Inhibition of Golgi mannosidase II with mannostatin A analogues: Synthesis, biological evaluation, and structure-activity relationship studies

ChemBioChem

Volumn 5, Issue 9, 2004, Pages 1220-1227

  Li, Bing ^a   Kawatkar, Sameer P ^a   George, Shaji ^a   Strachan, Heather ^a   Woods, Robert J ^a   Siriwardena, Aloysius ^a   Moremen, Kelley W ^a   Boons, Geert Jan ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Inhibitors; Mannosidases; Molecular modeling; Structure activity relationships; Substituent effects

Indexed keywords

ALPHA MANNOSIDASE; ALPHA MANNOSIDASE II; AMINE; AMINOCYCLOPENTITETROL; AMINOCYCLOPENTITETROL DERIVATIVE; ARGININE; BENZYL DERIVATIVE; CYCLOPENTANE DERIVATIVE; LYSOSOME ENZYME; MANNOSE; MANNOSIDASE INHIBITOR; MANNOSTATIN A; MANNOSTATIN B; MANNOSYL OXOCARBENIUM ION; SWAINSONINE; TYROSINE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; AMINO ACID SUBSTITUTION; ARTICLE; CELL LINE; DRUG ACTIVITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO CELL; ENERGY; ENZYME INHIBITION; EVALUATION; GOLGI COMPLEX; GROWTH INHIBITION; HUMAN; HUMAN CELL; HYDROPHOBICITY; LYSOSOME; PREDICTION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ALPHA-MANNOSIDASE; AMINES; ANIMALS; COMPUTATIONAL BIOLOGY; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; DROSOPHILA; ENZYME INHIBITORS; GOLGI APPARATUS; HUMANS; INDICATORS AND REAGENTS; LYSOSOMES; MANNOSIDASES; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4644342294     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300842     Document Type: Article

References (56)

1. J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
2. P. E. Goss, M. A. Baker, J. P. Carver, J. W. Dennis, Clin. Cancer Res. 1995, 1, 935.
3. D. R. P. Tulsiani, S. C. Hubbard, P. W. Robbins, O. Touster, J. Biol. Chem. 1982, 257, 3660.
4. A. Vasella, G.J. Davies, M. Bohm, Curr. Opin. Chem. Biol. 2002, 6, 619.
5. T. D. Heightman, A. T. Vasella, Angew. Chem. 1999, 111, 794; Angew. Chem. Int. Ed. 1999, 38, 750.
6. T. D. Heightman, A. T. Vasella, Angew. Chem. 1999, 111, 794; Angew. Chem. Int. Ed. 1999, 38, 750.
7. D. L. Zechel, S. G. Withers, Acc. Chem. Res. 2000, 33, 11.
8. D. L. Zechel, S. G. Withers, Curr. Opin. Chem. Biol. 2001, 5, 643.
9. J. D. McCarter, S. G. Withers, Curr. Opin. Struct. Biol. 1994, 4, 885.
10. J. M. H. van den Elsen, D. A. Kuntz, D. R. Rose, EMBO J. 2001, 20, 3008.
11. J.W. Dennis, K. Koch, S. Yousefi, I. Vanderelst, Cancer Res. 1990, 50, 1867.
12. T. L. Bowlin, P. S. Sunkara, Biochem. Biophys. Res. Commun. 1988, 151, 859.
13. K. Olden, P. Breton, K. Grzegorzewski, Y. Yasuda, B. L. Gause, O. A. Oredipe, S. A. Newton, S. L. White, Pharmacol. Ther. 1991, 50, 285.
14. P. E. Goss, C. L. Reid, D. Bailey, J. W. Dennis, Clin. Cancer Res. 1997, 3, 1077.
15. T. Aoyagi, T. Yamamoto, K. Kojiri, H. Morishima, M. Nagai, M. Hamada, T. Takeuchi, H. Umezawa, J. Antibiot. 1989, 42, 883.
16. S. B. King, B. Ganem, J. Am. Chem. Soc. 1994, 116, 562.
17. S. Ogawa, T. Morikawa, Bioorg. Med. Chem. Lett. 1999, 9, 1499.
18. S. Ogawa, T. Morikawa, Bioorg. Med. Chem. Lett. 2000, 10, 1047.
19. M. Kleban, P. Hilgers, J. N. Greul, R. D. Kugler, J. Li, S. Picasso, P. Vogel, V. Jager, ChemBioChem 2001, 2, 365.
20. O. Boss, E. Leroy, A. Blaser, J. L. Reymond, Org. Lett. 2000, 2, 151.
21. F. Popowycz, S. Gerber-Lemaire, R. Demange, E. Rodriguez-Garcia, A. T. C. Asenjo, I. Robina, P. Vogel, Bioorg. Med. Chem. Lett. 2001, 11, 2489.
22. S. Ogawa, K. Washida, Eur. J. Org. Chem. 1998, 1929.
23. S. Ogawa, T. Morikawa, Eur. J. Org. Chem. 2000, 1759.
24. C. Uchida, H. Kimura, S. Ogawa, Bioorg. Med. Chem. 1997, 5, 921.
25. A. K. Szardenings, T. S. Burkoth, G. C. Look, D. A. Campbell, J. Org. Chem. 1996, 61, 6720.
26. M. K. Schwarz, D. Tumelty, M.A. Gallop, J. Org. Chem. 1999, 64, 2219.
27. R. N. Salvatore, A. S. Nagle, K. W. Jung, J. Org. Chem. 2002, 67, 674.
28. M. Misago, Y. F. Liao, S. Kudo, S. Eto, M. G. Mattei, K. W. Moremen, M. N. Fukuda, Proc. Natl. Acad. Sci. USA 1995, 92, 11 766.
29. Y. F. Liao, A. Lal, K. W. Moremen, J. Biol. Chem. 1996, 271, 28 348.
30. P. Lalegerie, G. Legler, J. M. Yon, Biochimie 1982, 64, 977.
31. S. Knapp, T. G. M. Dhar, J. Org. Chem. 1991, 56, 4096.
32. C. Rabouille, D. A. Kuntz, A. Lockyer, R. Watson, T. Signorelli, D. R. Rose, M. van den Heuvel, D. B. Roberts, J. Cell Sci. 1999, 112, 3319.
33. J. E. Kilpatrick, K. S. Pitzer, R. Spitzer, J. Am. Chem. Soc. 1947, 69, 2483.
34. K. S. Pitzer, W. E. Donath, J. Am. Chem. Soc. 1959, 81, 3213.
35. A. Chung-Phillips, Y. Y. Chen, J. Phys. Chem. A 1999, 103, 953.
36. F. Cloran, I. Carmichael, A. S. Serianni, J. Phys. Chem. A 1999, 103, 3783.
37. M. T. Gordon, T. L. Lowary, C. M. Hadad, J. Org. Chem. 2000, 65, 4954.
38. D. J. Tannor, B. Marten, R. Murphy, R. A. Friesner, D. Sitkoff, A. Nicholls, M. Ringnalda, W.A. Goddard, B. Honig, J. Am. Chem. Soc. 1994, 116, 11 875.
39. B. Marten, K. Kim, C. Cortis, R. A. Friesner, R. B. Murphy, M. N. Ringnalda, D. Sitkoff, B. Honig, J. Phys. Chem. 1996, 100, 11 775.
40. Jaguar 4.2, Schrodinger, Inc., Portland, OR, 2001.
41. A. B. Boraston, P. Chiu, R. A. J. Warren, D. G. Kilburn, Biochemistry 2000, 39, 11 129.
42. I. L. Alberts, K. Nadassy, S. J. Wodak, Protein Sci. 1998, 7, 1700.
43. R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373.
44. R. U. Lemieux, L. T. J. Delbaere, H. Beierbeck, U. Spohr, Ciba Foundation Symposia 1991, 158, 231.
45. G. B. McGaughey, M. Gagne, A. K. Rappe, J. Biol. Chem. 1998, 273, 15 458.
46. Gaussian (Revision E.2), M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
47. A. D. Becke, Phys. Rev. A 1988, 38, 3098.
48. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
49. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
50. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213.
51. M. Sundaralingam, J. Am. Chem. Soc. 1971, 93, 6644.
52. D. S. Goodsell, G. M. Morris, A. J. Olson, J. Mol. Recognit. 1996, 9, 1.
53. G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Comput. Chem. 1998, 19, 1639.
54. L. Chiche, L. M. Gregoret, F. E. Cohen, P. A. Kollman, Proc. Natl. Acad. Sci. USA 1990, 87, 3240.
55. J. Gasteiger, M. Marsili, Tetrahedron 1980, 36, 3219.
56. E. L. Mehler, T. Solmajer, Protein Eng. 1991, 4, 903.