The binding of β-d-glucopyranosyl-thiosemicarbazone derivatives to glycogen phosphorylase: A new class of inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 22, 2010, Pages 7911-7922

  Alexacou, Kyra Melinda ^a,b   Tenchiu, Alia Cristina ^a   Chrysina, Evangelia D ^a   Charavgi, Maria Despoina ^a   Kostas, Ioannis D ^a   Zographos, Spyros E ^a   Oikonomakos, Nikos G ^a   Leonidas, Demetres D ^a,c  

^a INSTITUTE OF BIOLOGY   (Greece)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c UNIVERSITY OF THESSALY   (Greece)

Author keywords

Glucopyranosyl thiosemicarbazones; Glycogen phosphorylase; Inhibition; Type 2 diabetes; X ray crystallography

Indexed keywords

4 FLUOROBENZALDEHYDE 4 (BETA GLUCOPYRANOSYL)THIOSEMICARBAZONE; GLYCOGEN PHOSPHORYLASE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN;

ANIMALS; BINDING SITES; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; GLUCOSE; GLUCOSEPHOSPHATES; GLYCOGEN PHOSPHORYLASE, MUSCLE FORM; HALOGENS; KINETICS; MOLECULAR CONFORMATION; PROTEIN BINDING; PYRIDINES; RABBITS; THIOSEMICARBAZONES;

ORYCTOLAGUS CUNICULUS;

EID: 78449256484     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.09.039     Document Type: Article

References (42)

1. A. Green, N. Christian Hirsch, and S.K. Pramming Diabetes Metab. Res. Rev. 19 2003 3
2. S. Aiston, B. Andersen, and L. Agius Diabetes 52 2003 1333
3. S. Aiston, M.P. Coghlan, and L. Agius Eur. J. Biochem. 270 2003 2773
4. N.G. Oikonomakos Curr. Protein Pept. Sci. 3 2002 561
5. N.G. Oikonomakos, and L. Somsak Curr. Opin. Invest. Drugs 9 2008 379
6. J.L. Treadway, P. Mendys, and D.J. Hoover Expert Opin. Invest. Drugs 10 2001 439
7. D.J. Baker, J.A. Timmons, and P.L. Greenhaff Diabetes 54 2005 2453
8. L. Somsak, K. Czifrak, M. Toth, E. Bokor, E.D. Chrysina, K.M. Alexacou, J.M. Hayes, C. Tiraidis, E. Lazoura, D.D. Leonidas, S.E. Zographos, and N.G. Oikonomakos Curr. Med. Chem. 15 2008 2933
9. N.G. Oikonomakos, V.T. Skamnaki, K.E. Tsitsanou, N.G. Gavalas, and L.N. Johnson Structure 8 2000 575
10. V.L. Rath, M. Ammirati, D.E. Danley, J.L. Ekstrom, E.M. Gibbs, T.R. Hynes, A.M. Mathiowetz, R.K. McPherson, T.V. Olson, J.L. Treadway, and D.J. Hoover Chem. Biol. 7 2000 677
11. N.G. Oikonomakos, M. Kosmopoulou, S.E. Zographos, D.D. Leonidas, E.D. Chrysina, L. Somsak, V. Nagy, J.P. Praly, T. Docsa, B. Toth, and P. Gergely Eur. J. Biochem. 269 2002 1684
12. H. Beraldo, and D. Gambino Mini-Rev. Med. Chem. 4 2004 31
13. M. Belicchi-Ferrari, F. Bisceglie, C. Casoli, S. Durot, I. Morgenstern-Badarau, G. Pelosi, E. Pilotti, S. Pinelli, and P. Tarasconi J. Med. Chem. 48 2005 1671
14. D. Kovala-Demertzi, A. Papageorgiou, L. Papathanasis, A. Alexandratos, P. Dalezis, J.R. Miller, and M.A. Demertzis Eur. J. Med. Chem. 44 2009 1296
15. D. Kovala-Demertzi, P.N. Yadav, J. Wiecek, S. Skoulika, T. Varadinova, and M.A. Demertzis J. Inorg. Biochem. 100 2006 1558
16. A.-C. Tenchiu (Deleanu), I.D. Kostas, D. Kovala-Demertzi, and A. Terzis Carbohydr. Res. 344 2009 1352
17. S.S. Zhang, S.J. Ye, X.M. Li, S.S. Gu, and Q. Liu Chem. Res. Chin. U 21 2005 545
18. S. Ghosh, A.K. Misra, G. Bhatia, M.M. Khan, and A.K. Khanna Bioorg. Med. Chem. Lett. 19 2009 386
19. G. Zemplén, A. Gerecs, and I. Hadácsy Ber. Dtsch. Chem. Ges. 69 1936 1827
20. L.N. Johnson FASEB J. 6 1992 2274
21. M. OReilly, K.A. Watson, R. Schinzel, D. Palm, and L.N. Johnson Nat. Struct. Biol. 4 1997 405
22. K.A. Watson, R. Schinzel, D. Palm, and L.N. Johnson EMBO J. 16 1997 1
23. D. Barford, and L.N. Johnson Nature 340 1989 609
24. J.L. Martin, K. Veluraja, K. Ross, L.N. Johnson, G.W.J. Fleet, N.G. Ramsden, I. Bruce, M.G. Orchard, N.G. Oikonomakos, A.C. Papageorgiou, D.D. Leonidas, and H.S. Tsitoura Biochemistry (USA) 30 1991 10101
25. K.M. Alexacou, J.M. Hayes, C. Tiraidis, S.E. Zographos, D.D. Leonidas, E.D. Chrysina, G. Archontis, N.G. Oikonomakos, J.V. Paul, B. Varghese, and D. Loganathan Proteins 71 2008 1307
26. J.A.K. Howard, V.J. Hoy, D. OHagan, and G.T. Smith Tetrahedron 52 1996 12613
27. V.G. Tsirkone, E. Tsoukala, C. Lamprakis, S. Manta, J.M. Hayes, V.T. Skamnaki, C. Drakou, S.E. Zographos, D. Komiotis, and D.D. Leonidas Bioorg. Med. Chem. 18 2010 3413
28. P. Auffinger, F.A. Hays, E. Westhof, and P.S. Ho Proc. Natl. Acad. Sci. U.S.A. 101 2004 16789
29. P. Politzer, P. Lane, M.C. Concha, Y.G. Ma, and J.S. Murray J. Mol. Model. 13 2007 305
30. T.K. Lindhorst, and C. Kieburg Synthesis-Stuttgart 1995 1228
31. F. Cateni, P. Bonivento, G. Procida, M. Zacchigna, L.G. Favretto, G. Scialino, and E. Banfi Bioorg. Med. Chem. 15 2007 815
32. Although it is a known compound, full analytical data is not accessible: K. Cao, Z. Wang, and X. Zhao Shiyou Daxue Xuebao, Ziran Kexueban 28 2004 100
33. A.E. Melpidou, and N.G. Oikonomakos FEBS Lett. 154 1983 105
34. S. Saheki, A. Takeda, and T. Shimazu Anal. Biochem. 148 1985 277
35. N.G. Oikonomakos, A.E. Melpidou, and L.N. Johnson Biochim. Biophys. Acta 832 1985 248
36. Z. Otwinowski, and W. Minor C.W.J. Carter, R.M. Sweet, Methods Enzymology Vol. 276 1997 Academic Press New York 307
37. G.N. Murshudov, A.A. Vagin, and E.J. Dodson Acta Crystallogr., Sect. D 53 1997 240
38. R.A. Laskowski, M.W. MacArthur, D.S. Moss, and J.M. Thornton J. Appl. Crystallogr. 26 1993 283
39. CCP4 Acta Crystallogr., Sect. D 50 1994 760
40. P.J. Kraulis J. Appl. Crystallogr. 24 1991 946
41. R.M. Esnouf J. Mol. Graphics Modell. 15 1997 132
42. E.A. Merritt, and D.J. Bacon Macromol. Crystallogr. B277 1997 505