Liposome-like fucopeptides as sialyl Lewis X mimetics

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 22, 1996, Pages 2755-2760

  Lin, Chun Cheng ^a   Kimura, Teiji ^a   Wu, Shih Hsiung ^a,b   Weitz Schmidt, Gabriele ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; GLYCOPEPTIDE; LIPOSOME; LYMPHOCYTE ANTIGEN RECEPTOR;

ARTICLE; CELL SURFACE; DRUG SYNTHESIS; PROTEIN DOMAIN; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

EID: 0030593888     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00509-4     Document Type: Article

References (38)

1. 1. (a) Levy, D. E.; Tang, P. C.; Musser, J. H. Annu. Rep. Med. Chem. 1994, 215.
2. (b) Lasky, L. A. Science 1992, 258, 6224.
3. 2. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1132.
4. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Bevilacqua, M.; Seed, B. Science 1990, 250, 1130.
5. (c) Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Mark, R. M. Cell 1990, 63, 474.
6. (d) Lasky, L. A. Annu. Rev. Biochem. 1995, 64, 113.
7. (e) Springer, T. A. Cell 1994, 76, 301.
8. 3. (a) Buerke, M.; Weyrich, A. S.; Zheng, Z.; Gaeta, F. C. A.; Forrest, M. J.; Lefer, A. M. J. Clin. Invest. 1994, 1140.
9. (b) Mulligan, M. S.; Paulson, J. C.; Frees, S. D.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149.
10. (c) Murohara, T.; Margiotta, J.; Phillips, L. M.; Paulson, J. C.; DeFrees, S.; Zalipsky, S.; Guo, L. S. S.; Lefer, A. M. Cardiorascular Res. 1995, 30, 965.
11. 4. Ichikawa, Y.; Lin, Y.-C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283.
12. x is sensitive to α-fucosidase and neuraminidase.
13. 6. (a) Dupré, B.; Bui, H.; Scott, I. L.; Market, R. V.; Keller, K. M.; Beck, P. J.; Kogan, T. P. Bioorg. Med. Chem. Lett. 1996, 6, 569.
14. (b) Ramphal, J. Y.; Hiroshige, M.; Lou, B.; Gaudino, J. J.; Hayashi, M.; Chen, S. M.; Chiang, L. C.; Gaeta, F. C. A.; DeFrees, S. A. J. Med. Chem. 1996, 39, 1359.
15. (c) Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826 (also ref 18 cited there).
16. (d) Wang, R.; Wong, C.-H. Tetrahedron Lett. 1996, 31, 5427.
17. 7. Scheffler, K.; Ernst, B.; Katopodis, A.; Magnani, J. L.; Wang, W. T.; Weisemann., R.; Peters, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 1841.
18. (b) Cooke, R. M.; Hale, R. S.; Lister, S. G.; Shah, G.; Weir, M. P. Biochemistry, 1994, 33, 10591.
19. (c) Hensley, P.; McDevitt, P. J.; Brooks, I.; Trill, J. J.; Feild, J. A.; McNulty, D. E.; Connor, J. R.; Griswold, D. E.; Vasant Kumar; N.; Kopple, K. D.; Carr, S. A.; Dalton, B. J.; Johanson, K. J. Biol. Chem. 1994, 269, 23949
20. 8. (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 2096.
21. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459.
22. (c) DeFrees, S. A.; Kosch, W.; Way, W.; Paulson J. C., Sabesan, S.; Halcomb, R. L.; Huang, D.-H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 60.
23. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633.
24. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372.
25. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
26. (g) Graves, B. J.; Crowther, R. L.; Chandran, C.; Rumberger, J. M.; Li, S.; Huang, K.-S.; Presky, D. H.; Familletti, P. C.; Wolitzky, B. A.; Burns, D. K. Nature, 1994, 367, 532.
27. (h) Kogan, T. P.; Revelle, B. M.; Tapp, S.; Scott, D.; Beck, P. J. J. Biol. Chem. 1995, 270, 14047
28. 9. Weitz-Schmidt, G.; Stokmaier, D.; Scheel, G.; Nifant'ev, N. E.; Tuzikov, A. B.; Bovin, N. V. Anal. Biochem. 1996, 238, 184. All compounds were tested three times and an average value was taken (±10% error). All compounds show a dose-dependent response.
29. x liposome was shown to be much more active than the monomer; DeFrees, S. A.; Phillips, M, L.; Guo, L.; Zalipsky, S. J. Am. Chem. Soc. 1996, 118, 1601.
30. x: Spevak, W.; Foxall, C.; Charych, D. H.; Dasgupta, F.; Nagy, J. O. J. Med. Chem. 1996, 39, 1018.
31. 11Cs (M+Cs): 637.1373.
32. 13. Sasaki, A.; Murahashi, N.; Yamada, H.; Morikawa, A. Biol. Pharm. Bull. 1994, 17, 680.
33. 14. Beradt, P.; Fields, G. B.; Tirrell, M. J. Am. Chem. Soc. 1995, 117, 9515.
34. 15. Compounds 12 and 16 were obtained as reported in ref 6c. Compound 17 was purchased from Toronto Research Chemicals Inc., Canada
35. 16Cs (M+Cs): 1259.6658, found 1259.6620
36. 17. New, R. R. C. In Liposomes: A Practical Approach; New, R. R. C., Ed.; Oxford University press: Oxford, 1990, p 33-104.
37. +): 1159.5406, found 1159.5438.
38. 19. Storrs, R. W.; Tropper, F. D.; Li, H. Y.; Song, C. K.; Kuniyoshi, J. K.; Sipkins, D. A.; Li, K. C. P.; Bednarski, M. D. J. Am. Chem. Soc. 1995, 117, 7301.