Synthesis and immunochemical characterization of protein conjugates of carbohydrate and carbohydrate-mimetic peptides as experimental vaccines

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 13, 2004, Pages 3743-3754

  Hossany, Rehana B ^a   Johnson, Margaret A ^a   Eniade, Adewale A ^a   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

Carbohydrate mimetic peptides; Group A Streptococcus; Polysaccharide conjugate vaccine; Protein conjugate vaccines; Shigella flexneri Y

Indexed keywords

1,3 PROPANEDIAMINE; BACTERIAL VACCINE; BOVINE SERUM ALBUMIN; CARRIER PROTEIN; HAPTEN; MONOCLONAL ANTIBODY; OLIGOPEPTIDE; POLYSACCHARIDE; SQUARIC ACID DERIVATIVE; TETANUS TOXOID;

AMINATION; ARTICLE; CELL SURFACE; CONTROLLED STUDY; DRUG BINDING; DRUG CONJUGATION; DRUG SYNTHESIS; IMMUNOCHEMISTRY; NONHUMAN; PROTEIN ANALYSIS; REDUCTION KINETICS; SHIGELLA FLEXNERI; STREPTOCOCCUS;

AMINO ACID SEQUENCE; ANTIBODIES; ANTIGENS; BIOMIMETIC MATERIALS; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; GLYCOCONJUGATES; INHIBITORY CONCENTRATION 50; LIPOPOLYSACCHARIDES; PEPTIDES; PROTEINS; SHIGELLA FLEXNERI; STREPTOCOCCUS PYOGENES; VACCINES;

BOVINAE; SHIGELLA; SHIGELLA FLEXNERI; STREPTOCOCCUS; STREPTOCOCCUS SP. 'GROUP A';

EID: 2942573498     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.03.075     Document Type: Article

References (64)

1. Janeway C.A., Travers P. Austin P., Lawrence E., Robertson M. Immunobiology: The Immune System in Health and Disease. 3rd ed. 1997;Garland, New York
2. Mackett M., Williamson J.D. Human Vaccine. 1995;Bios Scientific, Oxford
3. Brown F. Vaccine Design Chichester. 1993;Wiley
4. Cruz S.J. Immunotherapy and Vaccines. 1997;Weinhein, VCH
5. Mims C.A. The Pathogenesis of Infectious Disease. 1976;Academic, London
6. Lerner R.A. Sci. Am. 248:1983;48
7. Jennings H.J. Curr. Top. Microbiol. Immunol. C 125:1990;373
8. Jennings H.J. Adv. Exp. Med. Biol. 228:1988;495
9. Lee C.-J. Mol. Immunol. 24:1987;1005
10. Lindberg A.A. Vaccine 17 Suppl. 2:1999;S28
11. Benaissa-Trouw B., Lefeber D.J., Kamerling J.P., Vliegenthart J.F.G., Kraaijeveld K., Snippe H. Infect. Immun. 69:2001;4698-4701
12. Pozsgay V. Adv. Carbohydr. Chem. Biochem. 56:2001;153
13. Peeters C.A., Tenbergen-Meekes A.M., Poolman J.T., Beurret M., Zegers B.J.M., Rijkers G.T. Infect. Immun. 59:1991;3504
14. Barington T., Gyhrs A., Kristensen K., Heilmann C. Infect. Immun. 62:1994;9
15. Johnson M.A., Pinto B.M. Aust. J. Chem. 55:2002;13
16. Zwick M.B., Shen J., Scott J.K. Curr. Opin. Biotechnol. 9:1998;427
17. Bisno A.L. Mandell G.L., Douglas R.G., Benett J.E. Principles and Practice of Infectious Diseases. 2nd ed. 1985;Wiley, New York. Chapter 160, p.133
18. Read S.E., Zabriskie J.B. Read S.E., Zabriskie J.B. Streptococcus Diseases and the Immune Response. 1980;Academic, New York
19. Weiss K.A., Laverdiere M. Can. J. Surg. 40:1997;18
20. Stevens D.L. Immunol. Invest. 26:1997;129
21. Nowak R. Science. 264:1994;1665
22. Blake, M. S.; Zabriskie, J. B.; Tai, J. Y.; Michon, F. U.S. Patent 5,866,135, 1999
23. Hale T.L. Hansler W.J., Shumman M. Topley and Wilson's Microbiology and Microbial Infections. Vol. 3:1998;479 Arnold, London
24. Coligan J.E., Kindt T.J., Krause R.M. Immunochemistry. 15:1978;755
25. Huang D.H., Krishna N.R., Pritchard D.G. Carbohydr. Res. 155:1986;193
26. Kenne L., Lindberg B., Petersson K., Romanowska E. Carbohydr. Res. 56:1977;363
27. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 76:1977;327
28. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 91:1978;279
29. Carlin N.I.A., Lindberg A.A., Bock K., Bundle D.R. Eur. J. Biochem. 139:1984;189
30. Harris S.L., Craig L., Mehroke J.S., Rashed M., Zwick M.B., Kenar K., Toone E.J., Greenspan N., Auzanneau F.-I., Marino-Albernas J.-R., Pinto B.M., Scott J.K. Proc. Natl. Acad. Sci. U.S.A. 94:1997;2454
31. Bundle D.R., Gidney M.A.J., Josephson S., Wessel H.-P. Synthesis of Shigella flexneri O-Antigenic Repeating Units. Anderson H.-P., Unger F.M. Conformational Probes and Aids to Monoclonal Antibody Production. ACS Symp. Ser. 231. Vol. 83:1983;American Chemical Society, Washington
32. Bundle D.R. Pure Appl. Chem. 61:1989;1171
33. Bundle D.R., Altman E., Auzanneau F.-I., Baumann H., Eichler E., Sigurskjold B.W. The Structure of Oligosaccharide-Antibody Complexes and Improved Inhibitors of Carbohydrate-Protein Binding in Complex Carbohydrates in Drugs Research. Bock K., Clausen H. Alfred Benzon Symp. Ser. 36. 1994;Munksgaard, Copenhagen
34. Hecht S. Recognition of Carbohydrate Antigens by Antibody Binding Sites in Carbohydrates. 1998;Oxford University Press Inc. Oxford
35. Vyas M.N., Vyas N.K., Meikle P.J., Sinnott B., Pinto B.M., Bundle D.R., Quiocho F.A. J. Mol. Biol. 231:1993;133
36. Vyas N.K., Vyas M.N., Chervenak M.C., Johnson M.A., Pinto B.M., Bundle D.R., Quoicho F.A. Biochemistry. 41:2002;13575
37. Rhodes G., Houghten R., Taulane J.P., Carson D., Vaughan J. Molec. Immun. 21:1984;1047
38. Dyson J.H., Cross K.J., Houghten R.H., Wilson I.A., Wright P.E., Lerner R.A. Nature. 318:1985;480
39. Geysen H.M., Meloen R.H., Barteling S.J. Proc. Natl. Acad. Sci. U.S.A. 81:1984;3998
40. Dyrberg T., Oldstone M.B.A. J. Exp. Med. 164:1986;1344
41. Schaaper W.M.M., Lankhof H., Puijk W.C., Meleon R.H. Molec. Immun. 26:1989;81
42. Mezo G., Dalmadi B., Mucsi I., Bosze S., Rajnavolgyi E., Hudecz F. J. Peptide Sci. 8:2002;107
43. Batzloff M.R., Hayman W.A., Davies M.R., Zeng M., Pruksakorn S., Brandt E.R., Good M.F. J. Infect. Dis. 187:2003;1598
44. Goetsch L., Haeuw J.F., Champion T., Lacheny C., N'Guyen T., Beck A., Corvaia N. Clin. Diagn. Lab. Immunol. 10:2003;125
45. Geoghegan K.F., Stroh J.G. Bioconjugate Chem. 3:1992;138
46. Johnson M.A., Rotondo A., Pinto B.M. Biochemistry. 41:2002;2149
47. Johnson M.A., Pinto B.M. Bioorg. Med. Chem. 12:2004;295
48. Johnson M.A., Eniade A.A., Pinto B.M. Bioorg. Med. Chem. 11:2003;781
49. Tieze L.F., Schroter C., Gabius S., Brinck U., Goerlach-Graw A., Gabius H.-J. Bioconjugate Chem. 2:1991;148
50. Auzanneau F.-I., Pinto B.M. Bioorg. Med. Chem. 4:1996;2003
51. Kamath V.P., Diedrich P., Hindsgaul O. Glycoconj. J. 13:1996;315
52. Atherton E., Sheppard R.C. Solid Phase Peptide Synthesis: A Practical Approach. 1989;IRL, New York
53. Rink H. Tetrahedron Lett. 28:1987;3787
54. Bernatowicz M.S., Daniels S.B., Koster H. Tetrahedron Lett. 30:1989;4645
55. Cammish L.E., Kates S.A. Chan W.C., White P.D. Fmoc Solid Phase Peptide Synthesis: A Practical Approach. 2000;Oxford University Press, Oxford, England
56. Dourtoglou V., Ziegler J.C., Gross B. Tetrahedron Lett. 19:1978;1269
57. Dourtoglou V., Cross B., Lambropoulou V., Zioudrou C. Synthesis. 1984;572
58. Knorr R., Trzeciak A., Bannwarth W., Gillessen D. Tetrahedron Lett. 30:1989;1927
59. Sinnott, B.; Bundle, D. R., unpublished results
60. Altman E., Bundle D.R. Methods Enzym. 247:1994;243
61. Colescott R.L., Bossinger C.D., Cook P.I., Kaiser E. Anal Biochem. 34:1970;595
62. Dubois M., Gilles K.H., Hamilton J.K., Rebers P.A., Smith F. Anal. Chem. 28:1956;1988
63. Johnston, B. D.; Pinto, B. M., unpublished results
64. Perrin D.D., Armarego W.L.F. Purification of Laboratory Chemicals. 3rd ed. 1988;Pergamon, London