"Multivalent" saccharides: Development of new approaches for inhibiting the effects of glycosphingolipid-binding pathogens

Biochemical Pharmacology

Volumn 65, Issue 5, 2003, Pages 699-707

  Schengrund, Cara Lynne ^a  

^a PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

Dendrimers; Gangliosides; Glycosphingolipid binding pathogens; Glycosphingolipids; Multivalent saccharides

Indexed keywords

BACTERIAL TOXIN; CARBOHYDRATE; CARBOHYDRATE BINDING PROTEIN; GLYCOSPHINGOLIPID; LECTIN; LIGAND;

BACTERIUM; BINDING SITE; CELL SURFACE; NONHUMAN; PATHOGENESIS; PRIORITY JOURNAL; PROTEIN BINDING; REVIEW; VIRUS;

EID: 0037333208     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(02)01553-8     Document Type: Note

References (80)

1. 1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid synthesis in cultured neurons in situ. J. Biol. Chem. 268:1993;27299-27306.
2. Platt F.M., Neises G.R., Karlsson G.B., Dwek R.A., Butters T.D. N-Butyldeoxygalactonojirimycin inhibits glycolipid biosynthesis but does not affect N-linked oligosaccharide processing. J. Biol. Chem. 269:1994;27108-27114.
3. Vunnam R.R., Radin N.S. Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain. Chem. Phys. Lipids. 26:1980;265-278.
4. Abe A., Inokuchi J., Jimbo M., Shimeno H., Nagamatsu J.A., Shukla G.S., Radin N.S. Improved inhibitors of glucosylceramide synthase. J. Biochem. (Tokyo). 111:1992;191-196.
5. Ledeen R.W., Yu R.K. Gangliosides: structure, isolation, and analysis. Methods Enzymol. 83:1982;139-191.
6. Hansson G.C., Karlsson K.-A., Larson G., Stromberg N., Thurin J. Carbohydrate-specific adhesion of bacteria to thin-layer chromatograms: a rationalized approach to the study of host cell glycolipid receptors. Anal. Biochem. 146:1985;158-163.
7. Kasai N., Naiki M., Yu R.K. Autoradiography of ganglioside antigens separated by high-performance thin-layer chromatography with their antibodies. J. Biochem. (Tokyo). 96:1984;261-264.
8. Schengrund C.-L., Ringler N.J. Binding of Vibrio cholera toxin and the heat-labile enterotoxin of Escherichia coli to GM1, derivatives of GM1, and non-lipid, oligosaccharide polyvalent ligands. J. Biol. Chem. 264:1989;13233-13237.
9. van Heyningen W.E., Carpenter C.C.J., Pierce N.F., Greenough W.B. III Deactivation of cholera toxin by ganglioside. J. Infect. Dis. 124:1971;415-418.
10. Cuatrecasas P. Interaction of Vibrio cholerae enterotoxin with cell membranes. Biochemistry. 12:1973;3547-3558.
11. Moss J., Fishman P.H., Manganiello V.C., Vaughan M., Brady R.O. Functional incorporation of ganglioside into intact cells: induction of choleragen responsiveness. Proc. Natl. Acad. Sci. U.S.A. 73:1976;1034-1037.
12. Simons K., Ikonen E. Functional rafts in cell membranes. Nature. 387:1997;569-572.
13. Lee Y.C., Lee R.T. Carbohydrate-protein interactions: basis of glycobiology. Acc. Chem. Res. 28:1995;321-327.
14. Lee R.T., Lee Y.C. Affinity enhancement by multivalent lectin-carbohydrate interaction. Glycoconj. J. 17:2000;543-551.
15. Pritchett T.J., Paulson J.C. Basis for the potent inhibition of influenza virus infection by equine and guinea pig α-2 macroglobulin. J. Biol. Chem. 264:1989;9850-9858.
16. Sixma T.K., Kalk K.H., van Zanten B.A.M., Dauter Z., Kingma J., Witholt B., Hol W.G.J. Refined structure of Escherichia coli heat-labile enterotoxin, a close relative of cholera toxin. J. Mol. Biol. 230:1993;890-918.
17. Merritt E.A., Sixma T.K., Kalk K.H., van Zanten B.A.M., Hol W.G.J. Galactose-binding site in Escherichia coli heat-labile enterotoxin (LT) and cholera toxin (CT). Mol. Microbiol. 13:1994;745-753.
18. Yamamoto T., Nakazawa T., Miyata T., Kaji A., Yokota T. Evolution and structure of two ADP-ribosylation enterotoxins, Escherichia coli heat-labile toxin and cholera toxin. FEBS Lett. 169:1984;241-246.
19. Holmgren J., Mansson J.-E., Svennerholm L. Tissue receptor for cholera exotoxin. Structural requirements of G11 ganglioside in toxin binding and inactivation. Med. Biol. 52:1974;229-233.
20. Gtet 1 and its derivatives with choleragen. Eur. J. Biochem. 48:1974;103-110.
21. Schwarzmann G., Mraz W., Sattler J., Schindler R., Wiegandt H. Comparison of the interaction of mono- and oligovalent ligands with cholera toxin. Demonstration of aggregate formation at low concentrations. Hoppe. Seylers. Z. Physiol. Chem. 359:1978;1277-1286.
22. Lee Y.C., Stowell C.P., Krantz M.J. 2-Imino-2-methoxyethyl 1-thioglycosides: new reagents for attaching sugars to proteins. Biochemistry. 15:1976;3956-3963.
23. De Brabander-van den Berg E.M.M., Meijer E.W. Poly(propylene imine) dendrimers: large-scale synthesis by heterogeneously catalyzed hydrogenations. Angew. Chem. Int. Ed. Engl. 32:1993;1308-1311.
24. Turnbull W.B., Stoddart J.F. Design and synthesis of glycodendrimers. Rev. Mol. Biotechnol. 90:2002;231-255.
25. Duncan R., Malik N. Dendrimers: biocompatability and potential for delivery of anticancer agents. Proc. Int. Symp. Control Release Bioact. Mater. 23:1996;105-106.
26. Ashton P.R., Boyd S.E., Brown C.L., Nepogodiev S.A., Meijer E.W., Peerlings H.W.I., Stoddart J.F. Synthesis of glycodendrimers by modification of poly(propylene imine) dendrimers. Chem. Eur. J. 3:1997;974-984.
27. Roy R., Baek M.-G., Rittenhouse-Olson K. Synthesis of N,N′-bis(acrylamido)acetic acid based T-antigen glycodendrimers and their mouse monoclonal IgG antibody binding properties. J. Am. Chem. Soc. 123:2001;1809-1816.
28. Roy R., Baek M.-G. Glycodendrimers: novel glycotope isosteres unmasking sugar coding. Case study with T-antigen markers from breast cancer MUC1 glycoprotein. Rev. Mol. Biotechnol. 90:2002;291-309.
29. Kitov P.I., Sadowska J.M., Mulvey G., Armstrong G.D., Ling H., Pannu N.S., Read R.J., Bundle D.R. Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands. Nature. 403:2000;669-672.
30. Kamath V.P., Diedrich P., Hindsgaul O. Use of diethyl squarate for the coupling of oligosaccharide amines to carrier proteins and characterization of the resulting neoglycoproteins by MALDI-TOF mass spectrometry. Glycoconj. J. 13:1996;315-319.
31. McBroom C.R., Samanen C.H., Goldstein I.J. Carbohydrate antigens: coupling of carbohydrates to proteins by diazonium and phenylisothiocyanate reactions. Methods Enzymol. 28:1972;212-219.
32. Elofsson M., Walse B., Kihlberg J. Building blocks for glycopeptide synthesis: glycosylation of 3-mercaptopropionic acid and Fmoc amino acids with unprotected carboxyl groups. Tetrahedron Lett. 51:1991;7613-7616.
33. Chernyak A., Karavanov A., Ogawa Y., Kovac P. Conjugating oligosaccharides to proteins by squaric acid diester chemistry: rapid monitoring of the progress of conjugation, and recovery of the unused ligand. Carbohydr. Res. 330:2001;479-486.
34. Mylvaganam M., Lingwood C.A. A convenient oxidation of natural glycosphingolipids to their "ceramide acids" for neoglycoconjugation. J. Biol. Chem. 274:1999;20725-20732.
35. Gray G.R. Antibodies to carbohydrates: preparation of antigens by coupling carbohydrates to proteins by reductive amination with cyanoborohydride. Methods Enzymol. 50:1978;155-160.
36. von der Lieth C.-W., Frank M., Lindhorst T.K. Molecular dynamics simulations of glycoclusters and glycodendrimers. Rev. Mol. Biotechnol. 90:2002;311-337.
37. Thompson J.P., Schengrund C.-L. Oligosaccharide-derivatized dendrimers: defined multivalent inhibitors of the adherence of the cholera toxin B subunit and the heat labile enterotoxin of E. coli to GM1. Glycoconj. J. 14:1997;837-845.
38. Fan E., Zhang Z., Minke W.E., Hou Z., Verlinde C.L.M.J., Hol W.G.J. High-affinity pentavalent ligands of Escherichia coli heat-labile enterotoxin by modular structure-based design. J. Am. Chem. Soc. 122:2000;2663-2664.
39. Minke W.E., Roach C., Hol W.G.J., Verlinde C.L.M.J. Structure-based exploration of the ganglioside GM1 binding sites of Escherichia coli heat-labile enterotoxin and cholera toxin for the discovery of receptor antagonists. Biochemistry. 38:1999;5684-5692.
40. Kuziemko G.M., Stroh M., Stevens R.C. Cholera toxin binding affinity and specificity for gangliosides determined by surface plasmon resonance. Biochemistry. 35:1996;6375-6384.
41. MacKenzie C.R., Hirama T., Lee K.K., Altman E., Young N.M. Quantitative analysis of bacterial toxin affinity and specificity for glycolipid receptors by surface plasmon resonance. J. Biol. Chem. 272:1997;5533-5538.
42. Dubois A., Berg D., Incecik E., Fiala N., Herman-Ackah L., Yang M., Wirth H.P., Perez-Perez G.I., Blaser M.J. Host specificity of Helicobacter pylori strains and host responses in experimentally challenged nonhuman primates. Gastroenterology. 116:1999;90-96.
43. Mysore J.V., Wigginton T., Simon P.M., Zopf D., Heman-Ackah L.M., Dubois A. Treatment of Helicobacter pylori infection in Rhesus monkeys using a novel antiadhesion compound. Gastroenterology. 117:1999;1316-1325.
44. Simon P.M., Goode P.L., Mobasseri A., Zopf D. Inhibition of Helicobacter pylori binding to gastrointestinal epithelial cells by sialic acid-containing oligosaccharides. Infect. Immun. 65:1997;750-757.
45. Reuter J.D., Myc A., Hayes M.H., Gan Z., Roy R., Qin D., Yin R., Piehler L.T., Esfand R., Tomalia D.A., Baker J.R. Jr. Inhibition of viral adhesion and infection by sialic-acid-conjugated dendritic polymers. Bioconjug. Chem. 10:1999;271-278.
46. Thompson J.P., Schengrund C.-L. Inhibition of the adherence of cholera toxin and the heat-labile enterotoxin of Escherichia coli to cell-surface GM1 by oligosaccharide-derivatized dendrimers. Biochem. Pharmacol. 56:1998;591-597.
47. Sears P., Wong C.-H. Toward automated synthesis of oligosaccharides and glycoproteins. Science. 291:2001;2344-2350.
48. Endo T., Koizumi S. Large-scale production of oligosaccharides using engineered bacteria. Curr. Opin. Struct. Biol. 10:2000;536-541.
49. Kitamura M., Iwamori M., Nagai Y. Interaction between Clostridium botulinum neurotoxin and gangliosides. Biochim. Biophys. Acta. 628:1980;328-335.
50. Walker R.I., Caldwell M.B., Lee E.C., Guerry P., Trust T.J., Ruiz-Palacios G.M. Pathophysiology of Campylobacter enteritis. Microbiol. Rev. 50:1986;81-94.
51. Suzuki S., Kawaguchi M., Mizuno K., Takama T., Yuki N. Immunological properties and ganglioside recognitions by Campylobacter jejuni-enterotoxin and cholera toxin. FEMS Immunol. Med. Microbiol. 8:1994;207-212.
52. Jolivet-Reynaud C., Hauttecoeur B., Alouf J.E. Interaction of Clostridium perfringens δ toxin with erythrocyte and liposome membranes and relation with the specific binding to the ganglioside GM2. Toxicon. 10:1989;1113-1126.
53. Donta S.T., Viner J.P. Inhibition of the steroidogenic effects of cholera and heat-labile Escherichia coli enterotoxin by GM1 ganglioside: evidence for a similar receptor site for the two toxins. Infect. Immun. 11:1975;982-985.
54. Teneberg S., Hirst T.R., Angstrom J., Karlsson K.-A. Comparison of the glycolipid-binding specificities of cholera toxin and porcine Escherichia coli heat-labile enterotoxin: identification of a receptor-active non-ganglioside glycolipid for the heat-labile toxin in infant rabbit small intestine. Glycoconj. J. 11:1994;533-540.
55. Chary P., Prasad R., Chopra A.K., Peterson J.W. Location of the enterotoxin gene from Salmonella typhimurium and characterization of the gene products. FEMS Microbiol. Lett. 111:1993;87-92.
56. k antigen) and a novel platelet glycosphingolipid. Infect. Immun. 66:1998;4355-4366.
57. Rogers T.B., Snyder S.H. High affinity binding of tetanus toxin to mammalian brain membranes. J. Biol. Chem. 256:1981;2402-2407.
58. Kiarash A., Boyd B., Lingwood C.A. 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. 269:1994;11138-11146.
59. Suzuki Y., Kato H., Naeve C.W., Webster R.G. Single-amino-acid substitution in an antigenic site of influenza virus hemagglutinin can alter the specificity of binding to cell membrane-associated gangliosides. J. Virol. 63:1989;4298-4302.
60. Matrosovich M., Miller-Podraza H., Teneberg S., Robertson J., Karlsson K.-A. Influenza viruses display high-affinity binding to human polyglycosylceramides represented on a solid-phase assay surface. Virology. 223:1996;413-416.
61. Cooling L.L.W., Koerner T.A.W., Naides S.J. Multiple glycosphingolipids determine the tissue tropism of Parvovirus B19. J. Infect. Dis. 172:1995;1198-1205.
62. Delorme C., Brussow H., Sidoti J., Roche N., Karlsson K.-A., Neeser J.-R., Teneberg S. Glycosphingolipid binding specificities of Rotavirus: identification of a sialic acid-binding epitope. J. Virol. 75:2001;2276-2287.
63. Epand R.M., Nir S., Parolin M., Flanagan T.D. The role of ganglioside GD1a as a receptor for Sendai virus. Biochemistry. 34:1995;1084-1089.
64. Brennan M.J., Joralmon R.A., Cisar J.O., Sandberg A.L. Binding of Actinomyces naeslundii to glycosphingolipids. Infect. Immun. 55:1987;487-489.
65. Backenson P.B., Coleman J.L., Benach J.L. Borrelia burgdorferi shows specificity of binding to glycosphingolipids. Infect. Immun. 63:1995;2811-2817.
66. Garcia-Monco J.C., Fernandez Villar B., Rogers R.C., Szczepanski A., Wheeler C.M., Benach J.L. Borrelia burgdorferi and other related spirochetes bind to galactocerebroside. Neurology. 42:1992;1341-1348.
67. 2 . Biochem. Biophys. Res. Commun. 175:1991;1082-1089.
68. Bailey G.B., Nudelman E.D., Day D.B., Harper C.F., Gilmour J.R. Specificity of glycosphingolipid recognition by Entamoeba histolytica trophozoites. Infect. Immun. 58:1990;43-47.
69. Krivan H.C., Roberts D.D., Ginsburg V. Many pulmonary pathogenic bacteria bind specifically to the carbohydrate sequence GalNAcβ1-4Gal found in some glycolipids. Proc. Natl. Acad. Sci. U.S.A. 85:1988;6157-6161.
70. Lanne B., Uggla L., Stenhagen G., Karlsson K.-A. Enhanced binding of enterotoxigenic Escherichia coli K99 to amide derivatives of the receptor ganglioside NeuGc-GM3. Biochemistry. 34:1995;1845-1850.
71. 3 ganglioside receptor. Infect. Immun. 61:1993;4518-4522.
72. Lanne B., Olsson B.-M., Jovall P.-A., Angstrom J., Linder H., Marklund B.-I., Bergstrom J., Karlsson K.-A. Glycoconjugate receptors for P-fimbriated Escherichia coli in the mouse. An animal model of urinary tract infection. J. Biol. Chem. 270:1995;9017-9025.
73. Evans D.G., Evans D.J. Jr., Moulds J.J., Graham D.Y. N-Acetylneuraminyllactose-binding fibrillar hemagglutinin of Campylobacter pylori: a putative colonization factor antigen. Infect. Immun. 56:1988;2896-2906.
74. Karlsson H., Johansson L., Miller-Podraza H., Karlsson K.-A. Fingerprinting of large oligosaccharides linked to ceramide by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry: highly heterogeneous polyglycosylceramides of human erythrocytes with receptor activity for Helicobacter pylori. Glycobiology. 9:1999;765-778.
75. Neeser J.-R., Granato D., Rouvet M., Servin A., Teneberg S., Karlsson K.-A. Lactobacillus johnsonii LA1 shares carbohydrate-binding specificities with several enteropathogenic bacteria. Glycobiology. 10:2000;1193-1199.
76. Krivan H.C., Olson L.D., Barile M.F., Ginsburg V., Roberts D.D. Adhesion of Mycoplasma pneumoniae to sulfated glycolipids and inhibition by dextran sulfate. J. Biol. Chem. 264:1989;9283-9288.
77. Stromberg N., Deal C., Nyberg G., Normark S., So M., Karlsson K.-A. Identification of carbohydrate structures that are possible receptors for Neisseria gonorrhoeae. Proc. Natl. Acad. Sci. U.S.A. 85:1988;4902-4906.
78. Karlsson K.-A. Animal glycolipids as attachment sites for microbes. Chem. Phys. Lipids. 42:1986;153-172.
79. Bernet M.F., Brassart D., Neeser J.R., Servin A.L. Lactobacillus acidophilus LA 1 binds to cultured human intestinal cell lines and inhibits cell attachment and cell invasion by enterovirulent bacteria. Gut. 35:1994;483-489.
80. Cundell D., Tuomanen E.I. Receptor specificity of adherence of Streptococcus pneumoniae to human type-II pneumocytes and vascular endothelial cells in vitro. Microb. Pathog. 17:1994;361-374.