Recent developments in synthetic oligosaccharide-based bacterial vaccines

Current Topics in Medicinal Chemistry

Volumn 8, Issue 2, 2008, Pages 126-140

  Pozsgay, Vince ^a  

^a EUNICE KENNEDY SHRIVER NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT   (United States)

Author keywords

Haemophilus influenzae; Keyhole limpet hemocyanin; Oligosaccharides; Shigella Dysenteriae Type 1; Streptococcus Pneumoniae

Indexed keywords

ANTHRAX VACCINE; B LYMPHOCYTE RECEPTOR; BACTERIAL VACCINE; BORRELIA BURGDORFERI VACCINE; DIPHTHERIA PERTUSSIS TETANUS HAEMOPHILUS INFLUENZAE TYPE B VACCINE; HAEMOPHILUS INFLUENZAE TYPE B VACCINE; IMMUNOGLOBULIN G ANTIBODY; MENINGOCOCCUS VACCINE; MYCOBACTERIUM TUBERCULOSIS VACCINE; OLIGOSACCHARIDE; PNEUMOCOCCUS VACCINE; POLYSACCHARIDE VACCINE; PSEUDOMONAS VACCINE; QUIMI HIB; SHIGELLA FLEXNERI 2A VACCINE; SHIGELLA VACCINE; STREPTOCOCCUS PNEUMONIAE TYPE 14 VACCINE; STREPTOCOCCUS PNEUMONIAE TYPE 3 VACCINE; STREPTOCOCCUS PNEUMONIAE TYPE 6B VACCINE; TEICHOIC ACID; VIBRIO CHOLERAE VACCINE; RECOMBINANT VACCINE;

ANTIGENICITY; B LYMPHOCYTE; CLINICAL TRIAL; DRUG EFFICACY; DRUG ISOLATION; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; HAEMOPHILUS INFLUENZAE TYPE B; HUMAN; IMMUNOREACTIVITY; INFECTION CONTROL; MAJOR HISTOCOMPATIBILITY COMPLEX; MENINGITIS; MOLECULAR WEIGHT; NONHUMAN; REVIEW; STRUCTURE ANALYSIS; UNSPECIFIED SIDE EFFECT; ANIMAL; BACTERIAL INFECTION; BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; IMMUNOLOGY; SYNTHESIS;

ANIMALS; BACTERIA; BACTERIAL INFECTIONS; BACTERIAL VACCINES; HUMANS; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; VACCINES, SYNTHETIC;

EID: 40549121341     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802608783378864     Document Type: Review

References (101)

1. Francis, T. Jr.; Tillet, W. S. J. Exp. Med. 1930, 52, 573-585.
2. Heidelberger, M.; Dilapi, M. M.; Siegel, M.; Walter, A. W. J. Immunol. 1950, 65, 535-541.
3. MMWR 1997, 46, 1-24.
4. Vinuesa, C. G.; MacLennan, I. C. M. Antibody responses to polysaccharides. In Immunobiology of Carbohydrates, Wong, S. Y. C., Arsequell, G., Eds.; Landes Bioscience/Eurekah.com: Georgetown, TX; New Yqrk, NY, 2003; pp 128-147.
5. Mond, J. J.; Lees, A.; Snapper, C. M. Ann. Rev. Immunol. 1995, 13, 655-692.
6. Snapper, C. M.; Rosas, A. L.; Kehry, M. R.; Mond, J. J.; Wetzler, L. M. Infect. Immun. 1997, 65, 3203-3208.
7. Jones, C. An. Acad. Bras. Cienc. 2005, 77, 293-324.
8. Musher, D. M.; Luchi, M. I.; Watson, D. A.; Hamilton, R.; Baughn, R. E. J. Inf. Dis. 1990, 161, 728-735.
9. Lortan, J. E.; Kaniuk, A. S.; Monteil, M. A. Clin. Exp. Immunol. 1993, 91, 54-57.
10. Chu, R. S.; McCool, T.; Greenspan, N. S.; Schreiber, J. R.; Harding, C. V. Infect. Immun. 2000, 68, 1450-1456.
11. Persson, M. A. A.; Brown, S. E.; Steward, M. W.; Hammarström, L.; Smith, C. I. E.; Howard, C. R.; Wahl, M.; Rynnel-Dagöö, B.; Lefranc, G.; Carbonara, A. O. J. Immunol. 1988, 140, 3875-3879.
12. Fedson, D. S.; Musher, D. M. Pneumococcal vaccine. In Vaccines, Plotkin, S. S., Mortimer, E. A. Jr., Eds.; WB Saunders Company: Philadelphia, 1994; pp 517-564.
13. Jennings, H. J. Curr. Top. Microbiol. Immunol. 1990, 150, 97-127.
14. Peeters, C. C. A. M.; Lagerman, P. R.; de Weers, O.; Oomen, L, A.; Hoogerhout, P.; Beurret, M.; Poolman, J. T. Polysaccharide-Conjugate Vaccines. In Vaccine Protocols, Robinson, A., Farrar, G., Wiblin, C., Eds.; Humana Press Inc., Totowa,N.J., 1996; pp 111-133.
15. Goebel, W. F.; Avery, O. T.J. Exp. Med. 1931, 54, 431-436.
16. Schneerson, R.; Barrera, O.; Sutton, A.; Robbins, J. B. J. Exp. Med. 1980, 152, 361-376.
17. Robbins, J. B.; Schneerson, R.; Anderson, P.; Smith, D. H. J. Am. Med. Assoc. 1996, 276, 1181-1185.
18. Claesson, A.; Schneerson, R.; Trollfors, B.; Lagergard, T.; Taranger, J.; Robbins, J. B. J. Pediatrics. 1990, 116, 929-931.
19. Werdelin, O.; Meldal, M.; Jensen, T. P. N. A. S. USA 2002, 99, 9611-9613.
20. Carbone, F. R.; Gleeson, P. A. Glycobiology 1997, 7, 725-730.
21. Deck, B.; Elofsson, M.; Kihlberg, J.; Unanue, E. R. J. Immunol. 1995, 155, 1074-1078.
22. Harding, C. V.; Kihlberg, J.; Elofsson, M.; Magnusson, G.; Unanue, E. R. J. Immunol. 1993, 151, 2419-2425.
23. Cemerski, S.; Shaw, A. Curr. Op. Immunol. 2006, 18, 298-304.
24. Seppälä, I.; Sarkas, H.; Mäkelä, O.; Eskola, J.; Käyhty, H. Scand. J. Immunol. 1988, 28, 471-479.
25. Mäkelä, O.; Mattila, P.; Rautonen, N.; Seppälä, I,; Eskola, J.; Käyhty, H. J. Immunol. 1987, 139, 1999-2004.
26. Miller, E.; Salisbury, D.; Ramsay, M. Vaccine 2001, 20, S58-67.
27. http://www.cdc.gov/Nip/vaccine/mening/mcv4mcv4_acip.htm 2006.
28. Poolman, J. T. Expert Rev. Vaccines 2004, 3, 597-604.
29. Lockhart, S.; Hackell, J. G.; Fritzell, B. Expert Rev. Vaccines 2006, 5, 553-564.
30. Black, S.; Shinefield, H.; Fireman, B.; Lewis, E.; Ray, P.; Hansen, J. R.; Elvin, L.; Ensor, K. M.; Hackell, J,; Siber, G.; Malinoski, F.; Madore, D.; Chang, I.; Kohberger, R.; Watson, W.; Austrian, R.; Edwards, K. Pediatr. Infect. Dis. J. 2000, 19, 187-195.
31. de Schutter, I.; Malfroot, A.; Piérard, D.; Lauwers, S. Pediatr. Pulmonol. 2006, 41, 765-770.
32. Prymula, R.; Motlova, J.; Kriz, P. Indian J. Med. Res. 2004, 119(Suppl), 168-170.
33. Levine, O. S.; Klein, K. L.; Butler, J. C. Pneumococcal protein-polysaccharide conjugate vaccines. In New Generation Vaccines, Third Edition ed.; Levine, M. M., Kaper, J. B., Rappuoli, R., Liu, M. A., Good, M. F., Eds.; Marcel Dekker Inc.: New York, 2004; pp 443-457.
34. Robbins, J. B.; Schneerson, R. N. Engl. J. Med. 1990, 323, 1415-1416.
35. Seid, R. C.; Boykins, R. A.; Liu, D.-F.; Kimbrough, K. W.; Hsieh, C.-L.; Eby, R. Glycoconj. J. 1989, 6, 489-498.
36. Goebel, W. F. J. Exp. Med. 1938, 68, 469-484.
37. Demchenko, A. V. Letters in Organic Chemistry 2005, 2, 580-589.
38. Pozsgay, V. Tetrahedron-Asymmetry 2000, 11, 151-172.
39. Matsuzaki, Y.; Ito, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1993, 34, 1061-1064.
40. Pozsgay, V.; Kubler-Kielb, J. ACS Symp. Ser. 2006, 960, 238-252.
41. Pozsgay, V.; Kubler-Kielb, J. ACS Symp. Ser. 2008, 989, 36-70.
42. Snippe, H.; van Houte, A.-J.; van Dam, J. E. G.; De Reuver, M. J.; Jansze, M.; Willers, J. M. N. Infect. Immun. 1983, 40, 856-861.
43. Pozsgay, V. Adv. Carbohydr. Chem. Biochem. 2000, 56, 153-199.
44. Pozsgay, V. Chemical synthesis of bacterial carbohydrates. In Immunobiology of Carbohydrates, Wong, S. Y. C., Arsequell, G., Eds.; Landes Bioscience/Eurekah.com: Georgetown, TX; New York, NY, 2003; pp 192-273.
45. Vliegenhart, J. F. G. FEBS Lett. 2006, 580, 2945-2950.
46. Lucas, A. H.; Apicella, M. A.; Taylor, C. E. Clin. Infect. Dis. 2005, 41, 705-712.
47. Jansen, W. T. M.; Snippe, H. IndianJ. Med. Res. 2004, 119, 7-12 Suppl.
48. Evenberg, D.; Hoogerhout, P.; van Boeckel, C. A. A.; Rijkers, G. T.; Beuvery, E. C.; van Boom, J. H.; Poolman, J. T. J. Inf. Dis. 1992, 165 (suppl. 1), S152-S155.
49. Chan, L.; Just, G. Tetrahedron 1990, 46, 151-162
50. Fernandez-Santana, V.; Cardoso, F.; Rodriguez, A.; Carmenate, T.; Pena, L.; Valdes, Y.; Hardy, E.; Mawas, F.; Heynngnezz, L.; Rodriguez, M. C.; Figueroa, I.; Chang, J. N.; Toledo, M. E.; Musacchio, A.; Hernandez, I.; Izquierdo, M.; Cosme, K.; Roy, R.; Verez-Bencomo, V. Infect. Immun. 2004, 72, 7115-7123.
51. Verez-Bencomo, V.; Fernandez-Santana, V.; Hardy, E.; Toledo, M. E.; Rodriguez, M. C.; Heynngnezz, L.; Rodriguez, A.; Baly, A.; Herrera, L.; Izquierdo, M.; Villar, A.; Valdes, Y.; Cosme, K.; Deler, M. L.; Montane, M.; Garcia, E.; Ramos, A.; Aguilar, A.; Medina, E.; Torano, G.; Sosa, I.; Hernandez, I.; Martinez, R.; Muzachio, A.; Carmenates, A.; Costa, L.; Cardoso, F.; Campa, C.; Diaz, M.; Roy, R. Science 2004, 305, 522-525.
52. Vérez-Bencomo, V. G.; Roy, R. United States Patent 2004, 6,765,091 B1.
53. Verez-Bencomo, V.; et al Development of a conjugate vaccine against Haemophilus influenzae type b based on synthetic antigens. In 23rd International Carbohydrate Symposium, 4 July 23-28, 2006, Whistler, Canada, 2006; p THU-C4-PM.5.
54. http://gndp.cigb.cu/QuimiHib/%20hybprodescription.htm 2007.
55. Taylor, D. N.; Trofa, A. C.; Sadoff, J.; Chu, C.; Bryla, D.; Shiloach, J.; Cohen, D.; Ashkenazi, S.; Lerman, Y.; Egan, W.; Schneerson, R.; Robbins, J. B. Infect. Immun. 1993, 61, 3678-3687
56. Szu, S.; Robbins, J. B.; Schneerson, R.; Pozsgay, V.; Chu, C. Polysaccharide-based conjugate vaccines for enteric bacterial infections: Typhoid fever, nontyphoidal salmonellosis, shigellosis, cholera and Escherichia coli O157. In New Generation Vaccines, Levine, M. M., Kaper, J. B., Rappuoli, R., Liu, M. A., Good, F., Eds.; Marcel Dekker: New York, 2004; pp 471-478.
57. Dmitriev, B. A.; Knirel, Y. A.; Kochetkov, N. K.; Hofman, I. Eur. J. Biochem. 1976, 66, 559-566.
58. Pozsgay, V. J. Org. Chem. 1998, 63, 5983-5999.
59. Pozsgay, V. Tetrahedron-Asymmetry 2000, 11, 151-172.
60. Kubler-Kielb, J.; Pozsgay, V. J. Org. Chem 2005, 70, 6987-6990, 2006, 71, 5422-5422.
61. Pozsgay, V.; Chu, C.; Pannell, L.; Wolfe, J.; Robbins, J. B.; Schneerson, R. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 5194-5197.
62. Pozsgay, V.; Kubler-Kielb, J.; Schneerson, R.; Robbins, J.B. In preparation 2007, 104, 14478-14482.
63. Ashkenazi, S.; Passwell, J. H.; Harlev, E.; Miron, D.; Dagan, R.; Farzan, N.; Ramon, R.; Majadly, F.; Bryla, D. A.; Karpas, A, B.; Robbins, J. B.; Schneerson, R. J. Infect. Dis. 1999, 179, 1565 -1568.
64. Belot, F.; Wright, K.; Costachel, C.; Phalipon, A.; Mulard, L. A. J. Org. Chem. 2004, 69, 1060-1074.
65. Gurreiro, C.; Guerreiro, C.; Laurent, I.; Baleax, F.; Mulard, L. A. Org. Bioorg. Chem. 2004, 2, 1519-1527.
66. Bélot, F.; Guerreiro, C.; Baleux, F.; Mulard, L. A. Chem. Eur. J. 2005, 11, 1625-1635.
67. Phalipon, A.; Costachel, C.; Grandjean, C.; Thuizat, A.; Guerreiro, C.; Tanguy, M.; Nato, F.; Normand, V. V. L.; Bélo, F.; Wright, K.; Marcel-Peyre, V.; Sansonetti, P. J.; Mulard, L. A. J. Immunol. 2006, 176, 1686-1694.
68. Benaissa-Trouw, B.; Lefeber, D. J.; Kamerling, J. P.; Vliegenthart, J. F. G.; Kraaijeveld, K.; Snippe, H. Infect. Immun. 2001, 69, 4698-4701.
69. Jansen, W. T. M.; Hogenboom, S.; Thijssen, M. J. L.; Kamerling, J. P.; Vliegenthart, J. F. G.; Verhoef, J.; Snippe, H.; Verheul, A. F. M. Infect. Immun. 2001, 69, 787-793.
70. Mawas, F.; Niggemann, J.; Jones, C.; Corbel, M. J.; Kamerling, J. P.; Vliegenthart, J. F. G. Infect. Immun. 2002, 70, 5107-5114.
71. Kovác, P. Studies toward a rationally designed conjugate vaccine for cholera using synthetic carbohydrate antigens. In Protein-carbohydrate interactions in infectious diseases, Bewley, C. A., Ed.; RSC Publishing: Cambridge, 2006; pp 175-220.
72. Chemyak, A.; Kondo, S.; Wade, T. K.; Meeks, M. D.; Alzari, P. M.; Fournier, J. M.; Taylor, R. K.; Kovic, P.; Wade, W. F. J. Inf. Dis. 2002, 185, 950-962.
73. Saksena, R.; Ma, X.; Wade, T. K.; Kovác, P.; Wade, W. F. FEMS Immunol. Med. Mic. 2006, 47, 116-128.
74. Lyczak, J. B.; Cannon, C. L.; Pier, G. B. Microbes Infect 2000, 2, 1051-1060.
75. Reiter, A.; Brade, L.; Sanchez-Carballo, P.; Brade, H.; Kosma, P. J. Endotoxin. Res. 2001, 7, 125-131.
76. Moayeri, M.; Leppla, S. H. Curr, Op. Microbiol. 2004, 7, 19-24.
77. Mock, M.; Fouet, A. Annu. Rev. Microbiol. 2001, 55, 647-671.
78. http://www.niaid.nih.gov/factsheets/anthrax.htm 2007.
79. Daubenspeck, J. M; Zeng, H.; Chen, P.; Dong, S.; Steichen, C.T.; Krishna, N. R.; Pritchard, D. G.; Turnbough, C. L. J. Biol. Chem. 2004, 279, 30945-30953.
80. Werz, D. B.; Seeberger, P. H. Angew. Chem. Int. Ed. 2005, 44, 6315-6318.
81. Adamo, R.; Saksena, R.; Kovác, P. Helv. Chim. Acta 2006, 89, 1074-1089.
82. Tamborrini, M.; Werz, D. B.; Frey, J.; Pluschke, G.; Seeberger, P. H. Angew. Chem. Int. Ed. 2006, 45, 6581-6582.
83. Mehta, A. S.; Saile, E.; Zhong, W.; Buskas, T.; Carlson, R.; Kannenberg, E.; Reed, Y.; Quinn, C. P.; Boons, G.-J. Chem. Eur. J. 2006, 12, 9136-9149.
84. http://www3. niaid.nih.gov/research/topics/lyme/ research/antibiotic/antibiotich. htm 2006
85. Behera, A. K.; Hildebrand, E.; Szafranski, J.; Hung, H. H.; Grodzinsky, A. J.; Lafyatis, R.; Koch, A. E.; Kalish, R.; Perides, G.; Steere, A. C. Arthritis Rheam. 2006, 54, 3319-3329.
86. Pozsgay, V.; Kubler-Kielb, J.; Coxon, B.; Ekborg, G. Tetrahedron 2005, 61, 10470-10481.
87. Pozsgay, V.; Kubler-Kielb, J. Carbohydr. Res. 2007, 342, 621-626.
88. Ben-Menachem, G.; Kubler-Kielb, J.; Coxon, B.; Yergey, A.; Schaeerson, R. Proc. Natl. Acad. Sci. USA 2003, 100, 7913-7918.
89. Pauillac, S.; Naar, J.; Mouratou, B.; Guesdon, J. L. J Immun. Methods 2002, 263, 75-83.
90. Hamasur, B.; Haile, M.; Pawlowski, A.; Schroder, U.; Williams, A.; Hatch, G.; Marsh, P.; Kallenius, G.; Svenson, S. B. Vaccine 2003, 21, 4081-4093.
91. Gadikota, R. R.; Callam, C. S.; Appelmelk, B. J.; Lowary, T. L. J. Carbohydr. Chem. 2003, 22, 459-480.
92. Porcelli, S. A.; Besra, G. S. In Intracellular pathogens in membrane interactions biogenesis, Vacuole Gorvel, J. P., Ed.; Kluwer Academie Pienum Publishers: New York, 2004; pp 230-249.
93. Jayaprakash, K. N.; Lu, J.; Fraser-Reid, B. Angew. Chem. Int. Ed. 2005, 44, 5894-5898.
94. Höleman, A.; Stocker, B. L; Seeberger, P. H. J. Chem. 2006, 71, 8071-8088.
95. Kubler-Kielb, J.; Coxon, B.; Schneerson, R. J. Bacteriol. 2004, 186, 6891-6901.
96. Maloughney, B.; Ruthnum, P.; Chan, E. Clin. Infect Dis. 1997, 23-11, 81-84.
97. Hammitt, L. L.; Hennessey, T. W.; Romero-Steiner, S.; Butler, J. C. Clin. Infect. Dis. 2006, 43, 386-387.
98. Fekete, A.; Hoogerhout, P.; Zomer, G.; Kubler-Kielb, J.; Schneerson, R.; Robbins, J. B.; Pozsgay, V. Carobphydr. Res. 2006, 341, 2037-2048.
99. Cox, A. D.; Perry, M. B. Carbohydr. Res. 1996, 290, 59-65s.
100. Turek, D.; Sundgren, A.; Lahmann, M.; Oscarson, S. Org. Biomol. Chem. 2006, 4, 1236-1241.
101. Ruttens, B.; Kovác, P. Carbohydr. Res. 2006, 341, 1077-1080.