Glycosylation pathways as drug targets for cancer: Glycosidase inhibitors

Mini-Reviews in Medicinal Chemistry

Volumn 6, Issue 9, 2006, Pages 1043-1052

  Gerber Lemaire, Sandrine ^a   Juillerat Jeanneret, Lucienne ^b  

^a EPFL   (Switzerland)

^b UNIVERSITY INSTITUTE OF PATHOLOGY   (Switzerland)

Author keywords

Cancer; Glucosidase; Glycosidases; Inhibitors; Mannosidase

Indexed keywords

1 DEOXY N METHYLNOJIRIMYCIN; 1 DEOXYMANNONOJIRIMYCIN; ALPHA GLUCOSIDASE INHIBITOR; ALPHA MANNOSIDASE; ALPHA MANNOSIDASE INHIBITOR; ANTINEOPLASTIC AGENT; CARBOHYDRATE; CASTANOSPERMINE; GLYCOPROTEIN; GLYCOSIDASE; GLYCOSIDASE INHIBITOR; GLYCOSYLTRANSFERASE; SWAINSONINE; SWAINSONINE DERIVATIVE; UNCLASSIFIED DRUG;

CANCER CELL; CANCER THERAPY; CARBOHYDRATE ANALYSIS; CELL SURFACE; CELLULAR DISTRIBUTION; DRUG STRUCTURE; DRUG TARGETING; ENZYME MECHANISM; GLYCOSYLATION; HUMAN; LUNG EDEMA; MELANOMA; NEUROLOGIC DISEASE; NONHUMAN; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN LOCALIZATION; PROTEIN METABOLISM; PROTEIN SECRETION; PROTEIN STABILITY; PROTEIN TARGETING; REVIEW; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; GLYCOSIDE HYDROLASES; GLYCOSYLATION; HUMANS; MOLECULAR STRUCTURE; NEOPLASMS;

EID: 33748661509     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955706778195162     Document Type: Review

References (93)

1. Endo, T. Biochem. Biophys. Acta, 1999, 1473, 237.
2. Bernacki, R.J.; Niedbala, M.J.; Korytnyk, W. Cancer Metab. Rev., 1985, 4, 81.
3. Corfield, A.P.; Myerscough, N. Meth. Mol. Biol., 2000, 125, 403.
4. Freeze, H.H.; Aebi, M. Curr. Op. Struct. Biol., 2005, 15, 490.
5. Peyrard, M.; Seroussi, E.; Sandberg-Nordqvist, A.C.; Xie, Y.G.; Han, F.Y.; Fransson, L; Collins, J.; Dunham, I.; Kost-Alimova, M.; Imreh, S.; Dumanski, J.P. Proc. Nat. Acad. Sci. USA, 1999, 96, 598.
6. Helenius,A.; Aebi, M. Ann. Rev. Biochem., 2004, 73, 1019.
7. Oh-eda, M.; Nakagawa, H.; Akama, T. O.; Lowitz, K.; Misago, M.; Moremen, K.W.; Fukuda, M.N. Eur. J. Biochem., 2001, 268, 1280.
8. Hamilton, S.R.; Li, H.; Wischnewski H.; Prasad, A.; Kerley-Hamilton, J.S.; Mitchell, T.; Walling, A.J.; Daividson, R.C.; Wildt, S.; Gerngross, T.U. Glycobiology, 2005, 15, 615.
9. Parham, P. Trends Biochem. Sci., 1996, 21, 427.
10. Wahrenbrock, M.G.; Varki, A. Cancer Res., 2006, 66, 2433.
11. Hakamori, S. Proc. Nat. Acad. Sci. USA, 2002, 99, 10231.
12. Paszkiewicz-Gadek, A.; Porowska, H.; Lemancewicz, D.; Wolczynski, S.; Gindzienski, A. Int. J. Mol. Med., 2006, 17, 669.
13. Dwek, M.V.; Brooks, S.A. Curr. Cancer Drug Targets, 2004, 4, 425.
14. Vlad, A.M.; Finn, O.J. Breast Dis., 2004, 20, 73.
15. Asano, N. J. Enzyme Inhib., 2000, 15, 215.
16. Asano, N. Glycobiology, 2003, 13, 93R.
17. Asano, N.; Nash, R.J.; Molyneux, R.J.; Fleet, G.W.J. Tetrahedron Assymetry, 2000, 11, 1645.
18. Couldrey, C.; Green, J.E. Breast Cancer Res., 2000, 2, 321.
19. Freire, T.; Ray, S.; von Mensdroff-Pouilly, S; Osinaga, F. Cancer Res., 2005, 65, 7880.
20. Ho, J.J.; Jaituni, R.S.; Crawley, S.C.; Yang, S.C.; Gum, J.R.; Kim, Y. S. Int. J. Oncol., 2003, 23, 585.
21. Dennis, J.W.; Granovski, M.; Warren, C.E. Bioessays, 1999, 21, 412.
22. Ito, Y.; Hagihara, S.; Matsuo, I.; Totani, K. Curr. Opin. Struct. Biol., 2005, 15, 481.
23. Liu, F.T.; Rabinovich, G.A. Nat. Rev. Cancer, 2005, 5, 29.
24. Hollingsworth, M.A.; Swanson, B.J. Nat. Rev. Cancer, 2004, 4, 45.
25. Fuster, M.M.; Esko, J.D. Nat. Rev. Cancer, 2005, 5, 526.
26. Dube, D.H.; Bertozzi, C.R. Nat. Rev. Drug Discov., 2005, 4, 477.
27. Dwek, R.A.; Butters, T.D.; Platt, F.M.; Zitzmann, N. Nat. Rev. Drug Discov., 2002, 1, 65.
28. Scanlin, T.F.; Glick, M.C. Glycoconjugate J., 2000, 17, 617.
29. Rudd, P.M.; Wormald, M.R.; Stanfield, R.L.; Huang, M.; Mattsson, N.; Speir, J.A.; DiGennaro, J.A.; Fetrow, J.S.; Dwek, R.A.; Wilson I.A. J. Mol. Biol., 1999, 293, 351.
30. Baldus, S.E.; Engelmann, K.; Hanisch, F.G. Crit. Rev. Clin. Lab. Sci., 2004, 41, 189.
31. Dwek, M.V.; Ross, H.A.; Leathem, A.J. Proteomics. 2001, 1, 756.
32. Yonezawa. S.: Sato, E. Pathol. Int 1997, 47, 813.
33. Day, A.J.; Prestwich, G.D. J. Biol. Chem., 2002, 277, 4585.
34. Hwang, J.B.; Hernandez, J.; Leduc, R.; Frost, S.C. Biochim. Biophys. phys. Acta., 2000, 1499, 74.
35. Siddals, K.W.; Marshman, E.; Westwood, M.; Gibson, J.M. J. Biol. Chem., 2004, 279, 38353.
36. Przybylo, M.; Hoja-Lukowicz, D.; Litynska, A.; Laidler, P. Cancer Cell Int., 2002, 2, 6.
37. Simizu, S.; Takagi, S.; Tamura, Y.; Osada, H. Cancer Res., 2005, 65, 7455.
38. Garcia, M.; Platet, N.; Liaudet, V.; Derocq, D.; Brouillet, J.P.; Rochefort, H. Stem Cells, 1996, 14, 642.
39. Tabares, G.; Radcliffe, C.M.; Barrabes, S.; Ramirez, M.; Aleixandre, R.N.; Hoesel, W.; Dwek, R.A.; Rudd, P.M.; Peracaula, R.; de Llorens, R. Glycobiology, 2006, 16, 132.
40. Carlberg, M.; Dricu A.; Blegen H.; Wang M.; Hjertman M.; Zickert P.; Höög, A.; Larsson O. J. Biol. Chem., 1996, 271, 17453.
41. Noda, I.; Fujieda, S.; Seki, M.; Tanaka, N.; Sunaga, H.; Ohtsubo, T.; Tsuzuki, H.; Fan, G. K.; Saito, H. Int. J. Cancer, 1999, 80, 279.
42. Chen, F.W.; Gordon, R.E.; Ioannou, Y.A. Biochem. J., 2005, 390, 549.
43. Fiaux, H.; Popowycz, F.; Favre, S.; Schütz, C.; Vogel, P.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L. J. Med Chem., 2005, 48, 4237.
44. Hanessian, S.; Zhan, L.; Bovey, R.; Saavedra, O.M.; Juillerat-Jeanneret, L. J Med. Chem., 2003, 46, 3600.
45. Aguilera, B.; Romero-Ramirez, L.; Abad-Rodriguez, J.; Corrales, G.; Nieto-Sampietro, M.; Fernandez-Mayoralas, A. J. Med. Chem., 1998, 41, 4599.
46. Nieto-Sampietro, M.; Bailon, C.; Fernandez-Mayoralas, A.; Martin-Lomas, M.; Mellstrom, B.; Naranjo, J.R. J. Neuropath. Exp. Neurol., 1996, 55, 169.
47. Goss, P.E.; Baker, M.A.; Carver, J.P.; Dennis, J.W. Clin. Cancer Res., 1995, 1, 935.
48. Goss, P.E.; Reid, C.L.; Bailey, D.; Dennis, J.W. Clin. Cancer Res., 1997, 3, 1077.
49. Henrissat, B. Biochem. Soc. Trans., 1998, 26, 153.
50. Ayude, D.; Fernandez-Rodriguez, J.; Rodriguez-Berrocal, F.J.; Martinez-Zorzano, V.S.; de Carlos, A.; Gil, E.; Paez de la Cadena, M. Oncology, 2000, 59, 310.
51. Dusseau, C.; Murray, G.I.; Keenan, R.A.; O'Kelly, T.; Krokan, H.E.; McLeod, H.L. Int. J. Oncol., 2001, 18, 393,
52. Franci, C.; Egea, G.; Arribas, R.; Reuser, A.J.; Real, F.X. Biochem. J., 1996, 314, 33.
53. Gil-Martin, E.; Gil-Seijo. S.; Nieto-Novoa. C.; Fernandez-Briera, A. Int. J. Biochem. Cell Biol., 1997, 28, 651.
54. Gil-Martin, E.; Rodriguez-Berrocal, F.J.; Paez de la Cadena, M.; Fernandez-Briera, A. Oncology, 1999, 56, 142.
55. Kakugawa, Y.; Wada, T.; Yamaguchi, K.; Yamanami, H.; Ouchi, K.; Sato, I.; Miyagi. T. Proc. Nat. Acad. Sci. USA, 2002, 99, 10718.
56. Kato, T.; Wang, Y.; Yamaguchi, K.; Milner, C.M.; Shineda, R.; Satomi, S.; Miyagi, T. Int. J. Cancer, 2001, 92, 797.
57. Reddi, A.L.; Sankaranarayanan, K.; Arulraj, H.S.; Devaraj, N.; Devaraj, H. Cancer Lett., 2000, 158, 61.
58. Slawson, C.; Pidala, J.; Potter, R. Biochim. Biophys. Acta, 2001, 1537, 147.
59. Sperker B.; Werner U.; Murdter, T.F.; Tekkaya C.; Fritz P.; Wacke, R.; Adam, U.; Gerken, M.; Drewelow, B.; Kroemer, H.K. Naunyn-Schmiedbergs Arch. Pharm., 2000, 362, 110.
60. Van den Elsen, J.M.; Kuntz, D.A.; Rose, D.R EMBO J., 2001, 20, 3008.
61. Vlodavsky, I.; Friedmann, Y.; Elkin, M.; Aingom, H.; Atzmon, R.; Ishai-Micaeli, R.; Bita, M.; Pappo, O.;. Peretz, T.; Michal, I; Spector, L.; Pecker, I. Nat. Med., 1999, 5, 793.
62. Winchester, B. Glycobiology, 2005, 15, 1R.
63. Beratis, N.G.; Kaperonis, A.; Eliopoulou, M.I.; Kourounis, G.; Tzingounis, V.A. J. Cancer Res. Clin. Oncol., 2005, 131, 371.
64. Wang, X.; Tsao, S.W.; Wong, Y.C.; Cheung, A.L. Curr. Cancer Drug Targets, 2003, 3, 153.
65. Cheng, H.; Cao, X.; Xian, M.; Fang, L.; Cai, T.B., Ji, J.J.; Tunac, J.B.; Sun, D.; Wang, P.G. J. Med. Chem., 2005, 48, 845.
66. Vasella, A.; Davies, G.J.; Böhm, M. Curr. Op. Struct. Biol., 2002, 6, 619.
67. Howard, S.; He, S.; Withers, S.G. J. Biol. Chem., 1998, 273, 2067.
68. Lillelund, V.H.; Jensen, H.H.; Liang, X.; Bols, M. Chem. Rev., 2002, 102, 515.
69. Popowycz, F.; Gerber-Lemaire, S.; Demange, R.; Rodriguez-Garcia. E.: Carmona Asenio, A.T.: Robina, I.: Vogel, P. Bioorg. Med. Chem. Lett., 2001, 11, 2489.
70. Gerber-Lemaire, S.; Popowycz, F.; Rodriguez-Garcia, E.; Carmona Asenjo, A.T.; Robina, I.; Vogel, P. Chembiochem., 2002, 3, 466.
71. Moreno-Vargas, A.J.; Schuetz, C.; Scopelliti, R.; Vogel, P. J. Org. Chem., 2003, 68, 5632.
72. Moreno-Vargas, A.J.; Vogel, P. Tetrahedron Lett., 2003, 44, 5069.
73. Popowycz, F.; Gerber-Lemaire, S.; Rodriguez-Garcia, E.; Schuetz, C.; Vogel, P. Helv. Chem. Acta, 2003, 86, 1914.
74. Popowycz, F.; Gerber-Lemaire, S.; Schütz, C.; Vogel, P. Helv. Chim. Acta, 2004, 87, 800.
75. Reddy, B.G.; Vankar, Y.D. Angw. Chemie, Int. Ed., 2005, 44, 2001.
76. Aft, R.L.; Zhang, F.W.; Gius, D. Br. J. Cancer, 2002, 87, 805.
77. Jacob, G.S. Curr. Opin. Struct. Biol., 1995, 5, 605.
78. El Ashry, E.S.H.; Rashed, N.; Shobier, A.H.S. Pharmazie, 2000, 55, 251.
79. El Ashry, E.S.H.; Rashed, N.; Shobier, A.H.S. Pharmazie, 2000, 55, 331.
80. El Ashry, E.S.H.; Rashed, N.; Shobier, A.H.S. Pharmazie, 2000, 55, 403.
81. Tomich, C.H.; da Silva, P.; Carvalho, I.; Taft, C.A. J. Comp. Aided Mol. Des., 2005, 19, 83.
82. Spearman, M.A.; Ballon, B.C.; Gerrard, J,M.; Greenberg, A.H.; Wright, J.A. Cancer Lett., 1991, 60, 185.
83. Pili, R.; Chang, J.; Parris, R.A.; Mueller, R.A.; Chrest, F.J.; Passaniti, A. Cancer Res., 1995, 55, 2920.
84. Hu, L.H.; Zou, H.B.; Gong, J.X.; Li, H.B.; Yang, L.X; Cheng, W.; Zhou, C.X.; Bai, H.; Guéritte, F.; Zhao, Y. J. Nat. Prod., 2005, 68, 342.
85. Yeo, T.K.; Yeo, K.T.; Parent, J.B.; Olden, K. J. Biol. Chem., 1985, 260, 2565.
86. Humphries, M.J.; Matsumoto, K.; White, S.L.; Olden, K. Proc. Natl. Acad. Sci. USA, 1986, 83, 1752.
87. Olden, K.; Breton, P.; Grzegorzewski, K.; Yasuda, Y.; Gause, B. L.; Oredipe, O.A.; Newton, S.A.; White, S.L. Pharmacol Ther., 1991, 50, 285.
88. Dennis, J.W.; White, S.L.; Freer, A.M.; Dime, D. Biochem. Pharmacol, 1993, 46, 1459.
89. Przybylo M.; Litynska A.; Pochec E. Biochimie, 2005, 87, 133.
90. Hembre, E.J.; Pearson, W.H. Tetrahedron, 1997, 53, 11021.
91. Pearson, W.H.; Guo, L. Tetrahedron Lett., 2001, 42, 8267.
92. Pearson, W.H.; Hembre, E.J. Tetrahedron Lett., 2001, 42, 8273.
93. Pearson, W.H.; Hembre, E.J. J. Org. Chem., 1996, 61, 5537.