Efficient sialyltransferase inhibitors based on transition-state analogues of the sialyl donor

Angewandte Chemie - International Edition

Volumn 37, Issue 20, 1998, Pages 2893-2897

  Müller, Bernd ^a   Schaub, Christoph ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Enzyme inhibitors; Neuraminic acids; Phosphonates; Transition states

Indexed keywords

SIALIC ACID; SIALYLTRANSFERASE; SIALYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; B LYMPHOCYTE ACTIVATION; CHEMICAL REACTION KINETICS; ENZYME INHIBITION; REACTION ANALYSIS; SIALYLATION; STRUCTURE ANALYSIS;

EID: 0032476814     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981102)37:20<2893::AID-ANIE2893>3.0.CO;2-W     Document Type: Article

References (37)

1. a) A. Rosenberg, Biology of Sialic Acids, Plenum, New York, 1995;
2. b) F. Dall'Olio, N. Malagolini, F. Serafini-Cessi, Int. J. Cancer 1992, 50, 325-330;
3. c) J. Morgenthaler, W. Kemmner, R. Brossmer, Biochem. Biophys. Res. Commun. 1990, 171, 860-866.
4. a) R. J. Bernacki, Science 1977, 195, 557-580;
5. b) Q. Zhou, S. Hakomori, K. Kitamura, Y. Igarashi, J. Biol. Chem. 1994, 209, 1959-1965;
6. c) J. W. Dennis in Cell Surface Carbohydrates and Cell Development (Ed.: M. Fukuda), CRC, Boca Raton, FL, USA, 1991, pp. 174-175;
7. d) W. Kemmner, D. Kruck, P. M. Schlag, Clin. Exp. Metastasis 1994, 12, 245-254.
8. a) T. Kawai, A. Kato, H. Higashi, S. Kato, M. Naiki, Cancer Res. 1991, 51, 1242-1246;
9. b) F.-G. Hanisch, B. Witter, G. Crombach, W. Schänzer, G. Uhlenbruck, Tumor-Associated Antigens, Oncogenes, Receptors, Cytokines in Tumor Diagnosis and Therapy at the Beginning of the Nineties. Cancer of the Breast-Stale and Trends in Diagnosis and Therapy (Ed.: R. Klapder), Zuckerschwerdt, München, 1992, pp. 367-370.
10. a) E. Sjoberg, A. Manzi, K. Khoo, A. Varki, J. Biol. Chem. 1992, 267, 16200-16211;
11. b) T. Kageshita, S. Hirai, T. Kimura, Cancer Res. 1995, 55, 1748-1751.
12. T. Hennet, D. Chui, J. C. Paulson, J. D. Marth, Proc. Natl. Acad. Sci. USA 1998, 95, 4504-4509.
13. A. Harduin-Lepers, A. Recchi, P. Delaunnoy, Glycobiology 1995, 5, 741-758.
14. a) C. Schaub, B. Müller, R. R. Schmidt, Glycoconjugate J. 1998, 15, 345-354;
15. b) C. Schaub, R. R. Schmidt, Abstr. Pap. 2nd Eur. Conf. Carbohydr. Mimics (La Garda, Italy), 1996, p. C10.
16. F. Amann, C. Schaub, B. Müller, R. R. Schmidt, Chem. Eur. J. 1998, 4, 1106-1115.
17. B. Müller, T. J. Martin, C. Schaub, R. R. Schmidt, Tetrahedron Lett. 1998, 39, 509-512.
18. a) W. Korytnyk, N. Angelino, W. Klohs, R. J. Bernacki, Eur. J. Med. Chem. 1980, 15, 77-84;
19. b) I. Kijima-Suda, Y. Migamata, S. Toyoshima, M. Itoh, T. Osawa, Cancer Res. 1986, 46, 858-862;
20. c) S. H. Khan, K. L. Matta in Glycoconjugates, Composition, Structure, Function (Eds.: H. J. Allen, E. C. Kisailus), Dekker, New York, 1992, pp. 361-378, and references therein.
21. a) H. Hashimoto, K. Sato, T. Wakabayashi, H. Kodama, Y. Kajihara, Carbohydr. Res. 1993, 247, 179-193;
22. b) M. Imamoto, H. Hashimoto, Tetrahedron Lett. 1996, 37, 1451-1454.
23. a) R. G. Kleineidam, T. Schmelter, R. T. Schwarz, R. Schauer, Glycoconjugate J. 1997, 14, 57-66;
24. b) D. H. van den Eijnden, T. J. Martin, R. R. Schmidt, unpublished results;
25. c) G. Dufner, Dissertation, Universität Konstanz, 1997.
26. Recently antisense technology has been investigated in order to decrease sialyltransferase expression: W. Kemmner, K. Hohaus, P. M. Schlag, FEBS Lett. 1997, 409, 347-350.
27. Other examples of transition-state analogues of sugar nucleotides: UDP-Gal: a) K. Frische, Dissertation, Universität Konstanz, 1992;
28. b) K. Frische, R. R. Schmidt, Bioorg. Med. Chem. Lett. 1993, 5, 1747-1750;
29. GDP-Fuc: c) S. Cai, M. R. Strond, S. Hakomori, T. Toyokuni, J. Org. Chem. 1992, 57, 6693-6696.
30. B. A. Horenstein, M. Bruner, J. Am. Chem. Soc. 1996, 118, 10371-10379;
31. b) B. A. Horenstein, M. Bruner, Biochemistry 1998, 37, 289-297, and references therein.
32. M. Hoffmann, Synthesis 1988, 62-64.
33. a) Y. Kajihara, K. Koseki, T. Ebata, H. Kodama, H. Matsusita, H. Hashimoto, Carbohydr. Res. 1994, 264, C1-C5;
34. b) Y. Kajihara, K. Koseki, T. Ebata, H. Kodama, H. Matsusita, H. Hashimoto, J. Org. Chem. 1995, 60, 5732-5735.
35. i values, see ref. [7a].
36. Commercially available from Aldrich.
37. Investigation of inhibition with a recombinant rat liver α(2-3)-sialyltransferase led to similar results: C. Schaub, Dissertation, in preparation.