Glycomimetic ligands for the human asialoglycoprotein receptor

Journal of the American Chemical Society

Volumn 134, Issue 4, 2012, Pages 1978-1981

  Mamidyala, Sreeman K ^a   Dutta, Sanjay ^a   Chrunyk, Boris A ^b   Préville, Cathy ^b   Wang, Hong ^b   Withka, Jane M ^b   McColl, Alexander ^b   Subashi, Timothy A ^b   Hawrylik, Steven J ^b   Griffor, Matthew C ^b   Kim, Sung ^b   Pfefferkorn, Jeffrey A ^b   Price, David A ^b   Menhaji Klotz, Elnaz ^b   Mascitti, Vincent ^b   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERICS; ASIALOGLYCOPROTEIN RECEPTORS; BINDING AFFINITIES; BINDING POCKETS; COVALENT ATTACHMENT; FUNCTIONAL UNITS; GLYCOMIMETIC; HEPATOCYTES; HIGH-CAPACITY; PYRANOSE; THERAPEUTIC AGENTS;

BINDING ENERGY;

LIGANDS;

ACETAMIDE DERIVATIVE; ASIALOGLYCOPROTEIN RECEPTOR; GALACTOSE; LIGAND; N ACETYLGALACTOSAMINE; PYRANOSIDE;

ARTICLE; BINDING AFFINITY; CARBOHYDRATE ANALYSIS; CONTROLLED STUDY; HUMAN;

ACETYLGALACTOSAMINE; ASIALOGLYCOPROTEIN RECEPTOR; HUMANS; LIGANDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84863023590     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2104679     Document Type: Article

References (30)

1. Zelensky, A. N.; Gready, J. E. FEBS J. 2005, 272, 6179-6217
2. Wang, S. L.; Yu, F. B.; Jiang, T. Y.; Sun, C. S.; Wang, T.; Zhang, J. H. J. Drug Targeting 2008, 16, 233-242
3. Zhang, Y.; Qi, R.; Gao, Y.; Wei, L.; Maitani, Y. J. Controlled Release 2007, 117, 281-290
4. Bernardes, G. J. L.; Kikkeri, R.; Maglinao, M.; Laurino, P.; Collot, M.; Hong, S. Y.; Lepenies, B.; Seeberger, P. H. Org. Biomol. Chem. 2010, 8, 4987-4996
5. Yang, Y.; Zhao, Y.; Yan, T.; Yu, M.; Sha, Y.; Zhao, Z.; Li, Z. Tetrahedron Lett. 2010, 51, 4182-4185
6. Rozema, D. B.; Lewis, D. L.; Wakefield, D. H.; Wong, S. C.; Klein, J. J.; Roesch, P. L.; Bertin, S. L.; Reppen, T. W.; Chu, Q.; Blokhin, A. V.; Hagstrom, J. E.; Wolff, J. A. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 12982-12987
7. Kim, E. M.; Jeong, H. J.; Park, I. K.; Cho, C. S.; Moon, H. B.; Yu, D. Y.; Bom, H. S.; Sohn, M. H.; Oh, I. J. J. Contr. Rel. 2005, 108, 557-567
8. Carver, J. P. Pure Appl. Chem. 1993, 65, 763-770
9. Valentijn, A. R. P. M; van der Marel, G. A.; Sliedregt, L. A. J. M.; van Berkel, T. J. C.; Biessen, E. A. L.; van Boom, J. H. Tetrahedron 1997, 53, 759-770
10. Sliedregt, L. A. J. M.; Rensen, P. C. N.; Rump, E. T.; van Santbrink, P. J.; Bijsterbosch, M. K.; Valentjin, A. R. P. M; van der Marel, G. A.; van Boom, J. H.; van Berkel, T. J. C.; Biessen, E. A. L. J. Med. Chem. 1999, 42, 609-618
11. Khorev, O.; Stokmaier, D.; Schwardt, O.; Cutting, B.; Ernst, B. Bioorg. Med. Chem. 2008, 16, 5216-5231
12. Lee, R. T.; Lee, Y. C. Glycoconjugate J. 2000, 17, 543-551
13. Meier, M.; Bider, M. D.; Malashkevich, V. N.; Spiess, M.; Burkhard, P. J. Mol. Biol. 2000, 300, 857-865
14. Kolatkar, A. R.; Leung, A. K.; Isecke, R.; Brossmer, R.; Drickamer, K.; Weis, W. I. J. Biol. Chem. 1998, 273, 19502-19508
15. Feinberg, H.; Torgersen, D.; Drickamer, K.; Weis, W. I. J. Biol. Chem. 2000, 275, 35176-35184
16. Kolatkar, A. R.; Weis, W. I. J. Biol. Chem. 1996, 271, 6679-6685
17. Iobst, S. T.; Drickamer, K. J. Biol. Chem. 1996, 271, 6686-6693
18. Stokmaier, D.; Khorev, O.; Cutting, B.; Born, R.; Ricklin, D.; Ernst, T. O. G.; Boni, F.; Schwingruber, K.; Gentner, M.; Wittwer, M.; Spreafico, M.; Vedani, A.; Rabbani, S.; Schwardt, O.; Ernst, B. Bioorg. Med. Chem. 2009, 17, 7254-7264 and references therein
19. Riva, C. Targeting the liver via the asialoglycoprotein-receptor: synthesis of directed small-molecule libraries for the H1-CRD. Ph.D. Thesis, University of Basel, 2006.
20. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855
21. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
22. d is generally used, such values are more properly defined as the inverse of the adsorption isotherm because one binding partner is confined to a surface. See, for example: Smith, E. A.; Thomas, W. D.; Kiessling, L. L.; Corn, R. M. J. Am. Chem. Soc. 2003, 125, 6140-6148
23. Connolly, D. T.; Townsend, R. R.; Kawaguchi, K.; Bell, W. R.; Lee, Y. C. J. Biol. Chem. 1982, 257, 939-945
24. Wong, T. C.; Townsend, R. R.; Lee, Y. C. Carbohydr. Res. 1987, 170, 27-46
25. Lu, H.; Tonge, P. J. Curr. Opin. Chem. Biol. 2010, 14, 467-474
26. Ng, K.K.-S.; Kolatkar, A. R.; Park-Snyder, S.; Feinberg, H.; Clark, D. A.; Drickamer, K.; Weis, W. I. J. Biol. Chem. 2002, 277, 16088-16095
27. Wall, D. A.; Wilson, G.; Hubbard, A. L. Cell 1980, 21, 79-93
28. Breitfeld, P. P.; Simmons, C. F., Jr.; Strous, G. J. A. M.; Geuze, H. J.; Schwartz, A. L. Int. Rev. Cytol. 1985, 97, 47-95
29. Geffen, I.; Spiess, M. Int. Rev. Cytol. 1992, 137B, 181-219
30. Sato, H.; Kato, Y.; Hayashi, E.; Tabata, T.; Suzuki, M.; Takahara, Y.; Sugiyama, Y. Pharm. Res. 2002, 19, 1736-1744