Persubstituted Cyclodextrin-Based Glycoclusters as Inhibitors of Protein-Carbohydrate Recognition Using Purified Plant and Mammalian Lectins and Wild-Type and Lectin-Gene-Transfected Tumor Cells as Targets

Bioconjugate Chemistry

Volumn 15, Issue 1, 2004, Pages 87-98

  André, Sabine ^a   Kaltner, Herbert ^a   Furuike, Tetsuya ^b   Nishimura, Shin Ichiro ^b   Gabius, Hans Joachim ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CELL MEMBRANES; CYCLODEXTRINS; LIGANDS; MAMMALS; SUGARS; TOPOLOGY; TUMORS;

CARBOHYDRATE RECOGNITION; CARBOHYDRATE-RECOGNITION DOMAINS; GALECTINS; MACROCYCLES; NUCLEOPHILIC SUBSTITUTIONS; SOLID PHASIS; SPATIAL FACTORS; THIOLATES; TUMOUR CELLS; WILD TYPES;

PROTEINS;

3 (3 THIOACETYLPROPIONAMIDO)PROPYL GLYCOSIDE; BETA CYCLODEXTRIN DERIVATIVE; CARBOHYDRATE; CELL RECEPTOR; CHIMERIC PROTEIN; CYCLODEXTRIN; GALACTOSE; GALECTIN; GALECTIN 3; GLYCOCONJUGATE; GLYCOPROTEIN; GLYCOSIDE; HEPTAKIS 6 DEOXY 6 IODO BETA CYCLODEXTRIN; HUMAN IMMUNOGLOBULIN; IMMUNOGLOBULIN G; IODIDE; LACTOSE; LECTIN; LIGAND; MACROCYCLIC COMPOUND; N ACETYLLACTOSAMINE; PLANT LECTIN; PLANT TOXIN; PROTEIN; UNCLASSIFIED DRUG; VISCUM ALBUM EXTRACT;

ARTICLE; ASSAY; BIOSENSOR; CARBOHYDRATE SYNTHESIS; CELL CLONE; CELL SURFACE; CHEMOREACTIVITY; COMPETITIVE INHIBITION; DRUG DESIGN; GENETIC TRANSFECTION; GEOMETRY; GLYCOSIDE SYNTHESIS; HUMAN; HUMAN CELL; HYPERACUTE GRAFT REJECTION; LIGAND BINDING; METASTASIS; MOLECULAR RECOGNITION; PROTEIN BINDING; PROTEIN STRUCTURE; SOLID; SOLID PHASE ASSAY; TUMOR CELL; TUMOR CELL CLONE;

MAMMALIA; STAPHYLOCOCCUS PHAGE 3A; VISCUM; VISCUM ALBUM;

EID: 0842328412     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0340666     Document Type: Article

References (92)

1. Ahmad, N., Gabius, H.-J., Kaltner, H., André, S., Kuwabara, I., Liu, F.-T., Oscarson, S., Norberg, T., and Brewer, C. F. (2002) Thermodynamic binding studies of cell surface carbohydrate epitopes to galectins-1, -3 and -7: evidence for differential binding specificities. Can. J. Chem. 80, 1096-1104.
2. André, S., Unverzagt, C., Kojima, S., Dong, X., Fink, C., Kayser, K., and Gabius, H.-J. (1997) Neoglycoproteins with the synthetic complex biantennary nonasaccharide or its α2, 3/α-2,6-sialylated derivatives: their preparation, assessment of their ligand properties for purified lectins, for tumor cells in vitro, and in tissue sections, and their biodistribution in tumor-bearing mice. Bioconjugate Chem. 8, 845-855.
3. André, S., Ortega, P. J., Perez, M. A., Roy, R., and Gabius, H.-J. (1999a) Lactose-containing starburst dendrimers: influence of dendrimer generation and binding-site orientation of receptors (plant/animal lectins and immunoglobulins) on binding properties. Glycobiology 9, 1253-1261.
4. André, S., Kojima, S., Yamazaki, N., Fink, C., Kaltner, H., Kayser, K., and Gabius, H.-J. (1999b) Galectins-1 and -3 and their ligands in tumor biology. J. Cancer Res. Clin. Oncol. 125, 461-474.
5. André, S., Pieters, R. J., Vrasidas, I., Kaltner, H., Kuwabara, I., Liu, F.-T., Liskamp, R. M. J., and Gabius, H.-J. (2001) Wedgelike glycodendrimers as inhibitors of binding of mammalian galectins to glycoproteins, lactose maxiclusters, and cell surface glycoconjugates. ChemBioChem 2, 822-830.
6. André, S., Liu, B., Gabius, H.-J., and Roy, R. (2003) First demonstration of differential inhibition of lectin binding by synthetic tri- and tetravalent glycoclusters from cross-coupling of rigidified 2-propynyl lactoside. Org. Biomol. Chem. 1, 3909-3916.
7. Ashton, P. R., Hounsell, E. F., Jayaraman, N., Nilsen, T. M., Spencer, N., Stoddart, J. F., and Young, M. (1998) Synthesis and biological evaluation of α-D-mannopyranoside-containing dendrimers. J. Org. Chem. 63, 3429-3437.
8. Baek, M.-G., and Roy, R. (2002) Synthesis and protein binding properties of T-antigen containing glycoPAMAM dendrimers. Bioorg. Med. Chem. 10, 11-17.
9. Baussanne, I., Benito, J. M., Ortiz Mellet, C., García Fernández, J. M., and Defaye, J. (2001) Dependence of concanavalin A binding on anomeric configuration, linkage type, and ligand multiplicity for thiourea-bridged mannopyranosyl-β-cyclodextrin conjugates. ChemBioChem 2, 777-783.
10. Bharadwaj, S., Kaltner, H., Korchagina, E. Y., Bovin, N. V., Gabius, H.-J., and Surolia, A. (1999) Microcalorimetric indications for ligand binding as a function of the protein for galactoside-specific plant and avian lectins. Biochim. Biophys. Acta 1472, 191-196.
11. Biessen, E. A. L., Noorman, F., van Teijlingen, M. E., Kuiper, J., Barrett-Bergshoeff, M., Bijsterbosch, M. K., Rijken, D. C., van Berkel, and T. J. (1996) Lysine-based cluster mannosides that inhibit ligand binding to the human mannose receptor at nanomolar concentration. J. Biol. Chem. 271, 28024-28030.
12. Bovin, N. V., and Gabius, H.-J. (1995) Polymer-immobilized carbohydrate ligands: versatile chemical tools for biochemistry and medical sciences. Chem. Soc. Rev. 24, 413-421.
13. Brewer, C. F. (2002) Binding and cross-linking properties of galectins. Biochim. Biophys. Acta 1572, 255-262.
14. Cairo, C. W., Gestwicki, J. E., Kanai, M., and Kiessling, L. L. (2002) Control of multivalent interactions by binding epitope density. J. Am. Chem. Soc. 124, 1615-1619.
15. Camby, I., Belot, N., Rorive, S., Lefranc, F., Maurage, C.-A., Lahm, H., Kaltner, H., Hadari, Y., Ruchoux, M.-M., Brotchi, J., Zick, Y., Salmon, I., Gabius, H.-J., and Kiss, R. (2001) Galectins are differentially expressed in supratentorial pilocytic astrocytomas, astrocytomas, anaplastic astrocytomas and glioblastomas, and significantly modulate tumor astrocyte migration. Brain Pathol. 11, 12-26.
16. Camby, I., Belot, N., Lefranc, F., Sadeghi, N., de Launoit, Y., Kaltner, H., Musette, S., Darro, F., Danguy, A., Salmon, I., Gabius, H.-J., and Kiss, R. (2002) Galectin-1 modulates human glioblastoma cell migration into the brain through modifications to the actin cytoskeleton and levels of expression of small GTPases. J. Neuropathol. Exp. Neurol. 61, 585-596.
17. Cao, Z., Said, N., Amin, S., Wu, H. K., Bruce, A., Garate, M., Hsu, D. K., Kuwabara, I., Liu, F.-T., and Panjwani, N. (2002) Galectins-3 and -7, but not galectin-1, play a role in re-epithelialization of wounds. J. Biol. Chem. 277, 42299-42305.
18. Cloninger, M. J. (2002) Biological applications of dendrimers. Curr. Opin. Chem. Biol. 6, 742-748.
19. Cooper, D. N. W. (2002) Galectinomics: finding themes in complexity. Biochim. Biophys. Acta 1572, 209-231.
20. Danguy, A., Camby, I., and Kiss, R. (2002) Galectins and cancer. Biochim. Biophys. Acta 1572, 285-293.
21. Davis, B. G., and Robinson, M. A. (2002) Drug delivery systems based on sugar-macromolecule conjugates. Curr. Opin. Drug Discovery Dev. 5, 279-288.
22. Dettmann, W., Grandbois, M., André, S., Benoit, M., Wehle, A. K., Kaltner, H., Gabius, H.-J., and Gaub, H. E. (2000) Differences in zero-force and force-driven kinetics of ligand dissociation from β -galactoside-specific proteins (plant and animal lectins, immunoglobulin G) monitored by plasmon resonance and dynamic single molecule force microscopy. Arch. Biochem. Biophys. 383, 157-170.
23. East, L., and Isacke, C. (2002) The mannose receptor family. Biochim. Biophys. Acta 1572, 364-386.
24. Endo, Y. (1989) Mechanism of action of ricin and related toxic lectins on the inactivation of eukaryotic ribosomes. Adv. Lectin Res. 2, 60-73.
25. Fulton, D. A., and Stoddart, J. F. (2001a) Neoglycoconjugates based on cyclodextrins and calixarenes. Bioconjugate Chem. 12, 655-672.
26. Fulton, D. A., and Stoddart, J. F. (2001b) Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions. J. Org. Chem 66, 8309-8319.
27. Furuike, T., Aiba, S., and Nishimura, S.-I. (2000) A highly practical synthesis of cyclodextrin-based glycoclusters having enhanced affinity with lectins. Tetrahedron 56, 9909-9915.
28. Gabius, H.-J. (1990) Influence of type of linkage and spacer on the interaction of β-galactoside-binding proteins with immobilized affinity ligands. Anal. Biochem. 189, 91-94.
29. Gabius, H.-J. (1991) Detection and functions of mammalian lectins - with emphasis on membrane lectins. Biochim. Biophys. Acta 1071, 1-18.
30. Gabius, H.-J. (1997) Animal lectins. Eur. J. Biochem. 243, 543-576.
31. Gabius, H.-J. (2001a) Glycohistochemistry: the why and how of detection and localization of endogenous lectins. Anat. Histol. Embryol. 30, 3-31.
32. Gabius, H.-J. (2001b) Probing the cons und pros of lectin-induced immunomodulation: case studies for the mistletoe lectin and galectin-1. Biochimie 83, 659-666.
33. Gabius, H.-J., Engelhardt, R., Rehm, S., and Cramer, F. (1984) Biochemical characterization of endogenous carbohydrate-binding proteins from spontaneous murine rhabdomyosarcoma, mammary adenocarcinoma and ovarian teratoma. J. Natl. Cancer Inst. 73, 1349-1357.
34. Gabius, H.-J., Engelhardt, R., Rehm, S., Barondes, S. H., and Cramer, F. (1986) Presence and relative distribution of three endogenous β-galactoside-specific lectins in different tumor types of rat. Cancer J. 1, 19-22.
35. Gabius, S., Schirrmacher, V., Franz, H., Joshi, S. S., and Gabius, H.-J. (1990) Analysis of cell-surface sugar receptor expression by neoglycoenzyme binding and adhesion to plastic-immobilized neoglycoproteins for related weakly and strongly metastatic cell lines of murine tumor model systems. Int. J. Cancer 46, 500-507.
36. Gabius, S., Joshi, S. S., Gabius, H.-J., and Sharp, J. G. (1991) Establishment, characterization and determination of cell surface sugar receptor (lectin) expression by neoglycoenzymes of a human myeloid marker-expressing B-lymphoblastoid cell line. Anticancer Res. 11, 793-800.
37. Gabius, H.-J., Darro, F., Remmelink, M., André, S., Kopitz, J., Danguy, A., Gabius, S., Salmon, I., and Kiss, R. (2001) Evidence for stimulation of tumor proliferation in cell lines and histotypic cultures by clinically relevant low doses of the galactoside-binding mistletoe lectin, a component of proprietary extracts. Cancer Invest. 19, 114-126.
38. Gabius, H.-J., André, S., Kaltner, H., and Siebert, H.-C. (2002) The sugar code: functional lectinomics. Biochim. Biophys. Acta 1572, 165-177.
39. Galanina, O. E., Kaltner, H., Khraltsova, L. S., Bovin, N. V., and Gabius, H.-J. (1997) Further refinement of the description of the ligand-binding characteristics for the galactoside-binding mistletoe lectin, a plant agglutinin with immunomodulatory potency. J. Mol. Recogn. 10, 139-147.
40. García-López, J. J., Hernández-Mateo, F., Isac-Garciá, J., Kim, J. M., Roy, R., Santoyo-González, F., and Vargas-Berenguel, A. (1999) Synthesis of per-glycosylated β-cyclodextrins having enhanced lectin binding affinity. J. Org. Chem. 64, 522-531.
41. Grandjean, C., Angyalosi, G., Loing, E., Adriaenssens, E., Melnyk, O., Pancre, V., Auriault, C., and Gras-Masse, H. (2001) Novel hyperbranched glycomimetics recognized by the human mannose receptor: quinic or shikimic acid derivatives as mannose bioisosteres. ChemBioChem 2, 747-757.
42. Gupta, D., Kaltner, H., Dong, X., Gabius, H.-J., and Brewer, C. F. (1996) Comparative cross-linking activities of lactose-specific plant and animal lectins and a natural lactose-binding immunoglobulin G fraction from human serum. Glycobiology 6, 843-849.
43. Hajto, T., Hostanska, K., Frei, K., Rordorf, C., and Gabius, H.-J. (1990) Increased secretion of tumor necrosis factor-α, interleukin-1, and interleukin-6 by human mononuclear cells exposed to the galactoside-specific lectin from clinically applied mistletoe extract. Cancer Res. 50, 3322-3326.
44. Hirabayashi, J., Ed. (1997) Recent topics on galectins. Trends Glycosci. Glycotechnol. 9, 1-180.
45. Hirabayashi, J., Hashidate, T., Arata, Y., Nishi, N., Nakamura, T., Hirashima, M., Urashima, T., Oka, T., Futai, M., Müller, W. E. G., Yagi, F., and Kasai, K.-i. (2002) Oligosaccharide specificity of galectins: a search by frontal affinity chromatography. Biochim. Biophys. Acta 1572, 232-254.
46. Horan, N., Yan, L., Isobe, H., Whitesides, G. M., and Kahne, D. (1999) Nonstatistical binding of a protein to clustered carbohydrates. Proc. Natl. Acad. Sci. U.S.A. 96, 11782-11786.
47. Houseman, B. T., and Mrksich, M. (2002) Model systems for studying polyvalent carbohydrate binding interactions. Top. Curr. Chem. 218, 1-44.
48. Ichikawa, M., Woods, A. S., Mo, H., Goldstein, I. J., and Ichikawa, Y. (2000) Simple preparation of multivalent cyclodextrin-carbohydrate conjugates. Tetrahedron: Asymmetry 11, 389-392.
49. Kaltner, H., and Stierstorfer, B. (1998) Animal lectins as cell adhesion molecules. Acta Anat. 161, 162-179.
50. Kaltner, H., Seyrek, K., Heck, A., Sinowatz, F., and Gabius, H.-J. (2002) Galectin-1 and galectin-3 in fetal development of bovine respiratory and digestive tracts. Cell Tissue Res. 307, 35-46.
51. Kiessling, L. L., Gestwicki, J. E., and Strong, L. E. (2000) Synthetic multivalent ligands in the exploration of cell-surface interactions. Curr. Opin. Chem. Biol. 4, 696-703.
52. Kilpatrick, D. C. (2002) Animal lectins: a historical introduction and overview. Biochim. Biophys. Acta 1572, 187-197.
53. Kojima, S., André, S., Korchagina, E. Y., Bovin, N. V., and Gabius, H.-J. (1997) Tyramine-containing poly(4-nitrophenylacrylate) as iodinatable ligand carrier in biodistribution analysis. Pharmaceut. Res. 14, 879-886.
54. Kopitz, J., von Reitzenstein, C., André, S., Kaltner, H., Uhl, J., Ehemann, V., Cantz, M., and Gabius, H.-J. (2001) Negative regulation of neuroblastoma cell growth by carbohydrate-dependent surface binding of galectin-1 and functional divergence from galectin-3. J. Biol. Chem. 276, 35917-35923.
55. Kopitz, J., André, S., von Reitzenstein, C., Versluis, K., Kaltner, H., Pieters, R. J., Wasano, K., Kuwabara, I., Liu, F.-T., Cantz, M., Heck, A. J. R., and Gabius, H.-J. (2003) Homodimeric galectin-7 (p53-induced gene 1) is a negative growth regulator for human neuroblastoma cells. Oncogene 22, 6277-6288.
56. Lahm, H., André, S., Hoeflich, A., Fischer, J. R., Sordat, B., Kaltner, H., Wolf, E., and Gabius, H.-J. (2001) Comprehensive galectin fingerprinting in a panel of 61 human tumor cell lines by RT-PCR and its implications for diagnostic and therapeutic procedures. J. Cancer Res. Clin. Oncol. 127, 375-386.
57. Laine, R. A. (1997) The information-storing potential of the sugar code. In Glycosciences: Status and Perspectives (H.-J. Gabius and S. Gabius, Eds.) pp 1-14, Chapman & Hall, London.
58. Lee, R. T., and Lee, Y. C. (1994) Enhanced biochemical affinities of multivalent neoglycoconjugates. In Neoglycoconjugates. Preparation and Applications (Y. C. Lee and R. T. Lee, Eds.) pp 23-50, Academic Press, San Diego.
59. Lee, R. T., Ichikawa, Y., Allen, H. J., and Lee, Y. C. (1990) Binding characteristics of galactoside-binding lectin (galaptin) from human spleen. J. Biol. Chem. 265, 7864-7871.
60. Lee, R. T., Gabius, H.-J., and Lee, Y. C. (1992) Ligand binding characteristics of the major mistletoe lectin. J. Biol. Chem. 267, 23722-23727.
61. Loris, R. (2002) Principles of structures of animal and plant lectins. Biochim. Biophys. Acta 1572, 198-208.
62. Mann, D. A., Kanai, M., Maly, D. J., and Kiessling, L. L. (1998) Probing low affinity and multivalent interactions with surface plasmon resonance: ligands for concanavalin. A. J. Am. Chem. Soc. 120, 10575-10582.
63. Nagy, N., Bronckart, Y., Camby, I., Legendre, H., Lahm, H., Kaltner, H., Hadari, Y. R., Van Ham, P., Yeaton, P., Pector, J.-C., Zick, Y., Salmon, I., Danguy, A., Kiss, R., and Gabius, H.-J. (2002) Galectin-8 expression decreases in cancer compared with normal and dysplastic human colon tissue and acts significantly on human colon cancer cell migration as a suppressor. Gut 50, 392-401.
64. Nagy, N., Legendre, H., Engels, O., André, S., Kaltner, H., Wasano, K., Zick, Y., Pector, J.-C., Decaestecker, C., Gabius, H.-J., Salmon, I., and Kiss, R. (2003) Refined prognostic evaluation in colon cancer using immunohistochemical galectin fingerprinting. Cancer 97, 1849-1858.
65. Nangia-Makker, P., Hogan, V., Honjo, Y., Baccarini, S., Tait, L., Bresalier, R., and Raz, A. (2002) Inhibition of human cancer cell growth and metastasis in nude mice by oral intake of modified citrus pectin. J. Natl. Cancer Inst. 94, 1854-1862.
66. Niwa, H., Tonevitsky, A. G., Agapov, I. I., Saward, S., Pfüller, U., and Palmer, R. A. (2003) Crystal structure at 3 Å of mistletoe lectin I, a dimeric type-II ribosome-inactivating protein, complexed with galactose. Eur. J. Biochem. 270, 2739-2749.
67. Nishimura, S.-I. (2001) Combinatorial syntheses of sugar derivatives. Curr. Opin. Chem. Biol. 5, 325-335.
68. Ohannesian, D. W., and Lotan, R. (1997) Galectins in tumor cells. In Glycosciences: Status and Perspectives (H.-J. Gabius and S. Gabius, Eds.) pp 459-469, Chapman & Hall, London.
69. Ortega-Caballero, F., Giménez-Martínez, J. J., García-Fuentes, L., Ortiz-Salmerón, E., Santoyo-González, F., and Vargas-Berenguel, A. (2001) Binding affinity properties of dendritic glycosides based on a β-cyclodextrin core toward guest molecules and concanavalin A. J. Org. Chem. 66, 7786-7795.
70. Ortiz Mellet, C., Defaye, J., and García Fernández, J. M. (2002) Multivalent cyclooligosaccharides: versatile carbohydrate clusters with dual role as molecular receptors and lectin ligands. Chem. Eur. J. 8, 1982-1990.
71. Rabinovich, G. A., Rubinstein, N., and Toscano, M. A. (2002) Role of galectins in inflammatory and immunomodulatory processes. Biochim. Biophys. Acta 1572, 274-284.
72. Ramström, O., Bunyapaiboonsri, T., Lohmann, S., and Lehn, J.-M. (2002) Chemical biology of dynamic combinatorial libraries. Biochim. Biophys. Acta 1572, 178-186.
73. Reuter, G., and Gabius, H.-J. (1999) Eukaryotic glycosylation: whim of nature or multipurpose tool? Cell. Mol. Life Sci. 55, 368-422.
74. Rice, K. G. (1997) Glycoconjutate-mediated drug targeting. In Glycosciences: Status and Perspectives (H.-J. Gabius and S. Gabius, Eds.) pp 471-483, Chapman & Hall, London.
75. Roy, R. (1996) Blue-prints, synthesis and applications of glycopolymers. Trends Glycosci. Glycotechnol. 8, 79-99.
76. Roy, R. (2002) Designing novel multivalent glycotools for biochemical investigations related to sialic acid. J. Carbohydr. Chem. 21, 769-798.
77. Rüdiger, H., Gabius, H.-J. (2001) Plant lectins. Glycoconjugate J. 18, 589-613.
78. Rüdiger, H., Siebert, H.-C., Solís, D., Jimé nez-Barbero, J., Romero, A., von der Lieth, C.-W., Díaz-Mauriño, T., and Gabius, H.-J. (2000) Medicinal chemistry based on the sugar code: fundamentals of lectinology and experimental strategies with lectins as targets. Curr. Med. Chem. 7, 389-416.
79. Schengrund, C.-L. (2003) "Multivalent" saccharides: development of new approaches for inhibiting the effects of glycosphingolipid-binding pathogens. Biochem. Pharmacol. 65, 699-707.
80. Sheikholeslam-Zadeh, R., Decaestecker, C., Delbrouck, C., Danguy, A., Salmon, I., Zick, Y., Kaltner, H., Hassid, S., Gabius, H.-J., Kiss, R., and Choufani, G. (2001) The levels of expression of galectin-3, but not of galectins-1 and -8, correlate with apoptosis in human cholesteatomas. Laryngoscope 111, 1042-1047.
81. Timoshenko, A. V., Gorudko, I. V., Kaltner, H., and Gabius, H.-J. (1999) Dissection of the impact of various intracellular signaling pathways on rat thymocytes after initial lectin-dependent cell association using a plant lectin as model and target-selective inhibitors. Mol. Cell. Biochem. 197, 137-145.
82. Timoshenko, A. V., Gorudko, I. V., Maslakova, O. V., André, S., Kuwabara, I., Liu, F.-T., Kaltner, H., and Gabius, H.-J. (2003) Analysis of selected blood and immune cell responses to carbohydrate-dependent surface binding of proto- and chimera-type galectins. Mol. Cell. Biochem. 259, 139-149.
83. Unverzagt, C., André, S., Seifert, J., Kojima, S., Fink, C., Srikrishna, G., Freeze, H., Kayser, K., and Gabius, H.-J. (2002) Structure-activity profiles of complex biantennary glycans with core fucosylation and with/without additional α2, 3/α2,6-sialylation: synthesis of neoglycoproteins and their properties in lectin assays, cell binding and organ uptake. J. Med. Chem. 45, 478-491.
84. Vrasidas, I., André, S., Valentini, P., Böck, C., Lensch, M., Kaltner, H., Liskamp, R. M. J., Gabius, H.-J., and Pieters, R. J. (2003) Rigidified multivalent lactose molecules and their interactions with mammalian galectins: a route to selective inhibitors. Org. Biomol. Chem. 1, 803-810.
85. Wang, J.-Q., Chen, X., Zhang, W., Zacharek, S., Chen, Y., and Wang, P. G. (1999) Enhanced inhibition of human antigal antibody binding to mammalian cells by synthetic α-gal epitope polymers. J. Am. Chem. Soc. 121, 8174-8181.
86. Weigel, P. H., and Yik, J. H. N. (2002) Glycans as endocytosis signals: the cases of the asialoglycoprotein and hyaluronan/chondroitin sulfate receptors. Biochim. Biophys. Acta 1572, 341-363.
87. Winterburn, P. J., and Phelps, C. F. (1972) The significance of glycosylated proteins. Nature 236, 147-151.
88. Yamazaki, N., Kojima, S., Bovin, N. V., André, S., Gabius, S., and Gabius, H.-J. (2000) Endogenous lectins as targets in drug delivery. Adv. Drug Delivery Rev. 43, 225-244.
89. Yamazaki, N., Jigami, Y., Gabius, H.-J., and Kojima, S. (2001) Preparation and characterization of neoglycoprotein-liposome conjugates: a promising approach to developing drug delivery materials applying sugar chain ligands. Trends Glycosci. Glycotechnol. 13, 319-329.
90. Yasuda, N., Aoki, N., Abe, H., and Hattori, K. (2000) Per-C-6 oligosaccharide-branched cyclodextrin interacting with both the lectin and drug. Chem. Lett. 6, 706-707.
91. Zanini, D., and Roy, R. (1997a) Chemoenzymatic synthesis and lectin binding properties of dendritic N-acetyllactosamine. Bioconjugate Chem. 8, 187-192.
92. Zanini, D., and Roy, R. (1997b) Synthesis of new α -thiosialodendrimers and their binding properties to the sialic acid specific lectin from Limax flavus. J. Am. Chem. Soc. 119, 2088-2095.