Studies on selectin blockers. 5. Design, synthesis, and biological profile of sialyl Lewis x mimetics based on modified serine-glutamic acid dipeptides

Journal of Medicinal Chemistry

Volumn 40, Issue 22, 1997, Pages 3534-3541

  Tsukida, Takahiro ^a   Hiramatsu, Yasuyuki ^a   Tsujishita, Hideki ^a   Kiyoi, Takao ^a   Yoshida, Masahiro ^a   Kurokawa, Kiriko ^a   Moriyama, Hideki ^a   Ohmoto, Hiroshi ^a   Wada, Yukihisa ^a   Saito, Tadayuki ^a   Kondo, Hirosato ^a  

^a KANEBO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE DERIVATIVE; ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; GLUTAMIC ACID DERIVATIVE; L SELECTIN; L SELECTIN BLOCKING AGENT; N (2 TETRADECYLHEXADECANOYL) O (ALPHA L FUCOPYRANOSYL) DEXTRO SERYL DEXTRO GLUTAMIC ACID 1 METHYLAMIDE; N (2 TETRADECYLHEXADECANOYL) O (ALPHA L FUCOPYRANOSYL) DEXTRO SERYLGLUTAMIC ACID 1 METHYLAMIDE; N (2 TETRADECYLHEXADECANOYL) O (ALPHA L FUCOPYRANOSYL)SERYL DEXTRO GLUTAMIC ACID 1 METHYLAMIDE; N (2 TETRADECYLHEXADECANOYL) O (ALPHA L FUCOPYRANOSYL)SERYLGLUTAMIC ACID 1 METHYLAMIDE; PADGEM PROTEIN; SERINE DERIVATIVE; SIALYL LEWIS X DERIVATIVE; UNCLASSIFIED DRUG; 5 ACETYLNEURAMINYL (2 3) GALACTOSYL (1 4) (FUCOPYRANOSYL (1 3)) N ACETYLGLUCOSAMINE; 5-ACETYLNEURAMINYL-(2-3)-GALACTOSYL-(1-4)-(FUCOPYRANOSYL-(1-3))-N-ACETYLGLUCOSAMINE; DIPEPTIDE; GLUTAMYL GLUTAMIC ACID; GLUTAMYL-GLUTAMIC ACID; IMMUNOGLOBULIN E; NONSTEROID ANTIINFLAMMATORY AGENT; OLIGOSACCHARIDE; SELECTIN; SERINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG EFFECT; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; INTRAVENOUS DRUG ADMINISTRATION; MOLECULAR DYNAMICS; MOUSE; NONHUMAN; SKIN INFLAMMATION; STRUCTURE ACTIVITY RELATION; ANIMAL; BAGG ALBINO MOUSE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; FEMALE; INFLAMMATION; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DIPEPTIDES; DRUG DESIGN; FEMALE; IMMUNOGLOBULIN E; INFLAMMATION; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED BALB C; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; SELECTINS; SERINE; STEREOISOMERISM;

EID: 0030612363     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970262k     Document Type: Article

References (33)

1. (a) Berg, E. L.; Yoshino, T.; Rott, L. S.; Robinson, M. K.; Warnock, R. A.; Kishimoto, T. K.; Picker, L. J.; Butcher, E. C. The Cutaneous Lymphocyte Antigen is a Skin Lymphocyte Homing Receptor for the Vascular Lectin Endothelial Cell-Leukocyte Adhesion Molecule 1. J. Exp. Med. 1991, 174, 1461-1466.
2. (b) Picker, L. J.; Kishimoto, T. K.; Smith, C. W.; Warnock, R. A.; Butcher, E. C. ELAM-1 is an Adhesion Molecule for Skin-Homing T Cells. Nature 1991, 349, 796-799.
3. Lorant, D. E.; Topham, M. K.; Whatley, R. E.; McEver, R. P.; Mclntyre, T. M.; Prescott, S. M.; Zimmerman, G. A. Inflammatory Roles of P-selectin. J. Clin. Invest. 1993, 92, 559-570.
4. Symon, F. A.; Walsh, G. M.; Watson, S. R.; Wardlaw, A. J. Eosinophil Adhesion to Nasal Polyp Endothelium is P-Selectin-Dependent. J. Exp. Med. 1994, 80, 371-376.
5. (e) Akbar, A. N.; Salmon, M.; Janossy, G. The Synergy Between Naive and Memory T Cells During Activation. Immunol. Today 1991, 12, 184-188.
6. (f) Duijvestijn, A. M.; Horst, E.; Pals, S. T.; Rouse, B. N.; Steere, A. C.; Picker, L. J.; Meijer, C. J. L. M.; Butcher, E. C. High Endothelial Differentiation in Human Lymphoid and Inflammatory Tissue Defined by Monoclonal Antibody HECA-452. Am. J. Pathol. 1988, 130, 147-155.
7. Nguyen, M.; Eilber, F. R.; DeFrees, S. Novel Synthetic Analogs of Sialyl Lewis X Can Inhibit Angiogenesis in Vitro and in Vivo. Biochem. Biophys. Res. Commun. 1996, 228, 716-723.
8. Wada, Y.; Saito, T.; Matsuda, N.; Ohmoto, H.; Yoshino, K.; Ohashi, M.; Kondo, H.; Ishida, H.; Kiso, M.; Hasegawa, A. Studies on Selectin Blockers. 2. Novel Selectin Blocker as Potential Therapeutics for Inflammatory Disorders. J. Med. Chem. 1996, 39, 2055-2059.
9. Tsujishita, H.; Hiramatsu, Y.; Kondo, N.; Ohmoto, H.; Kondo, H.; Kiso, M.; Hasegawa, A. Selectin-Ligand Interactions Revealed by Molecular Dynamics Simulation in Solution. J. Med. Chem. 1997, 40, 362-369.
10. 4
11. (a) Dauber-Osguthorpe, P.; Jones, D. K.; Cambell, M. M.; Semple, G.; Osguthorpe, D. J. Reduced and Retro-reduced Peptide Analogues-Conformations and Energies. Tetrahedron Lett. 1990, 31, 917-920.
12. (b) Flynn, G. A.; Beight, D. W.; Mehdi, S.; Koehl, J. R.; Giroux, E. L.; French, J. F.; Hake, P. W.; Dage, R. C. Application of a Conformationally Restricted Phe-Leu Dipeptide Mimetic to the Design of a Combined Inhibitor of Angiotensin I-Converting Enzyme and Neutral Endopeptidase 24.11. J. Med. Chem. 1993, 36, 2420-2423.
13. Kessler, H. Conformational and Biological Activity of Cyclic Peptides. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523.
14. Lim, M. S. L.; Johnston, E. R; Kettner, C. A. The Solution Conformation of (D)Phe-Pro-containing Peptides: Implications on the Activity of Ac-(D)Phe-Pro-boroArg-OH, a Potent Thrombin Inhibitor. J. Med. Chem. 1993, 36, 1831-1838,
15. (e) McDowell, R. S.; Gadek, T. R.; Baker, P. L.; Burdick, D. J.; Chan, K. S.; Quan, C. L.; Skelton, N.; Struble, M.; Thorsett, E. D.; Tischler, M.; Tom, J. Y. K.; Webb, T. R.; Burnier, J. P. From Peptide to Non-peptide. 1. The Elucidation of a Bioactive Conformation of the Arginine-Glycine-Aspartic Acid Recognition Sequence. J. Am. Chem. Soc. 1994, 116, 5069-5076.
16. (f) Ripka, W. C.; De Lucca, G. V.; Bach, A. C. L; Pottorf, R. S.; Blaney, J. M. Protein beta-Turn Mimetics. 1. Design, Synthesis, and Evaluation in Model Cyclic Peptides. Tetrahedron 1993, 49, 3593-3608.
17. (g) Simmerling, C. L.; Elber, R. Computer Determination of Peptide Conformations in Water: Different Roads to Structure. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3190-3193.
18. Bruccoleri, R. E.; Karplus, M. Conformational Sampling Using High Temperature Molecular Dynamics. Biopolymers 1990, 29, 1847-1862.
19. 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. Insight into E-selectin/Ligand Interaction from the Crystal Structure and Mutagenesis of the Lec/EGF Domains. Nature 1994, 367, 532-538.
20. (a) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Chain Reversals in Proteins. Biochim. Biophys. Acta 1973, 303, 211-229.
21. (b) Chou, P. Y.; Fasman, G. D. β-Turn in Proteins. J. Mol. Biol. 1977, 115, 135-175.
22. Aubry, A.; Curg, M. T.; Marrand, M. βI- and βII-Turn Conformations in Model Dipeptides with the Pro-Xaa Sequences. J. Am. Chem. Soc. 1985, 107, 7640-7647.
23. 2: Spectroscopic Evidence for a Peptide with Significant β-Turn Character in Water and in Dimethyl Sulfoxide. J. Am. Chem. Soc. 1992, 114, 3182-3188.
24. Boissonnas, R. A. Une Nouvelle Methode de Synthise Peptidique. (A New Method of Synthesizing Peptides.) Helv. Chim. Acta 1951, 34, 874-879.
25. x Ganglioside Analogues Sulfated at C-6 of Either the Galactose or N-Acetylglucosamine Residues, and at Both of the Galactose and N-Acetylglucosamine Residues: Probes for Clarifying the Real Carbohydrate Ligand of L-Selectin. Carbohydr. Res. 1996, 285, C1-C8.
26. Erbe, D. V.; Watson, S. R.; Presta, L. G.; Wolitzky, B. A.; Foxall, C.; Brandley, B. K.; Lasky, L. A. P- and E-selectin Use Common Sites for Carbohydrate Ligand Recognition and Cell Adhesion. J. Cell. Biol. 1993, 720 (5), 1227-1235.
27. Venkatachalam, C. M. Stereochemical Criteria for Polypeptides and Proteins. V. Conformation of a System of Three Linked Peptide Units. Biopolymers 1968, 6, 1425-1436.
28. Unpublished data.
29. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J.; Impey, R. W.; Klein, M. L. Comparison of Simple Potential Functions for Simulating Liquid Water. J. Chem. Phys. 1983, 79, 926-935.
30. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A Second Generation Force Field for the Simulation of proteins, Nucleic Acids, and Organic Molecules. J. Am. Chem. Soc. 1995, 117, 5179-5197.
31. Richmond, T. J. Solvent Accessible Surface Area and Excluded Volume in Proteinsl. J. Mol. Biol. 1984, 778, 63-89.
32. Wesson, L.; Eisengerg, D. Atomic Solvation Parameters Applied to Molecular Dynamics of Proteins in Solution. Proteins Sci. 1992, 1, 227-235.
33. Dunnett, C. W. New Tables For Multiple Comparisons with a Control. Biometrics 1964, 20, 482-491.