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Chemical Compound Review

SLea     (2S,4S,5R,6R)-5-acetamido-2- [(2S,3R,4S,5S...

Synonyms: HMDB06579, Sialyl Lea tri, Sialyl Lewis a, FT-0674576, AC1LD8E9, ...
 
 
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Disease relevance of Sialyl Lewis a

 

High impact information on Sialyl Lewis a

 

Chemical compound and disease context of Sialyl Lewis a

 

Biological context of Sialyl Lewis a

 

Anatomical context of Sialyl Lewis a

  • Two mucin-type glycoproteins detected by the monoclonal antibody C50, which reacts with the carcinoma-associated sialyl-Lewis a and sialyl-lactotetraose epitopes, were found in secreted and solubilized materials from the colon carcinoma cell line COLO 205 [16].
  • Influence of Lewis alpha1-3/4-L-fucosyltransferase (FUT3) gene mutations on enzyme activity, erythrocyte phenotyping, and circulating tumor marker sialyl-Lewis a levels [17].
  • Like BBAI, L-CanAg can inhibit leukocyte HL-60 cell adhesion to E-selectin-transfected COS-I cells, and this inhibition can be blocked by a F(ab')2 fragment directed against the sialyl-Lewis a epitope [18].
  • Secreted MUC1 mucins lacking their cytoplasmic part and carrying sialyl-Lewis a and x epitopes from a tumor cell line and sera of colon carcinoma patients can inhibit HL-60 leukocyte adhesion to E-selectin-expressing endothelial cells [19].
  • These findings suggest that some sialylglycoconjugates, perhaps sialyl Lewis A in particular, play an important role in the initial interaction of RAW117-H10 cells with the hepatic endothelium, leading to metastasis [20].
 

Associations of Sialyl Lewis a with other chemical compounds

  • To investigate the role of such mechanisms in cutaneous tumors, whole skin biopsies were examined immunohistochemically for a variety of selectin ligands including sialyl-Lewis-X, sialyl-Lewis-A (S-Le(a)), sulfatides, and CD15 [21].
  • We observed the following: (i) The functional group at the anomeric position of carbohydrates plays an important role during selectin recognition, since sLe(X) and sialyl Lewis-a (sLe(a)) were approximately 5-7-fold poorer inhibitors of L-selectin mediated cell adhesion compared to their methyl glycosides [22].
  • Here we show that biotinylated polyacrylamide-type glycoconjugates which contain sialyl Lewis X (sLex-polymer) or sialyl Lewis A (sLea-polymer) are ligands for E-selectin. sLea-polymer bound E-selectin with higher affinity than sLex-polymer [23].
  • Both the MUC1 and CD43 mucins became sialyl-Lewis a reactive, but after different times as revealed by pulse-chase studies [24].
  • Both glycoproteins carry sialyl-Lewis a epitopes and could bind transfected COS cells expressing E-selectin in a Ca(2+)- and E-selectin-dependent way [25].
 

Gene context of Sialyl Lewis a

 

Analytical, diagnostic and therapeutic context of Sialyl Lewis a

References

  1. Hypoxia induces adhesion molecules on cancer cells: A missing link between Warburg effect and induction of selectin-ligand carbohydrates. Koike, T., Kimura, N., Miyazaki, K., Yabuta, T., Kumamoto, K., Takenoshita, S., Chen, J., Kobayashi, M., Hosokawa, M., Taniguchi, A., Kojima, T., Ishida, N., Kawakita, M., Yamamoto, H., Takematsu, H., Suzuki, A., Kozutsumi, Y., Kannagi, R., Kanangi, R. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  2. Sialyl Lewis X-dependent lung colonization of B16 melanoma cells through a selectin-like endothelial receptor distinct from E- or P-selectin. Zhang, J., Nakayama, J., Ohyama, C., Suzuki, M., Suzuki, A., Fukuda, M., Fukuda, M.N. Cancer Res. (2002) [Pubmed]
  3. Tumor-microenvironment interactions: the fucose-generating FX enzyme controls adhesive properties of colorectal cancer cells. Zipin, A., Israeli-Amit, M., Meshel, T., Sagi-Assif, O., Yron, I., Lifshitz, V., Bacharach, E., Smorodinsky, N.I., Many, A., Czernilofsky, P.A., Morton, D.L., Witz, I.P. Cancer Res. (2004) [Pubmed]
  4. Restoration of alpha(1,2) fucosyltransferase activity decreases adhesive and metastatic properties of human pancreatic cancer cells. Aubert, M., Panicot, L., Crotte, C., Gibier, P., Lombardo, D., Sadoulet, M.O., Mas, E. Cancer Res. (2000) [Pubmed]
  5. Post-translational fate of a mucin-like leukocyte sialoglycoprotein (CD43) aberrantly expressed in a colon carcinoma cell line. Baeckström, D. J. Biol. Chem. (1997) [Pubmed]
  6. Cyclooxygenase-2 activity altered the cell-surface carbohydrate antigens on colon cancer cells and enhanced liver metastasis. Kakiuchi, Y., Tsuji, S., Tsujii, M., Murata, H., Kawai, N., Yasumaru, M., Kimura, A., Komori, M., Irie, T., Miyoshi, E., Sasaki, Y., Hayashi, N., Kawano, S., Hori, M. Cancer Res. (2002) [Pubmed]
  7. Increased expression of UDP-galactose transporter messenger RNA in human colon cancer tissues and its implication in synthesis of Thomsen-Friedenreich antigen and sialyl Lewis A/X determinants. Kumamoto, K., Goto, Y., Sekikawa, K., Takenoshita, S., Ishida, N., Kawakita, M., Kannagi, R. Cancer Res. (2001) [Pubmed]
  8. Contribution of carbohydrate antigens sialyl Lewis A and sialyl Lewis X to adhesion of human cancer cells to vascular endothelium. Takada, A., Ohmori, K., Yoneda, T., Tsuyuoka, K., Hasegawa, A., Kiso, M., Kannagi, R. Cancer Res. (1993) [Pubmed]
  9. beta 1,3-Galactosyltransferase beta 3Gal-T5 acts on the GlcNAcbeta 1-->3Galbeta 1-->4GlcNAcbeta 1-->R sugar chains of carcinoembryonic antigen and other N-linked glycoproteins and is down-regulated in colon adenocarcinomas. Salvini, R., Bardoni, A., Valli, M., Trinchera, M. J. Biol. Chem. (2001) [Pubmed]
  10. The GPI-linked Ly-6 antigen E48 regulates expression levels of the FX enzyme and of E-selectin ligands on head and neck squamous carcinoma cells. Eshel, R., Zanin, A., Sagi-Assif, O., Meshel, T., Smorodinsky, N.I., Dwir, O., Alon, R., Brakenhoff, R., van Dongen, G., Witz, I.P. J. Biol. Chem. (2000) [Pubmed]
  11. Expression of the leukocyte-associated sialoglycoprotein CD43 by a colon carcinoma cell line. Baeckström, D., Zhang, K., Asker, N., Rüetschi, U., Ek, M., Hansson, G.C. J. Biol. Chem. (1995) [Pubmed]
  12. Human intestinal M cells display the sialyl Lewis A antigen. Giannasca, P.J., Giannasca, K.T., Leichtner, A.M., Neutra, M.R. Infect. Immun. (1999) [Pubmed]
  13. Phenotypic and genotypic characteristics of aberrant crypt foci in human colorectal mucosa. Nucci, M.R., Robinson, C.R., Longo, P., Campbell, P., Hamilton, S.R. Hum. Pathol. (1997) [Pubmed]
  14. Expression of specific markers and particle transport in a new human intestinal M-cell model. Gullberg, E., Leonard, M., Karlsson, J., Hopkins, A.M., Brayden, D., Baird, A.W., Artursson, P. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  15. Tissue distribution of 2-3 and 2-6 sialyl Lewis A antigens and significance of the ratio of two antigens for the differential diagnosis of malignant and benign disorders of the digestive tract. Itai, S., Nishikata, J., Yoneda, T., Ohmori, K., Yamabe, H., Arii, S., Tobe, T., Kannagi, R. Cancer (1991) [Pubmed]
  16. Purification and characterization of a membrane-bound and a secreted mucin-type glycoprotein carrying the carcinoma-associated sialyl-Lea epitope on distinct core proteins. Baeckström, D., Hansson, G.C., Nilsson, O., Johansson, C., Gendler, S.J., Lindholm, L. J. Biol. Chem. (1991) [Pubmed]
  17. Influence of Lewis alpha1-3/4-L-fucosyltransferase (FUT3) gene mutations on enzyme activity, erythrocyte phenotyping, and circulating tumor marker sialyl-Lewis a levels. Orntoft, T.F., Vestergaard, E.M., Holmes, E., Jakobsen, J.S., Grunnet, N., Mortensen, M., Johnson, P., Bross, P., Gregersen, N., Skorstengaard, K., Jensen, U.B., Bolund, L., Wolf, H. J. Biol. Chem. (1996) [Pubmed]
  18. A secreted mucin carrying sialyl-Lewis a from colon carcinoma cells binds to E-selectin and inhibits HL-60 cell adhesion. Zhang, K., Baeckström, D., Hansson, G.C. Int. J. Cancer (1994) [Pubmed]
  19. Secreted MUC1 mucins lacking their cytoplasmic part and carrying sialyl-Lewis a and x epitopes from a tumor cell line and sera of colon carcinoma patients can inhibit HL-60 leukocyte adhesion to E-selectin-expressing endothelial cells. Zhang, K., Baeckström, D., Brevinge, H., Hansson, G.C. J. Cell. Biochem. (1996) [Pubmed]
  20. Role of sialylglycoconjugate(s) in the initial phase of metastasis of liver-metastatic RAW117 lymphoma cells. Kikkawa, H., Miyamoto, D., Imafuku, H., Koike, C., Suzuki, Y., Okada, S., Tsukada, H., Irimura, T., Oku, N. Jpn. J. Cancer Res. (1998) [Pubmed]
  21. Expression of selectin ligands by cutaneous squamous cell carcinoma. Groves, R.W., Allen, M.H., Ross, E.L., Ahsan, G., Barker, J.N., MacDonald, D.M. Am. J. Pathol. (1993) [Pubmed]
  22. Affinity and kinetics of sialyl Lewis-X and core-2 based oligosaccharides binding to L- and P-selectin. Beauharnois, M.E., Lindquist, K.C., Marathe, D., Vanderslice, P., Xia, J., Matta, K.L., Neelamegham, S. Biochemistry (2005) [Pubmed]
  23. An E-selectin binding assay based on a polyacrylamide-type glycoconjugate. Weitz-Schmidt, G., Stokmaier, D., Scheel, G., Nifant'ev, N.E., Tuzikov, A.B., Bovin, N.V. Anal. Biochem. (1996) [Pubmed]
  24. Tumor cell MUC1 and CD43 are glycosylated differently with sialyl-Lewis a and x epitopes and show variable interactions with E-selectin under physiological flow conditions. Fernandez-Rodriguez, J., Dwir, O., Alon, R., Hansson, G.C. Glycoconj. J. (2001) [Pubmed]
  25. Comparison of sialyl-Lewis a-carrying CD43 and MUC1 mucins secreted from a colon carcinoma cell line for E-selectin binding and inhibition of leukocyte adhesion. Zhang, K., Baeckström, D., Brevinge, H., Hansson, G.C. Tumour Biol. (1997) [Pubmed]
  26. Enhancement of metastatic activity of colon cancer as influenced by expression of cell surface antigens. Okazaki, K., Nakayama, Y., Shibao, K., Hirata, K., Nagata, N., Itoh, H. J. Surg. Res. (1998) [Pubmed]
  27. Modulation of MUC1 and blood group antigen expression in gastric adenocarcinoma cells by cytokines. Grohmann, G.P., Schirmacher, P., Manzke, O., Hanisch, F.G., Dienes, H.P., Baldus, S.E. Cytokine (2003) [Pubmed]
  28. Cloning, expression, and characterization of a novel UDP-galactose:beta-N-acetylglucosamine beta1,3-galactosyltransferase (beta3Gal-T5) responsible for synthesis of type 1 chain in colorectal and pancreatic epithelia and tumor cells derived therefrom. Isshiki, S., Togayachi, A., Kudo, T., Nishihara, S., Watanabe, M., Kubota, T., Kitajima, M., Shiraishi, N., Sasaki, K., Andoh, T., Narimatsu, H. J. Biol. Chem. (1999) [Pubmed]
  29. Distinct sub-populations of carcinoma-associated MUC1 mucins as detected by the monoclonal antibody 9H8 and antibodies against the sialyl-Lewis a and sialyl-Lewis x epitopes in the circulation of breast-cancer patients. Sikut, R., Zhang, K., Baeckström, D., Hansson, G.C. Int. J. Cancer (1996) [Pubmed]
  30. MUC5B glycosylation in human saliva reflects blood group and secretor status. Thomsson, K.A., Schulz, B.L., Packer, N.H., Karlsson, N.G. Glycobiology (2005) [Pubmed]
  31. Detection of ligands for selectins in the oligosaccharide fraction of human milk. Rudloff, S., Stefan, C., Pohlentz, G., Kunz, C. European journal of nutrition. (2002) [Pubmed]
 
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