α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II

European Journal of Medicinal Chemistry

Volumn 46, Issue 3, 2011, Pages 944-952

  Poláková, Monika ^a   Šesták, Sergej ^a   Lattová, Erika ^b   Petruš, Ladislav ^a   Mucha, Ján ^a   Tvaroška, Igor ^a   Kóňa, Juraj ^a  

^a INSTITUTE OF CHEMISTRY   (Slovakia)

^b UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Mannosidase inhibitors; Mannopyranosyl sulfones; Mannopyranosyl sulfoxides; Molecular modeling; Oxidation; Synthetic d mannopyranosides

Indexed keywords

ALPHA MANNOSIDASE; MANNOSE; RECOMBINANT ENZYME;

ARTICLE; GOLGI COMPLEX;

ALPHA-MANNOSIDASE; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MANNOSE; MANNOSIDASES; MODELS, MOLECULAR; PROTEIN BINDING; RECOMBINANT PROTEINS; SULFUR COMPOUNDS;

EID: 79951674558     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.012     Document Type: Article

References (39)

1. M. Bols, O. Lopez, and F. Ortega-Caballero Glycosidase inhibitors: structure, activity, synthesis, and medical relevance J.P. Kamerling, Comprehensive Glycoscience vol. 1 2007 Elsevier Oxford 815 867
2. K.W. Moremen BBA 1573 2002 225 235
3. P.E. Goss, M.A. Baker, J.P. Carver, and J.W. Dennis Clin. Cancer Res. 1 1995 935 944
4. D.A. Kuntz, S. Nakayama, K. Shea, H. Hori, Y. Uto, H. Nagasawa, and D.R. Rose Chembiochem 11 2010 673 680
5. D.A. Kuntz, W. Zhong, J. Guo, D.R. Rose, and G.J. Boons Chembiochem 10 2009 268 277
6. A. Siriwardena, H. Strachan, S. El-Daher, G. Way, B. Winchester, J. Glushka, K. Moremen, and G.J. Boons Chembiochem 6 2005 845 848
7. B. Li, S.P. Kawatkar, S. George, H. Strachan, R.J. Woods, A. Siriwardena, K.W. Moremen, and G.J. Boons Chembiochem 5 2004 1220 1227
8. H. Fiaux, D.A. Kuntz, D. Hoffman, R.C. Janzer, S. Gerber-Lemaire, D.R. Rose, and L. Juillerat-Jeanneret Bioorg. Med. Chem. 16 2008 7337 7346
9. P. Englebienne, H. Fiaux, D.A. Kuntz, C.R. Corbeil, S. Gerber-Lemaire, D.R. Rose, and N. Moitessier Proteins 69 2007 160 176
10. N.S. Kumar, D.A. Kuntz, X. Wen, B.M. Pinto, and D.R. Rose Proteins 71 2008 1484 1496
11. L.M. Kavlekar, D.A. Kuntz, X. Wen, B.D. Johnston, B. Svensson, D.R. Rose, and B.M. Pinto Tetrahedron Asymmetry 16 2005 1035 1046
12. D.A. Kuntz, C.A. Tarling, S.G. Withers, and D.R. Rose Biochemistry 47 2008 10058 10068
13. N. Shah, D.A. Kuntz, and D.R. Rose Biochemistry 42 2003 13812 13816
14. W.H. Pearson, and E.J. Hembre Tetrahedron Lett. 42 2001 8273 8276
15. E.J. Hembre, and W.H. Pearson Tetrahedron 53 1997 11021 11032
16. J.B. Behr, C. Chevrier, A. Defoin, C. Tarnus, and J. Streith Tetrahedron 59 2003 543 553
17. H. Fiaux, F. Popowycz, S. Favre, C. Schutz, P. Vogel, S. Gerber-Lemaire, and L. Juillerat-Jeanneret J. Med. Chem. 48 2005 4237 4246
18. R. Shah, J. Carver, J. Marino-Albernas, I. Tvaroška, F.D. Tropper, J. Dennis, GlycoDesign Inc., Toronto (CA), Novel 3, 5, and/or 6 substituted analogues of swainsonine processes for their preparation and their use as therapeutic agents, U.S. Patent US 2003/0236229 A1.
19. T. Fujita, H. Nagasawa, Y. Uto, T. Hashimoto, Y. Akasawa, and H. Hori Org. Lett. 6 2004 827 830
20. J.M.H. van den Elsen, D.A. Kuntz, and D.R. Rose Embo J 20 2001 3008 3017
21. W. Zhong, D.A. Kuntz, B. Ernber, H. Singh, K.W. Moremen, D.R. Rose, and G.J. Boons J. Am. Chem. Soc. 130 2008 8975 8983
22. N. Shah, D.A. Kuntzt, and D.R. Rose Proc. Natl. Acad. Sci. U.S.A. 105 2008 9570 9575
23. J.W. Dennis, K. Koch, S. Yousefi, and I. Vanderelst Cancer Res. 50 1990 1867 1872
24. P.K. Sharma, R.N. Shah, and J.P. Carver Org. Process Res. Dev. 12 2008 831 836
25. P.L. Durette, and T.Y. Shen Carbohydr. Res. 81 1980 261 274
26. M. Poláková, M. Beláňová, L. Petruš, and K. Mikušová Carbohydr. Res. 345 2010 1339 1347
27. G.R. Morais, A.J. Humphrey, and R.A. Falconer Tetrahedron Lett. 64 2008 7426 7431
28. M.C. Aversa, A. Barattucci, M.C. Bilardo, P. Bonaccorsi, P. Giannetto, P. Rollin, and A. Tatibouët J. Org. Chem. 70 2005 7389 7396
29. S. Numao, D.A. Kuntz, S.G. Withers, and D.R. Rose J. Biol. Chem. 278 2003 48074 48083
30. P. Heikinheimo, R. Helland, H.K.S. Leiros, I. Leiros, S. Karlsen, G. Evjen, R. Ravelli, G. Schoehn, R. Ruigrok, O.K. Tollersrud, S. McSweeney, and E. Hough J. Mol. Biol. 327 2003 631 644
31. C. Park, L. Meng, L.H. Stanton, R.E. Collins, S.W. Mast, H. Strachan, and K.W. Moremen J. Biol. Chem. 280 2005 37204 37214
32. R.A. Friesner, J.L. Banks, R.B. Murphy, T.A. Halgren, J.J. Klicic, D.T. Mainz, M.P. Repasky, E.H. Knoll, M. Shelley, J.K. Perry, D.E. Shaw, P. Francis, and P.S. Shenkin J. Med. Chem. 47 2004 1739 1749
33. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, and D.T. Mainz J. Med. Chem. 49 2006 6177 6196
34. Glide, Version 5.5 2009 Schrödinger, LLC New York, NY
35. Epik, Version 2.0 2009 Schrödinger, LLC New York, NY
36. Y. Zhao, N.E. Schultz, and D.G. Truhlar J. Chem. Theory Comput. 2 2006 364 382
37. Y. Zhao, N.E. Schultz, and D.G. Truhlar J. Chem. Phys. 123 2005 161103
38. Qsite, Version 5.5 2009 Schrödinger, LLC New York, NY
39. Maestro, Version 9.0 2009 Schrödinger, LLC New York, NY