Recognition of novel amphiphiles with many pendent mannose residues by con A

Bioconjugate Chemistry

Volumn 10, Issue 3, 1999, Pages 354-360

  Tagawa, Koji ^a   Sendai, Naoko ^a   Ohno, Kohji ^a   Kawaguchi, Tomoaki ^a   Kitano, Hiromi ^a   Matsunaga, Takayuki ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b Toyama Prefectural University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILES; ASSOCIATION REACTIONS; CHAINS; MOLECULES; PROTEINS;

CANAVALIA ENSIFORMIS; DEGREES OF POLYMERIZATIONS; MANNOPYRANOSIDES; POLYMER MAIN CHAIN; RADICAL INITIATORS; SIDE-CHAINS; SPECIFIC RECOGNITION; SUGAR RESIDUES; SURFACE DENSITY; TELOMERIZATION;

LIPOSOMES;

CANAVALIA ENSIFORMIS;

EID: 0033136224     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc980083x     Document Type: Article

References (37)

1. Jones, M. N. (1994) Carbohydrate-Mediated Liposomal Targeting and Drug Delivery. Adv. Drug Delivery Rev. 13, 215-250.
2. (a) Connolly, D. T., Townsend, R. R., Kwaduchi, K., Bell, W. R., and Lee, Y. C. (1982) Binding and Endocytosis of Cluster Glycosides by Rabbit Hepatocytes. J. Biol. Chem. 257, 939-945.
3. (b) Spanjer, H. H., Van Berkel, T. J., Scherphof, G. L., and Kempen, H. J. M. (1985) The Effect of a Water-Soluble Tris-Galactose Terminated Cholesterol Derivative on the in Vivo Fate of Small Unilamellar Vesicles in Rats. Biochim. Biophys. Acta 816, 396-402.
4. (a) Muller, C. D., and Schubor, F. (1989) Neo-Mannosylated Liposomes: Synthesis and Interaction with Mouse Kupffer Cells and Resident Peritoneal Macrophages. Biochim. Biophys. Acta 986, 97-105.
5. (b) Ghosh, P., Das, P. K., and Bachhawant, B. K. (1982) Targeting of Liposomes towards Different Cell Types of Rat Liver through the Involvement of Liposomal Surface Glycolipids. Arch. Biochem. Biophys. 213, 266-270.
6. (a) Hoppe, C. A., and Lee, Y. C. (1983) The Binding and Processing of Mannose-Bovine Serum Albumin Derivatives by Rabbit Alveolar Macrophages. J. Biol. Chem. 258, 14193-14199.
7. (b) Stahl, P. D., Rodman, J. S., Miller, M. J., and Schlesinger, P. H. (1978) Evidence for Receptor-Mediated Binding of Glycoproteins, Glycoconjugates, and Lysosomal Glycosidase by Alveolar Macrophages. Proc. Natl. Acad. Sci. U.S.A. 75, 1399-1403.
8. (c) Barratt, G., Tenu, J. P., Yapo, A., and Petit, J. F. (1986) Preparation and Characterization of Liposomes Containing Mannosylated Phospholipids Capable of Targeting Drugs to Macrophages. Biochim. Biophys. Acta 862, 153-164.
9. Allen, T. M. (1989) Stealth Liposomes: Avoiding Reticuloendothelial Uptake in Liposomes in the Therapy of Infection Diseases and Cancer (G. Lopez Berestain, and I. J. Fidler, Eds.) pp 405-415, Alan R. Liss, New York.
10. Kitano, H., Akatsuka, Y., and Ise, N. (1991) pH-Responsive Liposomes Which Contain Amphiphiles Prepared by Using Lipophilic Radical Initiator. Macromolecules 24, 42-46.
11. Kitano, H., Maeda, Y., Takeuchi, S., Ieda, K, and Aizu, Y. (1994) Liposomes Containing Amphiphiles Prepared by Using a Lipophilic Chain Transfer Reagent: Responsiveness to External Stimuli. Langmuir 10, 403-406.
12. Kitano, H., and Ohno, K. (1994) Sugar-Containing Lipids Prepared by Using a Lipophilic Radical Initiator: Interfacial Recognition by Lectin as Studied by Using the Multiple Internal Reflection Fluorescence Method. Langmuir 10, 4131-4135.
13. Kitano, H., Sohda, K, and Kosaka, A. (1995) Galactose-Containing Amphiphiles Prepared with a Lipophilic Radical Initiator. Bioconjugate Chem. 6, 131-134.
14. Ohno, K, Sohda, K., Kosaka, A., and Kitano, H. (1995) Galactose-Containing Amphiphiles Prepared with a Lipophilic Radical Initiator: Association Processes between Liposomes Triggered by Enzymatic Reaction. Bioconjugate Chem. 6, 361-366.
15. (a) Ohno, K., and Kitano, H. (1998) Catalytic Properties of Galactose Oxidase to Liposome-Forming Amphiphiles Which Have Many Pendent Galactose Residues. Bioconjugate Chem. 9, 548-554.
16. (b) Kawaguchi, T., Tagawa, K., Senda, F., Matsunaga, T., and Kitano, H. (1999) Recognition of Amphiphiles with Many Pendent Galactose Residues by Ricinus communis Agglutinin. J. Colloid Interface Sci. 210, 290-295.
17. Kitano, H., Wolf, H., and Ise, N. (1990) pH-Responsive Release of Fluorophore from Homocysteine-Carrying Polymerized Liposomes. Macromolecules 23, 1958-1961.
18. Kuwamura, T. (1961) Long Chain Aliphatic Derivatives of Glyceryl α,α′-Diethers. Kogyo Kagaku Zasshi 64, 1958-1964.
19. Lee, R. T., and Lee, Y. C. (1974) Synthesis of 3-(2-Aminoethylthio)propyl Glycosides. Carbohydr. Res. 37, 193-201.
20. Minamikawa, H., Murakami, T., and Hato, M. (1994) Synthesis of 1,3-Di-O-alkyl-2-O-(β-glycosyl)glycerols Bearing Oligosaccharides as Hydrophilic Groups. Chem. Phys. Lipids 72, 111-118.
21. Kalb, A. J., and Lusting, A. (1968) The Molecular Weight of Concanavalin A. Biochim. Biophys. Acta 168, 366-367.
22. Bartlett, G. R. (1959) Phosphorus Assay in Column Chromatography. J. Biol. Chem. 234, 466-468.
23. Dubois, M., Gilles, K., Hamilton, J. K., Rebers, P. A., and Smith, F. (1956) Colorimetric Method for Determination of Sugars and Related Substances. Anal. Chem. 28, 350-356.
24. (a) Ringsdorf, H., Schlarb, B., and Venzmer, J. (1988) Molecular Architecture and Function of Polymeric Oriented Systems: Models for the Study of Organization, Surface Recognition, and Dynamics of Biomembranes. Angew. Chem., Int. Ed. Eng. 27, 113-158.
25. (b) Kitano, H., Kato, N., Tanaka, N., and Ise, N. (1988) Mutual Recognition between Polymerized Liposomes: Enzyme and Enzyme Inhibitor System. Biochim. Biophys. Acta 942, 131-138.
26. (c) Kitano, H., Kato, N., and Ise, N. (1988) Mutual Recognition between Polymerized Liposomes: Macrophage Model System by Polymerized Liposomes. J. Am. Chem. Soc. 111, 6809-6813.
27. Wagner, N., Does, K., Koch, H., and Ringsdorf, H. (1981) Incorporation of ATP Synthetase into Long-Term Stable Lipsomes of a Polymerizable Synthetic Sulfolipid. FEBS Lett. 132, 313-318.
28. Goldstein, I. J., Hollerman, C. E., and Smith, E. E. (1965) Protein-Carbohydrate Interaction. II. Inhibition Studies on the Interaction of Concanavalin A with Polysaccharides. Biochemistry 4, 876-883.
29. Curatolo, W., Yau, A. O., Small, D. M., and Sears, B. (1978) Lectin-Induced Agglutination of Phospholipid/Glycolipid Vesicles. Biochemistry 17, 5740-5744.
30. Mandal, D. K., N. Kishore, N., and Brewer, C. F. (1994) Thermodynamics of Lectin-Carbohydrate Interactions. Titration Microcalorimetry Measurements of Binding of N-Linked Carbohydrates and Ovalbumin to Concanavalin A. Biochemistry 33, 1149-1156.
31. Lee, R. T., and Lee, Y. C. (1994) in Neoglycoconjugates: Preparation and Application (Y. C. Lee, and R. T. Lee, Eds.) pp 23-50, Academic Press, San Diego.
32. Schwarz, F. P., Puri, K. B., Bhat, R. G., and Surolia, A. (1993) Thermodynamics of Monosaccharide Binding to Concanavalin A, Pea (Pisum sativum) Lectin, and Lentil (Lens culinaris) Lectin. J. Biol. Chem. 268, 7668-7677.
33. (a) Bessler, W., Shafer, J. A., and Goldstein, I. J. (1974) A Spectrophotometric Study of the Carbohydrate Binding Site of Concanavalin A. J. Biol. Chem. 249, 2819-2822.
34. (b) Schwarz, F. P., Puri, K. B., and Surolia, A. (1991) Thermodynamics of the Binding of Galactopyranoside Derivatives to the Basic Lectin from Winged Bean (Psophocarpus tetrogonolobus). J. Biol. Chem. 266, 24344-24350.
35. Ramkumar, R., Surolia, A., and Podder, S. K. (1995) Energetics of Carbohydrate Binding by a 14 kDa S-Type Mammalian Lectin. Biochem. J. 308, 237-241.
36. (a) Fidler, I. J. (1985) Macrophages and Metastasis Biological Approach to Cancer Therapy. Presidential Address. Cancer Res. 45, 4714-4726.
37. (b) Sone, S. (1986) Role of Alveolar Macrophages in Pulmonary Neoplasias. Biochim. Biophys. Acta 823, 227-245.