Massive in vitro synthesis of tagged oligosaccharides in 1-benzyl-2-acetamido-2-deoxy-α-D-galactopyranoside treated HT-29 cells

Glycobiology

Volumn 10, Issue 6, 2000, Pages 565-575

  Zanetta, Jean Pierre ^c   Gouyer, Valérie ^a   Maes, Emmanuel ^c   Pons, Alexandre ^c   Hemon, Brigitte ^a   Zweibaum, Alain ^b   Delannoy, Philippe ^c   Huet, Guillemette ^a  

^a INSERM   (France)

^b CENTRE DE RECHERCHE DES CORDELIERS   (France)

^c UNIV LILLE   (France)

Author keywords

Aryl N acetyl D galactosaminide; HT 29; Oligosaccharide; Onco fetal

Indexed keywords

MUCIN; OLIGOSACCHARIDE; ORCINOL; PYRANOSIDE; RESORCINOL; SIALIC ACID;

ARTICLE; BIOSYNTHESIS; BRUSH BORDER; CELL STRAIN CACO 2; CONTROLLED STUDY; CULTURE MEDIUM; HUMAN; HUMAN CELL; INTESTINE CELL; PRIORITY JOURNAL;

EID: 0034046830     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/10.6.565     Document Type: Article

References (33)

1. Brockhausen, I. (1995) In Montreuil, J., Vliegenthart, J.F.G. and Schachter, H. (eds.), Glycoproteins. New Comprehensive Biochemistry, Vol. 29a. Elsevier Science B.V., Amsterdam, pp. 201-259.
2. Byrd, J.C., Dahiya, R., Huang, J. and Kim, Y.S. (1995) Inhibition of mucin synthesis by benzyl-α-GalNAc in KATO III gastric cancer and Caco-2 colon cancer cells. Eur. J. Cancer, 9, 1498-1505.
3. Ciucanu, I. and Kerek, F. (1984) A single and rapid method for the permethylation of cabohydrates. Carbohydr. Res., 131, 209-217.
4. Delannoy, P., Kim, I., Emery, N., De Bolos, C., Verbert, A., Degand, P. and Huet, G. (1996) Benzyl-N-acetyl-α-D-galactosaminide inhibits the sialylation and the secretion of mucins by a mucin secreting HT-29 cell subpopulation. Glycoconj. J., 13, 717-726.
5. Duronio, V., Jacobs, S., Romero, P.A. and Herscovics, A. (1988) Effects of inhibitors of N-linked oligosaccharide processing on the biosynthesis and function of insulin and insulin-like growth factor-I receptors. J. Biol. Chem., 263, 5436-5445.
6. Elbein, A.D., Pan, Y.T., Solf, R. and Vosbeck, K. (1983) Effect of swainsonine, an inhibitor of glycoprotein processing, on cultured mammalian cells. J. Cell Physiol., 115, 265-275.
7. Elbein, A.D., Tropea, J.E., Mitchell, M. and Kaushal, G.P. (1990) Kifunensine, a potent inhibitor of the glycoprotein processing mannosidase I. J. Biol. Chem., 265, 15599-15605.
8. Green, R.F., Meiss, H.K. and Rodriguez-Boulan, E. (1981) Glycosylation does not determine segregation of viral envelope proteins in the plasma membrane of epithelial cells. J. Cell Biol., 89, 230-239.
9. Hennebicq-Reig, S., Lesuffleur, T., Capon, C., de Bolos, C., Kim, I., Moreau, O., Richet, C., Hémon, B., Recchi, M.-A., Maës, E., Aubert, J.P., Real, F.X., Zweibam, A., Delannoy, P., Degand, P. and Huet, G. (1998) Permanent exposure of mucin-secreting HT-29 cells to benzyl-N-acetyl-α-d-galactosaminide induces abnormal O-glycosylation of mucins and inhibits constitutive and stimulated MUC5AC secretion. Biochem. J., 334, 283-295.
10. Hounsell, E.F., Lawson, A.M., Feeney, J., Gooi, C., Pickering, N.J., Stoll, M.S., Lui, S.C. and Feizi, T. (1985) Structural analysis of the O-glycosidically linked core-region oligosaccharides of human meconium glycoproteins which express oncofoetal antigens. Eur. J. Biochem., 148, 367-377.
11. Huang, J., Byrd, J.C., Yoor, W.H. and Kim, Y.S. (1992) Effect of benzyl-alpha-GalNAc, an inhibitor of mucin glycosylation, on cancer-associated antigens in human colon cancer cells. Oncol. Res., 4, 507-515.
12. Huet, G., Hennebicq-Reig, S., de Bolos, C., Ulloa, F., Lesuffleur, T., Barbat, A., Carrière, V., Kim, I., Real, F.X., Delannoy, P. and Zweibaum, A. (1998) GalNAc-α-O-benzyl inhibits NeuAcα2-3 glycosylation and blocks the intracellular transport of apical glycoproteins and mucus in differentiated HT-29 cells. J. Cell Biol., 15, 1311-1322.
13. Huet, G., Kim, I., de Bolos, J.M., Lo-Guidice, M., Moreau, O., Hemon, B., Richet, C., Delannoy, P., Real, F.X. and Degand, P. (1995) Characterization of mucins and proteoglycans synthesized by a mucin-secreting HT-29 cell subpopulation. J. Cell Science, 108, 1275-1285.
14. Kornfeld, R. and Kornfeld, S. (1985). Assembly of asparagine-linked oligosaccharides. Annu. Rev. Biochem., 54, 631-664.
15. Kuan, S.F., Byrd, J.C., Basbaum, C. and Kim, Y.S. (1989) Inhibition of mucin glycosylation by aryl-N-acetyl-α-galactosaminides in human colon cancer cells. J. Biol. Chem., 264, 19271-19277.
16. Kudo, T., Ikehara, Y., Togayachi, A., Kaneko, M., Hiraga, T., Sasaki, K. and Narimatsu, H. (1998) Expression cloning and characterization of a novel murine α1. 3-fucosyltransferase, mFuc-TIX, that synthesizes the Lewis x (CD15) epitope in brain and kidney. J. Biol. Chem., 273, 26729-26738.
17. Lesuffleur, T., Barbat, A., Dussaulx, E. and Zweibaum, A. (1990) Growth adaptation to methotrexate of HT-29 human colon carcinoma cells is associated with their ability to differentiate into columnar absorptive and mucussecreting cells. Cancer Res., 50, 6334-6343.
18. Lesuffleur, T., Kornowski, A., Augeron, C., Dussaulx, E., Barbat, A., Laboisse, C. and Zweibaum, A. (1991) Increased growth adaptability to 5-fluorouracil and methotrexate of HT-29 sub-populations selected for their commitment to differentiation. Int. J. Cancer, 49, 731-737.
19. Majuri, M.L., Niemela, R., Tiisala, S., Renkonen, O. and Renkonen, R. (1995) Expression and function of α 2,3-sialyl- and α 1,3/1,4-fucosyltransferases in colon adenocarcinoma cell lines: role in synthesis of E-selectin counter-receptors. Int. J. Cancer, 63, 551-9.
20. Michalski, J.-C. and Strecker, G. (1995) Methylation analysis of carbohydrate. In Verbert, A. (ed.), Methods on Glycoconjugates. Harwood Academic, Chur, Switzerland, pp. 93-100.
21. Mollicone, R., Candelier, J.J., Mennesson, B., Couillin, P., Venot, A.P. and Oriol, R. (1992). Five specificity patterns of (1-3)-α-L-fucosyltransferase activity defined by use of synthetic oligosaccharide acceptors. Differential expression of the enzymes during human embryonic development and in adult tissues. Carbohydr. Res., 228, 265-276.
22. Natsuka, S., Gersten, K.M., Zenita, K., Kannagi, R. and Lowe, J.B. (1994) Molecular cloning of a cDNA encoding a novel human leukocyte α-1,3-fucosyltransferase capable of synthesizing the sialyl Lewis x determinant. J. Biol. Chem., 269, 16789-16794.
23. Papac, D.I., Wong, A. and Jones, A.J. (1996) Analysis of acidic oligosaccharides and glycopeptides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal. Chem., 68, 3215-3223.
24. Pinto, M., Robine-Léon, S., Appay, M.D., Kedinger, M., Triadou, N., Dussaulx, E., Lacroix, B., Simon-Assmann, P., Haffen, K., Fogh, J. and Zweibaum, A. (1983) Enterocytic differentiation of cultured human colon cancer cells by replacement of glucose by galactose in the medium. Biol. Cell., 47, 323-330.
25. Powell, A.K. and Harvey, D.J. (1996) Stabilization of sialic acids in N-linked oligosaccharides and gangliosides for analysis by positive ion matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun. Mass. Spectrom., 10, 1027-1032.
26. Sasaki, K., Kurata, K., Funayama, K., Nagata, M., Watanabe, E., Ohta, S., Hanai, N. and Nishi, T. (1994) Expression cloning of a novel α1,3-fucosyltransferase that is involved in biosynthesis of the sialyl Lewis x carbohydrate determinants in leukocytes. J. Biol. Chem., 269, 14730-14737.
27. Schachter, H. and Brockhausen, I. (1992) The biosynthesis of serine (threonine)-N-acetylgalactosamine-linked carbohydrate moities. In Allen, H.J. and Kisialus, E.C. (eds.), Glycoconjugates: Composition, Structure and Function. Marcel Dekker, New York, pp. 269-332.
28. Scheiffele, P., Peranen, J. and Simons, K. (1995) N-Glycans as apical sorting signals in epithelial cells. Nature, 378, 96-98.
29. Sjoberg, E.R., Kitagawa, H., Glushka, J., van Halbeek, H. and Paulson, J.C. (1996) Molecular cloning of a developmentally regulated N-acetylgalactosamine α2,6-sialyltransferase specific for sialylated glycoconjugates. J. Biol. Chem., 271, 7450-7459.
30. Sobue, M., Habuchi, H., Ito, K., Yonekura, H., Oguri, K., Sakurai, K., Kamohara, S., Ueno, Y., Noyori, R. and Suzuki, S. (1987) β-D-xylosides and their analogues as artificial initiators of glycosaminoglycan chain synthesis. Aglycone-related variation in their effectiveness in vitro and in ovo. Biochem. J., 241, 591-601.
31. Yazawa, S., Abbas, S.A., Madiyalakan, R., Barlow, J.J. and Matta, K.L. (1986) N-Acetyl-β-D-glucosaminyltransferases related to the synthesis of mucin-type glycoproteins in human ovarian tissue. Carbohydr. Res., 149, 241-252.
32. Zanetta, J.-P., Vitiello, F. and Vincendon, G. (1980) Gangliosides from rat cerebellum: demonstration of considerable heterogeneity using a new solvent for thin layer chromatography. Lipids, 15, 1055-1061.
33. Zanetta, J.-P., Timmerman, P. and Leroy, Y. (1999) Gas-liquid chromatography of the heptafluorobutyrate derivatives of the O-methyl-glycosides on capillary columns: a method for the quantitative determination of the monosaccharide composition of glycoproteins and glycolipids. Glycobiology, 9, 255-266.