Alkynyl sugar analogs for the labeling and visualization of...

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process...

Reexamination Certificate

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C435S007100, C435S007200

Reexamination Certificate

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07960139

ABSTRACT:
The present disclosure relates to a method for metabolic oligosaccharide engineering that incorporates derivatized alkyne-bearing sugar analogs as “tags” into cellular glycoconjugates. The disclosed method incorporates alkynyl derivatized Fuc and alkynyl derivatized ManNAc sugars into a cellular glycoconjugate. A chemical probe comprising an azide group and a visual probe or a fluorogenic probe is used to label the alkyne-derivatized sugar-tagged glycoconjugate. In one aspect, the chemical probe binds covalently to the alkynyl group by Cu(I)-catalyzed [3+2] azide-alkyne cycloaddition and is visualized at the cell surface, intracellularly, or in a cellular extract. The labeled glycoconjugate is capable of detection by flow cytometry, SDS-PAGE, Western blot, ELISA or confocal microscopy, and mass spectrometry.

REFERENCES:
patent: 5625124 (1997-04-01), Falk et al.
Hsu TL, Hanson SR, Kishikawa K, Wang SK, Sawa M, Wong CH, Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells, (2007) Proc Natl Acad Sci 104:2614-2619.
Varki A, Cummings R, Esko JD, Freeze H, Hart GW, Marth J (1999) in Essentials of Glycobiology (Cold Spring Harbor Lab Press, Cold Spring Harbor, NY), pp. 1-635.
Axford JS, Glycosylation and rheumatic disease, (1999) Biochim Biophys Acta 1455:219-229.
Dube, D. H. & Bertozzi, C. R., Glycans in cancer and inflammation—potential for therapeutics and diagnostics, (2005) Nat. Rev. Drug Discov. 4, 477-488.
Mackiewicz A, Mackiewicz K, Glycoforms of serum a1-acid glycoprotein as markers of inflammation and cancer, (1995) Glycoconj J 12:241-247.
Meezan E, Wu HC, Black PH, Robbins PW, Comparative Studies on the Carbohydrate-Containing Membrane Components of Normal and Virus-Transformed Mouse Fibroblasts. II. Separation of Glycoproteins and Glycopeptides by Sephadex Chromatography*, (1969) Biochemistry 8:2518-2524.
Turner GA, N-Glycosylation of serum proteins in disease and its investigation using lectins, (1992) Clin Chim Acta 208:149-171.
Orntoft TF, Vestergaard EM, Clinical aspects of altered glycosylation of glycoproteins in cancer, (1999) Electrophoresis 20:362-371.
Sell S, Cancer-Associated Carbonhydrates Identified by Monoclonal Antibodies, (1990) Hum Pathol 21:1003-1019.
Taylor-Papadimitriou J, Epenetos AA, Exploiting altered glycosylation patterns in cancer: progress and challenges in diagnosis and therapy, (1994) Trends Biotechnol 12:227-233.
Zhang S, Cordon-Cardo C, Zhang HS, Reuter VE, Adluri S, Hamilton WB, Lloyd KO, Livingston PO, Selection of tumor antigens as targets for immune attack using immunohistochemistry: I. Focus on gangliosides, (1997) Int J Cancer 73:42-49.
Zhang S, Zhang HS, Cordon-Cardo C, Reuter VE, Singhal AK, Lloyd KO, Livingston PO, Selection of tumor antigens as targets for immune attack using immunohistochemistry: II. Blood group-related antigens, (1997) Int J Cancer 73:50-56.
Mahal LK, Yarema KJ, Bertozzi CR, Engineering Chemical Reactivity on Cell Surfaces Through Oligosaccharide Biosynthesis, (1997) Science 276:1125-1128.
Tai HC, Khidekel N, Ficarro SB, Peters EC, Hsieh-Wilson LC, Parallel Identification of O-GlcNAc-Modified Proteins from Cell Lysates, (2004) J Am Chem Soc 126:10500-10501.
Saxon E, Bertozzi CR, Cell Surface Engineering by a Modified Staudinger Reaction, (2000) Science 287:2007-2010.
Sampathkumar SG, Li AV, Jones MB, Sun Z, Yarema KJ, Metabolic installation of thiols into sialic acis modulates adhesion and stem cell biology, (2006) Nat Chem Biol 2:149-152.
Agard NJ, Baskin JM, Prescher JA, Lo A, Bertozzi CR, A Comparative Study of Bioorthogonal Reactions with Azides, (2006) ACS Chem Biol 1:644-648.
Agard NJ, Prescher JA, Bertozzi CR, A Strain-Promoted [3 + 2] Azide-Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems, (2004) J Am Chem Soc 126:15046-15047.
Rabuka D, Hubbard SC, Laughlin ST, Argade SP, Bertozzi CR, A Chemical Reporter Strategy to Probe Glycoprotein Fucosylation, (2006) J Am Chem Soc 128:12078-12079.
Sawa M., Hsu T. L., Itoh T., Sugiyama M., Hanson S. R. , Vogt P. K. , Wong C. H. , Glycoproteomic probes for fluorescent imaging of fucosylated glycansin vivo, (2006) Proc. Natl. Acad. Sci. USA 103, 12371-12376.
Dube DH, Prescher JA, Quang CN, Bertozzi CR, Probing mucin-type O-linked glycosylation in living animals, (2006) Proc Natl Acad Sci USA 103:4819-4824.
Hang HC, Yu C, Kato DL, Bertozzi CR, A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation, (2003) Proc Natl Acad Sci USA 100:14846-14851.
Becker, D. J. & Lowe, J. B., Fucose: biosynthesis and biological function in mammals, (2003) Glycobiology 13, 41R-53R.
Keppler OT, Horstkorte R, Pawlita M, Schmidt C, Reutter W, Fucose: biosynthesis and biological function in mammals, (2001) Glycobiology 11:11R-18R.
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB, A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes**, (2002) Angew Chem Int Ed Engl 41:2596-2599.
Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG, Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition, (2003) J Am Chem Soc 125:3192-3193.
Jacobs CL, Yarema KJ, Mahal LK, Nauman DA, Charters NW, Bertozzi CR, Metabolic Labeling of Glycoproteins with Chemical Tags through Unnatural Sialic Acid Biosynthesis, (2000) Methods Enzymol 327:260-275.
Sarkar AK, Fritz TA, Taylor WH, Esko JD, Disaccharide uptake and priming in animal cells: Inhibition of sialyl Lewis Xby acetylated GaIII1-4GIcNAc13-Onaphthalenemethanol, (1995) Proc Natl Acad Sci USA 92:3323-3327.
Sivakumar K, Xie F, Cash BM, Long S, Barnhill HN, Wang Q, A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes, (2004) Org Lett 6:4603-4606.
Yarema KJ, Mahal LK, Bruehl RE, Rodriguez EC, Bertozzi CR, Metabolic Delivery of Ketone Groups to Sialic Acid Residues, (1998) J Biol Chem 273:31168-31179.
Speers AE, Cravatt BF, Profiling Enzyme Activities In Vivo Using Click Chemistry Methods, (2004) Chem Biol 11:535-546.
Hanson S, Best M, Bryan MC, Wong CH, Chemoenzymatic synthesis of oligosaccharides and glycoproteins (2004) Trends Biochem Sci 29:656-663.
Luchansky SJ, Bertozzi CR, Azido Sialic Acids Can Modulate Cell-Surface Interactions, (2004) Chembiochem 5:1706-1709.
Fujihashi M, Peapus DH, Kamiya N, Nagata Y, Miki K, Crystal Structure of Fucose-Specific Lectin fromAleuria aurantiaBinding Ligands at Three of Its Five Sugar Recognition Sites, (2003) Biochemistry 42:11093-11099.
Wimmerova M, Mitchell E, Sanchez JF, Gautier C, Imberty A, Crystal Structure of Fungal Lectin, (2003) J Biol Chem 278:27059-27067.
Simanek EE, McGarvey GJ, Jablonowski JA, Wong CH, Selectin-Carbohydrate Interactions: From Natural Ligands to Designed Mimics, (1998) Chem Rev 98:833-862.
Yang L, McRae R, Henary MM, Patel R, Lai B, Vogt S, Fahrni CJ, Imaging of the intracellular topography of copper with a fluorescent sensor and by synchrotron x-ray fluorescence microscopy, (2005) Proc Natl Acad Sci USA 102:11179-11184.
Apweiler, R., Hermjakob, H. & Sharon, N., On the frequency of protein glycosylation, as deduced from analysis of the SWISS-PROT database, (1999) Biochim. Biophys. Acta 1473, 4-8.
Staudacher, E., α 1,3-Fucosyltransferases, (1996) Trends Glycosci. Glycotechnol. 8, 391-408.
Sears, P. & Wong, C.-H., Enzyme action in glycoprotein synthesis, (1998) Cell. Mol. Life Sci. 54, 223-252.
Haltiwanger, R. S. & Lowe, J. B., Role of glycosylation in development, (2004) Annu. Rev. Biochem. 73, 491-537.
Hirabayashi, J., Lectin-based structural glycomics: Glycoproteomics and glycan profiling, (2004) Glycoconj. J. 21, 35-40.
Shriver, Z., Raguram, S. & Sasisekharan, R., Glycomics: a pathway to a class of new and improved therapeutics, (2004) Nat. Rev. Drug Discov. 3, 863-873.
Khidekel, N., Ficarro, S. B., Peters, E. C. & Hsieh-Wilson, L. C., Exploring the O-GlcNAc proteome: Direct identification ofO-GlcNAc-modified proteins from the brain, (2004) Proc. Natl. Acad. Sci. USA 101, 13132-13137.
Ratner, D. M., Adams, E

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