Synthetic glycosylphosphatidylinositol as tools for glycoparasitology research

OMICS A Journal of Integrative Biology

Volumn 14, Issue 4, 2010, Pages 445-454

  Azzouz, Nahid ^b   Kamena, Faustin ^b   Seeberger, Peter H ^a  

^a MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSYLPHOSPHATIDYLINOSITOL; OLIGOSACCHARIDE;

EPITOPE MAPPING; INCUBATION TIME; MEDICAL RESEARCH; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; REVIEW;

ANIMALS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; DATABASES, FACTUAL; GLYCOSYLPHOSPHATIDYLINOSITOLS; HUMANS; MICROARRAY ANALYSIS; MOLECULAR SEQUENCE DATA; PARASITES; POLYSACCHARIDES;

ANIMALIA;

EID: 77956016935     PISSN: 15362310     EISSN: None     Source Type: Journal    
DOI: 10.1089/omi.2009.0138     Document Type: Review

References (97)

1. Alavi, A., and Axford, J.S. (2008). Sweet and sour: the impact of sugars on disease. Rhematology (Oxford) 47, 760-770.
2. Almeida, A.M., Murakami, Y., Layton, D.M., Hillmen, P., Sellick, G.S., Maeda, Y., et al. (2006). Hypomorphic promoter mutation in PIGM causes inherited glycosylphosphatidylinositol deficiency. Nat Med 12, 846-851.
3. Axford, J. (2001). The impact of glycobiology on medicine. Trends Immunol 22, 237-239.
4. Azzouz, N., Shams-Eldin, H., and Schwarz, R.T. (2005). Removal of phospholipid contaminants through precipitation of glycosylphosphatidylinositols. Anal Biochem 343, 152-158.
5. Azzouz, N., Shams-Eldin, H., Niehus, S., Debierre-Grockiego, F., Bieker, U., Schmidt, J., et al. (2006). Toxoplasma gondii grown in human cells uses GalNAc-containing glycosylphosphatidylinositol precursors to anchor surface antigens while the immunogenic Glc-GalNAc-containing precursors remain free at the parasite cell surface. Int J Biochem Cell Biol 38, 1914-1925.
6. Barnes, D.A., Bonnin, A., Huang, J.X., Gousset, L., Wu, J., Gut, J., et al. (1998). A novel multi-domain mucin-like glycoprotein of Cryptosporidium parvum mediates invasion. Mol Biochem Parasitol 96, 93-110.
7. Berhe, S., Schofield, L., Schwarz, R.T., and Gerold, P. (1999). Conservation of structure among glycosylphosphatidylinositol toxins from different geographic isolates of Plasmodium falciparum. Mol Biochem Parasitol 103, 273-278.
8. Boonyarattanakalin, S., Liu, X., Michieletti, M., Lepenies, B., and Seeberger, P.H. (2008). Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis. J Am Chem Soc 130, 16791-16799.
9. Chang, T., Milne, K.G., Güther, M.L., Smith, T.K., and Ferguson, M.A. (2002). Cloning of Trypanosoma brucei and Leishmania major genes encoding the GlcNAc-phosphatidylinositol de-Nacetylase of glycosylphosphatidylinositol biosynthesis that is essential to the African sleeping sickness parasite. J Biol Chem 277, 50176-50182.
10. Chtanova, T., Han, S.J., Schaeffer, M., van Dooren, G.G., Herzmark, P., Striepen, B., et al. (2009). Dynamics of T cell, antigenpresenting cell, and pathogen interactions during recall responses in the lymph node. Immunity 31, 342-355.
11. Dell, A., Morris, H.R., Easton, R.L., Patankar, M., and Clark, G.F. (1999). The glycobiology of gametes and fertilization. Biochim Biophys Acta 1473, 196-205.
12. Delorenzi, M., Sexton, A., Shams-Eldin, H., Schwarz, R.T., Speed, T., and Schofield, L. (2002). Genes for glycosylphosphatidylinositol toxin biosynthesis in Plasmodium falciparum. Infect Immun 70, 4510-4522.
13. de Macedo, C.S., Shams-Eldin, H., Smith, T.K., Schwarz, R.T., and Azzouz, N. (2003). Inhibitors of glycosyl-phosphatidylinositol anchor biosynthesis. Biochimie 85, 465-472.
14. de Paz, J.L., and Seeberger, P.H. (2008).Deciphering the glycosaminoglycan code with the help of microarrays. Mol Biosyst 4, 707-711.
15. Dodd, R.B., and Drickmer, K. (2001). Lectin-like proteins in model organisms: implications for evolution of carbohydratebinding activity. Glycobiology 11, 71R-79R.
16. Dube, D.H., and Bertozzi, C.R. (2005). Glycans in cancer and inflammation-potential for therapeutics and diagnostics. Nat Rev Drug Discov Nat Rev Drug Discov 4, 477-488.
17. Eisenhaber, B., Maurer-Stroh, S., Novatchkova, M., Schneider, G., and Eisenhaber, F. (2003). Enzymes and auxiliary factors for GPI lipid anchor biosynthesis and post-translational transfer to proteins. BioEssays 4, 367-385.
18. Ferguson, M.A. (1999). The structure, biosynthesis and functions of glycosylphosphatidylinositol anchors, and the contributions of trypanosome research. J Cell Sci 112, 2799-2809.
19. Ferguson, M.A., Brimacombe, J.S., Brown, J.R., Crossman, A., Dix, A., Field, R.A., et al. (1999). The GPI biosynthetic pathway as a therapeutic target for African sleeping sickness. Biochim Biophys Acta 1455, 327-340.
20. Freeze, H.H., and Aebi, M. (2005). Altered glycan structures: the molecular basis of congenital disorders of glycosylation. Curr Opin Struct Biol 15, 490-498.
21. Fujita, M., and Jigami, Y. (2008). Lipid remodeling of GPIanchored proteins and its function. Biochem Biophys Acta 1780, 410-420.
22. Fukuda, M.N., and Akama, T.O. (2003). The role of N-glycans in spermatogenesis. Cytogenet Genome Res 103, 302-306.
23. Fuster, M.M., and Esko, J.D. (2005). The sweet and sour of cancer: glycans as novel therapeutic targets. Nat Rev Cancer 2005 5, 526-542.
24. Gagneux, P., and Varki, A. (1999). Evolutionary considerations in relating oligosaccharide diversity to biological function. Glycobiolgy 9, 747-755.
25. Horlacher, T., and Seeberger, P.H. (2008). Carbohydrate arrays as tools for research and diagnostics. Chem Soc Rev 37, 1414-1422.
26. Hong, Y., and Kinoshita, T. (2009). Trypanosome glycosylphosphatidylinositol Biosynthesis. Korean J Parasitol 47, 197-204.
27. Hsu, K.L., and Mahal, L.K. (2009). Sweet tasting chips: microarraybased analysis of glycans. Curr Opin Chem Biol 13, 427-432.
28. Hwa, K.Y. (2001). Glycosyl phosphatidylinositol-linked glycoconjugates: structure, biosynthesis and function. Adv Exp Med Biol 491, 207-214.
29. Ikezawa, H. (2002). Glycosylphosphatidylinositol (GPI)-anchored proteins. Biol Pharm Bull 4, 409-417.
30. Inoue, N., Izui-Sarumaru, T., Murakami, Y., Endo, Y., Nishimura, J.I., Kurokawa, K., et al. (2006). Molecular basis of clonal expansion of hematopoiesis in 2 patients with paroxysmal nocturnal hemoglobinuria (PNH). Blood 108, 4232-4236.
31. Jaeken, J., and Matthijs, G. (2007). Congenital disorders of glycosylation: a rapidly expanding disease family. Annu Rev Genomics Hum Genet 8, 261-278.
32. Kamena, F., Tamborrini, M., Liu, X., Kwon, Y.U., Thompson, F., Pluschke, G., et al. (2008). Synthetic GPI array to study antitoxic malaria response. Nat Chem Biol 4, 238-240.
33. Kinoshita, K., and Inoue, N. (2000). Dissecting and manipulating the pathway for glycosylphosphatidylinositol-anchor biosynthesis. Curr Opin Chem Biol 4, 632-638.
34. Kinoshita, T., Fujita, M., and Maeda, Y. (2008). Biosynthesis, remodelling and functions of mammalian GPI-anchored proteins: recent progress. J Biochem 144, 287-294.
35. Kobata, A. (2000). A journey to the world of glycobiology. Glycoconj J 17, 443-464.
36. Kravetz, J.D., and Federman, D.G. (2005). Toxoplasmosis in pregnancy. Am J Med. 118, 212-216.
37. Krishnamoorthy, L., and Mahal, L.K. (2009). Glycomic analysis: an array of technologies. ACS Chem Biol 4, 715-732.
38. Kwon, Y.U., Soucy, R.L., Snyder, D.A., and Seeberger, P.H. (2005). Assembly of a series of malarial glycosylphosphatidylinositol anchor oligosaccharides. Chem Eur J 11, 2493-2504.
39. Larsen, K., Thygesen, M.B., Guillaumie, F., Willats, W.G., and Jensen, K.J. (2006). Solid-phase chemical tools for glycobiology. Carbohydr Res 2006 341, 1209-1234.
40. Lau, K.S., and Denis, J.W. (2008). N-Glycans in cancer progression. Glycobiology 18, 750-760.
41. Lekutis, C., Ferguson, D.J., Grigg, M.E., Camps, M., and Boothroyd, J.C. (2001). Surface antigens of Toxoplasma gondii: variations on a theme. Int J Parasitol 31, 1285-1292.
42. Ley, K., and Kansas, G.S. (2004). Selectins in T-cell recruitment to non-lymphoid tissues and sites of inflammation. Nat Rev Immunol 4, 325-335.
43. Lim, J., Gowda, D.C., Krishnegowda, G., and Luckhart, S. (2005). Induction of nitric oxide synthase in Anopheles stephensi by Plasmodium falciparum: mechanism of signaling and the role of parasite glycosylphosphatidylinositols. Infect Immun 73, 2778-2789.
44. Lis, H.S., and Sharon, N. (1998). Lectins: carbohydrate-specific proteins that mediate cellular recognition. Chem Rev 98, 637-674.
45. Liu, Y., Palma, A.S., and Feizi, T. (2009). Carbohydrate microarrays: key developments in glycobiology. Biol Chem 390, 647-656.
46. Maeda, Y., Ashida, H., and Kinoshita, T. (2006). CHO glycosylation mutants: GPI anchor. Methods Enzymol 416, 182-205.
47. Magez, S., Stijlemans, B., Radwanska, M., Pays, E., Ferguson, M.A.J., and De Baetselier, P. (1998). The glycosyl-inositolphosphate and dimyristoylglycerol moieties of the glycosylphosphatidylinositol anchor of the trypanosome variant-specific surface glycoprotein are distinct macrophage-activating factors. J Immunol 160, 1949-1956.
48. McConville, M.J., and Menon, A.K. (2000). Recent developments in the cell biology and biochemistry of glycosylphosphatidylinositol lipids. Mol Membr Biol 17, 1-16.
49. Mendonça-Previato, L., Todeschini, A.R., Heise, N., and Jose Osvaldo Previato, J.O. (2005). Protozoan parasite-specific carbohydrate structures. Curr Opin Struct Biol 15, 499-505.
50. Naik, R.S., Branch, O.H., Woods, A.S., Vijaykumar, M., Perkins, D.J., Nahlen, B.L., et al. (2000). Glycosylphosphatidylinositol anchors of Plasmodium falciparum: molecular characterization and naturally elicited antibody response that may provide immunity to malaria pathogenesis. J Exp Med 192, 1563-1576.
51. Oppenheimer, S.B., Alvarez, M., and Nnoli, J. (2008). Carbohydrate-based experimental therapeutics for cancer, HIV=AIDS and other diseases. Acta Histochem Acta Histochem 110, 6-13.
52. Orlean, P., and Menon, A.K. (2007). Thematic review series: lipid posttranslational modifactions. GPI anchoring of protein in yeast in mammalian cells, or: how we learned to stop worrying and love glycophospholipids. J Lipid Res 48, 993-1011.
53. Oyelaran, O., and Gildersleeve, J.C. (2007). Application of carbohydrate array technology to antigen discovery and vaccine development. Expert Rev Vaccines 6, 957-969.
54. Oyelaran, O., McShane, L.M., Dodd, L., and Gildersleeve, J.C. (2009a). Profiling human serum antibodies with a carbohydrate antigen microarray. J Proteome Res 8, 4301-4310.
55. Oyelaran, O., and Gildersleeve, J.C. (2009b). Glycan arrays: recent advances and future challenges. Curr Opin Chem Biol 13, 406-413.
56. Paulick, M.G., and Bertozzi, C.R. (2008). The glycosylphosphatidylinositol anchor: a complex membrane-anchoring structure for proteins. Biochemistry 47, 6991-7000.
57. Plante, O.J., Andrade, R.B., and Seeberger, P.H. (1999). Synthesis and use of glycosyl phosphates as glycosyl donors. Org Lett 1, 211-214.
58. Plante, O.J., Palmacci, E.R., Andrade, R.B., and Seeberger, P.H. (2001). Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents. J Am Chem Soc 123, 9545-9554.
59. Powell, A.K., Zhi, Z.L., and Turnbull, J.E. (2009). Saccharide microarrays for high-throughput interrogation of glycanprotein binding interactions. Methods Mol Biol 534, 313-329.
60. Ree, van R. (2002). Carbohydrate epitopes and their relevance for the diagnosis and treatment of allergic diseases. Int Arch Allergy Immunol 129, 189-197.
61. Robinson, P.J. (1991). Signal transduction by GPI-anchored membrane proteins. Cell Biol Intern Rep 15, 761-767.
62. Roseman, S. (2001). Reflections on glycobiology. J Biol Chem 276, 41527-41542.
63. Rudd, P.M., Elliott, T., Cresswell, P., Wilson, I.A., and Dwek, R.A. (2001). Glycosylation and the immune system. Science 291, 2370-2376.
64. Rudd, P.M., Wormald, M.R., and Dwek, R.A. (2004). Sugarmediated ligand-receptor interactions in the immune system. Trends Biotechnol 22, 524-530.
65. Schmidt, A., Schwarz, R.T., and Gerold, P. (1998). Plasmodium falciparum: asexual erythrocytic stages synthesize two structurally distinct free and protein-bound glycosylphosphatidylinositols in a maturation-dependent manner. Exp Parasitol 88, 95-102.
66. Schmidt, R.R. (1986). New methods for the synthesis of glycosides and oligosaccharides. Are there alternatives to the Koenigs-Knorr method? Angew Chem Int Ed Engl 25, 212-235.
67. Schmidt, R.R., and Michel, J. (1980). Facile synthesis of R- and b-O-glycosyl imidates; preparation of glycosides and disaccharides. Angew Chem Int Ed Engl 19, 731-732.
68. Schofield, L. (1997). Malaria toxins revisited. Parasitol Today 13, 275-276.
69. Schofield, L. (2007). Rational approaches to developing an antidisease vaccine against malaria. Microbes Infect 9, 784-791.
70. Schofield, L., and Grau, G. (2005). Immunological processes in malaria pathogenesis. Nat Rev Immunol 9, 722-735.
71. Schofield, L., and Hackett, F. (1993). Signal transduction in host cells by a glycosylphosphatidylinositol toxin of malaria parasites. J Exp Med 177, 145-153.
72. Schofield, L., and Tachado, S.D. (1996). Regulation of host cell function by glycosylphosphatidylinositols of parasitic protozoa. Immunol Cell Biol 74, 555-563.
73. Schofield, L., Novakovic, S., Gerold, P., Schwarz, R.T., McConville, M.J., and Tachado, S.D. (1996). Glycosylphosphatidylinositol toxin of Plasmodium falciparum up-regulates intercellular adhesion molecule-1, vascular cell adhesion molecule-1, and E-selectin expression in vascular endothelial cells and increases leukocyte kinase-dependent signal transduction. J Immunol 156, 1886-1896.
74. Schofield, L., Hewitt, M.C., Evans, K., Siomos, M.-A., and Seeberger, P.H. (2002). Synthetic GPI as a candidate anti-toxic vaccine in a model of malaria. Nature 418, 785-789.
75. Seeberger, P.H., and Werz, D.B. (2005). Automated synthesis of oligosaccharides as a basis for drug discovery. Nat Rev Drug Discov 4, 751-763.
76. Seeberger, P.H., and Werz, D.B. (2007). Synthesis and medical applications of oligosaccharides. Nature 446, 1046-1051.
77. Smith, T.K., Milne, F.C., Sharma, D.K., Crossman, A., Brimacombe, J.S., and Ferguson, M.A. (1997a). Early steps in glycosylphosphatidylinositol biosynthesis in Leishmania major. Biochem J 326, 393-400.
78. Smith, T.K., Sharma, D.K., Crossman, A., Dix, A., Brimacombe, J.S., and Ferguson, M.A. (1997b). Parasite and mammalian GPI biosynthetic pathways can be distinguished using synthetic substrate analogues. EMBO J 16, 6667-6675.
79. Smith, T.K., Sharma, D.K., Crossman, A., Brimacombe, J.S., and Ferguson, M.A. (1999). Selective inhibitors of the glycosylphosphatidylinositol biosynthetic pathway of Trypanosoma brucei. EMBO J 18, 5922-5930.
80. Smith, T.K., Gerold, P., Crossman, A., Paterson, M.J., Borissow, C.N., Brimacombe, J.S., et al. (2002). Substrate specificity of the Plasmodium falciparum glycosylphosphatidylinositol biosynthetic pathway and inhibition by species-specific suicide substrates. Biochemistry 41, 12395-12406.
81. Smith, T.K., Crossman, A., Brimacombe, J.S., and Ferguson, M.A. (2004). Chemical validation of GPI biosynthesis as a drug target against African sleeping sickness. EMBO J 23, 4701-4708.
82. Springer, T.A., and Lasky, L.A. (1991). Cell adhesion. Sticky sugars for selectins. Nature 349, 196-197.
83. Stallforth, P., Lepenies, B., Adibekian, A., and Seeberger, P.H. (2009). Claude S. Hudson Award in carbohydrate chemistry. Carbohydrates: a frontier in medicinal chemistry. J Med Chem 52, 5561-5577.
84. Svarovsky, S.A., and Joshi, L. (2008). Biocombinatorial selection of carbohydrate binding agents of therapeutic significance. Curr Drug Discov Technol 5, 20-28.
85. Tachado, S.D., and Schofield, L. (1994). Glycosylphosphatidylinositol toxin of Trypanosoma brucei regulates IL-1 alpha and TNF-alpha expression in macrophages by protein tyrosine kinase mediated signal transduction. Biochem Biophys Res Commun 205, 984-991.
86. Tachado, S.D., Gerold, P., McConville, M.J., Baldwin, M.J., Quilici, D., Schwarz, R.T., et al. (1996). Glycosylphosphatidylinositol toxin of Plasmodium falciparum induces nitric oxide synthase expression in macrophages and vascular endothelial cells by a protein tyrosine kinase-dependent and protein kinase C-dependent signaling pathway. J Immunol 156, 1897-1907.
87. Tachado, S.D., Gerold, P., Schwarz, R.T., Novakovic, S., McConville, M.J., and Schofield, L. (1997). Signal transduction in macrophages by glycosylphosphatidylinositols of Plasmodium, Trypanosoma, and Leishmania: activation of protein tyrosine kinases and protein kinase C by inositolglycan and diacylglycerol moieties. Proc Natl Acad Sci USA 94, 4022-4027.
88. Tachado, S.D., Mazhari-Tabrizi, R., and Schofield, L. (1999). Specificity in signal transduction among glycosylphosphatidylinositols of Plasmodium falciparum, Trypanosoma brucei, Trypanosoma cruzi and Leishmania spp. Parasite Immunol 12, 609-617.
89. Tiede, A., Bastisch, I., Schubert, J., Orlean, P., and Schmidt, R. E. (1999). Biosynthesis of glycosylphosphatidylinositols in mammals and unicellular microbes. Biol Chem 380, 503-523.
90. Urbaniak, M.D., Yashunsky, D.V., Crossman, A., Nikolaev, A.V., and Ferguson, M.A. (2008). Probing enzymes late in the trypanosomal glycosylphosphatidylinositol biosynthetic pathway with synthetic glycosylphosphatidylinositol analogues. ACS Chem Biol 3, 625-634.
91. Uttamchandani, M., Neo, J.L., Ong, B.N., and Moochhala, S. (2009). Applications of microarrays in pathogen detection and biodefence. Trends Biotechnol 27, 53-61.
92. von Itzstein, M. (2008). Disease-associated carbohydraterecognising proteins and structure-based inhibitor design. Curr Opin Struct Biol 18, 558-566.
93. von Itzstein, M., Plebanski, M., Cooke, B.M., and Coppel, R.L. (2008). Hot, sweet and sticky: the glycobiology of Plasmodium falciparum. Trends Parasitol 24, 210-218.
94. Wichroski, M.J., and Ward, G.E. (2003). Biosynthesis of glycosylphosphatidylinositol is essential to the survival of the protozoan parasite Toxoplasma gondii. Eukaryot Cell 2, 1132-1136.
95. Wu, Q., and Guo, Z. (2009). Glycosylphosphatidylinositols are potential targets for the development of novel inhibitors for aerolysin-type of pore-forming bacterial toxins. Med Res Rev (in press).
96. Xu, G., and Lam, K.S. (2003). Protein and chemical microarrayspowerful tools for proteomics. J Biomed Biotechnol 2003, 257-266.
97. Zhang, H., Ma, Y., and Sun, X.L. (2009). Recent developments in carbohydrate-decorated targeted drug=gene delivery. Med Res Rev (in press).