 45: 399-409.
51. Hopfinger A J, Reaka A, Venkatarangan P, Duca J S, Wang S. Journal of Chemical Information and Computer Sciences 1999; 39: 1151-1160.
52. So S -S, Karplus M. Journal of Computer-Aided Molecular Design 2001; 15: 613-647.
53. Fuente C, Krülle T M, Watson K A, Gregoriou M, Johnson L N, Tsitsanou K E. et al. Synlett 1997; 485-487.
54. Osz E, Sós E, Somsák L, Szilágyi L, Dinya Z. Tetrahedron 1997; 53: 5813-5824.
55. Oikonomakos N G, Skamnaki V T, Osz E, Szilágyi L, Somsák L, Docsa T, et al. Bioorganic and Medicinal Chemistry 2002; 10: 261-268.
56. Somsák L, Nagy V. Tetrahedron: Asymmetry 2000; 11 1719-1727 Corrigendurn 2247.
57. Somsák L, Nagy V, Docsa T, Tóth B, Gergely P. Tetrahedron: Asymmetry 2000; 11: 405-408.
58. Agasimundin Y S, Mumper M W, Hosmane R S. Bioorganic and Medicinal Chemistry 1998; 6: 911-923.
59. Sprang S R, Goldsmith E J, Fletterick R J, Withers S G, Madsen N B. Biochemistry 1982; 21: 5364-5371.
60. Street I P, Armstrong C R, Withers S G. Biochemistry 1986; 25: 6021-6027.
61. Nhien A N V, Villa P, Ronco G, Postel D. Journal of Pharmacy and Pharmacology 2001; 53: 939-943.
62. Postel D, Nhien A N V, Villa P, Ronco G. Tetrahedron Letters 2001; 42: 1499-1502.
63. Kovács L, Osz E, Domokos V, Holzer W, Györgydeák Z. Tetrahedron 2001; 57: 4609-4621.
64. Somsák L, Nagy V, Hadady Z, Illyés T Z, Szilágyi L, Praly J-P, et al. unpublished results.
65. Oikonomakos N G, Kosmopolou M, Zographos S E, Leonidas D D, Somsák L, Nagy V, et al. European Journal of Biochemistry 2002; 269: 1684-1696.
66. Oikonomakos N G. personal communication.
67. Farkas I, Szabó I F, Bognár R. Carbohydrate Research 1977; 56: 404-406.
68. Szabó I F, Farkas I, Somsák L, Bognár R. Acta Chimica Academiae Scientiarium Hungaricae 1981; 106: 61-69.
69. Lillelund V H, Jensen H H, Liang X, Bols M. Chemical Reviews 2002; 102: 515-553.
70. Jakobsen P, Lundbeck J M, Kristiansen M, Breinholt J, Demuth H, Pawlas J, et al. Bioorganic and Medicinal Chemistry 2001; 9: 733-744.
71. Lohse A, Jensen K B, Lundgren K, Bols M. Bioorganic and Medicinal Chemistry 1999; 7: 1965-1971,
72. Liu H, Liang X, Sohoel H, Bülow A, Bols M. Journal of the American Chemical Society 2001; 123: 5116-5117.
73. Heightman T D, Vasella A, Tsitsanou K E, Zographos S E, Skamnaki V T, Oikonomakos N G. Helvetica Chimica Acta 1998; 81: 853-864.
74. Krülle T M, Fuente C, Pickering L, Aplin R T, Tsitsanou K E, Zographos S E, et al. Tetrahedron: Asymmetry 1997; 8: 3807-3820.
75. Tsitsanou K E, Oikonomakos N G, Zographos S E, Skamnaki V T, Gregoriou M, Watson K A, et al. Protein Science 1999; 8: 741-749.
76. Board M, Bollen M, Stalmans W, Kim Y, Fleet G W J, Johnson L N. Biochemical Journal 1995, 311: 845-852.
77. Docsa T, Tóth B, Somsák L, Gergely P. In Protein Modules in Cellular Signalling L Heilmeyer P Friedrich eds IOS Press: Amsterdam 2001; pp 142-149.
78. Docsa T, Tar K, Tóth B, Somsák L, Gergely P. Journal of Physiology - London 2000; 526: Suppl 92P.
79. Andersen B, Fosgerau K, Kristiansen M, Lundgren K, Westergaard N. Diabetes 1999; 48: A447.
80. Fosgerau K, Mittelman S D, Sunehag A, Dea M K, Lundgren K, Bergman R N. American Journal of Physiology - Endocrinology and Metabolism 2001; 281: E375-E383.
81. Fosgerau K, Breinholt J, McCormack J G, Westergaard N. Journal of Biological Chemistry 2002; 277: 28648-28655.
82. de Souza CJ, Burkey BF. Beta 3-adrenoceptor agonists as anti-diabetic and anti-obesity drugs in humans. Curr Pharm Des 2001; 7(14): 1433-49.
83. Drucker DJ. Development of glucagon-like peptide-l-based pharmaceuticals as therapeutic agents for the treatment of diabetes. Curr Pharm Des 2001; 7(14): 1399-412.
84. McCormack JG, Westergaard N, Kristiansen M, Brand CL, Lau J. Pharmacological approaches to inhibit endogenous glucose production as a means of anti-diabetic therapy. Curr Pharm Des 2001; 7(14): 1451-74.