Characterization of protein-glycolipid recognition at the membrane bilayer

Journal of Molecular Recognition

Volumn 12, Issue 3, 1999, Pages 155-168

  Evans, Stephen V ^a   MacKenzie, C Roger ^b  

^a UNIVERSITY OF OTTAWA   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Context dependent recognition; Liposomes; Protein glycolipid interaction; Surface plasmon resonance

Indexed keywords

CELL MEMBRANE; LIPID BILAYER; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN INTERACTION; X RAY CRYSTALLOGRAPHY;

ANTIBODIES, MONOCLONAL; ANTIGEN-ANTIBODY REACTIONS; BACTERIAL TOXINS; BINDING SITES; CARBOHYDRATE CONFORMATION; CARBOHYDRATE METABOLISM; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; CRYSTALLOGRAPHY, X-RAY; GANGLIOSIDES; GLYCOLIPIDS; GLYCOSPHINGOLIPIDS; HUMANS; IMMUNOTHERAPY; KINETICS; LIPID BILAYERS; LIPOSOMES; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MELANOMA; MEMBRANE LIPIDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN BINDING; PROTEINS; SHIGA-LIKE TOXIN I; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; SURFACE PLASMON RESONANCE; TRIHEXOSYLCERAMIDES;

EID: 0033136786     PISSN: 09523499     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1352(199905/06)12:3<155::AID-JMR456>3.0.CO;2-S     Document Type: Review

References (94)

1. Ahmed S. N., Brown D. A. and London E. (1997). On the origin of sphingolipid/cholesterol-rich detergent-insoluble cell membranes: physiological concentrations of cholesterol and sphingolipid induce formation of a detergent-insoluble, liquid-ordered lipid phase in model membranes. Biochemistry 36, 10944-10953.
2. Alving C. R. and Richards R. L. (1977). Immune reactivities of antibodies against glycolipids - I. Properties of anti-galactocerebroside antibodies purified by a novel technique of affinity binding to liposomes. Immunochemistry 14, 373-381.
3. Alving C. R., Fowble J. W. and Joseph K. C. (1974). Comparative properties of four galactosyl lipids as antigens in liposomes. Immunochemistry 11, 475-481.
4. Ångström J., Teneberg S. and Karlsson K.-A. (1994). Delineation and comparison of ganglioside-binding epitopes for the toxins of Vibrio cholerae, Escherichia coli, and Clostridium tetani: evidence for overlapping epitopes. Proc. Natl Acad. Sci. USA 91, 11859-11863.
5. Ångström J., Teneberg T., Milh M. A., Larsson T., Leonardsson I., Olsson B.-M., Halvarsson M. Ö., Danielsson D., Nåslund I., Ljungh Å., Wadström T., Karlsson K.-A. (1998). The lactosyl-ceramide binding specificity of Helicobacter pylori. Glycobiology 8, 297-309.
6. Bovin N. V. (1997). Carbohydrate-carbohydrate interaction. In: Gabius H.-J. and Gabius S., (eds), Glycosciences, Chapman and Hall, Weinheim, pp 277-289.
7. Bretscher M.S. and Munro S. (1993). Cholesterol and the Golgi apparatus. Science 261, 1280-1281.
8. Brockhausen I. and Kuhns W. (1997). Glycoproteins and Human Disease. Chapman and Hall, New York.
9. Bundle D. R. (1997). Antibody-oligosaccharide interactions determined by crystallography. In: Gabius H. -J. and Gabius S., (eds), Glycosciences, Chapman and Hall, Weinheim, pp 311-331.
10. Bundle D. R., Eichler E., Gidney M. A., Meldal M., Ragauskas A., Sigurskjold B. W., Sinnott B., Watson D. C., Yaguchi M. and Young N. M. (1994). Molecular recognition of a Salmonella trisaccharide epitope by monoclonal antibody Se155-4. Biochemistry 33, 5172-5182.
11. D3 ganglioside. J. Immunol. 145, 891-898.
12. Cooper L. J. N., Robertson D., Granzow R. and Greenspan N. S. (1994). Variable domain-identical antibodies exhibit IgG subclass-related differences in affinity and kinetic constants as determined by surface plasmon resonance. Mol. Immmunol. 31, 577-584.
13. Crook S. J., Boggs J. M., Vistnes A. I. and Koshy K. M. (1986). Factors affecting surface expression of glycolipids: influence of lipid environment and ceramide composition on antibody recognition of cerobroside sulfate in liposomes. Biochemistry 25, 7488-7494.
14. Cuatrecasas P. (1973). Interaction of Vibrio cholerae enterotoxin with cell membranes. Biochemistry 18, 3547-3558.
15. Cummings M. D., Ling H., Armstrong G. D., Brunton J. L. and Read R. J. (1998). Modeling the carbohydrate-binding specificity of pig edema toxin. Biochemistry 37, 1789-1799.
16. Cush R., Cronin J. M., Stewart W. J., Maule C. H., Molloy J. and Goddard N. J. (1993). The resonant mirror: a novel optical biosensor for direct sensing of biomolecular interactions. Part I: principle of operation and associated instrumentation. Biosens. Bioelectron. 8, 347-353.
17. Donohue-Rolfe A., Jacewicz M. and Keusch G. T. (1989). Isolation and characterization of functional shiga toxin subunits and renatured holotoxin. Mol. Microbiol. 3, 1231-1236.
18. Dwek R. A. (1996). Glycobiology: toward understanding the function of sugars. Chem. Rev. 96 , 683-720.
19. Eggens I., Fenderson B., Toyokuni T., Dean B., Stroud M. and Hakomori S. (1989). Specific interaction between Lex and Lex determinants. A possible basis for cell recognition in preimplantation embryos and in embryonal carcinoma cells. J. Biol. Chem 264, 9467-9484.
20. Endo Y., Tsurugi K., Yutsudo T., Takeda Y., Ogasawara T. and Igarashi K. (1988). Site of action of a vero toxin (VT2) from Escherichia coli O157:H7 and a Shiga toxin on eukaryotic ribosomes. RNA N-glycosidase activity of the toxins. Eur J. Biochem. 171, 45-50.
21. Evans S. V. (1993). SETOR: hardware-lighted three-dimensional structures of macromolecules. J. Mol. Graphics 11, 134-138.
22. Gahmberg C. T. and Hakomori S. (1973). External labelling of cell surface galactose and galactosamine in glycolipid and glycoprotein of human erythrocytes. J. Biol. Chem. 248, 4311-4317.
23. Greenspan N. S., Monafo W. J. and Davie J. M. (1987). Interaction of IgG3 anti-streptococcal group A carbohydrate (GAC) antibody with streptococcal group A vaccine: enhancing and inhibiting effects of anti-GAC, anti-isotypic, and anti-idiotypic antibodies. (1987). J. Immunol. 138, 285-292.
24. Hakomori S. and Kannagi R. (1983) Glycosphingolipids as tumor-associated and differentiation markers. J. Natl Cancer Inst. 71, 231-251.
25. Hakomori S., Igarashi Y., Kojima N., Okoshi K., Handa B., Fenderson B. (1991). Functional role of cell surface carbohydrates in ontogenesis and oncogenesis. Glycoconjugate J. 8, 178.
26. Harrison B. A., MacKenzie R., Hirama T., Lee K. K. and Altman E. (1998). A kinetics approach to the characterization of an IgM specific for the glycolipid asialo-GM1. J. Immunol. Meth. 212, 29-39.
27. Hooper N. M. (1998) Do glycolipid microdomains really exist? Curr. Biol. 8, R114-R116.
28. Inoue K., Kataoka T. and Kinsky S. C. (1971). Comparative responses of liposomes prepared with different ceramide antigens to antibody and complement. Biochemistry 10, 2574-2581.
29. IUPAC-IUB Commission on Biochemical Nomenclature (1977) The nomenclature of lipids. Recommendations, 1976. Eur. J. Biochem. 79, 11-21.
30. Iwabuchi K., Handa K. and Hakomori S. (1998a). Separation of "Glycosphingolipid signaling domain" from caveolin-containing membrane fraction in mouse melanoma B16 cells and its role in cell adhesion coupled with signaling. J. Biol. Chem. 273, 33766-33773.
31. Iwabuchi K., Yamamura S., Prinetti A., Handa K. and Hakomori S. (1998b). GMS-enriched microdomain involved in cell adhesion and signal transduction through carbohydrate-carbohydrate interaction in mouse melanoma B16 cells. J. Biol. Chem. 273, 9130-9138.
32. Jones D. H., Lingwood C. A., Barber K. R. and Grant C. W. M. (1997). Globoside as a membrane receptor: a consideration of oligosaccharide communication with the hydrophobic domain. Biochemistry 36, 8539-8547.
33. Jönsson U., Fägerstam L., Ivarsson B., Johnsson B., Karlsson R., Lundh K., Löfås S., Persson B., Roos H., Rönnberg I., Sjölander S., Stenberg E., Ståhlberg R., Urbaniczky C., Östlin H. and Malmqvist M. (1991). Real-time biospecific interaction analysis using surface plasmon resonance and a sensor chip technology. BioTechniques 11, 620-627.
34. H domains. J. Biol. Chem. 274, 5597-5604.
35. Kannagi R., Stroup R., Cochran N. A., Urdal D. L., Young W. W. and Hakomori S. (1983). Factors affecting expression of glycolipid tumor antigens: influence of ceramide composition and coexisting glycolipid on the antigenicity of gangliotriaosylceramide in murine lymphoma cells. Cancer Res. 43, 4997-5005.
36. Karlsson K.-A. (1995). Microbial recognition of target-cell glycoconjugates. Curr. Opin. Struct. Biol. 5 , 622-635.
37. Karlsson R. and Fält A. (1997). Experimental design for kinetic analysis of protein-protein interactions using surface plasmon resonance biosensors. J. Immunol. Meth. 200, 121-133.
38. Kiarash A., Boyd B. and Lingwood C. A. (1994). Glycosphingolipid receptor function is modified by fatty acid content: verotoxin 1 and verotoxin 2c preferentially recognize different globotriaosyl ceramide fatty acid homologues. J. Biol. Chem. 269, 11138-11146.
39. Kievit E., Pinedo H. M., Schluper H. M., Haisma H. J. and Boven E. (1996). Comparison of monoclonal antibodies 17A and 323/ A3: the influence of the affinity on tumour uptake and efficacy of radioimmunotherapy in human ovarian cancer xenographs. Br. J. Cancer 73, 457-464.
40. Kojima N. and Hakomori S. (1991). Cell adhesion, spreading, and motility of GM3-expressing cells based on glycolipid-glycolipid interaction. J. Biol. Chem. 266, 17552-17558.
41. Kopitz J. (1997). Glycolipids: Structure and Function. In: Gabius H.-J. and Gabius S., (eds), Glycosciences, Chapman and Hall, Weinheim, pp 163-189.
42. Koscielak J., Hakomori S. and Jeanloz R. W. (1968). Glycolipid antigen and its antibody. Immunochemistry 5, 441-455.
43. Kuziemko G. M., Stroh M. and Stevens R. C. (1996). Cholera toxin binding affinity and specificity for gangliosides determined by surface plasmon resonance. Biochemistry 35, 6375-6383.
44. 3. Biochemistry 37, 1777-1788.
45. Lingwood C. A. (1993). Verotoxins and their glycolipid receptors. Adv. Lipid Res. 25, 189-211.
46. Lingwood C. A. (1996). Aglycone modulation of glycolipid receptor function. Glycoconjugate J. 13, 495-503.
47. Lingwood C. A., Law H., Richardson S., Petric M., Brunton J. L., De Grandis S. and Karmali M. (1987). Glycolipid binding of purified and recombinant Escherichia coli produced verotox-in in vitro. J. Biol. Chem. 262, 8834-8839.
48. MacKenzie C. R. and Hirama T. (1999). Quantitative analyses of binding affinity and specificity for glycolipid receptors by surface plasmon resonance. Meth. Enzymol. (in press).
49. MacKenzie C. R., Hirama T., Deng S.-J., Bundle D. R., Narang S. A. and Young N. M. (1996). Analysis by surface plasmon resonance of the influence of valence on the ligand binding affinity and kinetics of an anti-carbohydrate antibody. J. Biol. Chem. 271, 1527-1533.
50. MacKenzie C. R., Hirama T., Lee K. K., Altman E. and Young N. M. (1997). Quantitative analysis of bacterial toxin affinity and specificity for glycolipid receptors by surface plasmon resonance. J. Biol. Chem. 272, 5533-5538.
51. Mammen M., Choi S.-K. and Whitesides G. M. (1998). Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem. Int. Ed. 37, 2754-2794.
52. 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.
53. Masibay A. S., Balaji P. V., Boeggeman E. E. and Qasba P. K. (1993). Mutational analysis of the Golgi retention signal of bovine β,4-galactosyltransferase. J. Biol. Chem. 268, 9908-9916.
54. Masserini M., Freire E., Palestini P., Calappi E. and Tettamanti G. (1992). FucGM1 ganglioside mimics the receptor function of GM1 for cholera toxin. Biochemistry 31, 2422-2426.
55. Masson L., Mazza A. and Brousseau R. (1994). Stable immobilization of lipid vesicles for kinetic studies using surface plasmon resonance. Anal. Biochem. 218, 405-412.
56. Masson L., Mazza A., Brousseau and Tabashnik B. (1995). Kinetics of Bacillus thuringiensis toxin binding with brush border membrane vesicles from susceptible and resistant larvae of Plutella xylostella. J. Biol. Chem. 270, 11887-11896.
57. 2+ with hydroxy and non-hydroxy fatty acid species of cerobroside sulfate by Fourier transform infrared spectroscopy and molecular modeling. Biochemistry 36, 3438-3447.
58. M1 pentasaccharide. Protein Sci. 3, 166-177.
59. Merritt E. A., Sarfaty S., Jobling M. G., Chang T., Holmes R. K., Hirst, T. R. and Hol W. G. J. (1997). Structural studies of receptor binding by cholera toxin mutants. Protein Sci. 6, 1516-1528.
60. Myszka D. (1997). Kinetic analysis of macromolecular interactions using surface plasmon resonance. Curr. Opin. Biotechnol. 8, 50-57.
61. 3 lactone as a possible immunogen: requirements for tumor-associated antigen and immunogen. J. Immunol. 139, 3171-3176.
62. Nyholm P.-G. and Pascher I. (1993). Orientation of the saccharide chains of glycolipids at the membrane surface: conformational analysis of the glucose-ceramide and the glucose-glyceride linkages using molecular mechanics (MM3). Biochemistry 32, 1225-1234.
63. 3) Int. J. Biol. Macromol. 17, 199-204.
64. Nyholm P.-G., Magnusson G., Zheng Z., Norel R., Binnington-Boyd B., Lingwood C. A. (1996). Two distinct binding sites for globotriaosyl ceramide on verotoxins: identification by molecular modelling and confirmation using deoxy analogues and a new glycolipid receptor for all verotoxins. Chem. Biol. 3, 263-275.
65. Otsuji E., Park Y. S., Tashiro K., Kojima N., Toyokuni T. and Hakomori S. (1995). Inhibition of B16 melanoma metastasis by administration of GM3 or Gg3 liposomes: blocking adhesion of melanoma cells to endothelial cells (anti-adhesion therapy) via inhibition of GM3-Gg3 Cer or GM3-LacCer interaction. Int. J. Oncol. 6 , 319-327.
66. Patenaude S. I., MacKenzie C. R., Bilous D., To R. J., Ryan S. E., Young N. M. and Evans S. V. (1998). Production, crystallization and diffraction to atomic resolution of an antibody Fv specific for the blood-group A oligosaccharide antigen. Acta Cryst. D54, 1456-1459.
67. Plant A. L., Brigham-Burke M., Petrella E. C. and O'shannessy D. J. (1995). Phospholipid/alkanethiol bilayers for cell-surface receptor studies by surface plasmon resonance. Anal. Biochem. 226, 342-348.
68. Ramotar K., Boyd B., Tyrrell G., Gariepy J., Lingwood C. and Brunton J. (1990). Charaterization of a Shiga-like toxin IB subunit purified from overproducing clones of the SLT-I B cistron. Biochem. J. 272, 805-811.
69. Richardson J. M., Evans P. D., Homans S. W. and Donohue-Rolfe A. (1997). Solution structure of the carbohydrate-binding B-homopentamer of verotoxin VT from E. coli. Nature Struct. Biol. 4, 190-193.
70. Rock P., Allietta M., Young W. W., Thompson T. E. and Tillack T. W. (1990). Organization of glycosphingolipids in phosphatidylcholine bilayers: use of antibody molecules and Fab fragments as morphologic markers. Biochemistry 29, 8484-8490.
71. St. Hilaire P. M., Boyd M. K. and Toone E. J. (1994). Interaction of the Shiga-like toxin type 1 B-subunit with its carbohydrate receptor. Biochemistry 33, 14452-14463.
72. Schafer D. E. and Thaker A. K. (1982). Quantitative description of the binding of GM1 oligosaccharide by cholera enterotoxin. Cell Biophys. 4, 25-40.
73. Sears P. and Wong C.-H. (1996). Intervention of carbohydrate recognition by proteins and nucleic acids. Proc. Natl Acad. Sci. USA93, 12086-12093.
74. Shimizu H., Field R. A., Homans S. W. and Donohue-Rolfe A. (1998). Solution structure of the complex between the B-subunit homopentamer of verotoxin VT from Escherichia coli and the trisaccharide moiety of globotriasylceramide. Biochemistry 37, 11078-11082.
75. Shin M. L., Paznekas W. A. and Mayer M. M. (1978). On the mechanism of membrane damage by complement: the effect of length and unsaturation of the acyl chains in liposomal bilayers and the effect of cholesterol concentation in sheep erythrocyte and liposomal membranes. J. Immunol. 120, 1996-2002.
76. Simanek E. E., McGarvey G. J., Jablonowski J. A. and Wong C.-H. (1998). Selectin-carbohydrate interactions: from natural ligands to designed mimics. Chem. Rev. 98 , 833-862.
77. 2H NMR study of the influence of ceramide fatty acid characteristics on the carbohydrate headgroup in phospholipid bilayers. Biochemistry 31, 2662-2669.
78. Sinowatz F., Töpper-Petersen E. and Calvete J. J. (1997). Glycobiology of fertilization. In: Gabius H. -J. and Gabius S., (eds), Glycosciences, Chapman and Hall, Weinheim, pp 595-610.
79. Sixma T. K., Pronk S. E., Kalk K. H., Wartna E. S., van Zanten B. A. M., Witholt B. and Hol W. G. J. (1991). Crystal structure of a cholera toxin-related heat-labile enterotoxin from E. coli. Nature 351, 371.
80. Sixma T. K., Pronk S. E., Kalk K. H., van Zanten B. A. M., Berguis A. M. and Hol W. G. J. (1992). Lactose binding to heat-labile enterotoxin revealed by X-ray crystallography. Nature 355, 561-564.
81. Stein P. E., Boodhoo A., Tyrrell G. J., Brunton J. L. and Read R. J. (1992). Crystal structure of the cell-binding B oligomer of verotoxin from E. coli. Nature 355, 748-750.
82. Stein P. E., Boodhoo A., Armstrong G. D., Cockle S. A., Klein M. H. and Read R. J. (1994). Structure of a pertussis toxin-sugar complex as a model for receptor binding. Nature Struct. Biol. 1 , 591-596.
83. Stenberg E., Persson B., Roos H. and Urbaniczky C. (1991). Quantitative determination of surface concentration of protein with surface plasmon resonance using radiolabeled proteins. J. Colloid Interface Sci. 143, 513-526.
84. Stewart R. J. and Boggs J. M. (1993a). Exposure of galactosylceramide to galactose oxidase in liposomes: dependence on lipid environment and ceramide composition. Biochemistry 32, 5605-5614.
85. Stewart R.J. and Boggs J.M. (1993b). A carbohydrate - carbohydrate interaction between galactosylceramide-containing liposomes and cerobroside sulfate-containing liposomes: dependence on the glycolipid ceramide composition. Biochemistry 32, 10666-10674.
86. Utsumi H., Suzuki T., Inoue K. and Nojima S. (1984). Haptenic activity of galactosyl ceramide and its topographical distribution on liposomal membranes. Effects of temperature and phospholipid composition. J. Biochem. 96, 97-105.
87. van den Akker F., Sarfaty S., Twiddy E. M., Connell T. D., Holmes R. K. and Hol W. G. J. (1996a). Crystal structure of a new heat-labile enterotoxin, LT-IIb. Structure 4, 665-678.
88. van den Akker F., Steensma E. and Hol W. G. J. (1996b). Tumor marker disaccharide D-gal-,3-GaINAc complexed to heat-labile enterotoxin from Escherichia coli. Protein Sci. 5, 1184-1188.
89. Velders M. P., van Rhijn C. M., Briaire I. H., Fleuren G. J., Warnaar S. O. and Litvinov S. V. (1995). Immunotherapy with low and high affinity monoclonal antibodies 17-1A and 323/A3 in a nude mouse xenograph carcinoma model. Cancer Res. 55, 4398-4403.
90. Waddell T., Head S., Petric M., Cohen A. and Lingwood C. A. (1988). Glogotriosyl ceramide is specifically recognized by the Escherichia coli verocytotoxin 2. Biochem. Biophys. Res. Commun. 152, 674-679.
91. Webb M. S., Tilcock C. P. S. and Green B. R. (1988). Salt-mediated interactions between vesicles of the thylakoid lipid digalactosyldiacylglycerol. Biochim. Biophys. Acta 938, 323-333.
92. H idiotope that results in in specific homophilic binding and increased avidity for antigen. J. Immunol. 157, 1582-1588.
93. Yiu S. C. and Lingwood C. A. (1992). Polyisobutylmethacrylate modifies glycolipid binding specificity of verotoxin 1 in thin-layer chromatogram overlay procedures. Anal. Biochem. 202, 188-192.
94. Zhang R.-G., Scott D. L., Westbrook M. L., Nance S., Spangler B. D., Shipley G. G. and Westbrook E. M. (1995). The three-dimensional crystal structure of cholera toxin. Mol. Biol. 251, 563-573.