Inhibition of selectin binding
Abstract
This invention provides compositions for inhibiting the binding between two cells, one expressing P- or L-selectin on the surface and the other expressing the corresponding ligand. A covalently crosslinked lipid composition is prepared having saccharides and acidic group on separate lipids. The composition is then interposed between the cells so as to inhibit binding. Inhibition can be achieved at an effective oligosaccharide concentration as low as 10.sup.6 fold below that of the free saccharide. Since selectins are involved in recruiting cells to sites of injury, these composition scan be used to palliate certain inflammatory and immunological conditions.
- Inventors:
-
- Rodeo, CA
- Albany, CA
- New Delhi, IN
- Issue Date:
- Research Org.:
- Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
- OSTI Identifier:
- 872672
- Patent Number(s):
- 5985852
- Assignee:
- Regents of University of California ()
- Patent Classifications (CPCs):
-
A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61P - SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- DOE Contract Number:
- AC03-76SF00098
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- inhibition; selectin; binding; provides; compositions; inhibiting; cells; expressing; p-; l-selectin; surface; corresponding; ligand; covalently; crosslinked; lipid; composition; prepared; saccharides; acidic; separate; lipids; interposed; inhibit; achieved; effective; oligosaccharide; concentration; 10; fold; below; free; saccharide; selectins; involved; recruiting; sites; injury; scan; palliate; inflammatory; immunological; conditions; recruiting cells; provides compositions; selectin binding; separate lipids; oligosaccharide concentration; expressing p-; fold below; free saccharide; lipid composition; effective oligosaccharide; covalently crosslinked; crosslinked lipid; corresponding ligand; immunological conditions; inhibit binding; /514/424/999/
Citation Formats
Nagy, Jon O, Spevak, Wayne R, Dasgupta, Falguni, and Bertozzi, Caroline. Inhibition of selectin binding. United States: N. p., 1999.
Web.
Nagy, Jon O, Spevak, Wayne R, Dasgupta, Falguni, & Bertozzi, Caroline. Inhibition of selectin binding. United States.
Nagy, Jon O, Spevak, Wayne R, Dasgupta, Falguni, and Bertozzi, Caroline. Fri .
"Inhibition of selectin binding". United States. https://www.osti.gov/servlets/purl/872672.
@article{osti_872672,
title = {Inhibition of selectin binding},
author = {Nagy, Jon O and Spevak, Wayne R and Dasgupta, Falguni and Bertozzi, Caroline},
abstractNote = {This invention provides compositions for inhibiting the binding between two cells, one expressing P- or L-selectin on the surface and the other expressing the corresponding ligand. A covalently crosslinked lipid composition is prepared having saccharides and acidic group on separate lipids. The composition is then interposed between the cells so as to inhibit binding. Inhibition can be achieved at an effective oligosaccharide concentration as low as 10.sup.6 fold below that of the free saccharide. Since selectins are involved in recruiting cells to sites of injury, these composition scan be used to palliate certain inflammatory and immunological conditions.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1999},
month = {1}
}
Works referenced in this record:
Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes
journal, January 1988
- Ringsdorf, Helmut; Schlarb, Bernhard; Venzmer, Joachim
- Angewandte Chemie International Edition in English, Vol. 27, Issue 1
Glycolipids as Immunomodulators: Syntheses and Properties
journal, December 1991
- Lockhoff, Oswald
- Angewandte Chemie International Edition in English, Vol. 30, Issue 12
Lymphocyte homing into lymph nodes: in vitro demonstration of the selective affinity of recirculating lymphocytes for high-endothelial venules.
journal, September 1976
- Stamper, H. B.; Woodruff, J. J.
- Journal of Experimental Medicine, Vol. 144, Issue 3
Synthesis of sialyl Lewis X mimetics: Use of O-α-fucosyl-(1R, 2R)-2-aminocyclohexanol as core structure
journal, July 1996
- Wang, Ruo; Wong, Chi-Huey
- Tetrahedron Letters, Vol. 37, Issue 31
Peptides Which Bind to E-selectin and Block Neutrophil Adhesion
journal, September 1995
- Martens, Christine L.; Cwirla, Steven E.; Lee, Rozanne Y. -W.
- Journal of Biological Chemistry, Vol. 270, Issue 36
Design and Synthesis of Glycomimetic Prototypes - A Model Sialyl Lewis x Ligand for E-Selectin
journal, January 1994
- Hanessian, Stephen; Prabhanjan, Hubli
- Synlett, Vol. 1994, Issue 10
Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs
journal, January 1995
- DeFrees, Shawn A.; Kosch, Winfried; Way, William
- Journal of the American Chemical Society, Vol. 117, Issue 1
ELAM-1 mediates cell adhesion by recognition of a carbohydrate ligand, sialyl-Lex
journal, November 1990
- Phillips, M.; Nudelman, E.; Gaeta, F.
- Science, Vol. 250, Issue 4984
Intervention of carbohydrate recognition by proteins and nucleic acids.
journal, October 1996
- Sears, P.; Wong, C. H.
- Proceedings of the National Academy of Sciences, Vol. 93, Issue 22
Lymphocyte homing and leukocyte rolling and migration are impaired in L-selectin-deficient mice
journal, July 1994
- Arbonés, Maria L.; Ord, David C.; Ley, Klaus
- Immunity, Vol. 1, Issue 4
Synthesis of phospholipid-inhibitor conjugates by enzymic transphosphatidylation with phospholipase D
journal, November 1993
- Wang, Peng; Schuster, Matthias; Wang, Yi Fong
- Journal of the American Chemical Society, Vol. 115, Issue 23
Supramolecular assemblies of diacetylenic aldonamides
journal, September 1991
- Frankel, David A.; O'Brien, David F.
- Journal of the American Chemical Society, Vol. 113, Issue 19
Synthesis of antigenic carbohydrate polymers recognized by lectins and antibodies
journal, January 1988
- Roy, Ren�; Tropper, Fran�ois D.
- Journal of the Chemical Society, Chemical Communications, Issue 15
P-selectin glycoprotein ligand-1 mediates rolling of human neutrophils on P-selectin.
journal, February 1995
- Moore, K. L.; Patel, K. D.; Bruehl, R. E.
- Journal of Cell Biology, Vol. 128, Issue 4
Cardioprotection by liposome-conjugated sialyl Lewisx-oligosaccharide in myocardial ischaemia and reperfusion injury
journal, December 1995
- Murohara, T.
- Cardiovascular Research, Vol. 30, Issue 6
Granule membrane protein 140 (GMP140) binds to carcinomas and carcinoma-derived cell lines.
journal, March 1992
- Aruffo, A.; Dietsch, M. T.; Wan, H.
- Proceedings of the National Academy of Sciences, Vol. 89, Issue 6
Structure--function studies on selectin carbohydrate ligands. Modifications to fucose, sialic acid and sulphate as a sialic acid replacement
journal, December 1993
- Brandley, B. K.; Kiso, M.; Abbas, S.
- Glycobiology, Vol. 3, Issue 6
Selectin-Carbohydrate Interactions and the Initiation of the Inflammatory Response
journal, June 1995
- Lasky, Laurence A.
- Annual Review of Biochemistry, Vol. 64, Issue 1
Liposome-like fucopeptides as sialyl lewis X mimetics
journal, November 1996
- Lin, Chun-Cheng; Kimura, Teiji; Wu, Shih-Hsiung
- Bioorganic & Medicinal Chemistry Letters, Vol. 6, Issue 22
Enzyme-catalyzed synthesis of carbohydrates
journal, January 1989
- Toone, Eric J.; Simon, Ethan S.; Bednarski, Mark D.
- Tetrahedron, Vol. 45, Issue 17
PSGL-1 recognition of P-selectin is controlled by a tyrosine sulfation consensus at the PSGL-1 amino terminus
journal, October 1995
- Pouyani, Tara; Seed, Brian
- Cell, Vol. 83, Issue 2
The three members of the selectin receptor family recognize a common carbohydrate epitope, the sialyl Lewis(x) oligosaccharide
journal, May 1992
- Foxall, C.; Watson, Sr; Dowbenko, D.
- Journal of Cell Biology, Vol. 117, Issue 4
A ‘litmus test’ for molecular recognition using artificial membranes
journal, February 1996
- Charych, Deborah; Cheng, Quan; Reichert, Anke
- Chemistry & Biology, Vol. 3, Issue 2
Selectins and their ligands: current concepts and controversies
journal, November 1996
- Kansas, Gs
- Blood, Vol. 88, Issue 9
Inositol polyanions. Noncarbohydrate inhibitors of L- and P-selectin that block inflammation.
journal, May 1994
- Cecconi, O.; Nelson, R. M.; Roberts, W. G.
- Journal of Biological Chemistry, Vol. 269, Issue 21, p. 15060-15066
Higher-affinity oligosaccharide ligands for E-selectin.
journal, March 1993
- Nelson, R. M.; Dolich, S.; Aruffo, A.
- Journal of Clinical Investigation, Vol. 91, Issue 3
Tumor necrosis factor participates in the pathogenesis of acute immune complex alveolitis in the rat.
journal, December 1989
- Warren, J. S.; Yabroff, K. R.; Remick, D. G.
- Journal of Clinical Investigation, Vol. 84, Issue 6
Molecular assemblies of functionalized polydiacetylenes
journal, January 1995
- Spevak, Wayne; Nagy, Jon O.; Charych, Deborah H.
- Advanced Materials, Vol. 7, Issue 1
Sialyl Lewis x Liposomes as a Multivalent Ligand and Inhibitor of E-Selectin Mediated Cellular Adhesion
journal, January 1996
- DeFrees, Shawn A.; Phillips, Laurie; Guo, Luke
- Journal of the American Chemical Society, Vol. 118, Issue 26
The chemical-enzymatic synthesis of a carbon glycoside of N-acetyl neuraminic acid
journal, August 1991
- Nagy, Jon O.; Bednarski, Mark D.
- Tetrahedron Letters, Vol. 32, Issue 32
Polymerizable Phospholipid Analogues—New Stable Biomembrane and Cell Models
journal, November 1980
- Hub, Hans-Henning; Hupfer, Bernd; Koch, Horst
- Angewandte Chemie International Edition in English, Vol. 19, Issue 11
Shear-dependent inhibition of granulocyte adhesion to cultured endothelium by dextran sulfate
journal, April 1989
- Ley, K.; Lundgren, E.; Berger, E.
- Blood, Vol. 73, Issue 5, p. 1324-1330
Heparin oligosaccharides bind L- and P-selectin and inhibit acute inflammation
journal, December 1993
- Nelson, Rm; Cecconi, O.; Roberts, Wg
- Blood, Vol. 82, Issue 11
Polymerized liposomes containing C-glycosides of sialic acid: potent inhibitors of influenza virus in vitro infectivity
journal, February 1993
- Spevak, Wayne; Nagy, Jon O.; Charych, Deborah H.
- Journal of the American Chemical Society, Vol. 115, Issue 3
Synthesis of bioactive sialosides
journal, January 1993
- Ito, Y.; Gaudino, J. J.; Paulson, J. C.
- Pure and Applied Chemistry, Vol. 65, Issue 4
Liposomes from polymerizable phospholipids
journal, November 1983
- Hupfer, Bernd; Ringsdorf, Helmut; Schupp, Hans
- Chemistry and Physics of Lipids, Vol. 33, Issue 4
Leukocyte accumulation promoting fibrin deposition is mediated in vivo by P-selectin on adherent platelets
journal, October 1992
- Palabrica, Theresa; Lobb, Roy; Furie, Barbara C.
- Nature, Vol. 359, Issue 6398
Tyrosine Sulfation of P-selectin Glycoprotein Ligand-1 Is Required for High Affinity Binding to P-selectin
journal, September 1995
- Wilkins, Patricia P.; Moore, Kevin L.; McEver, Rodger P.
- Journal of Biological Chemistry, Vol. 270, Issue 39
Polydiacetylene Liposomes Functionalized with Sialic Acid Bind and Colorimetrically Detect Influenza Virus
journal, January 1995
- Reichert, Anke; Nagy, Jon O.; Spevak, Wayne
- Journal of the American Chemical Society, Vol. 117, Issue 2
The complement binding-like domains of the murine homing receptor facilitate lectin activity.
journal, October 1991
- Watson, S. R.; Imai, Y.; Fennie, C.
- Journal of Cell Biology, Vol. 115, Issue 1
Myeloperoxidase activity as a quantitative assessment of neutrophil infiltration into ischemie myocardium
journal, November 1985
- Mullane, Kevin M.; Kraemer, Rosemary; Smith, Bruce
- Journal of Pharmacological Methods, Vol. 14, Issue 3
Leukocyte trafficking mediated by selectin-carbohydrate interactions
journal, May 1995
- McEver, Rp; Moore, Kl; Cummings, Rd
- Journal of Biological Chemistry, Vol. 270, Issue 19
Supramolecular assemblies, a crystal structure, and a polymer of N-diacetylenic gluconamides
journal, September 1991
- Fuhrhop, Juergen Hinrich; Blumtritt, Peter; Lehmann, Christian
- Journal of the American Chemical Society, Vol. 113, Issue 19
Direct colorimetric detection of a receptor-ligand interaction by a polymerized bilayer assembly
journal, July 1993
- Charych, D.; Nagy, J.; Spevak, W.
- Science, Vol. 261, Issue 5121
An Efficient Synthesis of N -Allylglycosylamides from Unprotected Carbohydrates
journal, January 1996
- Spevak, Wayne; Dasgupta, Falguni; Hobbs, Christopher J.
- The Journal of Organic Chemistry, Vol. 61, Issue 10
Sulphation requirement for GlyCAM-1, an endothelial ligand for L-selectin
journal, February 1993
- lmai, Yasuyuki; Lasky, Laurence A.; Rosen, Steven D.
- Nature, Vol. 361, Issue 6412
A sulfated peptide segment at the amino terminus of PSGL-1 is critical for P-selectin binding
journal, October 1995
- Sako, Dianne; Comess, Kenneth M.; Barone, Karen M.
- Cell, Vol. 83, Issue 2
Synthetic Bilayer Membranes with Anionic Head Groups
journal, June 1978
- Kunitake, Toyoki; Okahata, Yoshio
- Bulletin of the Chemical Society of Japan, Vol. 51, Issue 6
Glycomimetic selectin inhibitors: (α-D-mannopyranosyloxy)methylbiphenyls
journal, March 1996
- Dupré, Brian; Bui, Huong; Scott, Ian L.
- Bioorganic & Medicinal Chemistry Letters, Vol. 6, Issue 5
Rapid neutrophil adhesion to activated endothelium mediated by GMP-140
journal, February 1990
- Geng, Jian-Guo; Bevilacquat, Michael P.; Moore, Kevin L.
- Nature, Vol. 343, Issue 6260
Molecular cloning of a CD28 cDNA by a high-efficiency COS cell expression system.
journal, December 1987
- Aruffo, A.; Seed, B.
- Proceedings of the National Academy of Sciences, Vol. 84, Issue 23
Possible role for cell-surface carbohydrate-binding molecules in lymphocyte recirculation.
journal, March 1983
- Stoolman, L. M.; Rosen, S. D.
- Journal of Cell Biology, Vol. 96, Issue 3
Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin
journal, January 1996
- Hiruma, Kazumi; Kajimoto, Tetsuya; Weitz-Schmidt, Gabriel
- Journal of the American Chemical Society, Vol. 118, Issue 39
CD62/P-selectin recognition of myeloid and tumor cell sulfatides
journal, October 1991
- Aruffo, Alejandro; Kolanus, Waldemar; Walz, Gerd
- Cell, Vol. 67, Issue 1
Sulfated disaccharide with greater inhibitory potency for L-selectin than sialyl Lewis x
journal, November 1995
- Bertozzi, Carolyn R.; Fukuda, Shun; Rosen, Steven D.
- Biochemistry, Vol. 34, Issue 44
Calcium-dependent heparin-like ligands for L-selectin in nonlymphoid endothelial cells
journal, July 1993
- Norgard-Sumnicht, K.; Varki, N.; Varki, A.
- Science, Vol. 261, Issue 5120
Highly stereoselective c-allylation of glycopyranosides with allylsilanes catalyzed by silyl triflate or iodosilane
journal, January 1984
- Hosomi, Akira; Sakata, Yasuyuki; Sakurai, Hideki
- Tetrahedron Letters, Vol. 25, Issue 22
The HNK-1 reactive sulfoglucuronyl glycolipids are ligands for L-selectin and P-selectin but not E-selectin.
journal, February 1993
- Needham, L. K.; Schnaar, R. L.
- Proceedings of the National Academy of Sciences, Vol. 90, Issue 4
GMP-140 binds to a glycoprotein receptor on human neutrophils: evidence for a lectin-like interaction.
journal, February 1991
- Moore, K. L.; Varki, A.; McEver, R. P.
- Journal of Cell Biology, Vol. 112, Issue 3
Lifetime of the P-selectin-carbohydrate bond and its response to tensile force in hydrodynamic flow
journal, April 1995
- Alon, Ronen; Hammer, Daniel A.; Springer, Timothy A.
- Nature, Vol. 374, Issue 6522
Enzyme-catalyzed oligosaccharide synthesis
journal, May 1992
- Ichikawa, Yoshitaka; Look, Gary C.; Wong, Chi-Huey
- Analytical Biochemistry, Vol. 202, Issue 2