Endogenous lectins as targets for drug delivery

Advanced Drug Delivery Reviews

Volumn 43, Issue 2-3, 2000, Pages 225-244

  Yamazaki, N ^a   Kojima, S ^b   Bovin, N V ^c   Andre S ^d   Gabius, S ^e   Gabius, H J ^d  

^a Natl Inst M   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^d UNIVERSITY OF MUNICH   (Germany)

^e Sternstr 12   (Germany)

Author keywords

Agglutinin; Drug targeting; Lectin; Neoglycoconjugate; Sugar code

Indexed keywords

CELL CULTURE; NUCLEIC ACIDS; PROTEINS; SACCHARIFICATION; TISSUE CULTURE;

AGGLUTININ; ENDOGENOUS LECTINS;

DRUG THERAPY;

ASIALOGLYCOPROTEIN RECEPTOR; DRUG RECEPTOR; GLYCOCONJUGATE; GLYCOSIDE; LECTIN; LIGAND; LIPOSOME; OLIGOSACCHARIDE; TRISACCHARIDE;

DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG TARGETING; HISTOPATHOLOGY; HUMAN; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN GLYCOSYLATION; PROTEIN STRUCTURE; RECEPTOR AFFINITY; REVIEW; TARGET CELL;

EID: 0034734974     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(00)00071-5     Document Type: Article

References (110)

1. Lindahl U., Kjellen L. Heparin or heparan sulfate - what is the difference? Thromb. Haemost. 66:1991;44-48.
2. Yamada S., Sugahara K. Structure of oligosaccharides isolated from heparan sulfate/heparin and substrate specificities of the degrading enzymes of bacterial origin. Trends Glycosci. Glycotechnol. 10:1998;95-123.
3. Reuter G., Gabius H.-J. Sialic acids. Structure, analysis, metabolism, and recognition. Biol. Chem. Hoppe-Seyler. 377:1996;325-342.
4. Hooper L.V., Manzella S.M., Baenziger J.U. The biology of sulfated oligosaccharides. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;261-276 Chapman and Hall, London.
5. Laine R.A. The information-storing potential of the sugar code. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;1-14 Chapman and Hall, London.
6. Winterburn P.J., Phelps C.F. The significance of glycosylated proteins. Nature. 236:1972;147-151.
7. Varki A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology. 3:1993;97-130.
8. Sharon N., Lis H. Glycoproteins: structure and function. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1998;133-162 Chapman and Hall, London.
9. Reuter G., Gabius H.-J. Eukaryotic glycosylation: whim of nature or multipurpose tool? Cell. Mol. Life Sci. 55:1999;368-422.
10. Wormald M.R., Dwek R.A. Glycoproteins: glycan presentation and protein-fold stability. Structure. 7:1999;R155-160.
11. Apweiler R., Hermjakob H., Sharon N. On the frequency of protein glycosylation, as deduced from analysis of the SWISS-PROT database. Biochim. Biophys. Acta. 1473:1999;4-8.
12. Varki A., Marth J. Oligosaccharides in vertebrate development. Sem. Dev. Biol. 6:1995;127-138.
13. Brockhausen I., Schachter H. Glycosyltransferases involved in N- and O-glycan biosynthesis. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;79-113 Chapman and Hall, London.
14. Amado M., Almeida R., Schwientek T., Clausen H. Identification and characterization of large galactosyltransferase gene families: galactosyltransferases for all functions. Biochim. Biophys. Acta. 1473:1999;35-53.
15. Furukawa K., Sato T. β-1,4-Galactosylation of N-glycans is a complex process. Biochim. Biophys. Acta. 1473:1999;54-66.
16. Schrével J., Gros D., Monsigny M. Cytochemistry of cell glycoconjugates. Progr. Histochem. Cytochem. 14:(2):1981;1-269.
17. Caselitz J. Lectins and blood group substances as tumor markers. Curr. Top. Pathol. 77:1987;245-278.
18. Spicer S.S., Schulte B.A. Diversity of cell glycoconjugates shown histochemically: a perspective. J. Histochem. Cytochem. 40:1992;1-38.
19. Gabius H.-J., Gabius S. Lectins and Glycobiology. 1993;Springer, Berlin, New York.
20. Danguy A. Perspectives in modern glycohistochemistry. Eur. J. Histochem. 39:1995;5-14.
21. Cummings R.D. Lectins as tools for glycoconjugate purification and characterization. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;191-199 Chapman and Hall, London.
22. Watkins W.M. Blood group substances. Science. 152:1955;172-181.
23. Mitchell S.W. Researches upon the venom of the rattlesnake. Smithsonian Contributions to Knowledge. XII:1860;89-90.
24. Flexner S., Noguchi H. Snake venom in relation to haemolysis, bacteriolysis, and toxicity. J. Exp. Med. 6:1902;277-301.
25. 2+-dependent β-galactoside-specific lectins from snake venoms. Biochem. J. 224:1984;301-307.
26. Villalobo A., Gabius H.-J. Signaling pathways for transduction of the initial message of the glycocode into cellular responses. Acta Anat. 161:1998;110-129.
27. Gabius H.-J. Biological information transfer beyond the genetic code: the sugar code. Naturwissenschaften. 87:2000;108-121.
28. Bodmer J.L., Dean R.T. Carrier potential of glycoproteins. Methods Enzymol. 112:1985;298-306.
29. Gabius H.-J. Potential participation of tumor lectins in cancer diagnosis, therapy and biology. Adv. Lectin Res. 2:1989;87-106.
30. Fiume L., Busi C., Di Stefano G., Mattioli A. Targeting of antiviral drugs to the liver using glycoprotein carriers. Adv. Drug Deliv. Rev. 14:1994;51-65.
31. Molema G., Meijer D.K.F. Targeting of drugs to various blood cell types using (neo)glycoproteins, antibodies and other protein carriers. Adv. Drug Deliv. Rev. 14:1994;25-50.
32. Rice K.G. Glycoconjugate-mediated drug targeting. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;471-483 Chapman and Hall, London.
33. Rademacher T.W., Parekh R.B., Dwek R.A. Glycobiology. Annu. Rev. Biochem. 57:1988;785-838.
34. Parekh R.B., Dwek R.A., Edge C.J., Rademacher T.W. N-Glycosylation and the production of recombinant glycoproteins. Trends Biotechnol. 7:1989;117-122.
35. Cumming D.A. Glycosylation of recombinant protein therapeutics: control and functional implications. Glycobiology. 1:1991;115-130.
36. Lee Y.C. Neoglycoconjugates: general considerations. Lee Y.C., Lee R.T. Neoglycoconjugates. Preparation and Applications. 1994;3-21 Academic Press, San Diego, CA.
37. Stowell C.P., Lee Y.C. Neoglycoproteins: the preparation and application of synthetic glycoproteins. Adv. Carbohydr. Chem. Biochem. 37:1980;225-281.
38. Aplin J.D., Wriston J.C. Preparation, properties and applications of carbohydrate conjugates of proteins and lipids. CRC Crit. Rev. Biochem. 10:1981;259-306.
39. Lee Y.C., Lee R.T. Neoglycoconjugates. Preparation and Applications. 1994;Academic Press, San Diego, CA.
40. Gabius H.-J., Schröter C., Gabius S., Brinck U., Tietze L.-F. Binding of T-antigen-bearing neoglycoprotein and peanut agglutinin to cultured tumor cells and breast carcinomas. J. Histochem. Cytochem. 38:1990;1625-1631.
41. Schmidt R.R. Strategies for the chemical synthesis of glycoconjugates. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;31-53 Chapman and Hall, London.
42. Palcic M.M. Biocatalytic synthesis of oligosaccharides. Curr. Opin. Biotechnol. 10:1999;616-624.
43. André S., Unverzagt C., Kojima S., Dong X., Fink C., Kayser K., Gabius H.-J. Neoglycoproteins with the synthetic complex biantennary nonasaccharide or its α2,3/α2,6-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. 8:1997;845-855.
44. Gabius H.-J., Unverzagt C., Kayser K. Beyond plant lectin histochemistry: preparation and application of markers to visualize the cellular capacity for protein-carbohydrate recognition. Biotech. Histochem. 73:1998;263-277.
45. Bovin N.V., Korchagina E.Y., Zemlyanukhina T.V., Byramova N.E., Galanina O.E., Zemlyakov A.E., Ivanov A.E., Zubov V.P., Mochalova L.V. Synthesis of polymeric neoglycoconjugates based on N-substituted polyacrylamides. Glycoconjugate J. 10:1993;142-151.
46. Magnusson G., Chernyak A.Y., Kihlberg J., Kononov L.O. Synthesis of neoglycoconjugates. Lee Y.C., Lee R.T. Neoglycoconjugates. Preparation and Applications. 1994;53-143 Academic Press, San Diego, CA.
47. Bovin N.V., Gabius H.-J. Polymer-immobilized carbohydrate ligands: versatile chemical tools for biochemistry and medical sciences. Chem. Soc. Rev. 24:1995;413-421.
48. Kojima S., André S., Korchagina E.Y., Bovin N.V., Gabius H.-J. Tyramine-containing poly(4-nitrophenylacrylate) as iodinatable carrier in biodistribution analysis. Pharm. Res. 14:1997;879-886.
49. Gabius H.-J., Gabius S., Zemlyanukhina T.V., Bovin N.V., Brinck U., Danguy A., Joshi S.S., Kayser K., Schottelius J., Sinowatz F., Tietze L.-F., Vidal-Vanaclocha F., Zanetta J.-P. Reverse lectin histochemistry: design and application of glycoligands for detection of cell and tissue lectins. Histol. Histopathol. 8:1993;369-383.
50. Danguy A., Decaestecker C., Genten F., Salmon I., Kiss R. Applications of lectins and neoglycoconjugates in histology and pathology. Acta Anat. 161:1998;206-218.
51. Gabius H.-J. Concepts of tumor lectinology. Cancer Invest. 15:1997;454-464.
52. Gabius H.-J., André S., Danguy A., Kayser K., Gabius S. Detection and quantification of carbohydrate-binding sites on cell surfaces and in tissue sections by neoglycoproteins. Methods Enzymol. 242:1994;37-46.
53. Gabius H.-J. Endogenous lectins in tumors and the immune system. Cancer Invest. 5:1987;39-46.
54. Monsigny M., Roche A.C., Midoux P., Kieda C., Mayer R. Endogenous lectins of myeloid and tumor cells: characterization and biological implications. Gabius H.-J., Nagel G.A. Lectins and Glycoconjugates in Oncology. 1988;25-48 Springer, Berlin, New York.
55. Gabius H.-J., Engelhardt R., Hellmann T., Midoux P., Monsigny M., Nagel G.A., Vehmeyer K. Characterization of membrane lectins in human colon carcinoma cells by flow cytofluorometry, drug targeting and affinity chromatography. Anticancer Res. 7:1987;109-112.
56. Bordet H.-J., Gay F.P. Sur les relations des sensibilisatrices avec l'alexine. Ann. Inst. Pasteur. 20:1906;467-498.
57. Ashwell G., Harford J. Carbohydrate-specific receptors of the liver. Annu. Rev. Biochem. 51:1982;531-554.
58. Gabius H.-J. Detection and functions of mammalian lectins - with emphasis on membrane lectins. Biochim. Biophys. Acta. 1071:1991;1-18.
59. Weigel P.H. Mechanisms and control of glycoconjugate turnover. Allen H.J., Kisailus E.C. Glycoconjugates. Composition, Structure, and Function. 1992;421-497 Marcel Dekker, New York.
60. Kaltner H., Stierstorfer B. Animal lectins as cell adhesion molecules. Acta Anat. 161:1998;162-179.
61. Gabius H.-J. Animal lectins. Eur. J. Biochem. 243:1997;543-576.
62. Rini J.M., Lobsanov Y.D. New animal lectin structures. Curr. Opin. Struct. Biol. 9:1999;578-584.
63. Lee Y.C. Biochemistry of carbohydrate-protein interaction. FASEB J. 6:1992;3193-4000.
64. Lee R.T., Lee Y.C. Enhanced biochemical affinities of multivalent neoglycoconjugates. Lee Y.C., Lee R.T. Neoglycoconjugates. Preparation and Applications. 1994;23-50 Academic Press, San Diego, CA.
65. Lee R.T., Lee Y.C. Neoglycoconjugates. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;55-77 Chapman and Hall, London.
66. S. André, B. Frisch, H. Kaltner, D.L. Desouza, F. Schuber, H.-J. Gabius, Lectin-mediated drug targeting. Selection of valency, sugar type (Gal/Lac) and spacer length for cluster glycosides as parameters to distinguish ligand binding to C-type asialoglycoprotein receptors and galectins, Pharm. Res. (2000) (in press).
67. Mammen M., Choi S.-K., Whitesides G.M. Polyvalente Wechselwirkungen in biologischen Systemen: Auswirkungen auf das Design und die Verwendung multivalenter Liganden und Inhibitoren. Angew. Chem. 110:1998;2908-2953.
68. Roy R. Blue-prints, synthesis and applications of glycopolymers. Trends Glycosci. Glycotechnol. 8:1996;79-99.
69. Roy R. Recent developments in the rational design of multivalent glycoconjugates. Top. Curr. Chem. 187:1997;241-274.
70. Yi D., Lee R.T., Longo P., Boger E.T., Lee Y.C., Petri W.A., Schnaar R.L. Substructural specificity and polyvalent carbohydrate recognition by the Entamoeba histolytica and rat hepatic N-acetylgalactosamine/galactose lectins. Glycobiology. 8:1998;1037-1043.
71. André S., Ortego P.J.C., Perez M.A., Roy R., Gabius H.-J. Lactose-containing starburst glycodendrimers: influence of dendrimer generation and binding-site orientation of receptors (plant/animal lectins and immunoglobulins) on binding properties. Glycobiology. 9:1999;1253-1261.
72. Gabius H.-J., Bardosi A. Neoglycoproteins as tools in glycohistochemistry. Progr. Histochem. Cytochem. 22:(3):1991;1-66.
73. Gabius H.-J., Gabius S. Chemical and biochemical strategies for the preparation of glycohistochemical tools and their application in lectinology. Adv. Lectin Res. 5:1992;123-157.
74. Gabius H.-J. The how and why of protein-carbohydrate interaction: a primer to the theoretical concept and a guide to application in drug design. Pharm. Res. 15:1998;23-30.
75. Hasegawa A., Kiso M. Design and synthesis of cell adhesion carbohydrate ligands/inhibitors. Witczak Z.J., Nieforth K.A. Carbohydrates in Drug Design. 1997;137-157 Marcel Dekker, New York.
76. Roy R. Sialoside mimetics and conjugates as anti-inflammatory agents and inhibitors of flu virus infections. Witczak Z.J., Nieforth K.A. Carbohydrates in Drug Design. 1997;83-136 Marcel Dekker, New York.
77. Solís D., Diaz-Mauriño T. Analysis of protein-carbohydrate interaction using engineered ligands. Gabius H.-J., Gabius S. Glycosciences: Status and Perspectives. 1997;345-354 Chapman and Hall, London.
78. von Itzstein M., Kiefel M.J. Sialic acid analogues as potential antimicrobial agents. Witczak Z.J., Nieforth K.A. Carbohydrates in Drug Design. 1997;39-82 Marcel Dekker, New York.
79. Simanek E.E., McGarvey G.J., Jablonowski J.A., Wong C.-H. Selectin-carbohydrate interactions: from natural ligands to designed mimics. Chem. Rev. 98:1998;833-862.
80. von der Lieth C.-W., Siebert H.-C., Kozar T., Burchert M., Frank M., Gilleron M., Kaltner H., Kayser G., Tajkhorshid E., Bovin N.V., Vliegenthart J.F.G., Gabius H.-J. Lectin ligands: new insights into their conformations and their dynamic behaviour and the discovery of conformer selection by lectins. Acta Anat. 161:1998;91-109.
81. Rüdiger H., Siebert H.-C., Solís D., Jiménez-Barbero J., Romero A., von der Lieth C.-W., Diaz-Mauriño T., Gabius H.-J. Medicinal chemistry based on the sugar code: fundamentals of lectinology and experimental strategies with lectins as targets. Curr. Med. Chem. 7:2000;389-416.
82. Jones M.N. Carbohydrate-mediated liposomal targeting and drug delivery. Adv. Drug Deliv. Rev. 13:1994;215-250.
83. Ouchi T., Ohya Y. Drug delivery systems using carbohydrate recognition. Lee Y.C., Lee R.T. Neoglycoconjugates. Preparation and Applications. 1994;465-498 Academic Press, San Diego, CA.
84. Bovin N.V. Polyacrylamide-based neoglycoconjugates as tools in glycobiology. Glycoconjugate J. 15:1998;431-446.
85. Vodovozova E., Gayenko E., Razinkov V., Korchagina E., Bovin N., Molotkovsky J. Saccharide-assisted delivery of cytotoxic liposomes to human malignant cells. Biochem. Mol. Biol. Int. 44:1998;543-553.
86. Heath T.D., Macher B.A., Papahadjopoulos D. Covalent attachment of immunoglobulins to liposomes via glycosphingolipids. Biochim. Biophys. Acta. 640:1981;66-81.
87. Yamazaki N., Kojima S., Gabius S., Gabius H.-J. Studies on carbohydrate-binding proteins using liposome-based systems. Preparation of neoglycoprotein-conjugated liposomes and the feasibility of their use as drug-targeting devices. Int. J. Biochem. 24:1992;99-104.
88. Yamazaki N., Gabius S., Kojima S., Gabius H.-J. Neoglycoprotein-liposome conjugates for studies of membrane lectins. Gabius H.-J., Gabius S. Lectins and Glycobiology. 1993;319-326 Springer, Berlin, New York.
89. Yamazaki N., Kodama M., Gabius H.-J. Neoglycoprotein-liposome and lectin-liposome conjugates as tools for carbohydrate recognition research. Methods Enzymol. 242:1994;56-65.
90. x trisaccharides. Drug Deliv. Syst. 14:1999;498-505.
91. Kojima S., Gabius H.-J. Biodistribution of neoglycoproteins in mice bearing solid Ehrlich tumor. J. Cancer Res. Clin. Oncol. 114:1988;468-472.
92. x-terminated N-linked oligosaccharides in mice. J. Biol. Chem. 270:1995;24024-24031.
93. Kojima S., Ishido M., Kubota K., Kubodera A., Hellmann T., Kohnke-Godt B., Wosgien B., Gabius H.-J. Tissue distribution of radioiodinated neoglycoproteins and mammalian lectins. Biol. Chem. Hoppe-Seyler. 371:1990;331-338.
94. André S., Kojima S., Yamazaki N., Fink C., Kayser K., Gabius H.-J. Galectin-1 and -3 and their ligands in tumor biology. Non-uniform properties in cell surface presentation and modulation of adhesion to matrix glycoproteins for various tumor cell lines, in biodistribution of free and liposome-bound galectins and in their expression by breast and colorectal carcinomas with/without metastatic propensity. J. Cancer Res. Clin. Oncol. 125:1999;461-474.
95. Panés J., Perry M., Granger D.N. Leukocyte - endothelial cell adhesion: avenues for therapeutic intervention. Br. J. Pharmacol. 126:1999;537-550.
96. Rosen S.D. Endothelial ligands for L-selectin. From lymphocyte recirculation to allograft rejection. Am. J. Pathol. 155:1999;1013-1020.
97. Vestweber D., Blanks J.E. Mechanisms that regulate the function of the selectins and their ligands. Physiol. Rev. 79:1999;181-213.
98. Yang J., Furie B.C., Furie B. The biology of P-selectin glycoprotein ligand-1: its role as a selectin counterreceptor in leukocyte-endothelial and leukocyte-platelet interaction. Thromb. Haemost. 81:1999;1-7.
99. Paillard F. Glycotargeting: a receptor-mediated delivery using sugar ligands. Hum. Gene Ther. 10:1999;337-339.
100. Dintzis R.Z., Okajima M., Middleton M.H., Greene G., Dintzis H.M. The immunogenicity of soluble haptenated polymers is determined by molecular mass and hapten valency. J. Immunol. 143:1989;1239-1244.
101. Monsigny M., Roche A.C., Midoux P., Mayer R. Glycoconjugates as carriers for specific delivery of therapeutic drugs and genes. Adv. Drug Deliv. Rev. 14:1994;1-24.
102. Seymour L.W. Soluble polymers for lectin-mediated drug targeting. Adv. Drug Deliv. Rev. 14:1994;89-111.
103. Monsigny M., Midoux P., Mayer R., Roche A.C. Glycotargeting: influence of the sugar moiety on both the uptake and the intracellular trafficking of nucleic acid carried by glycosylated polymers. Biosci. Rep. 19:1999;125-132.
104. Balboni P.G., Minia A., Grossi M.P., Barbanti-Brodano G., Mattioli A., Fiume L. Activity of albumin conjugates of 5-fluorodeoxyuridine and cytosine arabinoside on poxviruses as a lysosomotropic approach to antiviral chemotherapy. Nature. 264:1976;181-183.
105. Kopecek J. Targetable polymeric anticancer drugs. Temporal control of drug activity. Ann. NY Acad. Sci. 681:1991;335-344.
106. Giannasca P.J., Boden J.A., Monath T.P. Targeted delivery of antigen to hamster nasal lymphoid tissue with M-cell-directed lectins. Infect. Immun. 65:1997;4288-4298.
107. Diebold S.S., Kursa M., Wagner E., Cotten M., Zenke M. Mannose polyethylenimine conjugates for targeted DNA delivery into dendritic cells. J. Biol. Chem. 274:1999;19087-19094.
108. Brady R.O., Barton N.W. Enzyme replacement therapy with macrophage-targeted human placental glucocerebrosidase in Gaucher disease. Gabius H.-J., Gabius S. Lectins and Cancer. 1991;237-250 Springer, Berlin, New York.
109. Friedman B., Vaddi K., Preston C., Mahon E., Cataldo J.R., McPherson J.M. A comparison of the pharmacologic properties of carbohydrate remodeled recombinant and placental-derived β-glucocerebrosidase: implications for clinical efficacy in treatment of Gaucher disease. Blood. 93:1999;2807-2816.
110. 4 binding. Proc. Natl. Acad. Sci. USA. 95:1998;2089-2093.