Epitope dissection of receptor-active gangliosides with affinity for Helicobacter pylori and influenza virus

• Autorzy: Miller-Podraza H. , Larsson T. , Nilsson J. , Teneberg S. , Matrosovich M. , Johansson L.
• Języki publikacji: EN

Abstrakty

EN

Receptor-active gangliosides with affinity for Helicobacter pylori and influenza virus were chemically modified and analyzed by negative ion fast atom bombardment mass spectrometry (FAB MS) or electron ionization mass spectrometry (EI MS) after permethylation. Derivatizations included mild periodate oxidation of the sialic acid glycerol tail or conversion of the carboxyl group to primary alcohol or amides. The modified gangliosides were then tested for binding affinity using thin-layer plates overlaid with labeled microbes or microbe-derived proteins. Mild periodate oxidation, which shortens sialic acid tail without destruction of sugar cores, abolished or drastically reduced binding of H. pylori and avian influenza virus to sialyl-3-paragloboside (S-3-PG). The same effect was observed in the case of binding of the human influenza virus to receptor-active gangliosides of human leukocytes. Conversion of S-3-PG or leukocyte gangliosides to primary alcohols or amides also abolished the binding. However, mild periodate oxidation had no effect on binding of NAP (neutrophil-activating protein of H. pylori) to the active ganglioside.

Słowa kluczowe

EN

sialic acid; man; virus; glycosphingolipid; binding epitope; ganglioside; leucocyte; influenza; Helicobacter pylori

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 1998
• Tom: 45
• Numer: 2
• Opis fizyczny: p.439-449,fig.

Twórcy

autor

Miller-Podraza H.

• Goteborg University, Medicinaregatan 9A, S-413 90 Goteborg, Sweden

autor

Larsson T.

autor

Nilsson J.

autor

Teneberg S.

autor

Matrosovich M.

autor

Johansson L.

Bibliografia

• 1. Svennerholm, L. (1984). Biological signifi­cance of gangliosides. INSERM 126, 21-44. which mediates the adsorption-fusion process of viral infection. J. Biol. Chenu 260. 1362- 1365.
• 2. Fishman, P.H. (1986) Recent advances in iden­tifying the functions of gangliosides. Chem. Phys. Lipids 42, 137-151.
• 3. Curatolo, W. (1987) Glycolipid function. Bio- chim. Biophys. Acta 906. 37-160.
• 4. Karlsson, K.-A. (1989) Animal glycosphin- golipids as membrane attachment sites for bacteria. Annu. Rev. Biochem. 58, 309-350.
• 5. Herrler, G., Hausmann, J. & Klenk, H.-D. (1995) Sialic acid as receptor determinant of ortho- and paramyxoviruses; in Biology of the Sialic Acids (Rosenberg, A., fid.) pp. 315-335, Plenum Press, New York.
• 6. Varki, A. (1992) Diversity in the sialic acids. Glycobiology 2, 25-40.
• 7. Suzuki, Y., Matsunaga, M. & Matsumoto, M. (1985) iV-Acetylneuraminyllactoceramide, GM3-NeuAc, a new influenza A virus receptor which mediates the adsorption-fusion process of viral infection. J. Biol. Chenu 260. 1362- 1365.
• 8. Suzuki, Y., Nakao, T., Ito, T., Watanabc, N., Toda, Y., Guiyun, X., Suzuki, T., Kobayashi, T., Kimura, Y., Yamada, A., Sugawara, K., Nishimura, H., Kitame, F., Nakamura, K., Deya, E., Kiso, M. & Hasegawa, A. (1992) Structural determination of gangliosides that bind to influenza A, B and C viruses by an im­proved binding assay: Strain-specific receptor epitopes in sialo-sugar chains. Virology 189, 121-131.
• 9. Bergelson, L.D., Bukrinskaya, A.G., Proka- zova, N.V., Shaposhnikova, G.I., Kocharov, S.L., Shevchenko, V.P., Kornilaeva, G.V. & Fomina-Ageeva, E.V. (1982) Role of ganglio­sides in reception of influenza virus. Eur. J. Biochem. 128, 467-474.
• 10. Muthing, J. (1996) Influenza A and Sendai vi­ruses preferentially bind to fucosylated gan­gliosides with linear poly-N-acetyllactosaminyl chains from human granulocytes. Carbohy­drate Res. 290, 217-224.
• 11. Słomiany, B.L., Piotrowski, J., Samanta, A., VanHorn, K., Murty, V.L.N. & Słomiany, A. (1989) Campylobacter pylon colonization fac­tor shows specificity for lactosylceramide sul­fate and ganglioside GM3. Biochem. Int. 19, 929-936.
• 12. Toshihito, S., Natomi, H., Zhao. W., Okuzumi, K., Sugano, K., Iwamori, M. & Nagai, Y. (1991) Identification of glycolipid receptors for Heli­cobacter pylori by TLC-immunostaining. FEBS Lett. 282, 385-387.
• 13. Evans, D.G. & Evans, D.J., Jr. (1995) Adhe­sion properties of Helicobacter pylori. Methods Enzymol. 253, 336-360.
• 14. Miller-Podraza, H., Abul Milh, M., Bergstrom, J. & Karlsson, K.-A. (1996) Recognition of gly- coconjugates by Helicobacter pylori: An appar­ently high-affinity binding of human polygly­cosylceramides, a second sialic acid-based specificity. Glycoconjugate J. 13, 453-460.
• 15. Miller-Podraza, H., Bergstrôm, J., Milh Abul, M. & Karlsson, K.-A. (1997) Recognition of gly- coconjugates by Helicobacter pylori. Compari­son of two sialic acid-dependent specificities based on haemagglutination and binding to human erythrocyte glycoconjugates. Glycocon- jugateJ. 14,467-471.
• 16. Miller-Podraza, H., Milh Abul, M., Teneberg, S. & Karlsson, K.-A. (1997) Binding of Helico­bacter pylori to sialic acid-containing glycolip- ids of various origins separated on thin-layer chromatograms. Infect. Jmmun. 65, 2480- 2482.
• 17. Teneberg, S., Miller-Podraza, H., Lampert, H.C., Evans, D.J., Jr., Evans, D.G. Danielsson, D. & Karlsson, K.-A. (1997) Carbohydrate binding specificity of the neutrophil-activating protein of Helicobacter pylori. J. Biol. Chem. 272, 19067-19071.
• 18. Karlsson, K.-A. (1987) Preparation of total nonacid glycolipids for overlay analysis of re­ceptors for bacteria and viruses and for other studies. Methods Enzymol 138, 212-220.
• 19. Miller-Podraza, H., Andersson, C. & Karlsson, K.-A. (1993) New method for the isolation of polyglycosylceramides from human erythro­cyte membranes. Biochim. Biophys. Acta 1168, 330-339.
• 20. Veh, R.W., Corfield, A.P., Sander. M. & Schauer, R. (1977) Neuraminic acid-specific modification and tritium labelling of ganglio- sides. Biochim. Biophys. Acta 486, 145-160.
• 21. Lanne, B., Uggla, L., Stenhagen, G. & Karls­son, K.-A. (1995) Enhanced binding of entero­toxigenic Escherichia coli K99 to amide deriva­tives of the receptor ganglioside NeuGc-GM3. Biochemistry 34, 1845-1850.
• 22. Matrosovich, M., Miller-Podraza, H., Tene­berg, S., Robertson, J. & Karlsson, K.-A. (1996) Influenza viruses display high-affinity binding to human polyglycosylceramides rep­resented on solid-phase assay surface. Virology 223, 413-416.
• 23. Miller-Podraza, H., Stenhagen, G., Larsson, T., Andersson, C. & Karlsson, K.-A. (1997) Screening for the presence of polyglycosylce­ramides in various tissues: Partial characteri­zation of blood group-active complex gly- cosphingolipids of rabbit and dog small intes­tines. Glycoconjugate J. 14, 231-239.
• 24. Evans, D.J., Jr., Evans. D.G., Takemura, T., Nakano, H., Lampert, H.C., Graham, D.Y., Granger, D.N. & Kvietys, P.R. (1995) Charac­terization of a Helicobacter pylori neutrophil- activating protein. Infect. Immun. 63, 2213- 2220.
• 25. Nakamura, K. & Handa, S. (1986) Biochemical properties of iV-methylamides of sialic acids in gangliosides. J. Biochem. 99, 219-226.
• 26. Handa, S. & Nakamura, K. (1984) Modifica­tion of sialic acid carboxyl group of ganglio­side. J. Biochem. (Tokyo) 95, 1323-1329.
• 27. Rogers, G.N. & D'Souza, B.L. (1989) Receptor binding properties of human and animal HI influenza virus isolates. Virology 173, 317- 322.
• 28. Matrosovich, M.N., Gambaryan, A.S., Tene­berg, S., Piskarev, V.E., Yamnikova, S.S. Lvov, D.K., Robertson, J.S. & Karlsson, K.-A (1997) Avian influenza viruses differ from hu man viruses by recognition of sialyloligosac charides and gangliosides and by a higher con servation of the HA receptor-binding site. Vi rology 233, 224-234.
• 29. Kelm, S., Paulson, J.C., Rose, U., Brossmer, R., Schmid, W., Bandgar, B.P., Schreiner, E., Hartmann, M. & Zbiral, E. (1992) Use of sialic acid analogues to define functional groups in­volved in binding to the influenza virus hemag­glutinin. Eur. J. Biochem. 205, 147-153.
• 30. Matrosovich, M.N., Gambaryan, A.S., Tuzi- kov, A.B., Byramova, N.E., Mochalova, L.V., Golbraikh, A.A., Shenderovich, M.D., Finne, J. & Bovin, N.V. (1993) Probing of the receptor-binding sites of the Hi and H3 influ­enza A and influenza B virus hemagglutinins by synthetic and natural sialosides. Virology 196, 111-121.
• 31. Wadström, T. (1995) An update on Helicobac­ter pylon. Cut. Upin. Gastroenterol 11, 69- 75.
• 32. Nedrud, J.G. & Czinn. S.J. (1996) An update on Helicobacter pylori. Curr. Opin. Gastroen­terol. 12. 62-67.
• 33. Goldstone, A.R., Quirke, P. & Dixon, M.F. (1996) Helicobacter pylori infection and gastric cancer. J. Pathol. 179, 129-137.
• 34. Simon, P.M., Goode, P.L., Mobasseri, A. & Zopf, D. (1997) Inhibition of Helicobacter pylori binding to gastrointestinal epithelial cells by sialic acid-containing oligosaccharides. Infect. Immun. 65, 750-757.
• 35. Evans, D.G., Evans, D.J., Jr.. Moulds, J.J. & Graham, D.Y. (1988) N-Acetylneuraminyl- lactose-binding fibrillar hemagglutinin of Campylobacter pylori: A putative colonization factor antigen. Infect. Immun. 56,2896-2906.
• 36. Lelwala-Guruge, J., Ljungh, A. & Wadström, T. (1992.) Haemagglutination patterns of Heli­cobacter pylori. AI'MIS 100, 908-913.
• 37. Hirmo, S., Keim, S., Schauer, R., Nilsson, B. & Wadström, T. (1996) Adhesion of Helicobacter pylori strains to a-2,3-linkcd sialic acids. Glyco- conjugate J. 13, 1005-1011.
• 38. Koscielak, J., Miller-Podraza, H., Krauze. R. & Piasek, A. (1976) Isolation and characteriza­tion of poly(glycosyl)ceramides (megalogly- colipids) with A, H and I blood-group activi­ties. Eur. J. Biochem 71, 9-18.
• 39. Koscielak, J.. Zdebska, E., Wilczyńska, Z., Miller-Podraza, H. & Dzierzkowa-Borodej, W. (1979) Immunochemistry of Ii-active gly- cosphingolipids of erythrocytes. Eur. J. Bio­chem 96. 331-337
• 40. Zdebska, E., Krauze. R. & Koscielak, J. (1983) Structure and blood group I activity of poly(glycosyl)ceramidcs. Carbohydrate Res. 120, 113-130.
• 41. Loomes, L.M., Uemura, K-i., Childs, R.A., Paulson, J.C., Rogers, G.N., Scudder, P.R., Mi­chalski, J.-C., Hounsell, E.F., Taylor-Robinson, D. & Feizi, T. (1984) Erythrocyte receptors for Mycoplasma pneumoniae are sialylated oligo­saccharides of Ii antigen type. Nature 307, 560-563.
• 42. Liukkonen, J.f Haataja, S., Tikkanen, K., Keim, S. & Finne, J. (1992) Identification of N- acetylneuraminyl#2-3poly-iV-acetyllactosamine glycans as the receptors of sialic-acid-binding Streptococcus suis strains. J. Biol Chem. 267, 21105-21111.