Studies on the specificity and sensitivity of the influenza C virus binding assay for 9-O-acetylated sialic acids and its application to human melanomas

Journal of Biochemistry

Volumn 127, Issue 6, 2000, Pages 1021-1031

  Hubl, Ulrike ^a,b   Ishida, Hideharu ^c   Kiso, Makoto ^c   Hasegawa, Akira ^c   Schauer, Roland ^b  

^a CALLAGHAN INNOVATION   (New Zealand)

^b UNIVERSITY OF KIEL   (Germany)

^c GIFU UNIVERSITY   (Japan)

Author keywords

9 O acetylated Neu5Ac; Gangliosides; Influenza C virus; Melanoma; Overlay assay; Sialic acid analogues; Solid phase assay

Indexed keywords

GANGLIOSIDE; GLYCOPROTEIN; NEURAMINIC ACID DERIVATIVE; SIALIC ACID;

ACCURACY; ACETYLATION; ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN TISSUE; INFLUENZA VIRUS; MELANOMA; MOLECULAR RECOGNITION; NONHUMAN;

HUMAN INFLUENZA VIRUS; INFLUENZA C VIRUS; INFLUENZA VIRUS;

EID: 0033920406     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/oxfordjournals.jbchem.a022693     Document Type: Article

References (64)

1. Svennerholm, L. (1963) Chromatographic separation of human brain gangliosides. J. Neurochem. 10, 613-623
2. Schauer, R. (1997) Origin and biological role of the great chemical diversity of natural sialic acids. Trends Glycosci. Glycotechnol. 9, 315-330
3. Schauer, R. and Kamerling, J.P. (1997) Chemistry, biochemistry and biology of sialic acids in Glycoproteins II (Montreuil, J., Vliegenthart, J.F.G., and Schachter, H., eds.) pp. 243-402, Elsevier, Amsterdam
4. Vandamme-Feldhaus, V. and Schauer, R. (1998) Characterization of the enzymatic 7-O-acetylation of sialic acids and evidence for enzymatic O-acetyl migration from C-7 to C-9 in bovine submandibular gland. J. Biochem. 124, 111-121
5. Schauer, R. (1985) Sialic acids and their role as biological masks. Trends Biochem. Sci. 10, 357-360
6. Varki, A. (1992) Diversity in the sialic acids. Glycobiology 1, 25-40
7. Schauer, R., Kelm, S., Reuter, G., Roggentin, P., and Shaw, L. (1995) Chemistry and biology of sialic acid in Biology of the Sialic Acids (Rosenberg, A. ed.) pp. 7-67, Plenum Press, New York
8. Kelm, S. and Schauer, R. (1997) Sialic acids in molecular and cellular interactionsin in International Review of Cytology (Jeon, K.W. and Jarvik, J.W., eds.) Vol. 175, pp. 137-240, Academic Press, San Diego
9. Schauer, R. (1982) Chemistry, metabolism and biological functions of sialic acids. Adv. Carbohydr. Chem. Biochem. 40, 131-234
10. Corfield, A.P., Sander-Wewer, M., Veh, R.W., Wember, M., and Schauer, R. (1986) The action of sialidases on substrates containing O-acetylated sialic acids. Biol. Chem. Hoppe-Seyler 367, 433-439
11. Rogers, G.N., Herrler, G., Paulson, J.C., and Henk, H.-D. (1986) Influenza C virus uses 9-O-acetyl-N-acetylneuraminic acids as a high affinity receptor determinant for attachment to cells. J. Biol. Chem. 261, 5947-5951
12. Vlasak, R., Luytjes, W., Spaan, W., and Palese, P. (1988) Human and bovine coronaviruses recognize sialic acid-containing receptors similar to those of influenza C virus. Proc. Natl. Acad. Sci. USA 85, 4526-4529
13. Ørskov, F., Ørskov, L., Sutton, A., Schneerson, R., Lin, W., Egan, W., Hoff, G., and Robbins, J. (1979) Form variation in E. coli K1: determined by O-acetylation of the capsular polysaccharide. Exp. Med. 149, 669-685
14. Shi, W.-X., Chammas, R., Varki, N.M., Powell, L., and Varki, A. (1996) Sialic acid 9-O-acetylation on murine erythroleukemia cells affects complement activation, binding to I-type lectins, and tissue homing. J. Biol. Chem. 271, 31526-31532
15. Herrler, G., Reuter, G., Rott, R., Klenk, H.-D., and Schauer, R. (1987) N-Acetyl-9-O-acetylneuraminic acid, the receptor determinant for influenza C virus, is a differentiation marker on chicken erythrocytes. Biol. Chem. Hoppe-Seyler 368, 451-454
16. Mendez-Otero, R. and Constantine-Patone, M. (1990) Granule cell induction of 9-O-acetyl gangliosides on cerebellar glia in microcultures. Dev. Biol. 138, 400-409
17. Cheresh, D.A., Varki, A.P., Varki, N.M., Stallcup, W.B., Levine, J., and Reisfeld, R.A. (1984) A monoclonal antibody recognizes an O-acetylated sialic acid in a human melanoma-associated ganglioside. J. Biol. Chem. 259, 7453-7459
18. Paller, A.S., Arnsmeier, S.L., Robinson, J.K., and Bremer, E.G. (1992) Alteration in keratinocyte ganglioside content in basal cell carcinomas. J. Invest. Dermatol. 98, 226-232
19. Hubl, U., Fahr, C., Proksch, E., and Schauer, R. (1997) Nachweis O-acetylierter Ganglioside mit Influenza C Viren in Melanomen und Basaliomen. Z. Hautkrankheiten 72, 701
20. Araujo, H., Menezes, M., and Mendez-Otero, R. (1997) Blockage of 9-O-acetyl gangliosides induces microtubule depolymerization in growth cones and neurites. Eur. J. Cell Biol. 72, 202-213
21. Yamamoto, M., Schwarting, G.A., and Crandall, J.G. (1994) Altered 9-O-acetylation of disialogangliosides in cerebellar Purkinje cells of the nervous mutant mouse. Brain Res. 662, 223-232
22. Schauer, R (1987) Analysis of sialic acids. Methods Enzymol. 138, 132-161
23. Shukla, A.K. and Schauer, R. (1982) Analysis of N,O-acylated neuraminic acids by high-performance liquid anion-exchange chromatography. J. Chromatogr. 244, 81-89
24. Hara, S., Takemori, Y., Yamaguchi, M., Nakamura, M., and Ohkura, Y. (1985) Determination of α-keto acids in serum and urine by high performance liquid chromatography with fluorescence detection. J. Chromatogr. 344, 33-39
25. Hara, S., Yamaguchi, M., Takemori, Y., Furuhata, K., Ogura, H., and Nakamura, M. (1989) Determination of mono-O-acetylated N-acetylneuraminic acids in human and rat sera by fluorimetric high-performance liquid chromatography. Anal. Biochem. 179, 162-166
26. Reuter, G. and Schauer, R. (1986) Comparison of electron and chemical ionization mass spectrometry of sialic acids. Anal. Biochem. 157, 39-46
27. Kamerling, J.P., Makovitzky, J., Schauer, R., Vliegenthart, J.F.G., and Wember, M. (1982) The nature of sialic acids in human lymphocytes. Biochim. Biophys. Acta 714, 351-355
28. Kamerling, J.P., Schauer, R., Shukla, A.K., Stoll, S., van Halbeek, H., and Vliegenthart, J.F.G. (1987) Migration of O-acetyl groups in N,O-acetylneuraminic acids. Eur. J. Biochem. 162, 601-607
29. Reuter, G. and Schauer, R. (1994) Determination of sialic acids. Methods Enzymol. 230, 168-199
30. Herrler, G. and Klenk, H.-D. (1985) Neuraminic acid is involved in the binding of influenza C virus to erythrocytes. Virology 141, 144-147
31. Herrler, G., Rott, R., Klenk, H.-D., Müller, H.-R, Shukla, A.K., and Schauer, R. (1985) The receptor-destroying enzyme of influenza C virus is neuraminate-O-acetylesterase. EMBO J. 4, 1503-1506
32. Schauer, R., Reuter, G., Stoll, S., Posadas del Rio, F., Herrler, G., and Klenk, H.-D. (1988) Isolation and characterization of sialate-9(4)-O-acetylesterase from influenza C virus. Biol. Chem. Hoppe Seyler 369, 1121-1130
33. Zimmer, G., Reuter, G., and Schauer, R. (1992) Use of influenza C virus for detection of 9-O-acetylated sialic acids on immobilized glycoconjugates by esterase activity Eur. J. Biochem. 204, 209-215
34. Roy, R., Andersson, F.O., Harms, G., Kelm, S., and Schauer, R. (1992) Synthesis of esterase-resistant 9-O-acetylated polysialosides as inhibitors of influenza C virus hemagglutinin. Angew. Chem. Int. Ed. Engl. 31, 1478-1481
35. Harms, G., Reuter, G., Corfield, A.P., and Schauer, R. (1996) Binding specificity of influenza C-virus to variably O-acetylated glycoconjugates and its use for histochemical detection of N-acetyl-9-O-acetylneuraminic acid in mammalian tissues. Glycoconjugate J. 13, 621-630
36. Klein, A., Krishna, M., Varki, N.M., and Varki, A. (1994) 9-O-Acetylated sialic acids have widespread but selective expression: Analysis using chimeric dual-function derived from influenza C hemagglutinin-esterase. Proc. Natl. Acad. Sci. USA 91, 7782-7786
37. Ogura, H., Furuhata, K., Sato, S., Anazawa, K., Itoh, M., and Shitori, Y. (1987) Synthesis of 9-O-acetyl and 4-O-acetyl-sialic acids. Carbohydr. Res. 167, 77-86
38. Sander, M., Veh, R.W., and Schauer, R. (1979) Partial purification and further characterization of glycoprotein-specific neuraminidase from horse liver in Glycoconjugates, Proc. 5th Int. Symp. (Schauer, R., Boer, P., Buddecke, E., Kramer, M.F., Vliegenthart, J.F.G., and Wiegandt, H., eds.) pp. 358-359, Thieme-Verlag, Stuttgart
39. Ledeen, R.W. and Yu, R.K. (1982) Gangliosides: Structure, isolation, and analysis. Methods Enzymol. 83, 139-191
40. Müthing, J. and Unland, F. (1994) Improved separation of isomeric gangliosides by anion-exchange high-performance liquid chromatography. J. Chromatogr. B. Biomed. Appl. 658, 39-45
41. Hasegawa, A. and Kiso, M. (1992) Systematic synthesis of gangliosides toward the elucidation and biomedical application of their biological functions in Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry (Ogura, H., Hasegawa, A., and Suami, T., eds.) pp. 243-266, Verlag Chemie, Weinheim
42. Crocker, P.R., Kelm, S., Dubois, C., Martin, B., McWilliam, A.S., Shotton, D.M., Paulson, J.C., and Gordon, S. (1991) Purification and properties of sialoadhesins, a sialic-binding receptor or murine tissues macrophages. EMBO J. 10, 1661-1669
43. Mawhinney, T.P. and Chance, D.L. (1994) Hydrolysis of sialic acids and O-acetylated sialic acids with propionic acid. Anal. Biochem. 223, 164-167
44. Reuter, G., Pfeil, R., Stoll, S., Schauer, R., Kamerling, J.P., Versluis, C., and Vliegenthart, J.F.G. (1983) Identification of new sialic acids derived from glycoprotein of bovine submandibular gland. Eur. J. Biochem. 134, 139-143
45. Laemmli, U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 681-685
46. Nielsen, S. and Reynolds, J.A. (1978) Measurements of molecular weights by gel electrophoresis. Methods Enzymol. 48, 3-10
47. Towbin, H., Staehelin, T., and Gordon, J. (1979) Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets. Procedure and some applications. Proc. Natl. Acad. Sci. USA 76, 4350-1354
48. 2. J. Biol. Chem. 267, 16200-16211
49. Stickl, H., Huber, W., Faillard, H., Becker, A., Holzhauser, R., and Graeff, H. (1991) Veränderung der Acylneuraminsäuregehalte auf T-Lymphozyten und im Plasma bei Erkrankung an Mamma-Karzinom. Klin. Wochenschr. 69, 5-9
50. Muchmore, E.A. and Varki, A. (1987) Selective inactivation of influenza C esterase: A probe for detection of 9-O-acetylated sialic acids. Science 236, 1293-1295
51. Manuguerra, J.-C., DuBois, C., and Hannoun, C. (1991) Analytical detection of 9(4)-O-acetylated sialoglycoproteins and gangliosides using influenza C virus. Anal. Biochem. 194, 425-432
52. Zimmer, G., Suguri, T., Yu, R.K., Schauer, R., and Herrler, G. (1994) Modification of sialic acids by 9-O-acetylation is detected in human leucocytes using the lectin property of influenza C virus. Glycobiology 4, 343-349
53. Manzi, A.E., Sjoberg, E.R., Diaz, S., and Varki, A. (1990) Biosynthesis and turnover of O-acetyl and N-acetyl groups in the gangliosides of human melanoma cells. J. Biol. Chem. 265, 13091-13103
54. Ravindranath, M.H., Higa, H.H., Cooper, E.L., and Paulson, J. (1985) Purification and characterization of an O-acetylsialic acid-specific lectin from a marine crab Cancer antennarius. J. Biol. Chem. 260, 8850-8856
55. Ravindranath, M.H., Paulson, J.C., and Irie, R.F. (1988) Human melanoma antigen O-acetylated ganglioside GD3 is recognized by Cancer antennarius lectin. J. Biol. Chem. 263, 2079-2086
56. Corti, M. Cantù, L., and Sonnino, S. (1987) Fundamentals of physico-chemical properties of gangliosides in solution in Gangliosides and Modulation of Neuronal Functions (Rahmann, H., ed.) Nato ASI Series, Vol. H7, pp. 101-118, Springer-Verlag Berlin, Heidelberg
57. 1-acid glycoprotein. Biochim. Biophys. Acta 492, 291-302
58. 1H-NMR spectroscopy and permethylation analysis. Biochemistry 17, 5206-5214
59. Portoukalian, J., Zwingelstein, G., and Dore, J.F. (1979) Lipid composition of human malignant melanoma tumors and various levels of malignant growth. Eur. J. Biochem. 94, 19-23
60. Heidenheim, M., Hansen, E.R., and Baadsgaard, O. (1995) CDw60, which identifies the acetylated form of Gni gangliosides, is strongly expressed in human basal cell carcinoma. Br J. Dermatol. 133, 392-397
61. Ariga, T., Blaine, G.M., Yoshino, H., Dawson, G., Kanda, T., Zeng, G.C., Kasama, T., Kushi, Y., and Yu, R.K. (1995) Glycosphingolipid composition of murine neuroblastoma cells: O-acetylesterase gene downregulates the expression of O-acetylated GD3. Biochemistry 34, 11500-11507
62. Marquina, G., Waki, H., Fernandez, L.E., Kon, K., Carr, A., Valiente, O., Perez, R., and Ando, S. (1996) Gangliosides expressed in human breast cancer. Cancer Res. 56, 5165-5171
63. Birklé, S., Ren, S., Slominski, A., Zeng, G., Gao, L., and Yu, R.K. (1999) Down-regulation of the expression of O-acetyl-GD3 by the O-acetylesterase cDNA in hamster melanoma cells: effects on cellular proliferation, differentiation, and melanogenesis. J. Neurochem. 72, 954-961
64. Corfield, A.P., Myerscough, N., Warren, B.F., Durdey, P., Paraskeva, C., and Schauer, R. (1999) Reduction of sialic acid O-acetylation in human colonic mucins in the adenoma-carcinoma sequence. Glycoconjugate J. 16, 307-317