An efficient combinatorial method for the discovery of glycosidase inhibitors

ChemBioChem

Volumn 3, Issue 5, 2002, Pages 466-470

  Gerber Lemaire, Sandrine ^a   Popowycz, Florence ^a   Rodríguez García, Eliazar ^a   Asenjo, Ana Teresa Carmona ^b   Robina, Inmaculada ^b   Vogel, Pierre ^a  

^a Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

^b UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Carbohydrat mimics; Combinatorial chemistry; Imines; Inhibitors; Mannosidases

Indexed keywords

3,4 DIHYDROXYPYRROLIDIN 2 YL DERIVATIVE; ALPHA MANNOSIDASE; GLYCOSIDASE INHIBITOR; PYRROLIDINE DERIVATIVE; SWAINSONINE; SWAINSONINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLINICAL TRIAL; ENZYME INHIBITION; HUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID TUMOR; SYNTHESIS;

ALDEHYDES; AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; ENZYME INHIBITORS; IMINES; MANNOSIDASES; MOLECULAR STRUCTURE;

EID: 0036903709     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/1439-7633(20020503)3:5<466::AID-CBIC466>3.0.CO;2-D     Document Type: Article

References (38)

1. S. L. White, T. Nagai, S. K. Akiyama, E. J. Reeves, K. Grzegorzewski, K. Olden, Cancer Commun. 1991, 3, 83; 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; N. Asano, Enzyme Inhib. 2000, 15, 215; J. Carver, J. W. Dennis, P. Shah, US 5773239A, June 30, 1998 [Chem. Abstr. 1998, 129, 95683].
2. S. L. White, T. Nagai, S. K. Akiyama, E. J. Reeves, K. Grzegorzewski, K. Olden, Cancer Commun. 1991, 3, 83; 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; N. Asano, Enzyme Inhib. 2000, 15, 215; J. Carver, J. W. Dennis, P. Shah, US 5773239A, June 30, 1998 [Chem. Abstr. 1998, 129, 95683].
3. S. L. White, T. Nagai, S. K. Akiyama, E. J. Reeves, K. Grzegorzewski, K. Olden, Cancer Commun. 1991, 3, 83; 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; N. Asano, Enzyme Inhib. 2000, 15, 215; J. Carver, J. W. Dennis, P. Shah, US 5773239A, June 30, 1998 [Chem. Abstr. 1998, 129, 95683].
4. S. L. White, T. Nagai, S. K. Akiyama, E. J. Reeves, K. Grzegorzewski, K. Olden, Cancer Commun. 1991, 3, 83; 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; N. Asano, Enzyme Inhib. 2000, 15, 215; J. Carver, J. W. Dennis, P. Shah, US 5773239A, June 30, 1998 [Chem. Abstr. 1998, 129, 95683].
5. S. M. Colegate, P. R. Dorling, C. R. Huxtable, Austr. J. Chem. 1979, 32, 2257.
6. A. D. Elbein, R. D. Molyneux in Iminosugars as Glycosidase Inhibitors; Nojirimycin and Beyond (Eds.: A. E. Stütz), Wiley-VCH, Weinheim, 1999, Chap. 11, p. 216.
7. P. E. Goss, J. Baptiste, B. Fernandes, M. Baker, J. W. Dennis, Cancer Res. 1994, 54, 1450; P. E. Goss, C. L. Reid, D. Bailey, J. W. Dennis, Clin. Cancer Res. 1997, 3, 1077; P. D. Rye, N. V. Bovin, E. V. Vlasova, R. A. Walker, Glycobiology 1995, 5, 385; J. W. Dennis, M. Granovsky, C. E. Warren, BioEssays 1999, 21, 412; J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
8. P. E. Goss, J. Baptiste, B. Fernandes, M. Baker, J. W. Dennis, Cancer Res. 1994, 54, 1450; P. E. Goss, C. L. Reid, D. Bailey, J. W. Dennis, Clin. Cancer Res. 1997, 3, 1077; P. D. Rye, N. V. Bovin, E. V. Vlasova, R. A. Walker, Glycobiology 1995, 5, 385; J. W. Dennis, M. Granovsky, C. E. Warren, BioEssays 1999, 21, 412; J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
9. P. E. Goss, J. Baptiste, B. Fernandes, M. Baker, J. W. Dennis, Cancer Res. 1994, 54, 1450; P. E. Goss, C. L. Reid, D. Bailey, J. W. Dennis, Clin. Cancer Res. 1997, 3, 1077; P. D. Rye, N. V. Bovin, E. V. Vlasova, R. A. Walker, Glycobiology 1995, 5, 385; J. W. Dennis, M. Granovsky, C. E. Warren, BioEssays 1999, 21, 412; J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
10. P. E. Goss, J. Baptiste, B. Fernandes, M. Baker, J. W. Dennis, Cancer Res. 1994, 54, 1450; P. E. Goss, C. L. Reid, D. Bailey, J. W. Dennis, Clin. Cancer Res. 1997, 3, 1077; P. D. Rye, N. V. Bovin, E. V. Vlasova, R. A. Walker, Glycobiology 1995, 5, 385; J. W. Dennis, M. Granovsky, C. E. Warren, BioEssays 1999, 21, 412; J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
11. P. E. Goss, J. Baptiste, B. Fernandes, M. Baker, J. W. Dennis, Cancer Res. 1994, 54, 1450; P. E. Goss, C. L. Reid, D. Bailey, J. W. Dennis, Clin. Cancer Res. 1997, 3, 1077; P. D. Rye, N. V. Bovin, E. V. Vlasova, R. A. Walker, Glycobiology 1995, 5, 385; J. W. Dennis, M. Granovsky, C. E. Warren, BioEssays 1999, 21, 412; J. W. Dennis, M. Granovsky, C. E. Warren, Biochim. Biophys. Acta 1999, 1473, 21.
12. W. H. Pearson, L. Guo, Tetrahedron Lett. 2001, 42, 8267; W. H. Pearson, E. J. Hembre, Tetrahedron Lett. 2001, 42, 8273.
13. W. H. Pearson, L. Guo, Tetrahedron Lett. 2001, 42, 8267; W. H. Pearson, E. J. Hembre, Tetrahedron Lett. 2001, 42, 8273.
14. C. W. Ekhart, M. H. Fechter, P. Hadwiger, E. Mlaker, A. E. Stütz, A. Tauss, T. M. Wrodnigg in Iminosugars as Glycosidase Inhibitors; Nojirimycin and Beyond (Eds.: A. E. Stütz), Wiley-VCH, Weinheim, 1999, Chap. 12, p. 253.
15. F. Popowycz, S. Gerber-Lemaire, R. Demange, E. Rodriguez-Garcia, A. T Carmona Asenjo, I. Robina, P. Vogel, Bioorg. Med. Chem. Lett. 2001, 11, 2489.
16. For a related study, see: C. Saotome, C. H. Wong, O. Kame, Chem. Biol. 2001, 138, 1; see also: G. Limberg, I. Lindt, J. Zavilla, Synthesis 1999, 178.
17. For a related study, see: C. Saotome, C. H. Wong, O. Kame, Chem. Biol. 2001, 138, 1; see also: G. Limberg, I. Lindt, J. Zavilla, Synthesis 1999, 178.
18. J. Hine, F. A. Via, J. Am. Chem. Soc. 1972, 94, 190; J. Hine, C. Y. Yeh, F. C. Schmalstieg, J. Org. Chem. 1970, 35, 340; J. Hine, C. Y. Yeh, J. Am. Chem. Soc. 1967, 89, 2669; E. Gout, M. Zador, C. G. Beguin, Nouv. J. Chim. 1984, 8, 243.
19. J. Hine, F. A. Via, J. Am. Chem. Soc. 1972, 94, 190; J. Hine, C. Y. Yeh, F. C. Schmalstieg, J. Org. Chem. 1970, 35, 340; J. Hine, C. Y. Yeh, J. Am. Chem. Soc. 1967, 89, 2669; E. Gout, M. Zador, C. G. Beguin, Nouv. J. Chim. 1984, 8, 243.
20. J. Hine, F. A. Via, J. Am. Chem. Soc. 1972, 94, 190; J. Hine, C. Y. Yeh, F. C. Schmalstieg, J. Org. Chem. 1970, 35, 340; J. Hine, C. Y. Yeh, J. Am. Chem. Soc. 1967, 89, 2669; E. Gout, M. Zador, C. G. Beguin, Nouv. J. Chim. 1984, 8, 243.
21. J. Hine, F. A. Via, J. Am. Chem. Soc. 1972, 94, 190; J. Hine, C. Y. Yeh, F. C. Schmalstieg, J. Org. Chem. 1970, 35, 340; J. Hine, C. Y. Yeh, J. Am. Chem. Soc. 1967, 89, 2669; E. Gout, M. Zador, C. G. Beguin, Nouv. J. Chim. 1984, 8, 243.
22. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
23. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
24. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
25. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
26. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
27. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
28. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
29. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
30. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
31. A. Ganessan, Angew. Chem. 1998, 110, 2989; Angew. Chem. Int. Ed. 1998, 37, 2828; J. M. Lehn, Chem. Eur. J. 1999, S, 2455; V. A. Polyakov, M. I. Nelen, N. Nazarpack-Kandlousy, A.D. Ryabov, A. V. Eliseev, J. Phys. Org. Chem. 1999, 12, 357; A. V. Eliseev, J. M. Lehn, Curr. Top. Microbial. Immunol. 1999, 213, 159; C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67; J. M. Lehn, Science 2001, 291, 2331, and references cited therein; P.A. Brady, R. P. Bonar-Law, S. J. Rowan, C. J. Suckling, J. K. Sanders, Chem. Commun. 1996, 319; S. J. Rowan, P. A. Brady, J. K. M. Sanders, Angew. Chem. 1996, 108, 2283; Angew. Chem. Int. Ed. Engl. 1996, 35, 2143.
32. For related studies showing similar autocatalytical effects, see: J. Hine, M. S. Cholob, W. K. Chess, Jr., J. Am. Chem. Soc. 1973, 95, 4270.
33. This commercially available enzyme is a useful model for α-mammalian α-mannosidases such as Golgi α-mannosidase II; see, for example: S. Howard, S. He, S. G. Withers, J. Biol. Chem. 1998, 273, 2067.
34. For details of the enzymatic assays, see: A. Brandi, S. Cicchi, F. M. Cordero, B. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 1995, 60, 6806; S. Picasso, Y. Chen, P. Vogel, Carbohydrate Lett. 1994, 1, 1; see also: J. E. Tropea, R. J. Molyneux, G. P. Kaushal, Y. T. Pan, M. Mitchell, A. D. Elbein, Biochemistry 1989, 28, 2027.
35. For details of the enzymatic assays, see: A. Brandi, S. Cicchi, F. M. Cordero, B. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 1995, 60, 6806; S. Picasso, Y. Chen, P. Vogel, Carbohydrate Lett. 1994, 1, 1; see also: J. E. Tropea, R. J. Molyneux, G. P. Kaushal, Y. T. Pan, M. Mitchell, A. D. Elbein, Biochemistry 1989, 28, 2027.
36. For details of the enzymatic assays, see: A. Brandi, S. Cicchi, F. M. Cordero, B. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 1995, 60, 6806; S. Picasso, Y. Chen, P. Vogel, Carbohydrate Lett. 1994, 1, 1; see also: J. E. Tropea, R. J. Molyneux, G. P. Kaushal, Y. T. Pan, M. Mitchell, A. D. Elbein, Biochemistry 1989, 28, 2027.
37. The same assays were made on N-methylpyrrol-2-carbaldehyde and N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxaldehyde. No significant inhibitory activities were observed.
38. G. W. J. Fleet, J. C. Son, D. St. C. Green, I. Cenci di Bello, B. Winchester, Tetrahedron 1988, 44, 2649.