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Angewandte Chemie - International Edition

Volumn 45, Issue 32, 2006, Pages 5345-5348

Selective inhibition of glycosidases by feedback prodrugs

(3) Guo, Jun a Asong, Jinkeng a Boons, Geert Jan a

a UNIVERSITY OF GEORGIA (United States)

Author keywords

Glycosidases; Inhibitors; Mannosidases; Prodrugs; Selectivity

Indexed keywords

GLYCOSIDASES; INHIBITORS; MANNOSIDASES; PRODRUGS; SELECTIVITY;

DRUG PRODUCTS; ENZYME INHIBITION; HYDROLYSIS;

ENZYMES;

GLYCOSIDASE; PRODRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; FEEDBACK SYSTEM; METABOLISM;

FEEDBACK, BIOCHEMICAL; FEEDBACK, PHYSIOLOGICAL; GLYCOSIDE HYDROLASES; MOLECULAR STRUCTURE; PRODRUGS;

EID: 33747881818 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200600808 Document Type: Article

Times cited : (11)

References (44)

1
- 0027318961
- A. Varki, Glycobiology 1993, 3, 97.
- (1993) Glycobiology , vol.3 , pp. 97
- Varki, A.¹

2
- 0001094662
- R. A. Dwek, Chem. Rev. 1996, 96, 683.
- (1996) Chem. Rev. , vol.96 , pp. 683
- Dwek, R.A.¹

3
- 0000591717
- T. Kolter, K. Sandhoff, Angew. Chem. 1999, 111, 1632;
- (1999) Angew. Chem. , vol.111 , pp. 1632
- Kolter, T.¹ Sandhoff, K.²

4
- 0033152727
- Angew. Chem. Int. Ed. 1999, 38, 1532.
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1532

5
- 0033135747
- J. W. Dennis, M. Granovsky, C. E. Warren, BioEssays 1999, 21, 412.
- (1999) BioEssays , vol.21 , pp. 412
- Dennis, J.W.¹ Granovsky, M.² Warren, C.E.³

6
- 21744431575
- M. M. Fuster, J. D. Esko, Nat. Rev. Cancer 2005, 5, 526.
- (2005) Nat. Rev. Cancer , vol.5 , pp. 526
- Fuster, M.M.¹ Esko, J.D.²

7
- 20844437106
- D. H. Dube, C. R. Bertozzi, Nat. Rev. Drug Discovery 2005, 4, 477.
- (2005) Nat. Rev. Drug Discovery , vol.4 , pp. 477
- Dube, D.H.¹ Bertozzi, C.R.²

8
- 0032714567
- J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
- (1999) Biochim. Biophys. Acta , vol.1473 , pp. 21
- Dennis, J.W.¹ Granovsky, M.² Warren, C.E.³

9
- 0029128356
- P. E. Goss, M. A. Baker, J. P. Carver, J. W. Dennis, Clin. Cancer Res. 1995, 1, 935.
- (1995) Clin. Cancer Res. , vol.1 , pp. 935
- Goss, P.E.¹ Baker, M.A.² Carver, J.P.³ Dennis, J.W.⁴

10
- 0036462605
- V. H. Lillelund, H. H. Jensen, X. F. Liang, M. Bols, Chem. Rev. 2002, 102, 515.
- (2002) Chem. Rev. , vol.102 , pp. 515
- Lillelund, V.H.¹ Jensen, H.H.² Liang, X.F.³ Bols, M.⁴

11
- 0033097654
- A. Berecibar, C. Grandjean, A. Siriwardena, Chem. Rev. 1999, 99, 779.
- (1999) Chem. Rev. , vol.99 , pp. 779
- Berecibar, A.¹ Grandjean, C.² Siriwardena, A.³

12
- 0034607947
- N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 2000,11, 1645.
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1645
- Asano, N.¹ Nash, R.J.² Molyneux, R.J.³ Fleet, G.W.J.⁴

13
- 0001216096
- T. D. Heightman, A. T. Vasella, Angew. Chem. 1999, 111, 794;
- (1999) Angew. Chem. , vol.111 , pp. 794
- Heightman, T.D.¹ Vasella, A.T.²

14
- 0033559148
- Angew. Chem. Int. Ed. 1999, 38, 750.
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 750

15
- 0030862827
- M. vonItzstein, R. J. Thomson, Curr. Med. Chem. 1997, 4, 185.
- (1997) Curr. Med. Chem. , vol.4 , pp. 185
- VonItzstein, M.¹ Thomson, R.J.²

16
- 0242287992
- N. Asano, Glycobiology 2003, 13, 93R.
- (2003) Glycobiology , vol.13
- Asano, N.¹

17
- 0031740403
- R. Perfetti, P. S. Barnett, R. Mathur, J. M. Egan, Diabetes/Metab. Rev. 1998, 14, 207.
- (1998) Diabetes/Metab. Rev. , vol.14 , pp. 207
- Perfetti, R.¹ Barnett, P.S.² Mathur, R.³ Egan, J.M.⁴

18
- 0027287506
- M. Von Itzstein, W. Y. Wu, G. B. Kok, M. S. Pegg, J. C. Dyason, B. Jin, T. V. Phan, M. L. Smythe, H. F. White, S. W. Oliver, P. M. Colman, J. N. Varghese, D. M. Ryan, J. M. Woods, R. C. Bethell, V. J. Hotham, J. M. Cameron, C. R. Penn, Nature 1993, 363, 418.
- (1993) Nature , vol.363 , pp. 418
- Von Itzstein, M.¹ Wu, W.Y.² Kok, G.B.³ Pegg, M.S.⁴ Dyason, J.C.⁵ Jin, B.⁶ Phan, T.V.⁷ Smythe, M.L.⁸ White, H.F.⁹ Oliver, S.W.¹⁰ Colman, P.M.¹¹ Varghese, J.N.¹² Ryan, D.M.¹³ Woods, J.M.¹⁴ Bethell, R.C.¹⁵ Hotham, V.J.¹⁶ Cameron, J.M.¹⁷ Penn, C.R.¹⁸

19
- 0030044141
- M. vonItzstein, J. C. Dyason, S. W. Oliver, H. F. White, W. Y. Wu, G. B. Kok, M. S. Pegg, J. Med. Chem. 1996, 39, 388.
- (1996) J. Med. Chem. , vol.39 , pp. 388
- VonItzstein, M.¹ Dyason, J.C.² Oliver, S.W.³ White, H.F.⁴ Wu, W.Y.⁵ Kok, G.B.⁶ Pegg, M.S.⁷

20
- 0031048319
- C. U. Kim, W. Lew, M. A. Williams, H. T. Liu, L. J. Zhang, S. Swaminathan, N. Bischofberger, M. S. Chen, D. B. Mendel, C. Y. Tai, W. G. Laver, R. C. Stevens, J. Am. Chem. Soc. 1997, 119, 681.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 681
- Kim, C.U.¹ Lew, W.² Williams, M.A.³ Liu, H.T.⁴ Zhang, L.J.⁵ Swaminathan, S.⁶ Bischofberger, N.⁷ Chen, M.S.⁸ Mendel, D.B.⁹ Tai, C.Y.¹⁰ Laver, W.G.¹¹ Stevens, R.C.¹²

21
- 0031916471
- W. X. Li, P. A. Escarpe, E. J. Eisenberg, K. C. Cundy, C. Sweet, K. J. Jakeman, J. Merson, W. Lew, M. Williams, L. J. Zhang, C. U. Kim, N. Bischofberger, M. S. Chen, D. B. Mendel, Antimicrob. Agents Chemother. 1998, 42, 647.
- (1998) Antimicrob. Agents Chemother. , vol.42 , pp. 647
- Li, W.X.¹ Escarpe, P.A.² Eisenberg, E.J.³ Cundy, K.C.⁴ Sweet, C.⁵ Jakeman, K.J.⁶ Merson, J.⁷ Lew, W.⁸ Williams, M.⁹ Zhang, L.J.¹⁰ Kim, C.U.¹¹ Bischofberger, N.¹² Chen, M.S.¹³ Mendel, D.B.¹⁴

22
- 0035818923
- P. Chand, P. L. Kotian, A. Dehghani, Y. El-Kattan, T. H. Lin, T. L. Hutchison, Y. S. Babu, S. Bantia, A. J. Elliott, J. A. Montgomery, J. Med. Chem. 2001, 44, 4379.
- (2001) J. Med. Chem. , vol.44 , pp. 4379
- Chand, P.¹ Kotian, P.L.² Dehghani, A.³ El-Kattan, Y.⁴ Lin, T.H.⁵ Hutchison, T.L.⁶ Babu, Y.S.⁷ Bantia, S.⁸ Elliott, A.J.⁹ Montgomery, J.A.¹⁰

23
- 8844262688
- G. Godin, P. Compain, O. R. Martin, K. Ikeda, L. Yu, N. Asano, Bioorg. Med. Chem. Lett. 2004, 14, 5991.
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5991
- Godin, G.¹ Compain, P.² Martin, O.R.³ Ikeda, K.⁴ Yu, L.⁵ Asano, N.⁶

24
- 0028176432
- F. M. Platt, G. R. Neises, R. A. Dwek, T. D. Butters, J. Biol. Chem. 1994, 269, 8362.
- (1994) J. Biol. Chem. , vol.269 , pp. 8362
- Platt, F.M.¹ Neises, G.R.² Dwek, R.A.³ Butters, T.D.⁴

25
- 0028171083
- F. M. Platt, G. R. Neises, G. B. Karlsson, R. A. Dwek, T. D. Butters, J. Biol. Chem. 1994, 269, 27 108.
- (1994) J. Biol. Chem. , vol.269 , pp. 27108
- Platt, F.M.¹ Neises, G.R.² Karlsson, G.B.³ Dwek, R.A.⁴ Butters, T.D.⁵

26
- 15644367080
- H. S. Overkleeft, G. H. Renkema, J. Neele, P. Vianello, I. O. Hung, A. Strijland, A. M. van der Burg, G. J. Koomen, U. K. Pandit, J. Aerts, J. Biol. Chem. 1998, 273, 26 522.
- (1998) J. Biol. Chem. , vol.273 , pp. 26522
- Overkleeft, H.S.¹ Renkema, G.H.² Neele, J.³ Vianello, P.⁴ Hung, I.O.⁵ Strijland, A.⁶ Van Der Burg, A.M.⁷ Koomen, G.J.⁸ Pandit, U.K.⁹ Aerts, J.¹⁰

27
- 33747873685
- C. Y. Wu, C. F. Chang, J. S. Y. Chen, C. H. Wong, C. H. Lin, Angew. Chem. 2003, 115, 5119;
- (2003) Angew. Chem. , vol.115 , pp. 5119
- Wu, C.Y.¹ Chang, C.F.² Chen, J.S.Y.³ Wong, C.H.⁴ Lin, C.H.⁵

28
- 0142119368
- Angew. Chem. Int. Ed. 2003, 42, 4661.
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4661

29
- 0037010811
- L. L. Johnson, T. A. Houston, Tetrahedron Lett. 2002, 43, 8905.
- (2002) Tetrahedron Lett. , vol.43 , pp. 8905
- Johnson, L.L.¹ Houston, T.A.²

30
- 0035903835
- I. Robina, A. J. Moreno-Vargas, J. G. Fernandez-Bolanos, J. Fuentes, R. Demange, P. Vogel, Bioorg. Med. Chem. Lett. 2001, 11, 2555.
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2555
- Robina, I.¹ Moreno-Vargas, A.J.² Fernandez-Bolanos, J.G.³ Fuentes, J.⁴ Demange, R.⁵ Vogel, P.⁶

31
- 27644473102
- R. Lysek, C. Schutz, P. Vogel, Helv. Chim. Acta 2005, 88, 2788.
- (2005) Helv. Chim. Acta , vol.88 , pp. 2788
- Lysek, R.¹ Schutz, C.² Vogel, P.³

32
- 0038170055
- T. D. Butters, R. A. Dwek, F. M. Platt, Curr. Top. Med. Chem. 2003, 3, 561.
- (2003) Curr. Top. Med. Chem. , vol.3 , pp. 561
- Butters, T.D.¹ Dwek, R.A.² Platt, F.M.³

33
- 0242577550
- A. B. Pardee, G. P. V. Reddy, Gene 2003, 321, 17.
- (2003) Gene , vol.321 , pp. 17
- Pardee, A.B.¹ Reddy, G.P.V.²

34
- 0028349238
- S. B. King, B. Ganem, J. Am. Chem. Soc. 1994, 116, 562.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 562
- King, S.B.¹ Ganem, B.²

35
- 0035966194
- F. M. H. de Groot, W. J. Loos, R. Koekkoek, L. W. A. van Berkom, G. F. Busscher, A. E. Seelen, C. Albrecht, P. de Bruijn, H. W. Scheeren, J. Org. Chem. 2001, 66, 8815.
- (2001) J. Org. Chem. , vol.66 , pp. 8815
- De Groot, F.M.H.¹ Loos, W.J.² Koekkoek, R.³ Van Berkom, L.W.A.⁴ Busscher, G.F.⁵ Seelen, A.E.⁶ Albrecht, C.⁷ De Bruijn, P.⁸ Scheeren, H.W.⁹

36
- 0034658141
- S. Ogawa, T. Morikawa, Bioorg. Med. Chem. Lett. 2000, 10, 1047.
- (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1047
- Ogawa, S.¹ Morikawa, T.²

37
- 0025765611
- S. Ogawa, Y. M. Yu, J. Chem. Soc. Chem. Commun. 1991, 890.
- (1991) J. Chem. Soc. Chem. Commun. , pp. 890
- Ogawa, S.¹ Yu, Y.M.²

38
- 0346323751
- T. Suami, Y. Sakota, K. Tadano, S. Nishiyam, Bull. Chem. Soc. Jpn. 1971, 44, 2222.
- (1971) Bull. Chem. Soc. Jpn. , vol.44 , pp. 2222
- Suami, T.¹ Sakota, Y.² Tadano, K.³ Nishiyam, S.⁴

39
- 0033549661
- J. C. Wilson, M. J. Kiefel, D. I. Angus, M. von Itzstein, Org. Lett. 1999, 1, 443.
- (1999) Org. Lett. , vol.1 , pp. 443
- Wilson, J.C.¹ Kiefel, M.J.² Angus, D.I.³ Von Itzstein, M.⁴

40
- 4644342294
- B. Li, S. P. Kawatkar, S. George, H. Strachan, R. J. Woods, A. Siriwardena, K. W. Moremen, G. J. Boons, ChemBioChem 2004, 5, 1220.
- (2004) ChemBioChem , vol.5 , pp. 1220
- Li, B.¹ Kawatkar, S.P.² George, S.³ Strachan, H.⁴ Woods, R.J.⁵ Siriwardena, A.⁶ Moremen, K.W.⁷ Boons, G.J.⁸

41
- 0026317511
- A. D. Elbein, FASEB J. 1991, 5, 3055.
- (1991) FASEB J. , vol.5 , pp. 3055
- Elbein, A.D.¹

42
- 0028899712
- A. K. Sarkar, T. A. Fritz, W. H. Taylor, J. D. Esko, Proc. Natl. Acad. Sci. USA 1995, 92, 3323.
- (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 3323
- Sarkar, A.K.¹ Fritz, T.A.² Taylor, W.H.³ Esko, J.D.⁴

43
- 0025342509
- J. W. Dennis, K. Koch, S. Yousefi, I. Vanderelst, Cancer Res. 1990, 50, 1867.
- (1990) Cancer Res. , vol.50 , pp. 1867
- Dennis, J.W.¹ Koch, K.² Yousefi, S.³ Vanderelst, I.⁴

44
- 33747887184
- note
- Treatment of compound 1 with cell lysate in the presence of the mannosidase inhibitors swainsonine and kifunensine did not lead to significant decomposition, therefore indicating that proteases or other enzymes do not decompose the prodrug.

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