Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1998-01-08
1999-11-02
Fonda, Kathleen K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
514 53, 514 61, 536 41, 536 185, 53612313, 536124, A61K 3170, C07H 1500
Patent
active
059770805
ABSTRACT:
Sulfated disaccharides characterized by the ability to inhibit the binding of selectin to its physiologically-relevant ligand are disclosed. Included are efficient and inexpensive methods for producing the sulfated disaccharides, and methods for their therapeutic use and in in vivo and in vitro assays.
REFERENCES:
patent: 5211937 (1993-05-01), Brandley et al.
patent: 5428025 (1995-06-01), Brandley et al.
Baumheuter, S., et al., (1993) "Binding of L-selectin to the Vascular Sialomucin CD43," Science 262:436-438.
Berg, E.L. et al., (1989) "Homing Receptors and Vascular Addressins: Cell Adhesion Molecules That Direct Lymphocyte Traffic," Immunol. Rev. 108:5-18.
Brandley, B.K., et al., (1993) "Structure-function Studies on Selectin Carbohydrate Ligands. Modifications to Fucose, Sialic Acid and Sulphate as a Sialic Acid Replacement," Glycobiology 3:633-639.
Briskin, M.J., et al., (1993) "MAdCAM-1 Homology to Immunoglobulin and Mucin-like Adhesion Receptors and to IgA1," Nature 363:461-464.
Buerke, M., et al., (1994) "Sialyl Lewis.sup.x -containing Oligosaccharide Attenuates Myocardial Reperfusion Injury in Cats," J. Clin. Invest. 93:1140-1148.
Capon, C., et al., (1989) "Structures of O-glycosidically Linked Oligosaccharides Isolated from Human Meconium Glycoproteins," Eur. J. Biochem. 182:139-52.
Duijvestijn, A., and Hamann, A., (1989) "Mechanisms and Regulation of Lymphocyte Migration," Immunol. Today 10:23-28.
Dumas, D.P., et al. (1991) "Enzymatic Substdata(ynthesis of Sialyl Le.sup.x and Derivatives Based on a Recombinant Fucosyltransferase," Biorg. Med. Chem. Lett. 1:425-428.
Gallatin, M.W., et al., (1983) "A Cell-surface Molecule Involved in Organ-specific Homing of Lymphocytes," Nature 304:30-34.
Gallatin, M.W., et al., (1986) "Lymphocyte Homing Receptors," Cell 44:673-680.
Green, P.J., et al., (1992) "High Affinity Binding of the Leukocyte Adhesion Molecule L-selectin to 3"-sulphated-Le.sup.a and -Le.sup.x Oligosaccharides and the Predominance of Sulphate in This Interaction Demonstrated by Binding Studies With a Series of Lipid-linked Oligosaccharides," Biochem. Biophys. Res. Commun. 188(1):244-251.
Hemmerich, S., et al., (1995) "Structure of the O-Glycans in GlyCAM-1, and Endothelial-derived Ligand for L-selectin," J. Biol. Chem. 270:12035-12047.
Imai, Y., et al., (1992) "Further Characterization of the Interaction Between L-selectin and Its Endothelial Ligands," Glycobiology 2:373-381.
Imai, Y., et al., (1993) "Sulphation Requirement for ICAM-1, and Endothelial Ligand for L-selectin," Nature 361:555-557.
Jacob, G.S., et al., (1995) "Binding of Sialyl Lewis X to E-selectin as Measured by Fluorescence Polarization," Biochemistry 34:1210-1217.
Langer, R., (1990) "New Methods of Drug Delivery," Science 249:1527-1533.
Lasky, L.A., et al., (1992) "An Endothelial Ligand for L-selectin Is a Novel Mucin-like Molecule," Cell 69:927-938.
Lewinsohn, D.M., et al., (1987) "Leukocyte-Endothelial Cell Recognition: Evidence of a Common Molecular Mechanism Shared by Neutrophils, Lymphocytes, and Other Leukocytes," J. Immunol. 138:4313-4321.
Ma, X. et al., (1993) "Monoclonal Antibody to L-selectin Attenuates Neutrophil Accumulation and Protects Ischemic Reperfused Cat Myocardium," Circulation 88:649-658.
Manning, D.D., et al., "Sulfation of Lewis X," Abstracts of Papers, Part 2. 206th. American Chemical Society National Meeting (Washington, D.C.) Abstract No. ORGN 61. Aug. 22-27, 1993.
Manning, et al., "Selectin-Saccharide Interactions: Revealing Structure-Function Relationships with Chemical Synthesis," J. Org. Chem. (October 6, 1995) vol. 60:6254-6255. See Footnote 16 and Scheme 1.
Mawhinney, T.P., et al., (1992) "Sulfated Sialyl-oligosaccharides Derived from Tracheobronchial Mucous Glycoproteins of a Patient Suffering from Cystic Fibrosis," Carbohydrate Res. 235:179-197.
Mihelcic, D., et al., (1994) "Inhibition of Leukocyte L-selectin Function With a Monoclonal Antibody Attenuates Reperfusion Injury to the Rabbit Ear," Blood 84:2322-2328.
Mulligan, M.S., et al., (1993) "Protective Effects of Sialylated Oligosaccharides in Immune Complex-induced Acute Lung Injury," J. Exp. Med. 178:623-631.
Mulligan, M.S., et al., (1993) "Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury," Nature 364:149-151.
Mulligan, M.S., et al., (1994) "Requirements for L-Selectin in Neutrophil-Mediated Lung Injury in Rats," J. Immunol. 152:832-840.
Needham, L. K., et al., (1993) "The HNK-1 Reactive Sulfoglucuronyl Glycolipids for L-selectin and P-selectin But Not E-selectin," Proc. Natl. Acad. Sci. USA 90:1359-1363.
Nicolaou, K.C., et al., (1991) "Sterocontrolled Synthesis of Sialyl Le.sup.x, the Oligosaccharide Binding Ligand to ELAM-1 (Sialyl=N-acetylneuramin)," J. Chem. Soc., Chem. Commun. pp. 870-872.
Nicolaou, K.C., et al., (1992) "Total Synthesis of Sialyl Dimeric Le.sup.x," J. Am. Chem Soc. 114:3126-3128.
Palcid, M.M., (1994) "Glycosyltransferases in Glycobiology," Meth. Enzymol. 230:300-316.
Rao, B.N.N., et al. (1994) "Sialyl Lewis X Mimics Derived from a Pharmacophore Search Are Selectin Inhibitors With Anti-inflammatory Activity," J. Biol. Chem. 269:19663-19666.
Rosen, S.D., (1989) "Lymphocyte Homing: Progress and Prospects," Curr. Opin. Cell. Biol. 1:913-919.
Rosen, S.D., and Bertozzi, C.R., (1994) "The Selectins and Their Ligands," Curr. Op. Cell Biol. 6:663-673.
Santos-Benito, et al., "Inhibition of Proliferation of Normal and Transformwd Neural Cells by Blood Group-related Oligosaccharides," J. Exp. Med. (Sep. 1992) vol. 176:915-18. See Table 1.
Scudder, P.R., et al., (1994) "Enzymatic Synthesis of a 6"-sulphated Sialyl-Lewis.sup.x Which Is an Inhibitor of L-Selectin Binding to Peripheral Addressin," Glycobiology 4:929-933.
Seekamp, A., et al., (1994) "Role of Selectins in Local Remote Tissue Injury Following Ischemia and Reperfusion," Am. J. Pathol. 144:592-598.
Singh, et al., "Synthesis of Oligosaccharides Structurally Related to E-Selectin Ligands," J. Chem. Soc. Chem. Commun., pp. 775-776. See compound 5. (1994).
Springer, T.A., (1990) "Adhesion Receptors of the Immune System," Nature 346:425-434.
Stahl, W., et al., (1994) "Synthesis of Deoxy Sialyl Lewis.sup.x Analogues, Potential Selectin Antagonists," Agnew. Chem. Int. Ed. Engl. 33:2096-2098.
Stoolman, L.M., (1989) "Adhesion Molecules Controlling Lymphocyte Migration," Cell 56:907-910.
Suzuki, Y., et al., 1993, "Sulfated Glycolipids Are Ligands for a Lymphocyte Homing Receptor, L-selectin (LECAM-1), Binding Epitope in Sulfated Sugar Chain," Biochem. Biophys. Res. Commun. 190(2):426-434.
Uchiyama, T., et al., (1995) "Design and Synthesis of Sialyl Lewis X Mimetics," J. Am Chem. Soc. 117:5395-5396.
Varki, A., (1994) "Selectin Ligands," Proc. Natl. Acad. Sci. USA 91:7390-7397.
Watson, S.R., et al., (1990 "A Homing Receptor-IgG Chimera as a Probe for Adhesive Ligands of Lymph Node High Endothelial Venules," J. Cell Biol. 110:2221-2229.
Woodruff, J.J., et al., (1987) "Specific Cell-Adhesion Mechanisms Determining Migration Pathways of Recirculating Lymphocytes," Ann. Rev. Immunol. 5:201-222.
Yang, X.-D., et al., (1993) "Inhibition of Insulitis and Prevention of Diabetes in Nonobese Diabetic Mice by Blocking L-selectin and Very Late Antigen 4 Adhesion Receptors," Proc. Natl. Acad. Sci. 90:10494-10498.
Yednock, T.A., and Rosen, S.D., (1989) "Lymphocyte Homing," Adv. Immunol. 54:313-378.
Yuen, C.T., et al., (1994) "Sulfated Blood Group Lewis.sup.a," J. Biol. Chem. 269:1595-1598.
Bertozzi Carolyn
Rosen Steven D.
Field Bret E.
Fonda Kathleen K.
The Regents of the University of California
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