Traveling for the glycosphingolipid path

Glycoconjugate Journal

Volumn 17, Issue 7-9, 2000, Pages 627-647

  Hakomori, Sen itiroh ^a,b  

^a PACIFIC NORTHWEST RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Carbohydrate carbohydrate interaction; Cell adhesion; Oncogenic transformation; Ontogenic development; Signal transduction; Tumor associated antigen

Indexed keywords

BLOOD GROUP A ANTIGEN; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; GANGLIOSIDE; GLYCOSPHINGOLIPID; GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE; SIALIC ACID DERIVATIVE; TUMOR ANTIGEN;

ANTIGEN DETECTION; CARBOHYDRATE ANALYSIS; CELL DIFFERENTIATION; CELL TRANSFORMATION; EMBRYO; HUMAN; HUMAN CELL; LIPID METABOLISM; ONTOGENY; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION; VACCINATION;

AMINO ACID SEQUENCE; ANIMALS; ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; CARBOHYDRATE SEQUENCE; CELL DIFFERENTIATION; EMBRYONIC AND FETAL DEVELOPMENT; FEMALE; GLYCOPEPTIDES; GLYCOSPHINGOLIPIDS; GLYCOSYLATION; HISTORY, 19TH CENTURY; HISTORY, 20TH CENTURY; HUMANS; MALE; MEMBRANE LIPIDS; MODELS, BIOLOGICAL; MOLECULAR SEQUENCE DATA;

EID: 0034444166     PISSN: 02820080     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011086929064     Document Type: Review

References (193)

1. 1 Thudichum JLW, A treatise on the chemical constitution of the brain. Bailliere, Tindall & Cox, London; German edition published in 1901 under the title 'Die chemische Konstitution des Gehirns des Menschen und der Tiere' (Franz Pieteker, Tubingen, Germany, 1884).
2. 2 Thierfelder H, Klenk E, Die Chemie der Cerebroside und Phosphatide, (Verlag von Julius Springer, Berlin, 1930).
3. 3 Hakomori S, Antigen structure and genetic basis of histo-blood groups A, B, and O: Their changes associated with human cancer, Biochim Biophys Acta 1473, 247-66 (1999).
4. 4 Papirmeister B, Mallette MF, The isolation and some properties of the Forssman hapten from sheep erythrocytes, Arch Biochem Biophys 57, 94-99 (1955).
5. 5 Rapport MM, Graf L, Cancer antigens: How specific should they be? Cancer Res 21, 1225-37 (1961).
6. 6 Rapport MM, Graf L, Immunochemical reactions of lipids, Prog Allergy 13, 273-331 (1969).
7. 7 Yamakawa T, Glycolipids of mammalian red blood cells. In Lipoide: 16 Colloquium der Gesellschaft Physiologische Chemie, edited by Schute E, (Springer-Verlag, Berlin, 1966), pp. 87-111.
8. 8 Yamakawa T, A reflection on the early history of glycosphingolipids, Glycoconj J 13, 123-26 (1996).
9. 9 Solter D, Knowles BB, Monoclonal antibody defining a stage-specific mouse embryonic antigen (SSEA-1 ), Proc Natl Acad Sci USA 75, 5565-69 (1978).
10. 10 Shevinsky LH, Knowles BB, Damjanov I, Solter D, Monoclonal antibody to murine embryos defines a stage-specific embryonic antigen expressed on embryos and human teratocarcinoma cells, Cell 30, 697-705 (1982).
11. 11 Fenderson BA, Eddy EM, Hakomori S, Glycoconjugate expression during embryogenesis and its biological significance, BioEssays 12, 173-79 (1990).
12. 12 Kannagi R, Levery SB, Ishigami F, Hakomori S, Shevinsky LH, Knowles BB, Solter D, New globoseries glycosphingolipids in human teratocarcinoma reactive with the monoclonal antibody directed to a developmentally regulated antigen, stage-specific embryonic antigen 3, J Biol Chem 258, 8934-42 (1983).
13. 13 Kannagi R, Cochran NA, Ishigami F, Hakomori S, Andrews PW, Knowles BB, Solter D, Stage-specific embryonic antigens (SSEA-3 and -4) are epitopes of a unique globo-series ganglioside isolated from human teratocarcinoma cells, EMBO J 2, 2355-61 (1983).
14. 14 Fenderson BA, Andrews PW, Nudelman ED, Clausen H, Hakomori S, Glycolipid core structure switching from globo-to lacto-and ganglio-series during retinoic acid-induced differentiation of TERA-2-derived human embryonal carcinoma cells, Dev Biol 122, 21-34 (1987).
15. 15 Gooi HC, Feizi T, Kapadia A, Knowles BB, Solter D, Evans MJ, Stage-specific embryonic antigen involves α1-3 fucosylated type 2 blood group chains, Nature 292, 156-58 (1981).
16. 16 Hakomori S, Nudelman ED, Levery SB, Solter D, Knowles BB, The hapten structure of a developmentally regulated glycolipid antigen (SSEA-1) isolated from human erythrocytes and adenocarcinoma: A preliminary note, Biochem Biophys Res Commun 100, 1578-86 (1981).
17. 17 Kannagi R, Nudelman ED, Levery SB, Hakomori S, A series of human erythrocyte glycosphingolipids reacting to the monoclonal antibody directed to a developmentally regulated antigen, SSEA-1, J Biol Chem 257, 14865-74 (1982).
18. 18 Watanabe K, Hakomori S, Status of blood group carbohydrate chains in ontogenesis and in oncogenesis, J Exp Med 144, 644-53 (1976).
19. 19 Fukuda M, Fukuda MN, Papayannopoulou T, Hakomori S, Membrane differentiation in human erythroid cells: Unique profiles of cell surface glycoproteins expressed in erythroblasts in vitro from three ontogenic stages, Proc Natl Acad Sci USA 77, 3474-78 (1980).
20. 20 Niemann H, Watanabe K, Hakomori S, Childs RA, Feizi T, Blood group i and I activities of 'lacto-N-norhexaosylceramide' and its analogues: The structural requirements for i-specificities, Biochem Biophys Res Commun 81, 1286-93 (1978).
21. 21 Watanabe K, Hakomori S, Childs RA, Feizi T, Characterization of blood group I-active ganglioside: Structural requirements for I-and i-specificities, J Biol Chem 254, 3221-28 (1979).
22. 22 Feizi T, Childs RA, Watanabe K, Hakomori S, Three types of blood group I specificity among monoclonal anti-I autoantibodies revealed by analogues of a branched erythrocyte glycolipid, J Exp Med 149, 975-80 (1979).
23. 23 Marsh WL, Anti-i: Cold antibody defining the Ii relationship in human red cells, Br J Haematol 7, 200-9 (1961).
24. 24 Giblett ER, Crookston MC, Aggutinability of red cells by anti-i in patients with thalassemia major and other haematological disorders, Nature 201, 1138 (1964).
25. 25 Klinman NR, Karush F, Equine anti-hapten antibody: V The non-precipitability of bivalent antibody, Immunochemistry 4, 387-90 (1967).
26. 26 Hornick CL, Karush F, Antibody affinity: III. The role of multivalence, Immunochemistry 9, 325-28 (1972).
27. 27 Gopalakrishnan PV, Karush F, Antibody affinity: VII. Multivalent interaction of antilactoside antibody, J Immunol 113, 769-71 (1974).
28. 28 Rosenfield RE, A-B hemolytic disease of newborn: Analysis of 1480 cord blood specimens, with special reference to the direct anti-globulin test and to the group O mother, Blood 10, 17 (1955).
29. 29 Romans DG, Tilley CA, Dorrington KJ, Monogamous bivalency of IgG antibodies: I. Deficiency of branched ABHI-active oligosaccharide chains on red cells of infants causes the weak anti-globulin reactions in hemolytic disease of the newborn due to ABO incompatibility, J Immunol 124, 2807-11 (1980).
30. 30 Clausen H, Levery SB, McKibbin JM, Hakomori S, Blood group A determinants with mono-and difucosyl type 1 chain in human erythrocyte membranes, Biochemistry 24, 3578-86 (1985).
31. 31 Clausen H, Levery SB, Nudelman ED, Baldwin M, Hakomori S, Further characterization of type 2 and type 3 chain blood group A glycosphingolipids from human erythrocyte membranes, Biochemistry 25, 7075-85 (1986).
32. 2 enzymes, and type 3 chain H expression in relation to secretor status, J Biol Chem 261, 1388-92 (1986).
33. 33 Hakomori S, Nudelman ED, Levery SB, Kannagi R, Novel fucolipids accumulating in human adenocarcinoma: I. Glycolipids with di-or trifucosylated type 2 chain, J Biol Chem 259, 4672-80 (1984).
34. 6) as human tumor-associated antigen, J Biol Chem 266, 8439-46 (1991).
35. a) epitope, Cancer Res 51, 2199-204 (1991).
36. 6), J Biol Chem 259, 10511-17 (1984).
37. 6), and a possible three-dimensional epitope structure, J Biol Chem 261, 11254-58 (1986).
38. 6), Eur J Biochem 203, 577-86 (1992).
39. 4 defined by monoclonal antibody 43-9F: Enzymatic synthesis, structural characterization, and comparative reactivity with various antibodies, Biochemistry 33, 10672-80 (1994).
40. 40 Kannagi R, Papayannopoulou T, Nakamoto B, Cochran NA, Yokochi T, Stamatoyannopoulas G, Hakomori S, Carbohydrate antigen profiles of human erythroleukemia cell lines HEL and K562, Blood 62, 1230-41 (1983).
41. 41 Kannagi R, Levery SB, Hakomori S, Sequential change of carbohydrate antigen associated with the differentiation of murine leukemia cells: i-I antigenic conversion and shifting of glycolipid synthesis, Proc Natl Acad Sci USA 80, 2844-48 (1983).
42. 42 Ichikawa Y, Differentiation of a cell line of myeloid leukemia, J Cell Physiol 74, 223-34 (1969).
43. 43 Sachs L, Control of normal cell differentiation and the phenotypic reversion of malignancy in myeloid leukaemia, Nature 274, 535-39 (1978).
44. 44 Gahmberg CG, Hakomori S, Surface carbohydrates of hamster fibroblasts: I. Chemical characterization of surface-labeled glycosphingolipids and a specific ceramide tetrasaccharide for transformants, J Biol Chem 250, 2438-46 (1975).
45. py tumor, Biochem Biophys Res Commun 68, 799-806 (1976).
46. 46 Rosenfelder G, Young WWJ, Hakomori S, Association of the glycolipid pattern with antigenic alterations in mouse fibroblasts transformed by murine sarcoma virus, Cancer Res 37, 1333-39 (1977).
47. 47 Hakomori S, Wang S-M, Young WWJ, Isoantigenic expression of Forssman glycolipid in human gastric and colonic mucosa: Its possible identity with 'A-like antigen' in human cancer, Proc Natl Acad Sci USA 74, 3023-27 (1977).
48. 48 Yoda Y, Ishibashi T, Makita A, Isolation, characterization, and biosynthesis of Forssman antigen in human lung and lung carcinoma, J Biochem (Tokyo) 88, 1887-90 (1980).
49. 49 Young WW, Jr, Hakomori S, Levine P, Characterization of anti-Forssman (anti-Fs) antibodies in human sera: Their specificity and possible changes in patients with cancer, J Immunol 123, 92-96 (1979).
50. 50 Hakomori S, Aberrant glycosylation in tumors and tumor-associated carbohydrate antigens, Adv Cancer Res 52, 257-331 (1989).
51. 51 Hakomori S, Cancer-associated glycosphingolipid antigens: Their structure, organization, and function, Acta Anatomica 161, 79-90 (1998).
52. 52 Young WWJ, Hakomori S, Therapy of mouse lymphoma with monoclonal antibodies to glycolipid: Selection of low antigenic variants in vivo, Science 211, 487-489 (1981).
53. D3 ganglioside: A phase I trial in patients with malignant melanoma, Proc Natl Acad Sci USA 82, 1242-46 (1985).
54. 54 Hakomori S, Tumor malignancy defined by aberrant glycosylation and sphingo(glyco)lipid metabolism, Cancer Res 56, 5309-18 (1996).
55. 55 Hakomori S, Tumor-associated carbohydrate antigens defining tumor malignancy: Basis for development of anti-cancer vaccines. In Molecular immunology of complex carbohydrate II, edited by Wu AM, (Kluwer, New York, 2000).
56. x (defined by MAb FH6) and LCP, Clin Expl Metastasis 9, 245-57 (1991).
57. 57 Takada A, Ohmori K, Takahashi N, Tsuyuoka K, Yago A, Zenita K, Hasegawa A, Kannagi R, Adhesion of human cancer cells to vascular endothelium mediated by a carbohydrate antigen, sialyl Lewis A, Biochem Biophys Res Commun 179, 713-19 (1991).
58. x is recognized by the endothelial cell leukocyte adhesion molecule ELAM-1, J Biol Chem 266, 14869-72 (1991).
59. 59 Takada A, Ohmori K, Yoneda T, Tsuyuoka K, Hasegawa A, Kiso M, Kannagi R, Contribution of carbohydrate antigens sialyl Lewis A and sialyl Lewis X to adhesion of human cancer cells to vascular endothelium, Cancer Res 53, 354-61 (1993).
60. 60 Ohyama C, Tsuboi S, Fukuda M, Dual roles of sialyl Lewis X oligosaccharides in tumor metastasis and rejection by natural killer cells, EMBO J 18, 1516-25 (1999).
61. 61 Hakomori S, Carbohydrate-carbohydrate interaction as an initial step in cell recognition, Pure & Appl Chem 63, 473-82 (1991).
62. 62 Kojima N, Shiota M, Sadahira Y, Handa K, Hakomori S, Cell adhesion in a dynamic flow system as compared to static system: Glycosphingolipid-glycosphingolipid interaction in the dynamic system predominates over lectin-or integrin-based mechanisms in adhesion of B16 melanoma cells to non-activated endothelial cells, J Biol Chem 267, 17264-70 (1992).
63. M3-LacCer interaction, Int J Oncol 6, 319-27 (1995).
64. 64 Crocker PR, Clark EA, Filbin M, Gordon S, Jones Y, Varki A, Siglecs: A family of sialic acid-binding lectins [Glyco-Forum section]. Glycobiology 8, v (1998).
65. 65 Brinkman-Van der Linden EC, Varki A, New aspects of siglec binding specificities, including the significance of fucosylation and of the sialyl-Tn epitope: Sialic acid-binding immunoglobulin superfamily lectins, J Biol Chem 275, 8625-32 (2000).
66. 66 Manfredi MG, Lim S, Claffey KP, Seyfried TN, Gangliosides influence angiogenesis in an experimental mouse brain tumor, Cancer Res 59, 5392-97 (1999) (2000).
67. 67 Zeng G, Gao L, Birkle S, Yu RK, Suppression of ganglioside GD3 expression in a rat F-11 tumor cell line reduces tumor growth, angiogenesis and vascular endothelial growth factor production, Cancer Res, in press (2000).
68. 68 Hakomori S, Novel endothelial cell activation factor(s) released from activated platelets which induce E-selectin expression and tumor cell adhesion to endothelial cells: A preliminary note, Biochem Biophys Res Commun 203, 1605-13 (1994).
69. 69 Khatib A-M, Kontogiannea M, Fallavollita L, Jamison B, Meterissian S, Brodt P, Rapid induction of cytokine and E-selectin expression in the liver in response to metastatic tumor cells, Cancer Res 59, 1356-61 (1999).
70. 70 Lavie Y, Cao H, Bursten SL, Giuliano AE, Cabot MC, Accumulation of glucosylceramides in multidrug-resistant cancer cells, J Biol Chem 271, 19530-36 (1996).
71. 71 Liu Y-Y, Han T-Y, Giuliano AE, Hansen N, Cabot MC, Uncoupling ceramide glycosylation by transfection of glucosylceramide synthase antisense reverses adriamycin resistance, J Biol Chem 275, 7138-43 (2000).
72. 72 Inokuchi J, Mason I, Radin NS, Antitumor activity via inhibition of glycosphingolipid biosynthesis, Cancer Lett 38, 23-30 (1987).
73. 73 Hakomori S, Possible new directions in cancer therapy based on aberrant expression of glycosphingolipids: Anti-adhesion and ortho-signaling therapy, Cancer Cells 3, 461-70 (1991).
74. 74 Kannagi R, Nudelman E, Hakomori S, Possible role of ceramide in defining structure and function of membrane glycolipids, Proc Natl Acad Sci USA 79, 3470-74 (1982).
75. 75 Watanabe K, Matsubara T, Hakomori S, α-L-fucopyranosylceramide, a novel glycolipid accumulated in some of the human colon tumors, J Biol Chem 251, 2385-87 (1976).
76. 76 Yoshino T, Watanabe K, Hakomori S, Chemical synthesis of α-L-fucopyranosylceramide and its analogues and preparation of antibodies directed to this glycolipid, Biochemistry 21, 928-34 (1982).
77. 77 Kannagi R, Stroup R, Cochran NA, Urdal DL, Young WWJ, Hakomori S, 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 (1983).
78. 78 Kiarash A, Boyd B, Lingwood CA, 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, 11138-46 (1994).
79. 79 Boyd B, Magnusson G, Zhiuyan Z, Lingwood CA, Lipid modulation of glycolipid receptor function: Availability of Gal(α1-4)Gal disaccharide for verotoxin binding in natural and synthetic glycolipids, Eur J Biochem 223, 873-78 (1994).
80. 80 Pascher I, Molecular arrangements in sphingolipids: Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability, Biochim Biophys Acta 455, 433-51 (1976).
81. 81 Hannun YA, Sphingolipid-mediated signal transduction, (R.G. Landes Co., Austin, TX, 1997).
82. 82 Fenderson BA, Zehavi U, Hakomori S, A multivalent lacto-N-fucopentaose III-lysyllysine conjugate decompacts preimplantation mouse embryos, while the free oligosaccharide is ineffective, J Exp Med 160, 1591-96 (1984).
83. 83 Rosenman SJ, Fenderson BA, Hakomori S, The role of glycoconjugates in embryogenesis, In Glycoconjugates in medicine, edited by Ohyama M, Muramatsu T. (Professional Postgraduate Services, Japan, 1988), pp. 43-50.
84. x determinants: A possible basis for cell recognition in preimplantation embryos and in embryonal carcinoma cells, J Biol Chem 264, 9476-84 (1989).
85. x expression, Glycoconj J 11, 238-48 (1994).
86. 2+-dependent carbohydrate association through ion spray mass spectrometry, J Am Chem Soc 115, 2877-81 (1993).
87. x trisaccharide, Carbohydr Lett 1, 475-82 (1996).
88. 88 Boubelik M, Dráberová L, Dráber P, Carbohydrate-mediated sorting in aggregating embryonal carcinoma cells, Biochem Biophys Res Commun 224, 283-88 (1996).
89. 89 Yu S, Withers DA, Hakomori S, Globoside-dependent adhesion of human embryonal carcinoma cells, based on carbohydrate-carbohydrate interaction, initiates signal transduction and induces enhanced activity of transcription factors AP1 and CREB, J Biol Chem 273, 2517-25 (1998).
90. 90 Takeichi M, Cadherins: A molecular family essential for selective cell-cell adhesion and animal morphogenesis, Trends Gen 3, 213-17 (1987).
91. 91 Larue L, Ohsugi M, Hirchenhain J, Kemler R, E-cadherin null mutant embryos fail to form a trophectoderm epithelium, Proc Natl Acad Sci USA 91, 8263-67 (1994).
92. 92 Draber P, Maly P, Mutants of embryonal carcinoma cells defective in the expression of embryoglycan, Proc Natl Acad Sci USA 84, 5798-802 (1987).
93. 93 Muramatsu T, Developmentally regulated expression of cell surface carbohydrates during mouse embryogenesis, J Cell Biochem 36, 1-14 (1988).
94. 94 Yamashita T, Wada R, Sasaki T, Deng C, Bierfreund U, Sandhoff K, Proia RL, A vital role for glycosphingolipid synthesis during development and differentiation, Proc Natl Acad Sci USA 96, 9142-47 (1999).
95. 95 Thomson JA, Kalishman J, Golos TG, Durning M, Harris CP, Becker RA, Hearn JP, Isolation of a primate embryonic stem cell line, Proc Natl Acad Sci USA 92, 7844-48 (1995).
96. 96 Kojima N, Hakomori S, Specific interaction between gangliotriaosylceramide (Gg3) and sialosyllactosylceramide (GM3) as a basis for specific cellular recognition between lymphoma and melanoma cells, J Biol Chem 264, 20159-62 (1989).
97. M3-expressing cells based on glycolipid-glycolipid interaction, J Biol Chem 266, 17552-58 (1991).
98. 98 Kojima N, Hakomori S, Synergistic effect of two cell recognition systems: Glycosphingolipid-glycosphingolipid interaction and integrin receptor interaction with pericellular matrix protein, Glycobiology 1, 623-30 (1991).
99. 99 Matsuura K, Kitakouji H, Sawada N, Ishida H, Kiso M, Kitajima K, Kobayashi K, A quantitative estimation of carbohydrate-carbohydrate interaction using clustered oligosaccharides of glycolipid monolayers and of artificial glycoconjugate polymers by surface plasmon resonance, J Am Chem Soc 122, 7406-07 (2000).
100. x, Science 250, 1130-32 (1990).
101. 101 Stroud MR, Handa K, Salyan MEK, Ito K, Levery SB, Hakomori S, Reinhold BB, Reinhold VN, Monosialogangliosides of human myelogenous leukemia HL60 cells and normal human leukocytes. 2. Characterization of E-selectin binding fractions, and structural requirements for physiological binding to E-selectin, Biochemistry 35, 770-78 (1996).
102. x epitope as the physiological myeloid cell ligand in E-selectin-dependent adhesion: Studies under static and dynamic flow conditions, Biochemistry 36, 12412-20 (1997).
103. 103 Leppanen A, Mehta P, Ouyang Y, Ju T, Helm J, Moore KL, van Die I, Canfield WM, McEver RP, Cummings RD, A novel glycosulfopeptide binds to P-selectin and inhibits leukocyte adhesion to P-selectin, J Biol Chem 274, 24838-48 (1999).
104. 104 Kleinman HK, Martin GR, Fishman PH, Ganglioside inhibition of fibronectin-mediated cell adhesion to collagen, Proc Natl Acad Sci USA 76, 3367-71 (1979).
105. 105 Cheresh DA, Pytela R, Pierschbacher MD, Klier FG, Ruoslahti E, Reisfeld RA, An Arg-Gly-Asp-directed receptor on the surface of human melanoma cells exists in a divalent cation-dependent functional complex with the disialoganglioside GD2, J Cell Biol 105, 1163-73 (1987).
106. M3 ganglioside in α5β1 integrin receptor for fibronectin-mediated adhesion of FUA169 cells, J Biol Chem 268, 2217-22 (1993).
107. 107 Hyuga S, Yamagata S, Tai T, Yamagata T, Inhibition of highly metastatic FBJ-LL cell migration by ganglioside GD1 a highly expressed in poorly metastatic FBJ-S1 cells, Biochem Biophys Res Commun 231, 340-43 (1997).
108. 108 Lingwood CA, Hakomori S, Selective inhibition of cell growth and associated changes in glycolipid metabolism induced by monovalent antibodies to glycolipids, Exp Cell Res 108, 385-91 (1977).
109. 3 ganglioside induces hamster fibroblast growth inhibition in chemically-defined medium: Ganglioside may regulate growth factor receptor function, Biochem Biophys Res Commun 106, 711-18 (1982).
110. y antigen expression is correlated with apoptosis (programmed cell death), Glycobiology 3, 381-90 (1993).
111. 111 Ono M, Handa K, Withers DA, Hakomori S, Motility inhibition and apoptosis are induced by metastasis-suppressing gene product CD82 and its analogue CD9, with concurrent glycosylation, Cancer Res 59, 2335-9 (1999).
112. 112 Bremer EG, Hakomori S, Bowen-Pope DF, Raines EW, Ross R, Ganglioside-mediated modulation of cell growth, growth factor binding, and receptor phosphorylation, J Biol Chem 259, 6818-25 (1984).
113. 3 on tyrosine phosphorylation of the epidermal growth factor receptor, J Biol Chem 261, 2434-40 (1986).
114. 114 Yates AJ, Rampersaud A, Sphingolipids as receptor modulators: An overview. In Sphingolipids as signaling modulators in the nervous system, edited by Ledeen RW, Hakomori S, Yates AJ, Schneider JS, Yu RK, (New York Acad Sci, New York, NY, 1998), pp. 57-71.
115. 115 Weis FMB, Davis RJ, Regulation of epidermal growth factor receptor signal transduction: Role of gangliosides, J Biol Chem 265, 12059-66 (1990).
116. 116 Anderson RGW, The caveolae membrane system, Annu Rev Biochem 61, 199-225 (1998).
117. 117 Yamamura S, Handa K, Hakomori S, A close association of GM3 with c-Src and Rho in GM3-enriched microdomains at the B16 melanoma cell surface membrane: A preliminary note, Biochem Biophys Res Commun 236, 218-22 (1997).
118. D3 in rat brain: Possible regulation of Lyn by glycosphingolipid in caveolae-like domains, J Biol Chem 272, 29947-53 (1997).
119. 119 Iwabuchi K, Handa K, Hakomori S, 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, 33766-73 (1998).
120. 120 Hakomori S, Handa K, Iwabuchi K, Yamamura S, Prinetti A, New insights in glycosphingolipid function: 'Glycosignaling domain,' a cell surface assembly of glycosphingolipids with signal transducer molecules, involved in cell adhesion coupled with signaling, Glycobiology 8, xi-xviii (1998).
121. 121 Zhang Y, Iwabuchi K, Nunomura S, Hakomori S, Effect of synthetic sialyl 2→1 sphingosine and other glycosylsphingosines on the structure and function of the 'glycosphingolipid signaling domain (GSD)' in mouse melanoma B16 cells, Biochemistry 39, 2459-68 (2000).
122. 122 Iwabuchi K, Zhang Y, Handa K, Withers DA, Sinaÿ P, Hakomori S, Reconstitution of membranes simulating 'glycosignaling domain' and their susceptibility to lyso-GM3, J Biol Chem 275, 15174-81 (2000).
123. 123 Mineo C, James GL, Smart EJ, Anderson RGW, Localization of epidermal growth factor-stimulated Ras/Raf-1 interaction to caveolae membrane, J Biol Chem 271, 11930-35 (1996).
124. 124 Liu P, Ying Y, Ko Y-G, Anderson RGW, Localization of platelet-derived growth factor-stimulated phosphorylation cascade to caveolae, J Biol Chem 271 10299-303 (1996).
125. 125 Coetzee T, Fujita N, Dupree J, Shi R, Blight A, Suzuki K, Suzuki K, Popko B, Myelination in the absence of galactocerebroside and sulfatide: Normal structure with abnormal function and regional instability, Cell 86, 209-19 (1996).
126. 126 Bosio A, Binczek E, Stoffel W, Functional breakdown of the lipid bilayer of the myelin membrane in central and peripheral nervous system by disrupted galactocerebroside synthesis, Proc Natl Acad Sci USA 93, 13280-85 (1996).
127. 127 Takamiya K, Yamamoto A, Furukawa K, Yamashiro S, Shin M, Okada M, Fukumoto S, Haraguchi M, Takeda N, Fujimura K, Sakae M, Kishikawa M, Shiku H, Furukawa K, Aizawa S, Mice with disrupted GM2/GD2 synthase gene lack complex gangliosides but exhibit only subtle defects in their nervous system, Proc Natl Acad Sci USA 93, 10662-67 (1996).
128. 128 Sheikh KA, Sun J, Liu Y, Kawai H, Crawford TO, Proia RL, Griffin JW, Schnaar RL, Mice lacking complex gangliosides develop Wallerian degeneration and myelination defects, Proc Natl Acad Sci USA 96, 7532-37 (1999).
129. 129 Charron M, Shaper JH, Shaper NL, The increased level of β1,4-galactosyltransferase required for lactose biosynthesis is achieved in part by translational control, Proc Natl Acad Sci USA 95, 14805-10 (1998).
130. 130 Withers DA, Hakomori S, Human α(1,3)-fucosyltransferase IV (FUTIV) gene expression is regulated by Elk-1 in the U937 myeloid cell line, J Biol Chem (2000) (in press).
131. 131 Ko JH, Miyoshi E, Noda K, Ekuni A, Kang R, Ikeda Y, Taniguchi N, Regulation of the GnT-V promoter by transcription factor Ets-1 in various cancer cell lines, J Biol Chem 274, 22941-48 (1999).
132. 132 Kominato Y, Tsuchiya T, Hata N, Takizawa H, Yamamoto F, Transcription of human ABO histo-blood group genes is dependent upon binding of transcription factor CBF/INF-Y to minisatellite sequence, J Biol Chem 272, 25890-98 (1997).
133. 133 Iwamoto S, Withers DA, Handa K, Hakomori S, Deletion of A-antigen in a human cancer cell line is associated with reduced promoter activity of CBF/INF-Y binding region, and possibly with enhanced DNA methylation of A transferase promoter, Glycoconj J 16, 659-66 (1999).
134. 134 Hood L, Huang HV, Dreyer WJ, The area-code hypothesis: The immune system provides clues to understanding the genetic and molecular basis of cell recognition during development. In Cell surface carbohydrates and biological recognition, edited by Marchesi VT, Ginsburg V, Robbins PW, Fox CF (Alan R. Liss, Inc., New York, 1977), pp. 531-59.
135. 135 Kopitz J, von Reitzenstein C, Burchert M, Cantz M, Gabius HJ, Galectin-1 is a major receptor for ganglioside GM1, a product of the growth-controlling activity of a cell surface ganglioside sialidase, on human neuroblastoma cells in culture, J Biol Chem 273, 11205-11 (1998).
136. 136 Schnaar RL, Collins BE, Wright LP, Kiso M, Tropak MB, Roder JC, Crocker PR, Myelin-associated glycoprotein binding to gangliosides: Structural specificity and functional implications. In Sphingolipids as signaling modulators in the nervous system, edited by Ledeen RW, Hakomori S, Yates AJ, Schneider JS, Yu RK (Ann NY Acad Sci, Vol. 845) (NY Acad Sci, New York, NY, 1998).
137. 137 Maecker HT, Todd SC, Levy S, The tetraspanin superfamily: Molecular facilitators, FASEB J 11, 428-42 (1997).
138. 138 Archibald DD, Mann S, Template mineralization of self-assembled anisotropic lipid microstructures, Nature 364, 430-33 (1993).
139. 139 Archibald DD, Mann S, Structural studies of lipid fibers formed by sphingosine, Biochim Biophys Acta 1166, 154-162 (1993).
140. 140 Imae T, Construction of helical structure by lipids and related compounds [in Japanese], Proteins, Nucleic Acids, & Enzymes [Japanese] 38, 731-40 (1993).
141. 141 Livingston PO, Wong GY, Adluri S, Tao Y, Padavan M, Parente R, Hanlon C, Calves MJ, Helling F, Ritter G, Improved survival in stage III melanoma patients with GM2 antibodies: A randomized trial of adjuvant vaccination with GM2 ganglioside, J Clin Oncol 12, 1036-44 (1994).
142. 142 MacLean GD, Miles DW, Rubens RD, Reddish MA, Longenecker BM, Enhancing the effect of THERATOPE STn-KLH cancer vaccine in patients with metastatic breast cancer by pretreatment with low-dose intravenous cyclophosphamide, J Immunother 19, 309-16 (1996).
143. 143 Slovin SF, Ragupathi G, Adluri S, Ungers G, Terry K, Kim S, Spassova M, Bornmann WG, Fazzari M, Dantis L, Olkiewicz K, Lloyd KO, Livingston PO, Danishefsky SJ, Scher HI, Carbohydrate vaccines in cancer: Immunogenicity of a fully synthetic globo H hexasaccharide conjugate in man, Proc Natl Acad Sci USA 96, 5710-15, (1999).
144. 144 Harding CV, Kihlberg J, Elofsson M, Magnusson G, Unanue ER, Glycopeptides bind MHC molecules and elicit specific T cell responses, J Immunol 151, 2419-25 (1993).
145. 145 Deck MB, Sjolin P, Unanue ER, Kihlberg J, MHC-restricted, glycopeptide-specific T cells show specificity for both carbohydrate and peptide residues, J Immunol 162 4740-44 (1999).
146. 146 Celis E, Tsai V, Crimi C, DeMars R, Wentworth PA, Chesnut RW, Grey HM, Sette A, Serra HM, Induction of anti-tumor cytotoxic T lymphocytes in normal humans using primary cultures and synthetic peptide epitopes, Proc Natl Acad Sci USA 91, 2105-09 (1994).
147. 147 Singhal AK, Fohn M, Hakomori S, Induction of Tn (α-N-acetylgalactosamine-O-serine/threonine) antigen-mediated cellular immune response for active immunotherapy in mice, Cancer Res 51, 1406-11 (1991).
148. 148 Lo-Man R, Bay S, Vichier-Guerre S, Deriaud E, Cantacuzene D, Leclerc C, A fully synthetic immunogen carrying a carcinoma-associated carbohydrate for active specific immunotherapy, Cancer Res 59, 1520-24 (1999).
149. 149 Toyokuni T, Dean B, Cai S, Boivin D, Hakomori S, Singhal AK, Synthetic vaccines: Synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins, J Am Chem Soc 116, 395-96 (1994).
150. 150 Toyokuni T, Hakomori S, Singhal AK, Synthetic carbohydrate vaccines: Synthesis and immunogenicity of Tn antigen conjugates, Bioorg Med Chem 2, 1119-32 (1994).
151. 151 del Guercio MF, Alexander J, Kubo RT, Arrhenius T, Maewal A, Appella E, Hoffman SL, Jones T, Valmori D, Sakaguchi K, Grey HM, Sette A, Potent immunogenic short linear peptide constructs composed of B cell epitopes and Pan DRT helper epitopes (PADRE) for antibody responses in vivo, Vaccine 15, 441-48 (1997).
152. 152 Kieber-Emmons T, Luo P, Qiu J, Chang TY, O I, Blaszczyk-Thurin M, Steplewski Z, Vaccination with carbohydrate peptide mimotopes promotes anti-tumor responses, Nature Biotechnol 17, 660-65 (1999).
153. 153 O'Hanley P, Low D, Romero I, Lark D, Vosti K, Falkow S, Schoolnik G, Gal-Gal binding and hemolysis phenotypes and genotypes associated with uropathogenic Escherichia coli, N Engl J Med 313, 414-20 (1985).
154. k antigen as receptor for the haemagglutination of pyelonephritic Escherichia coli, FEMS Microbiol Lett 7, 297-302 (1980).
155. 155 Leffler H, Svanborg-Eden C, Chemical identification of a glycosphingolipid receptor for Escherichia coli attaching to human urinary tract cells and agglutinating human erythrocytes, FEMS Microbiol Lett 8, 127-34 (1980).
156. 156 Stapleton A, Nudelman ED, Clausen H, Hakomori S, Stamm WE, Binding of uropathogenic Escherichia coli R45 to glycolipids extracted from vaginal epithelial cells is dependent on histo-blood group secretor status, J Clin Invest 90, 965-72 (1992).
157. 157 Stapleton AE, Stroud MR, Hakomori S, Stamm WE, The globo-series glycosphingolipid sialosyl galactosyl globoside is found in urinary tract tissues and is a preferred binding receptor in vitro for uropathogenic Escherichia coli expressing pap-encoded adhesins, Infect Immun 66, 3856-61 (1998).
158. 158 Isojima S, Graham RM, Graham JB, Sterility in female guinea pigs induced by injection with testis, Science 129, 44-5 (1959).
159. 159 Isojima S, Tsuchiya K, Koyama K, Tanaka C, Naka O, Adachi H, Further studies on sperm immobilizing antibody found in sera of unexplained cases of sterility in women, Am J Obstet Gynecol 112, 199-207 (1972).
160. 160 Isojima S, Kameda K, Tsuji Y, Shigeta M, Ikeda Y, Koyama K, Establishment and characterization of human hybridoma secreting monoclonal antibody with high titers of sperm immobilizing and agglutinating activity against human seminal plasma, J Reprod Immunol 10, 67-78 (1987).
161. 161 Tsuji Y, Clausen H, Nudelman E, Kaizu T, Hakomori S, Isojima S, Human sperm carbohydrate antigens defined by an antisperm human monoclonal antibody derived from an infertile women bearing antisperm antibodies in her serum, J Exp Med 168, 343-56 (1988).
162. 162 Schroter S, Den P, Conradt HS, Nimtz M, Hale G, Kirchhoff C, Male-specific modification of human CD52, J Biol Chem 274, 29862-73 (1999).
163. 163 Diekman AB, Norton EJ, Westbrook VA, Klotz KL, Naaby-Hansen S, Herr JC, Anti-sperm antibodies from infertile patients and their cognate sperm antigens: A review. Identity between SAGA-1, the H6-3C4 antigen, and CD52, Am J Reprod Immunol 43, 134-43 (2000).
164. 164 Mulligan MS, Lowe JB, Larsen RD, Paulson JC, Zheng Z-L, DeFrees S, Maemura K, Fukuda M, Ward PA, Protective effects of sialylated oligosaccharides in immune complex-induced acute lung injury, J Exp Med 178, 623-31 (1993).
165. 165 Mulligan MS, Paulson JC, DeFrees S, Zheng Z-L, Lowe JB, Ward PA, Protective effects of oligosaccharides in P-selectin-dependent lung injury, Nature 364, 149-51 (1993).
166. 166 O I, Kieber-Emmons T, Otvos L, Blaszczyk-Thurin M, Peptide mimicking sialyl-Lewis(a) with anti-inflammatory activity, Biochem Biophys Res Commun 268, 106-11 (2000).
167. 167 Fukuda MN, Ohyama C, Lowitz K, Matsuo O, Pasqualini R, Ruoslahti E, Fukuda M, A peptide mimic of E-selectin ligand inhibits sialyl Lewis X-dependent lung colonization of rumor cells, Cancer Res 60, 450-56 (2000).
168. 168 Taki T, Ishikawa D, Ogura M, Nakajima M, Handa S, Ganglioside GD1α functions in the adhesion of metastatic tumor cells to endothelial cells of the target tissue, Cancer Res 57, 1882-8 (1997).
169. 169 Ishikawa D, Kikkawa H, Ogino K, Hirabayashi Y, Oku N, Taki T, GD1α-replica peptides functionally mimic GD1α, an adhesion molecule of metastatic tumor cells, and suppress the tumor metastasis, FEBS Lett 441, 20-24 (1998).
170. 170 Hoess R, Brinkmann U, Handel T, Pastan I, Identification of a peptide which binds to the carbohydrate-specific monoclonal antibody B3, Gene 128, 43-49 (1993).
171. 171 Kahn M, Chen B, Methodology for the synthesis of mimetics of peptide β-turns, Tetrahedron Lett 28, 1623-26 (1987).
172. 172 Kahn M, Wilke S, Chen B, Fujita K, Lee YH, Johnson M, The design and synthesis of nonpeptide mimetics of β-turns, J Mol Recog 1, 75-79 (1988).
173. 173 Saragovi HU, Fitzpatrick D, Raktabutr A, Nakanishi H, Kahn M, Greene MI, Design and synthesis of a mimetic from an antibody complementarity determining region, Science 253, 792-95 (1991).
174. 174 Siddiqui B, Hakomori S, A ceramide tetrasaccharide of human erythrocyte membrane reacting with anti-type XIV pneumococcal polysaccharide antiserum, Biochim Biophys Acta 330, 147-155 (1973).
175. 175 Stellner K, Watanabe K, Hakomori S, Isolation and characterization of glycosphingolipids with blood group H-specificity from membranes of human erythrocytes, Biochemistry 12, 656-61 (1973).
176. 176 Watanabe K, Laine RA, Hakomori S, On neutral fucoglycolipids having long branch carbohydrate chains: H-active glycosphingolipids of human erythrocyte membranes, Biochemistry 14, 2725-33 (1975).
177. 177 Nudelman ED, Mandel U, Levery SB, Kaizu T, Hakomori S, A series of disialogangliosides with binary 2-3 sialosyllactosamine structure, defined by monoclonal antibody NUH2, are oncodevelopmentally regulated antigens, J Biol Chem 264, 18719-25 (1989).
178. 2 subgroups, J Biol Chem 257, 446-55 (1982).
179. 179 Yang H-J, Hakomori S, A sphingolipid having a novel type of ceramide and lacto-N-fucopentaose III, J Biol Chem 246, 1192-200 (1971).
180. x as a new tumor-associated antigen, Cancer Res 44, 5279-85 (1984).
181. 6), J Biol Chem 261, 11247-53 (1986).
182. 182 Handa K, Withers DA, Hakomori S, The α1→3 fucosylation at the penultimate GlcNAc catalyzed by fucosyltransferase VII is blocked by internally fucosylated residue in sialosyl long-chain poly-LacNAc: Enzymatic basis for expression of physiological E-selectin epitope, Biochem Biophys Res Commun 243, 199-204 (1998).
183. y) determinants in human blood cell membranes (ghosts): Evidence that type 2 chain can elongate repetitively but type 1 chain cannot, J Biol Chem 260, 6410-15 (1985).
184. 184 Mårtensson S, Due C, Påhlsson P, Nilsson B, Eriksson H, Zopf D, Olsson L, Lundblad A, A carbohydrate epitope associated with human squamous lung cancer, Cancer Res 48, 2125-31 (1988).
185. a glycosphingolipid, a novel extended type 1 chain antigen, Cancer Res 52, 3739-45 (1992).
186. 4) of human adenocarcinoma and the monoclonal antibody (FH9) defining this disialosyl structure, Biochemistry 25, 2859-66 (1986).
187. 187 Hakomori S, Siddiqui B, Li Y-T, Li S-C, Hellerqvist CG, Anomeric structures of 'globoside' and ceramide trihexoside of human erythrocytes and 'BHK' fibroblasts, J Biol Chem 246, 2271-7 (1971).
188. 188 Nudelman ED, Kannagi R, Hakomori S, Parsons M, Lipinski M, Wiels J, Fellous M, Tursz T, A glycolipid antigen associated with Burkitt lymphoma defined by a monoclonal antibody, Science 220, 509-11 (1983).
189. 189 Siddiqui B, Kawanami J, Li Y-T, Hakomori S, Structures of ceramide tetrasaccharides from various sources: Uniqueness of rat kidney ceramide tetrasaccharide, J Lipid Res 13, 657-662 (1972).
190. 190 Siddiqui B, Hakomori S, A revised structure for Forssman glycolipid hapten, J Biol Chem 246, 5766-69 (1971).
191. 191 Bremer EG, Levery SB, Sonnino S, Ghidoni R, Canevari S, Kannagi R, Hakomori S, Characterization of a glycosphingolipid antigen defined by the monoclonal antibody MBr1 expressed in normal and neoplastic epithelial cells of human mammary gland, J Biol Chem 259, 14773-7 (1984).
192. 192 Saito S, Levery SB, Salyan MEK, Goldberg RI, Hakomori S, Common tetrasaccharide epitope NeuAcα2→3Galβ1→3 (NeuAcα2→6)GalNAc, presented by different carrier glycosylceramides or O-linked peptides, is recognized by different antibodies and ligands having distinct specificities, J Biol Chem 269, 5644-52 (1994).
193. 193 Satoh M, Handa K, Saito S, Tokuyama S, Ito A, Miyao N, Orikasa S, Hakomori S, Disialosyl galactosylgloboside as an adhesion molecule expressed on renal cell carcinoma and its relationship to metastatic potential, Cancer Res 56, 1932-38 (1996).