Inhibition of glycogen phosphorylase in the context of type 2 diabetes, with focus on recent inhibitors bound at the active site

Mini-Reviews in Medicinal Chemistry

Volumn 10, Issue 12, 2010, Pages 1102-1126

  Praly, J P ^a,b,c,d   Vidal, S ^a,b,c,d  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ LYON 1   (France)

^c CNRS   (France)

^d CPE LYON   (France)

Author keywords

Diabetes; Enzymology; Glucose based inhibitors; Glycogen phosphorylase; Glycomimics; Hyperglycemia; Inhibitors; Type 2 diabetes mellitus

Indexed keywords

2 NAPHTHYLACETIC ACID; AMYLO 1,6 GLUCOSIDASE; GLUCAGON; GLUCOSE; GLYCOGEN PHOSPHORYLASE; IMINOSUGAR; SULFONIUM DERIVATIVE;

ALLOSTERISM; ARTICLE; BINDING SITE; ENZYME ACTIVE SITE; GLUCONEOGENESIS; GLUCOSE BLOOD LEVEL; HUMAN; INHIBITION KINETICS; LIVER CELL; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; PROTEIN MOTIF;

EID: 78549295877     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/1389557511009011102     Document Type: Article

References (161)

1. Saltiel, A. R.; Kahn, C. R. Insulin signalling and the regulation of glucose and lipid metabolism. Nature, 2001, 414, 799-806.
2. Abate, N.; Chandalia, M. The impact of ethnicity on type 2 diabetes. J. Diabetes Complications, 2003, 17, 39-58.
3. Chiu, K. C.; Cohan, P.; Lee, N. P.; Chuang, L.-M. Insulin sensitivity differs among ethnic groups with a compensatory response in β -cell function. Diabetes Care, 2000, 23, 1353-1358.
4. Petersen, K. F.; Dufour, S.; Feng, J.; Befroy, D.; Dziura, J.; Dalla Man, C.; Cobelli, C.; Shulman, G. I. Increased prevalence of insulin resistance and nonalcoholic fatty liver disease in Asian-Indian men. Proc. Natl. Acad. Sci. USA, 2006, 103, 18273-18277.
5. Cheng, T. O. Rising prevalence of diabetes in china. J. Nat. Med. Assoc., 2003, 95, 1115-1116.
6. Bril, A.; Ktorza, A. A better understanding of the pathophysiology of obesity and type 2 diabetes: a clue for new therapeutic approaches. Curr. Opin. Pharmacol., 2006, 6, 577-579.
7. Cornier, M.-A.; Dabelea, D.; Hernandez, T. L.; Lindstrom, R. C.; Steig, A. J.; Stob, N. R.; Van Pelt, R. E.; Wang, H.; Eckel, R. H. The Metabolic Syndrome. Endocr. Rev., 2008, 29, 777-822.
8. Zimmet, P.; Alberti, K. G. M. M.; Shaw, J. Global and societal implications of the diabetes epidemic. Nature, 2001, 414, 782-787.
9. Alberti, K. G. M. M.; Zimmet, P.; Shaw, J.; Bloomgarden, Z.; Kaufman, F.; Silink, M. Type 2 diabetes in the young: the evolving epidemic. Diabetes Care, 2004, 27, 1798-1811.
10. Ren, J.-M.; Semenkovich, C. F.; Gulve, E. A.; Goa, J.; Holloszy, J. O. Exercise induces rapid increases in GLUT4 expression, glucose transport capacity, and insulin-stimulated glycogen storage in muscle. J. Biol. Chem., 1994, 269, 14396-14401.
11. Krentz, A. J.; Bailey, C. J. Oral antidiabetic agents: current role in type 2 diabetes mellitus. Drugs, 2005, 65, 385-411.
12. Ross, S. A.; Gulve, E. A.; Wang, M. Chemistry and Biochemistry of Type 2 Diabetes. Chem. Rev., 2004, 104, 1255-1282.
13. Skyler, J. S. Diabetes Mellitus: Pathogenesis and Treatment Strategies. J. Med. Chem., 2004, 47, 4113-4117.
14. Radziuk, J.; Pye, S. Hepatic glucose uptake, gluconeogenesis and the regulation of glycogen synthesis. Diabetes Metab. Res. Rev., 2001, 17, 250-272.
15. Owen, O. E.; Morgan, A. P.; Kemp, H. G.; Sullivan, J. M.; Herrera, M. G.; Cahill, G. F. Brain Metabolism during Fasting. J. Clin. Invest., 1967, 46, 1589-1595.
16. Bernard, C. Leçons de physiologie experimentale appliquée à la médecine; Baillière et fils: Paris, 1854.
17. Schwartz, M. W.; Porte, D., Jr. Diabetes, Obesity, and the Brain. Science, 2005, 307, 375-379.
18. Migrenne, S.; Marsollier, N.; Cruciani-Guglielmacci, C.; Magnan, C. Importance of the gut-brain axis in the control of glucose homeostasis. Curr. Opin. Pharmacol., 2006, 6, 592-597.
19. Henke, B. R. Peroxisome Proliferator-Activated Receptor/Dual Agonists for the Treatment of Type 2 Diabetes. J. Med. Chem., 2004, 47, 4118-4127.
20. Zhang, B. B.; Moller, D. E. New approaches in the treatment of type 2 diabetes. Curr. Opin. Chem. Biol., 2000, 4, 461-467.
21. Heppner, K. M.; Habegger, K. M.; Day, J.; Pfluger, P. T.; Perez-Tilve, D.; Ward, B.; Gelfanov, V.; Woods, S. C.; DiMarchi, R.; Tschöp, M. Glucagon regulation of energy metabolism. Physiol. Behav., 2010, 100, 545-548.
22. Cohen, P. The twentieth century struggle to decipher insulin signalling. Nat. Rev. Mol. Cell. Biol., 2006, 7, 867-873.
23. Moller, D. E. New drug targets for type 2 diabetes and the metabolic syndrome. Nature, 2001, 414, 821-827.
24. Morral, N. Novel targets and therapeutic strategies for type 2 diabetes. Trends Endocrinol. Metab., 2003, 14, 169-175.
25. Nourparvar, A.; Bulotta, A.; Di Mario, U.; Perfetti, R. Novel strategies for the pharmacological management of type 2 diabetes. Trends Pharmacol. Sci., 2004, 25, 86-91.
26. Rotella, D. P. Novel Second-Generation Approaches for the Control of Type 2 Diabetes. J. Med. Chem., 2004, 47, 4111-4112.
27. Knudsen, L. B. Glucagon-like Peptide-1: The Basis of a New Class of Treatment for Type 2 Diabetes. J. Med. Chem., 2004, 47, 4128-4134.
28. Weber, A. E. Dipeptidyl Peptidase IV Inhibitors for the Treatment of Diabetes. J. Med. Chem., 2004, 47, 4135-4141.
29. Hooft van Huijsduijnen, R.; Sauer, W. H. B.; Bombrun, A.; Swinnen, D. Prospects for Inhibitors of Protein Tyrosine Phosphatase 1B as Antidiabetic Drugs. J. Med. Chem., 2004, 47, 4142-4146.
30. Montalibet, J.; Kennedy, B. P. Therapeutic strategies for targeting PTP1B in diabetes. Drug Discov. Today, 2005, 2, 129-135.
31. von Geldern, T. W.; Tu, N.; Kym, P. R.; Link, J. T.; Jae, H.-S.; Lai, C.; Apelqvist, T.; Rhonnstad, P.; Hagberg, L.; Koehler, K.; Grynfarb, M.; Goos-Nilsson, A.; Sandberg, J.; Osterlund, M.; Barkhem, T.; Hoglund, M.; Wang, J.; Fung, S.; Wilcox, D.; Nguyen, P.; Jakob, C.; Hutchins, C.; Farnegardh, M.; Kauppi, B.; Ohman, L.; Jacobson, P. B. Liver-Selective Glucocorticoid Antagonists: A Novel Treatment for Type 2 Diabetes. J. Med. Chem., 2004, 47, 4213-4230.
32. Kakinuma, H.; Oi, T.; Hashimoto-Tsuchiya, Y.; Arai, M.; Kawakita, Y.; Fukasawa, Y.; Iida, I.; Hagima, N.; Takeuchi, H.; Chino, Y.; Asami, J.; Okumura-Kitajima, L.; Io, F.; Yamamoto, D.; Miyata, N.; Takahashi, T.; Uchida, S.; Yamamoto, K. (1S)-1,5-Anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-D-glucitol (TS-071) is a Potent, Selective Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for Type 2 Diabetes Treatment. J. Med. Chem., 2010, 53, 3247-3261.
33. Kim, M. J.; Lee, J.; Kang, S. Y.; Lee, S.-H.; Son, E.-J.; Jung, M. E.; Lee, S. H.; Song, K.-S.; Lee, M.; Han, H.-K.; Kim, J.; Lee, J. Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: Pyridazinylmethylphenyl glucoside congeners. Bioorg. Med. Chem. Lett., 2010, 20, 3420-3425.
34. Combettes, M.; Kargar, C. Newly Approved and Promising Antidiabetic Agents. Thérapie, 2007, 62, 293-310.
35. Bernard, C. Leçons sur les phénomènes de la vie commune aux animaux et aux végétaux; Baillière et fils: Paris, 1878.
36. Bollen, M.; Keppens, S.; Stalmans, W. Specific features of glycogen metabolism in the liver. Biochem. J., 1998, 336, 19-31.
37. Radziuk, J.; Pye, S. Quantitation of basal endogenous glucose production in Type II diabetes: importance of the volume of distribution. Diabetologia, 2002, 45, 1053-1084.
38. Magnusson, I.; Rothman, D. L.; Gerard, D. P.; Katz, L. D.; Shulman, G. I. Contribution of hepatic glycogenolysis to glucose production in humans in response to a physiological increase in plasma glucagon concentration. Diabetes, 1995, 44, 185-189.
39. Diraison, F.; Large, V.; Brunengraber, H.; Beylot, M. Non-invasive tracing of liver intermediary metabolism in normal subjects and in moderately hyperglycaemic NIDDM subjects. Evidence against increased gluconeogenesis and hepatic fatty acid oxidation in NIDDM. Diabetologia, 1998, 41, 212-220.
40. Nuttall, F. Q.; Ngo, A.; Gannon, M., C. Regulation of hepatic glucose production and the role of gluconeogenesis in humans: is the rate of gluconeogenesis constant? Diabetes Metab. Res. Rev., 2008, 24, 438-458.
41. Bock, G.; Dalla Man, C.; Campioni, M.; Chittilapilly, E.; Basu, R.; Toffolo, G.; Cobelli, C.; Rizza, R. A. Pathogenesis of Pre-Diabetes. Mechanisms of Fasting and Postprandial Hyperglycemia in People With Impaired Fasting Glucose and/or Impaired Glucose Tolerance. Diabetes, 2006, 55, 3536-3549.
42. Basu, A.; Dalla Man, C.; Basu, R.; Toffolo, G.; Cobelli, C.; Rizza, R. A. Effect of type 2 diabetes on insulin secretion, insulin action, glucose effectiveness, and postprandial glucose metabolism. Diabetes Care, 2009, 32, 866-872.
43. Basu, R.; Schwenk, W. F.; Rizza, R. A. Both fasting glucose production and disappearance are abnormal in people with mild and severe type 2 diabetes. Am. J. Physiol. Endocrinol. Metab., 2004, 287, E55-E62.
44. Bock, G.; Chittilapilly, E.; Basu, R.; Toffolo, G.; Cobelli, C.; Chandramouli, V.; Landau, B. R.; Rizza, R. A. Contribution of Hepatic and Extrahepatic Insulin Resistance to the Pathogenesis of Impaired Fasting Glucose: Role of Increased Rates of Gluconeogenesis. Diabetes, 2007, 56, 1703-1711.
45. Shaw, R. J.; Lamia, K. A.; Vasquez, D.; Koo, S.-H.; Bardeesy, N.; DePinho, R. A.; Montminy, M.; Cantley, L. C. The Kinase LKB1 Mediates Glucose Homeostasis in Liver and Therapeutic Effects of Metformin. Science, 2005, 310, 1642-1646.
46. van Schaftingen, E.; Gerin, I. The glucose-6-phosphatase system. Biochem. J., 2002, 362, 513-532.
47. Agius, L. New hepatic targets for glycaemic control in diabetes. Best Pract. Res. Clin. Endocrinol. Metab., 2007, 21, 587-605.
48. Barf, T. Intervention of hepatic glucose production. Small molecule regulators of potential targets for type 2 diabetes. Mini-Rev. Med. Chem., 2004, 4, 897-908.
49. Meijer, L.; Flajolet, M.; Greengard, P. Pharmacological inhibitors of glycogen synthase kinase 3. Trends Pharmacol. Sci., 2004, 25, 471-480.
50. Martin, W. H.; Hoover, D. J.; Armento, S. J.; Stock, I. A.; McPherson, R. K.; Danley, D. E.; Stevenson, R. W.; Barretti, E. J.; Treadway, J. L. Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo. Proc. Natl. Acad. Sci. USA, 1998, 95, 1776-1781.
51. Cori, C. F.; Cori, G. T. Mechanism of formation of hexosemonophosphate in muscle and isolation of a new phosphate monoester. Proc. Soc. Exp. Biol. Med., 1936, 34, 702-705.
52. Johnson, L. N. Glycogen phosphorylase: control by phosphorylation and allosteric effectors. FASEB J., 1992, 6, 2274-2282.
53. Johnson, L. N. The regulation of protein phosphorylation. Biochem. Soc. Trans., 2009, 37, 627-641.
54. Hudson, J. W.; Golding, G. B.; Crerar, M. M. Evolution of Allosteric Control in Glycogen Phosphorylase. J. Mol. Biol., 1993, 234, 700-721.
55. Newgard, C. B.; Hwang, P. K.; Fletterick, R. J. The Family of Glycogen Phosphorylases: Structure and Function. Crit. Rev. Biochem. Mol. Biol., 1989, 24, 69-99.
56. Assaf, S. A.; Yunis, A. A. Subunit Structure and Amino-Acid Composition of Crystallized Human-Muscle Glycogen Phosphorylase. Eur. J. Biochem., 1973, 35, 282-289.
57. Coats, W. S.; Browner, M. F.; Fletterick, R. J.; Newgard, C. B. An Engineered Liver Glycogen Phosphorylase with AMP Allosteric Activation. J. Biol. Chem., 1991, 266, 16113-16119.
58. Newgard, C. B.; Littman, D. R.; van Genderen, C.; Smith, M.; Fletterick, R. J. Human Brain Glycogen Phosphorylase. Cloning, sequence analysis, chromosomal mapping, tissue expression, and comparison with the human liver anbd muscle isozymes. J. Biol. Chem., 1988, 263, 3850-3857.
59. Goldsmith, E. J.; Sprang, S. R.; Hamlin, R.; Xuong, N. H.; Fletterick, R. J. Domain separation in the activation of glycogen phosphorylase a. Science, 1989, 245, 528-532.
60. Rath, V. L.; Ammirati, M.; LeMotte, P. K.; Fennell, K. F.; Mansour, M. N.; Danley, D. E.; Hynes, T. R.; Schulte, G. K.; Wasilko, D. J.; Pandit, J. Activation of Human Liver Glycogen Phosphorylase by Alteration of the Secondary Structure and Packing of the Catalytic Core. Mol. Cell, 2000, 6, 139-148.
61. Lukacs, C. M.; Oikonomakos, N. G.; Crowther, R. L.; Hong, L.-N.; Kammlott, R. U.; Levin, W.; Li, S.; Liu, C.-M.; Lucas-McGady, D.; Pietranico, S.; Reik, L. The crystal structure of human muscle glycogen phosphorylase a with bound glucose and AMP: An intermediate conformation with T-state and R-state features. Proteins: Struct. Funct. Bioinfo., 2006, 63, 1123-1126.
62. Mair, J. Glycogen phosphorylase isoenzyme BB to diagnose ischaemic myocardial damage. Clin. Chim. Acta, 1998, 272, 79-86.
63. Tashima, S.; Shimada, S.; Yamaguchi, K.; Tsuruta, J.; Ogawa, M. Expression of brain-type glycogen phosphorylase is a potentially novel early biomarker in the carcinogenesis of human colorectal carcinomas. Am. J. Gastroenterol., 2000, 95, 255-263.
64. Hwang, P. K.; See, Y. P.; Vincentini, A. M.; Powers, M. A.; Fletterick, R. J.; Crerar, M. M. Comparative sequence analysis of rat, rabbit, and human muscle glycogen phosphorylase cDNAs. Eur. J. Biochem., 1985, 152, 267-274.
65. Guénard, D.; Morange, M.; Buc, H. Comparative Study of the Effect of 5'AMP and Its Analogs on Rabbit Glycogen Phosphorylase b Isoenzymes. Eur. J. Biochem., 1977, 76, 447-452.
66. Shimada, S.; Matsuzaki, H.; Marutsuka, T.; Shiomori, K.; Ogawa, M. Gastric and intestinal phenotypes of gastric carcinoma with reference to expression of brain (fetal)-type glycogen phosphorylase. J. Gastroenterol., 2001, 36, 457-464.
67. Mayer, D.; Letsch, I. Resolution of glycogen phosphorylase isoenzymes in precast Phastsystem polyacrylamide gels. Electrophoresis, 1991, 12, 297-302.
68. Rath, V. L.; Lin, K.; Hwang, P. K.; Fletterick, R. J. The evolution of an allosteric site in phosphorylase. Structure, 1996, 4, 463-473.
69. Bot, G.; Kovács, E.; Gergely, P. Role of tetramer in equilibrium dimer equilibrium in the dephosphorylation of phosphorylase a. Acta Biochim. Biophys. Acad. Sci. Hung., 1977, 12, 335-341.
70. Wang, Z.-X. Kinetic study on the dimer-tetramer interconversion of glycogen phosphorylase a. Eur. J. Biochem., 1999, 259, 609-617.
71. Oikonomakos, N. G. Glycogen Phosphorylase as a molecular target for type 2 diabetes therapy. Curr. Prot. Pept. Sci., 2002, 3, 561-586.
72. Johnson, L. N.; Hu, S.-H.; Barford, D. Catalytic mechanism of glycogen phosphorylase. Faraday Discuss., 1992, 93, 131-142.
73. Ekstrom, J. L.; Pauly, T. A.; Carty, M. D.; Soeller, W. C.; Culp, J.; Danley, D. E.; Hoover, D. J.; Treadway, J. L.; Gibbs, E. M.; Fletterick, R. J.; Day, Y. S. N.; Myszka, D. G.; Rath, V. L. Structure-Activity Analysis of the Purine Binding Site of Human Liver Glycogen Phosphorylase. Chem. Biol., 2002, 9, 915-924.
74. Hampson, L. J.; Arden, C.; Agius, L.; Ganotidis, M.; Kosmopoulou, M. N.; Tiraidis, C.; Elemes, Y.; Sakarellos, C.; Leonidas, D. D.; Oikonomakos, N. G. Bioactivity of glycogen phosphorylase inhibitors that bind to the purine nucleoside site. Bioorg. Med. Chem., 2006, 14, 7835-7845.
75. Oikonomakos, N. G.; Skamnaki, V. T.; Tsitsanou, K. E.; G Gavalas, N.; Johnson, L. N. A new allosteric site in glycogen phosphorylase b as a target for drug interactions. Structure, 2000, 8, 575-584.
76. Rath, V. L.; Ammirati, M.; Danley, D. E.; Ekstrom, J. L.; Gibbs, E. M.; Hynes, T. R.; Mathiowetz, A. M.; McPherson, R. K.; Olson, T. V.; Treadway, J. L.; Hoover, D. J. Human liver glycogen phosphorylase inhibitors bind at a new allosteric site. Chem. Biol., 2000, 7, 677-682.
77. Chrysina, E. D.; Kosmopoulou, M. N.; Tiraidis, C.; Kardakaris, R.; Bischler, N.; Leonidas, D. D.; Hadady, Z.; Somsák, L.; Docsa, T.; Gergely, P.; Oikonomakos, N. G. Kinetic and crystallographic studies on 2-(β-D-glucopyranosyl)-5-methyl-1,3,4-oxadiazole, -benzothiazole, and -benzimidazole, inhibitors of muscle glycogen phosphorylase b. Evidence for a new binding site. Protein Sci., 2005, 14, 873-888.
78. Pinotsis, N.; Leonidas, D. D.; Chrysina, E. D.; Oikonomakos, N. G.; Mavridis, I. M. The binding of β- and γ-cyclodextrins to glycogen phosphorylase b: Kinetic and crystallographic studies. Protein Sci., 2003, 12, 1914-1924.
79. Lin, K.; Hwang, P. K.; Fletterick, R. J. Distinct phosphorylation signals converge at the catalytic center in glycogen phosphorylases. Structure, 1997, 5, 1511-1523.
80. Johnson, L. N.; Acharya, K. R.; Jordan, M. D.; McLaughlin, P. J. Refined crystal structure of the phosphorylase-heptulose 2- phosphate-oligosaccharide-AMP complex. J. Mol. Biol., 1990, 211, 645-661.
81. Watson, K. A.; McCleverty, C.; Geremia, S.; Cottaz, S.; Driguez, H.; Johnson, L. N. Phosphorylase recognition and phosphorolysis of its oligosaccharide substrate: answers to a long outstanding question. EMBO J., 1999, 18, 4619-4632.
82. Barford, D.; Schwabe, J. W. R.; Oikonomakos, N. G.; Acharya, K. R.; Hajdu, J.; Papageorgiou, A. C.; Martin, J. L.; Knott, J. C. A.; Vasella, A.; Johnson, L. N. Channels at the catalytic site of glycogen phosphorylase b: binding and kinetic studies with the β- glycosidase inhibitor D-gluconohydroximo-1,5-lactone N- phenylurethane. Biochemistry, 1988, 27, 6733-6741.
83. Papageorgiou, A. C.; Oikonomakos, N. G.; Leonidas, D. D.; Bernet, B.; Beer, D.; Vasella, A. The binding of D-gluconohydroximo- 1,5-lactone to glycogen phosphorylase. Kinetic, ultracentrifugation and crystallographic studies. Biochem. J., 1991, 274, 329-338.
84. Heightman, T. D.; Vasella, A.; Tsitsanou, K. E.; Zographos, S. E.; Skamnaki, V. T.; Oikonomakos, N. G. Cooperative Interactions of the Catalytic Nucleophile and the Catalytic Acid in the Inhibition of β-Glycosidases. Calculations and their validation by comparative kinetic and structural studies of the inhibition of glycogen phosphorylase b. Helv. Chim. Acta, 1998, 81, 853-864.
85. Heightman, T. D.; Vasella, A. T. Recent Insights into Inhibition, Structure, and Mechanism of Configuration-Retaining Glycosidases. Angew. Chem. Int. Ed., 1999, 38, 750-770.
86. Buchbinder, J. L.; Fletterick, R. J. Role of the Active Site Gate of Glycogen Phosphorylase in Allosteric Inhibition and Substrate Binding. J. Biol. Chem., 1996, 271, 22305-22309.
87. Johnson, L. N.; Snape, P.; Martin, J. L.; Acharya, K. R.; Barford, D.; Oikonomakos, N. G. Crystallographic Binding Studies on the Allosteric Inhibitor Glucose-6-Phosphate to T State Glycogen Phosphorylase b. J. Mol. Biol., 1993, 232, 253-267.
88. Oikonomakos, N. G.; Tiraidis, C.; Leonidas, D. D.; Zographos, S. E.; Kristiansen, M.; Jessen, C. U.; Norskov-Lauritsen, L.; Agius, L. Iminosugars as Potential Inhibitors of Glycogenolysis: Structural Insights into the Molecular Basis of Glycogen Phosphorylase Inhibition. J. Med. Chem., 2006, 49, 5687-5701.
89. Andersen, B.; Westergaard, N. The effect of glucose on the potency of two distinct glycogen phosphorylase inhibitors. Biochem. J., 2002, 367, 443-450.
90. Latsis, T.; Andersen, B.; Agius, L. Diverse effects of two allosteric inhibitors on the phosphorylation state of glycogen phosphorylase in hepatocytes. Biochem. J., 2002, 368, 309-316.
91. Pautsch, A.; Stadler, N.; Wissdorf, O.; Langkopf, E.; Moreth, W.; Streicher, R. Molecular Recognition of the Protein Phosphatase 1 Glycogen Targeting Subunit by Glycogen Phosphorylase. J. Biol. Chem., 2008, 283, 8913-8918.
92. Aiston, S.; Green, A.; Mukhtar, M.; Agius, L. Glucose 6-phosphate causes translocation of phosphorylase in hepatocytes and inactivates the enzyme synergistically with glucose. Biochem. J., 2004, 377, 195-204.
93. Cohen, P. T. W. Protein phosphatase 1 - targeted in many directions. J. Cell. Sci., 2002, 115, 241-256.
94. Kelsall, I. R.; Munro, S.; Hallyburton, I.; Treadway, J. L.; Cohen, P. T. W. The hepatic PP1 glycogen-targeting subunit interaction with phosphorylase a can be blocked by C-terminal tyrosine deletion or an indole drug. FEBS Lett., 2007, 581, 4749-4753.
95. Alemany, S.; Cohen, P. Phosphorylase a is an allosteric inhibitor of the glycogen and microsomal forms of rat hepatic protein phosphatase-1. FEBS Lett., 1986, 198, 194-202.
96. Aiston, S.; Andersen, B.; Agius, L. Glucose 6-Phosphate Regulates Hepatic Glycogenolysis Through Inactivation of Phosphorylase. Diabetes, 2003, 52, 1333-1339.
97. Doherty, M. J.; Moorhead, G.; Morrice, N.; Cohen, P.; Cohen, P. T. W. Amino acid sequence and expression of the hepatic glycogenbinding (GL-subunit of protein phosphatase-1. FEBS Lett., 1995, 375, 294-298.
98. Kelsall, I. R.; Rosenzweig, D.; Cohen, P. T. W. Disruption of the allosteric phosphorylase a regulation of the hepatic glycogentargeted protein phosphatase 1 improves glucose tolerance in vivo. Cell Signal., 2009, 21, 1123-1134.
99. Treadway, J. L.; Mendys, P.; Hoover, D. J. Glycogen phosphorylase inhibitors for treatment of type 2 diabetes mellitus. Exp. Opin. Invest. Drugs, 2001, 10, 439-454.
100. Somsák, L.; Nagy, V.; Hadady, Z.; Docsa, T.; Gergely, P. Glucose analog inhibitors of glycogen phosphorylases as potential antidiabetic agents. Recents developments. Curr. Pharm. Des., 2003, 9, 1177-1189.
101. Somsák, L.; Nagy, V.; Hadady, Z.; Felföldi, N.; Docsa, T.; Gergely, P. Recents developments in the synthesis and evaluation of glucose analog inhibitors of glycogen phosphorylases as potential antidiabetic agents. Frontiers Med. Chem., 2005, 2, 253-272.
102. Khan, M. Sugar-derived Heterocycles and Their Precursors as Inhibitors Against Glycogen Phosphorylases (GP). Top. Heterocycl. Chem., 2007, 9, 33-52.
103. Oikonomakos, N. G.; Somsák, L. Advances in glycogen phosphorylase inhibitor design. Curr. Opin. Invest. Drugs, 2008, 9, 379-395.
104. Somsák, L.; Czifrák, K.; Tóth, M.; Bokor, E.; Chrysina, E. D.; Alexacou, K. M.; Hayes, J. M.; Tiraidis, C.; Lazoura, E.; Leonidas, D. D.; Zographos, S. E.; Oikonomakos, N. G. New inhibitors of glycogen phosphorylase as potential antidiabetic agents. Curr. Med. Chem., 2008, 15, 2933-2983.
105. Henke, B. R.; Sparks, S. M. Glycogen phosphorylase inhibitors. Mini-Rev. Med. Chem., 2006, 6, 845-857.
106. Baker, D. J.; Greenhaff, P. L.; Timmons, J. A. Glycogen phosphorylase inhibition as a therapeutic target: a review of the recent patent literature. Exp. Opin. Ther. Pat., 2006, 16, 459-466.
107. Oikonomakos, N. G.; Kontou, M.; Zographos, S. E.; Watson, K. A.; Johnson, L. N.; Bichard, C. J. F.; Fleet, G. W.; Acharya, K. R. N-Acetyl-β-D-glucopyranosylamine: A potent T-state inhibitor of glycogen phosphorylase. A comparison with -D-glucose. Protein Sci., 1995, 4, 2469-2477.
108. Board, M.; Bollen, M.; Stalmans, W.; Kim, Y.; Fleet, G. W.; Johnson, L. N. Effects of C-1-substituted glucose analogue on the activation states of glycogen synthase and glycogen phosphorylase in rat hepatocytes. Biochem. J., 1995, 311, 845-852.
109. Board, M. N-Acetyl-β-D-glucopyranosylamine 6-phosphate is a specific inhibitor of glycogen-bound protein phosphatase 1. Biochem. J., 1997, 328, 695-700.
110. Board, M.; Hadwen, M.; Johnson, L., N. Effects of Novel Analogues of D-Glucose on Glycogen Phosphorylase Activities in Crude Extracts of Liver and Skeletal Muscle. Eur. J. Biochem., 1995, 228, 753-761.
111. Blériot, Y.; Smelt, K. H.; Cadefau, J.; Bollen, M.; Stalmans, W.; Biggadike, K.; Johnson, L. N.; Oikonomakos, N. G.; Lane, A. L.; Crook, S.; Watkin, D. J.; Fleet, G. W. J. 7-Carbon mimics of D- glucose and L-fucose: Activation by 6R-, and inactivation by 6S, - 6C-methylglucose of glycogen synthase: Inhibition of glucokinase and/or glucose-6-phosphatase. Tetrahedron Lett., 1996, 37, 7155-7158.
112. 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. Potent inhibition of glycogen phosphorylase by a spirohydantoin of glucopyranose: First pyranose analogues of hydantocidin. Tetrahedron Lett., 1995, 36, 2145-2148.
113. Somsák, L.; Nagy, V.; Docsa, T.; Tóth, B.; Gergely, P. Gram-scale synthesis of a glucopyranosylidene-spiro-thiohydantoin and its effect on hepatic glycogen metabolism studied in vitro and in vivo. Tetrahedron: Asymmetry, 2000, 11, 405-408.
114. Docsa, T.; Tar, K.; Tóth, B.; Somsák, L.; Gergely, P. Regulation of hepatic metabolism by glycopyranosylidene-spiro-thiohydantoin. J. Physiol., 2000, 526, 92P.
115. Tsirkone, V. G.; Tsoukala, E.; Lamprakis, C.; Manta, S.; Hayes, J. M.; Skamnaki, V. T.; Drakou, C.; Zographos, S. E.; Komiotis, D.; Leonidas, D. D. 1-(3-Deoxy-3-fluoro-β-D-glucopyranosyl) pyrimidine derivatives as inhibitors of glycogen phosphorylase b: Kinetic, crystallographic and modelling studies. Bioorg. Med. Chem., 2010, 18, 3413-3425.
116. Oikonomakos, N. G.; Kosmopoulou, M. N.; Zographos, S. E.; Leonidas, D. D.; Chrysina, E. D.; Somsák, L.; Nagy, V.; Praly, J.-P.; Docsa, T.; Tóth, B.; Gergely, P. Binding of N-acetyl-N'-β-D- glucopyranosyl urea and N-benzoyl-N'-β-D-glucopyranosyl urea to glycogen phosphorylase b. Eur. J. Biochem., 2002, 269, 1684-1696.
117. Hadady, Z.; Tóth, M.; Somsák, L. C-(β-D-Glucopyranosyl) heterocycles as potential glycogen phosphorylase inhibitors. Arkivoc, 2004, vii, 140-149.
118. Alexacou, K. M.; Hayes, J. M.; Tiraidis, C.; Zographos, S. E.; Leonidas, D. D.; Chrysina, E. D.; Archontis, G.; Oikonomakos, N. G.; Paul, J. V.; Varghese, B.; Loganathan, D. Crystallographic and computational studies on 4-phenyl-N-(beta-D-glucopyranosyl)-1H-1,2,3-triazole-1-acetamide, an inhibitor of glycogen phosphorylase: Comparison with alpha-D-glucose, N-acetyl-beta-D-glucopyranosylamine and N-benzoyl-N'-beta-D-glucopyranosyl urea binding. Proteins: Struct. Funct. Bioinfomatics, 2008, 71, 1307-1323.
119. Osz, E.; Somsák, L.; Szilágyi, L.; Kovács, L.; Docsa, T.; Tóth, B.; Gergely, P. Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin. Bioorg. Med. Chem. Lett., 1999, 9, 1385-1390.
120. Krülle, T. M.; Watson, K. A.; Gregoriou, M.; Johnson, L. N.; Crook, S.; Watkin, D. J.; Griffiths, R. C.; Nash, R. J.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Specific inhibition of glycogen phosphorylase by a spirodiketopiperazine at the anomeric position of glucopyranose. Tetrahedron Lett., 1995, 36, 8291-8294.
121. Andersen, B.; Rassov, A.; Westergaard, N.; Lundgren, K. Inhibition of glycogenolysis in primary rat hepatocytes by 1, 4-dideoxy-1,4-imino-D-arabinitol. Biochem. J., 1999, 342, 545-550.
122. Fosgerau, K.; Westergaard, N.; Quistorff, B.; Grunnet, N.; Kristiansen, M.; Lundgren, K. Kinetic and Functional Characterization of 1,4-Dideoxy-1,4-imino-D-arabinitol: A Potent Inhibitor of Glycogen Phosphorylase with Anti-hyperglyceamic Effect in ob/ob Mice. Arch. Biochem. Biophys., 2000, 380, 274-284.
123. Walls, A. B.; Sickmann, H. M.; Brown, A.; Bouman, S. D.; Ransom, B.; Schousboe, A.; Waagepetersen, H. S. Characterization of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) as an inhibitor of brain glycogen shunt activity. J. Neurochem., 2008, 105, 1462-1470.
124. Bisht, S. S.; Fatima, S.; Tamrakar, A. K.; Rahuja, N.; Jaiswal, N.; Srivastava, A. K.; Tripathi, R. P. Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity. Bioorg. Med. Chem. Lett., 2009, 19, 2699-2703.
125. Bertus, P.; Szymoniak, J.; Jeanneau, E.; Docsa, T.; Gergely, P.; Praly, J.-P.; Vidal, S. Synthesis of a C-glucosylated cyclopropylamide and evaluation as a glycogen phosphorylase inhibitor. Bioorg. Med. Chem. Lett., 2008, 18, 4774-4778.
126. He, L.; Zhang, Y. Z.; Tanoh, M.; Chen, G.-R.; Praly, J.-P.; Chrysina, E. D.; Tiraidis, C.; Kosmopoulou, M. N.; Leonidas, D. D.; Oikonomakos, N. G. In the Search of Glycogen Phosphorylase Inhibitors: Synthesis of C-D-Glycopyranosylbenzo(hydro)quinones - Inhibition of and Binding to Glycogen Phosphorylase in the Crystal. Eur. J. Org. Chem., 2007, 596-606.
127. Praly, J.-P.; He, L.; Qin, B. B.; Tanoh, M.; Chen, G.-R. C-Glycopyranosyl-1,4-benzoquinones and -hydroquinones opening access to C-glycosylated analogs of vitamin E. Tetrahedron Lett., 2005, 46, 7081-7085.
128. Bialy, L.; Waldmann, H. Inhibitors of Protein Tyrosine Phosphatases: Next-Generation Drugs? Angew. Chem. Int. Ed., 2005, 44, 3814-3839.
129. Shrestha, S.; Shim, Y. S.; Kim, K. C.; Lee, K.-H.; Cho, H. Evans Blue and other dyes as protein tyrosine phosphatase inhibitors. Bioorg. Med. Chem. Lett., 2004, 14, 1923-1926.
130. Czifrák, K.; Somsák, L. Synthesis of anomeric sulfonamides and their behaviour under radical-mediated bromination conditions. Carbohydr. Res., 2009, 344, 269-277.
131. Watson, K. A.; Mitchell, E. P.; Johnson, L. N.; Bichard, C. J. F.; Orchard, M. G.; Fleet, G. W. J.; Oikonomakos, N. G.; Leonidas, D. D.; Son, J. C. Design of Inhibitors of Glycogen Phosphorylase: A Study of α- and β-C-Glucosides and 1-Thio-β-D-glucose Compounds. Biochemistry, 1994, 33, 5745-5758.
132. Nagy, V.; Czifrák, K.; Bényei, A.; Somsák, L. Synthesis of some O-, S- and N-glycosides of hept-2-ulopyranosonamides. Carbohydr. Res., 2009, 344, 921-927.
133. Juhász, L.; Docsa, T.; Brunyászki, A.; Gergely, P.; Antus, S. Synthesis and glycogen phosphorylase inhibitor activity of 2,3- dihydrobenzo[1,4]dioxin derivatives. Bioorg. Med. Chem., 2007, 15, 4048-4056.
134. Czakó, Z.; Juhász, L.; Kenéz, Á.; Czifrák, K.; Somsák, L.; Docsa, T.; Gergely, P.; Antus, S. Synthesis and glycogen phosphorylase inhibitory activity of N-β-D-glucopyranosyl)amides possessing 1,4-benzodioxane moiety. Bioorg. Med. Chem., 2009, 17, 6738-6741.
135. Felföldi, N.; Tóth, M.; Chrysina, E. D.; Charavgi, M.-D.; Alexacou, K.-M.; Somsák, L. Synthesis of new glycosyl biuret and urea derivatives as potential glycoenzyme inhibitors. Carbohydr. Res., 2010, 345, 208-213.
136. Pintér, I.; Kovács, J.; Tóth, G. Synthesis of sugar ureas via phosphinimines. Carbohydr. Res., 1995, 273, 99-108.
137. Nagy, V. Synthesis of Glycogen Phosphorylase Inhibitors. PhD Thesis, University of Debrecen/University of Lyon, 2003.
138. Tóth, M.; Kun, S.; Bokor, É.; Benltifa, M.; Tallec, G.; Vidal, S.; Docsa, T.; Gergely, P.; Somsák, L.; Praly, J.-P. Synthesis and structure-activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase. Bioorg. Med. Chem., 2009, 17, 4773-4785.
139. Benltifa, M.; Vidal, S.; Gueyrard, D.; Goekjian, P. G.; Msaddek, M.; Praly, J.-P. 1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4- oxadiazoles as glycogen phosphorylase inhibitors. Tetrahedron Lett., 2006, 47, 6143-6147.
140. Benltifa, M.; Vidal, S.; Fenet, B.; Msaddek, M.; Goekjian, P. G.; Praly, J.-P.; Brunyánszki, A.; Docsa, T.; Gergely, P. In Search of Glycogen Phosphorylase Inhibitors: 5-Substituted 3-C- Glucopyranosyl-1,2,4-oxadiazoles from β-D-Glucopyranosyl Cyanides upon Cyclization of O-Acylamidoxime Intermediates. Eur. J. Org. Chem., 2006, 4242-4256.
141. Meldal, M.; Tornoe, C. W. Cu-Catalyzed Azide-Alkyne Cycloaddition. Chem. Rev., 2008, 108, 2952-3015.
142. Bokor, É.; Docsa, T.; Gergely, P.; Somsák, L. Synthesis of 1-(D- glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors. Bioorg. Med. Chem., 2010, 18, 1171-1180.
143. Cecioni, S.; Argintaru, O.-A.; Docsa, T.; Gergely, P.; Praly, J.-P.; Vidal, S. Probing multivalency for the inhibition of an enzyme: glycogen phosphorylase as a case study. New J. Chem., 2009, 33, 148-156.
144. Cheng, K.; Liu, J.; Sun, H.; Bokor, E.; Czifrak, K.; Konya, B.; Toth, M.; Docsa, T.; Gergely, P.; Somsak, L. Tethered derivatives of D-glucose and pentacyclic triterpenes for homo/heterobivalent inhibition of glycogen phosphorylase. New J. Chem., 2010, 34, 1450-1464.
145. Chrysina, E. D.; Bokor, É.; Alexacou, K.-M.; Charavgi, M.-D.; Oikonomakos, G. N.; Zographos, S. E.; Leonidas, D. D.; Oikonomakos, N. G.; Somsák, L. Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case. Tetrahedron: Asymmetry, 2009, 20, 733-740.
146. Gueyrard, D.; Haddoub, R.; Salem, A.; Bacar, N. S.; Goekjian, P. G. Synthesis of Methylene Exoglycals Using a Modified Julia Olefination. Synlett, 2005, 520-522.
147. Bourdon, B.; Corbet, M.; Fontaine, P.; Goekjian, P. G.; Gueyrard, D. Synthesis of enol ethers from lactones using modified Julia olefination reagents: application to the preparation of tri- and tetrasubstituted exoglycals. Tetrahedron Lett., 2008, 49, 747-749.
148. Benltifa, M.; Hayes, J. M.; Vidal, S.; Gueyrard, D.; Goekjian, P. G.; Praly, J.-P.; Kizilis, G.; Tiraidis, C.; Alexacou, K.-M.; Chrysina, E. D.; Zographos, S. E.; Leonidas, D. D.; Archontis, G.; Oikonomakos, N. G. Glucose-based spiro-isoxazolines: A new family of potent glycogen phosphorylase inhibitors. Bioorg. Med. Chem., 2009, 17, 7368-7380.
149. Nagy, V.; Benltifa, M.; Vidal, S.; Berzsényi, E.; Teilhet, C.; Czifrák, K.; Batta, G.; Docsa, T.; Gergely, P.; Somsák, L.; Praly, J.-P. Glucose-based spiro-heterocycles as potent inhibitors of glycogen phosphorylase. Bioorg. Med. Chem., 2009, 17, 5696-5707.
150. Somsák, L.; Nagy, V.; Vidal, S.; Czifrák, K.; Berzsényi, E.; Praly, J.-P. Novel design principle validated: Glucopyranosylidene-spirooxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent. Bioorg. Med. Chem. Lett., 2008, 18, 5680-5683.
151. Praly, J.-P. Structure of anomeric glycosyl radicals and their transformations under reductive conditions. Adv. Carbohydr. Chem. Biochem., 2000, 56, 65-151.
152. El Ashry, E. S. H.; El Nemr, A. Synthesis of Naturally Occuring Nitrogen Heterocycles from Carbohydrates; Blackwell Publishing Ltd, 2005.
153. Compain, P.; Martin, O. R. Iminosugars: from synthesis to therapeutic applications John Wiley & Sons: New York, 2007.
154. Asano, N. Sugar-mimicking glycosidase inhibitors: bioactivity and application. Cell Mol. Life Sci., 2009, 66, 1479-1492.
155. Li, H.; Liu, T.; Zhang, Y.; Favre, S.; Bello, C.; Vogel, P.; Butters, T. D.; Oikonomakos, N. G.; Marrot, J.; Blériot, Y. New Synthetic Seven-Membered 1-Azasugars Displaying Potent Inhibition Towards Glycosidases and Glucosylceramide Transferase. ChemBioChem, 2008, 9, 253-260.
156. Rountree, J. S. S.; Terry, D. B.; Mark, R. W.; Stephanie, D. B.; Raymond, A. D.; Naoki, A.; Kyoko, I.; Emma, L. E.; Robert, J. N.; George, W. J. F. Design, Synthesis, and Biological Evaluation of Enantiomeric β-N-Acetylhexosaminidase Inhibitors LABNAc and DABNAc as Potential Agents against Tay-Sachs and Sandhoff Disease. ChemMedChem, 2009, 4, 378-392.
157. Best, D.; Wang, C.; Weymouth-Wilson, A. C.; Clarkson, R. A.; Wilson, F. X.; Nash, R. J.; Miyauchi, S.; Kato, A.; Fleet, G. W. J. Looking glass inhibitors: scalable syntheses of DNJ, DMDP, and (3R)-3-hydroxy-L-bulgecinine from D-glucuronolactone and of L-DNJ, L-DMDP, and (3S)-3-hydroxy-D-bulgecinine from L- glucuronolactone. DMDP inhibits -glucosidases and β-galactosidases whereas L-DMDP is a potent and specific inhibitor of β-glucosidases. Tetrahedron: Asymmetry, 2010, 21, 311-319.
158. Kuriyama, C.; Kamiyama, O.; Ikeda, K.; Sanae, F.; Kato, A.; Adachi, I.; Imahori, T.; Takahata, H.; Okamoto, T.; Asano, N. In vitro inhibition of glycogen-degrading enzymes and glycosidases by sixmembered sugar mimics and their evaluation in cell cultures. Bioorg. Med. Chem., 2008, 16, 7330-7336.
159. Minami, Y.; Kuriyama, C.; Ikeda, K.; Kato, A.; Takebayashi, K.; Adachi, I.; Fleet, G. W. J.; Kettawan, A.; Okamoto, T.; Asano, N. Effect of five-membered sugar mimics on mammalian glycogendegrading enzymes and various glucosidases. Bioorg. Med. Chem., 2008, 16, 2734-2740.
160. Mohan, S.; Pinto, B. M. Zwitterionic glycosidase inhibitors: salacinol and related analogues. Carbohydr. Res., 2007, 342, 1551-1580.
161. Mohan, S.; Pinto, B. M. Towards the elusive structure of kotalanol, a naturally occurring glucosidase inhibitor. Nat. Prod. Rep., 2010, 27, 481-488.