Peptide and glycopeptide dendrimers. Part I

Journal of Peptide Science

Volumn 5, Issue 1, 1999, Pages 5-23

  Vepřek, Pavel ^a   Ježek, Jan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Dendrimers; Glycodendrimers; Multiple antigen glycopeptides (MAGs); Multiple antigen peptides (MAPs); Regioselectively addressable functionalized templates (RAFTs); Sequential oligopeptide carriers (SOCs); Template assembled synthetic proteins (TASPs)

Indexed keywords

ANTIGEN; DENDRIMER; GLYCOPEPTIDE; PEPTIDE; VACCINE;

ANTIBODY PRODUCTION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG ISOLATION; DRUG MANUFACTURE; DRUG PURITY; IMMUNOCHEMISTRY; METHODOLOGY; PRIORITY JOURNAL; REVIEW; SERODIAGNOSIS;

EID: 2442752591     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199901)5:1<5::AID-PSC178>3.0.CO;2-R     Document Type: Review

References (188)

1. J.M.J. Fréchet (1994). Functional polymers and dendrimers: reactivity, molecular architecture, and interfacial energy. Science 263, 1710-1715.
2. D.A. Tomalia and H.D. Durst (1993). Genealogically directed synthesis: starburst/cascade dendrimers and hyperbranched structures. Top. Curr. Chem. 165, 193-313.
3. H.-B. Mekelburger, W. Jaworek and F. Vögtle (1992). Dendrimers, arborols and cascade molecules: breakthrough into generations of new materials. Angew. Chem. Int. Ed. Engl. 31, 1571-1576.
4. N.N. Androin and D. Astruc (1995). Molecular trees -from syntheses towards applications. Bull. Soc. Chim. Fr. 132, 875-909.
5. D.A. Tomalia, A.M. Naylor and W.A. Goddard (1990). Starburst dendrimers: molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter. Angew. Chem. Int. Ed. Engl. 29, 138-175.
6. S.C. Stinson (1997). Delving Into dendrimers. Chem. Eng. News 75, 28-30.
7. J.M. Lehn (1990). Perspectives in supramolecular chemistry - from molecular recognition towards molecular information processing and self-organization. Angew. Chem. Int. Ed. Engl. 29, 1304-1319.
8. J.M. Lehn (1994). Perspectives in supramolecular chemistry - from molecular recognition towards self-organisation. Pure Appl. Chem. 66, 1961-1966.
9. E. Buhleier, W. Wehner and F. Vögtle (1978). 'Cascade-' and 'Nonskld-Chain-like' syntheses of molecular cavity topologies. Synthesis, 155-158.
10. C.J. Hawker, K.L. Wooley and J.M.J. Fréchet (1993). Unimolecular micelles and globular amphiphiles: dendritic macromolecules as novel recyclable solubilization agents. J. Chem. Soc., Perkin Trans. I, 1287-1297.
11. S. Mattei, P. Seiler, F. Diederich and W. Gramlich (1995). Dendrophanes: water-soluble dendritic receptors. Helv. Chim. Acta 78, 1904-1912.
12. G.R. Newkome, R. Güther, C.N. Moorefield, F. Cardullo, L. Echegoyen, E. Pérez-Cordero and H. Luftmann (1995). Routes to dendritic networks: bis-dendimers by coupling of cascade macromolecules through metal centers. Angew. Chem. Int. Ed. Engl. 34, 2023-2026.
13. T. Nagasaki, O. Kimura, M. Ukon, S. Arimori, I. Hamachi and S. Shinkal (1994). Synthesis, metal-binding properties and polypeptide solubilization of 'crowned' arborols. J. Chem. Soc., Perkin Trans. I, 75-81.
14. J.P. Tam (1988). Synthetic peptide vaccine design: synthesis and properties of a high-density multiple antigenic peptide system. Proc. Natl. Acad. Sci. USA 85, 5409-5413.
15. R. Roy (1996). Glycodendrimers: a new class of biopolymers. Polymer News 21, 226-232.
16. G.R. Newkome, F. Cardullo, E.C. Constable, C.N. Moorefield and A.M.W. Cargill-Thompson (1993). Metallomicellanols: incorporation of ruthenium(II)-2,2′:6′,2″-terpyridme triads into cascade polymers. J. Chem. Soc., Chem. Commun., 925-927.
17. E.C. Constable (1991). Helices, supramolecular chemistry and metal-directed self-assembly. Angew. Chem. Int. Ed. Engl. 30, 1450-1451.
18. J.W. Knapen, A.W. van der Made, J.C. de Wilde, P.W.N.M. van Leeuwen, P. Wijkens, D.M. Grove and G. van Koten (1994). Homogenous catalysts based on silane dendrimers functionalized with arylnickel(II) complexes. Nature 372, 659-663.
19. K.L. Wooley (1997). From dendrimers to knedel-like structures. Chem. Eur. J. 3, 1397-1399.
20. F. Zeng and S.C. Zimmerman (1997). Dendrimers in supramolecular chemistry: from molecular recognition to self-assembly. Chem. Rev. 97, 1681-1712.
21. G.R. Newkome, C.N. Moorefield and F. Vögtle (1996). Dendritic Macromolecules: Concepts, Syntheses, Perspectives, VCH, Weinheim, Germany.
22. M. Mutter, E. Altmann, K.-H. Altmann, R. Hersperger, P. Koziej, K. Nebel, G. Tuchscherer and S. Vuilleumier (1988). The construction of new proteins. Part III. Artificial folding units by assembly of amphiphilic secondary structures on a template. Helv. Chim. Acta 71, 835-847.
23. R.G. Denkewalter, J.F. Kolc and W.J. Lukasavage, US Pat. 4410688 (1983); Chem. Abstr. 100, (1984) 103 907 p.
24. R.G. Denkewalter, J.F. Kolc and W.J. Lukasavage, US Pat. 4410688 (1983); Chem. Abstr. 100, (1984) 103 907 p.
25. D.N. Posnett, H. McGrath and J.P. Tam (1988). A novel method for producing anti-peptide antibodies. J. Biol. Chem. 263, 1719-1725.
26. J. Ježek. J. Velek, T. Trnka and M. Písačka. Solid phase synthesis of Tn antigens in both free and immobilized form, in: Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Libraries 1995, R. Epton, Ed., p. 427-428, Mayflower Scientific Ltd., Birmingham, 1997.
27. S. Bay, R. Lo-man, E. Osinaga, H. Nakada, C. Leclerc and D. Cantacuzéne (1997). Preparation of a multiple antigen glycopeptide (MAG) carrying the Tn antigen. J. Peptide Res. 49, 620-625.
28. V. Tsikaris, C. Sakarellos, M.T. Cung, M. Marraud and M. Sakarellos-Daitsiotis (1996). Concept and design of a new class of sequential oligopeptide carriers (SOC) for covalent attachment of multiple antigenic peptides. Biopolymers 38, 291-293.
29. M. Mutter and S. Vuilleumier (1989). A chemical approach to protein design-template-assembled synthetic proteins (TASP). Angew. Chem. Int. Ed. Engl. 28, 535-554.
30. P. Dumy, I.M. Eggleston, S. Cervigni, U. Sila, X. Sun and M. Mutter (1995). A convenient synthesis of cyclic peptides as regioselectively addressable functionalized templates (RAFT). Tetrahedron Lett. 36, 1255-1258.
31. R.A. Lemer (1982). Tapping the immunological repertoire to produce antibodies of predetermined specificity. Nature 299, 593-596.
32. J.G. Sutcliffe, T.M. Shinnick, N. Green and R.A. Lerner (1983). Antibodies that react with predetermined sites on proteins. Science 219, 660-666.
33. R. Arnon, E. Maron, M. Sela and C.B. Anfinsen (1971). Antibodies reactive with native lysozyme elicited by a completely synthetic antigen. Proc. Natl. Acad. Sci. USA 68, 1450-1455.
34. R.M. Hoksinson, R.D.G. Rigby, P.E. Mattner, V.L. Hyunh, M. D'Occhio, A. Neish, T.E. Trigg, B.A. Moss, M.J. Lindsey, G.D. Coleman and C.L. Schwartzkopf (1990). Vaxstrate: an anti-reproductive vaccine for cattle. Aust. J. Biotechnol. 4, 166-170.
35. M. Valero, L.R. Amador, C. Galindo, J. Figueroa, M.S. Bello, L.A. Murillo, A.L. Mora, G. Patarroyo, C.L. Rocha and M. Rojas (1993). Vaccination with SPf66, a chemically synthesised vaccine, against Plasmodium falciparum malaria in Colombia. Lancet 341, 705-710.
36. P.R. Hansen, H. Flyge, A. Holm, E. Lauritzen and B.D. Larsen (1996). Photochemical conjugation of peptides to carrier proteins using 1,2,3-thladiazole-4-carboxylic acid. Int. J. Peptide Protein Res. 47, 419-426.
37. G. Walter, K.H. Scheidtmann, A. Carbone, A.P. Laudano and R.F. Doolittle (1980). Antibodies specific for the carboxy-and amino-terminal regions of simian virus 40 large tumor antigen. Proc. Natl. Acad. Sci. USA 77, 5197-5120.
38. A.R. Neurath, S.B. Kent and N. Strick (1982). Specificity of antibodies elicited by a synthetic peptide having a sequence in common with a fragment of a virus protein, the hepatitis B surface antigen. Proc. Natl. Acad. Sci. USA 79, 7871-7875.
39. C.O. Jacob, R. Arnon and M.J. Sela (1985). Effect of carrier on the immunogenic capacity of synthetic cholera vaccine. Mol. Immunol. 22, 1333-1339.
40. G.H. Cohen, B. Dietzschold, M. Ponce de Leon, D. Long, E. Golub, A. Varrichio, L. Pereira and R.J. Elsenberg (1984). Localization and synthesis of an antigenic determinant of herpes simplex virus glycoprotein D that stimulates the production of neutralizing antibody. J. Virol. 49, 102-108.
41. E. Pfaff, M. Mussagy, H.O. Bohm, G.E. Schulz and H. Schauer (1982). Antibodies against a preselected peptide recognize and neutralize foot and mouth disease virus. EMBO J. 1, 869-874.
42. J.P. Briand, S. Muller and M.H. Van-Regenmortel (1985). Synthetic peptides as antigens: pitfalls of conjugation methods. J. Immunol. Methods 78, 56-69.
43. R. DiMarchi, G. Brooke, C. Gale, V. Cracknell, T. Doel and N. Mowat (1986). Protection of cattle against foot-and-mouth disease by a synthetic peptide. Science 232, 639-641.
44. H. MacArthur and G. Walter (1984). Monoclonal antibodies specific for the carboxy terminus of simian virus 40 large T antigen. J. Virol. 52, 483-491.
45. D. Di-John, S.S. Wasserman, J.R. Torres, M.J. Cortesia, J. Murillo, G.A. Losonsky, D.A. Herrington, D. Struchrer and M.M. Levine (1989). Effect of priming with carrier on response to conjugate vaccine. Lancet 2, 1415-1418.
46. M.P. Schutze, C. LeClerc, F. Jolivet, F. Audibert and L. Chedid (1985). Carrier-induced epitopic suppression, a major issue for future synthetic vaccines. J. Immunol. 135, 2319-2322.
47. A. Kumar, R. Arora, P. Kaur, V.S. Chauhan and P. Sharma (1992). 'Universal' T helper cell determinants enhance immunogenicity of a Plasmodium falciparum merozoite surface antigen peptide. J. Immunol. 148, 1499-1505.
48. D.M. Shaw, C.M. Stanley, C.D. Partidos and M.W. Steward (1993). Influence of the T-helper epitope on the titre and affinity of antibodies to B-cell epitopes after co-immunization. Mol. Immunol. 30, 961-968.
49. P. Sarobe, J.-J. Lasarte, J. Golvano, A. Gullon, M.-P. Civeira, J. Prieto and F. Borrás-Cuesta (1991). Induction of antibodies against a peptide hapten does not require covalent linkage between the hapten and a class II presentable T helper peptide. Eur. J. Immunol. 21, 1555-1558.
50. M. Bellone, P.I. Karachunski, N. Ostlie, S. Lei and B.M. Conti-Tronconi (1994). Preferential pairing of T and B cells for production of antibodies without covalent association of T and B epitopes. Eur. J. Immunol. 24, 799-804.
51. I. Prieto, S. Hervás-Stubbs, M. Garcia-Granero, C. Berasain, J.I. Riezu-Boj, J.-J. Lasarte, P. Sarobe, J. Prieto and F. Borrás-Cuesta (1995). Simple strategy to induce antibodies of distinct specifity. Application to the mapping of gp120 and inhibition of HIV-1 infectivity. Eur. J. Immunol. 25, 877-883.
52. M.J. Francis, G.Z. Hastings, A.D. Syred, B. McGinn, F. Brown and D.J. Rowland (1987). Non-responsiveness to a foot-and-mouth disease virus peptide overcome by addition of foreign helper T-cell determinants. Nature 330, 168-170.
53. S. Sad, V.S. Chauhan, K. Arunan and R. Raghupathy (1993). Synthetic gonadotrophin-releasing hormone (GnRH) vaccines incorporating GnRH and synthetic T-helper epitopes. Vaccine 11, 1145-1150.
54. M. Srinivasan, S.Z. Domanico, P.T.P. Kaumaya and S.K. Pierce (1993). Peptides of 23 residues or greater are required to stimulate a high affinity class II-restricted T cell response. Eur. J. Immunol. 23, 1011-1016.
55. N.D. Zegers, C. van Holten, E. Classen and W.J.A. Boersma (1993). Peptide-induced memory (IgG) response, cross-reactive with native proteins, require covalent linkage of a specific B cell epitope with a T cell epitope. Eur. J. Immunol. 23, 630-634.
56. J.J. Golvano, J.J. Lasarte, P. Sarobe, A. Gullon, J. Prieto and F. Borass-Cuesta (1990). Polarity of immunogens: implications for vaccine design. Eur. J. Immunol. 20, 2363-2366.
57. C. Partidos, C. Stanley and M. Steward (1992). The effect of orientation of epitopes on the immunogenicity of chimeric synthetic peptides representing measles virus protein sequences. Mol. Immunol. 29, 651-658.
58. M.E. Levely, M.A. Mitchell and J.A. Nicholas (1990). Synthetic immunogens constructed from T-cell and B-cell stimulating peptides (T:B chimeras): preferential stimulation of unique T-and B-cell specificities is influenced by immunogen configuration. Cell. Immunol. 125, 65-78.
59. F. Ria, B.M.C. Chan, M.T. Scherer, J.A. Smith and M.L. Gefter (1990). Immunological activity of covalently linked T-cell epitopes. Nature 343, 381-383.
60. J.P. Tam and F. Zavala (1989). Multiple antigen peptide. A novel approach to increase detection sensitivity of synthetic peptides in solid-phase immunoassays. J. Immunol. Methods 124, 53-61.
61. W. Huang, B. Nardelli and J.P. Tam (1994). Lipophilic multiple antigen peptide system for peptide immunogen and synthetic vaccine. Mol. Immunol. 31, 1191-1199.
62. J. Bernillon and S.M. Wallach (1993). Design of a new multiple antigen peptide system using 9-fluorenylmethyloxycarbonyl (Fmoc) strategy. Biotechnol. Tech. 7, 603-608.
63. 2; n = 1, 3, 7. J. Peptide Res. 51, 297-302.
64. J.P. Tam, P. Clavijo, Y.-A. Lu, V. Nussenzweig, R. Nussenzweig and F. Zavala (1990). Incorporation of T and B epitopes of the circumsporozoite protein in a chemically defined synthetic vaccine against malaria. J. Exp. Med. 171, 299-306.
65. G. Fassina and G. Cassani (1993). Peptide-based assay for the identification of endothelin-converting enzyme inhibitors. Peptide Res. 6, 73-78.
66. P. Simmonds, K.A. Rose, S. Graham, S.W. Chan, F. McOmish, B.C. Dow, E.A. Follett, P.L. Yap and H. Marsden (1993). Mapping of serotype-specific, immunodominant epitopes in the NS-4 region of hepatitis C virus (HCV): use of type-specific peptides to serologically differentiate infections with HCV types 1, 2, and 3. J. Clin. Microbiol. 31, 1493-1503.
67. G. Fassina (1992). Oriented Immobilization of peptide ligands on solid supports. J. Chromatogr. 591, 99-106.
68. S. Butz, S. Rawer, W. Rapp and U. Birsner (1994). Immunization and affinity purification of antibodies using resin-immobilized lysine-branched synthetic peptides. Peptide Res. 7, 20-23.
69. J.P. Briand, C. Andre, N. Tuaillon, L. Herve, J. Neimark and S. Muller (1992). Multiple autoepitope presentation for specific detection of antibodies in primary biliary cirrhosis. Hepatology 16, 1395-1403.
70. F. Sinigaglia, M. Guttinger, S. Graham, S.W. Chan, F. McOrnish, B. Dow, E.A. Follette, P. Yap and H. Marsden (1993). Mapping of serotype-specific, immunodominant epitopes in the NS-4 region of hepatitis C virus (HCV): use of type-specific peptides to serologically differentiate infections with HCV types 1, 2, and 3. J. Clin. Microbiol. 31, 1493-1503.
71. P. Ho, D. Mutch, K. Winkel, A.J. Saul, G.I. Jones, T.J. Doran and C.M. Rzepczyk (1990). Identification of two promiscuous T cell epitopes from tetanus toxin. Eur. J. Immunol 20, 477-483.
72. V.S. Ivanov, L.N. Kulik, A.E. Gabrielian, L.D. Tchikin, A.T. Kozich and V.T. Ivanov (1994). Synthetic peptides in the determination of hepatitis A virus T-cell epitopes. FEBS Lett. 345, 159-161.
73. R.W. Tindle, G.J. Fernando, J.C. Sterling and I.H. Frazer (1991). A 'public' T-helper epitope of the E7 transforming protein of human papillomavirus 16 provides cognate help for several E7 B-cell epitopes from cervical cancer-associated human papillomavirus genotypes. Proc. Natl. Acad. Sci. USA 88, 5887-5891.
74. N. Ahlborg (1995). Synthesis of a diepitope multiple antigen peptide containing sequences from two malaria antigens using Fmoc chemistry. J. Immunol. Methods 179, 269-275.
75. J.P. Tam and Y.-A. Lu (1989). Vaccine engineering: enhancement of immunogenicity of synthetic peptide vaccines related to hepatitis in chemically defined models consisting of T-and B-cell epitopes. Proc. Natl. Acad. Sci. USA 86, 9084-9088.
76. B. Nardelli, J.P. Defoort, W. Huang and J.P. Tam (1992). Design of a complete synthetic peptide-based AIDS vaccine with a built-in adjuvant. AIDS Res. Hum. Retroviruses 8, 1405-1407.
77. M. Levi, U. Ruden, D. Birx, L. Loomis, R. Redfield, K. Lovgren, L. Akerblom, E. Sandstrom and B. Wahren (1993). Effects of adjuvants and multiple antigen peptides on humoral and cellular immune responses to gp160 of HIV-1. J. Acquired Immune Defic. Syndr. 6, 855-864.
78. J.M. Calvo-Calle, G.A. de Oliveira, P. Clavijo, M. Maracic, J.P. Tam, Y.-A. Lu, E.H. Nardin, R.S. Nussenzweig and A.H. Cochrane (1993). Immunogenicity of multiple antigen peptides containing B and non-repeat T cell epitopes of the circumsporozoite protein of Plasmodium falciparum. J. Immunol. 150, 1403-1413.
79. E.H. Nardin and R.S. Nussenzweig (1993). T cell responses to pre-erythrocytic stages of malaria: role in protection and vaccine development against pre-erythrocytic stages. Annu. Rev. Immunol. 11, 687-727.
80. A. Pessi, D. Valmori, P. Migliorini, C. Tougne, E. Blanchi, P.H. Lambert, G. Corradin and G. Del Giudice (1991). Lack of H-2 restriction of the Plasmodium falciparum (NANP) sequence as multiple antigen peptide. Eur. J. Immunol. 21, 2273-2276.
81. S.K. Chai, P. Clavijo, J.P. Tam and F. Zavala (1992). Immunogenic properties of multiple antigen peptide systems containing defined T and B epitopes. J. Immunol. 149, 2385-2390.
82. J-.P. Briand, C. Barin, M.H.V. Van Regenmortel and S. Muller (1992). Applications and limitations of the multiple antigen peptide (MAP) system in the production and evaluation of anti-peptide and anti-protein antibodies. J. Immunol. Methods 156, 255-265.
83. F. Troalen, A. Razafindratsita, A. Puisieux, T. Voeltzel, C. Bohuon, D. Bellet and J.M. Bidart (1990). Structural probing of human lutropin using antibodies raised against synthetic peptides constructed by classical and multiple antigen peptide system approaches. Mol. Immunol. 27, 363-368.
84. S.D. Mahale, J. Pereira, U. Natraj and K.S.N. Iyer (1996). Comparison of antibodies raised against the peptide 10-24 of chicken riboflavin carrier protein (cRCP) by classical and multiple antigen peptide (MAP) approaches. J. Immunol. Methods 190, 215-219.
85. G.W. McLean, A.M. Owsianka, J.H. Subak-Sharpe and H.S. Marsden (1991). Generation of anti-peptide and anti-protein sera. Effect of peptide presentation on immunogenicity. J. Immunol. Methods 137, 149-157.
86. J. Freund (1951). The effect of paraffin and mycobacteria on antibody formation and sensation. A review. Am. J. Clin. Pathol. 21, 645-656.
87. J. Freund, G.E. Thompson and M.M. Lipton (1955). Aspermatogenesis, anaphylaxis, and cutaneous sensitization induced in the guinea pig by homologous testicular extract. J. Exp. Med. 101, 591-603.
88. A. Adam. Synthetic Adjuvants: Modern Concepts in Immunology Vol. 1, C-A. Bona, Ed., p. 1-58, John Wiley & Sons, New York, 1984.
89. A. Adam, R. Ciorbaru, F. Ellouz, J.F. Petit and E. Lederer (1974). Adjuvant activity of monomeric bacterial cell wall peptidoglycans. Biochem. Biophys. Res. Commun. 56, 561-567.
90. F. Ellouz, A. Adam, R. Ciorbaru and E. Lederer (1974). Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives. Biochem. Biophys. Res. Commun. 59, 1317-1325.
91. S. Kotani, Y. Wanatabe, F. Kinoshita, T. Shimono, I. Morisaki, T. Shiba, S. Kusumoto, Y. Tarumi and K. Ikenaka (1975). Immunoadjuvant activities of synthetic N-acetyl-muramyl-peptides or -amino acids. Biken J. 18, 105-111.
92. A. Adam and E. Lederer (1984). Muramyl peptides: immunomodulators, sleep factors, and vitamins. Med. Res. Rev. 4, 111-152.
93. C. Leclerc and F.R. Vogel (1986). Synthetic Immunomodulators and synthetic vaccines. Crit. Rev. Ther. Drug Carrier Syst. 2, 353-406.
94. K.H. Wiesmüller, W.G. Bessler and G. Jung (1983). Synthesis of the mitogenic S-[2,3-bis-(palmitoyloxy)propyl]-N-palmitoyl pentapeptide from Escherichia coli lipopeptide. Biol. Chem. Hoppe-Seyler's 364, 593-606.
95. A. Reitermann, J. Metzgler, K.H. Wiesmüller, G. Jung and W.G. Bessler (1989). Lipopeptide derivatives of bacterial lipoprotein constitute potent immune adjuvants combined with or covalently coupled to antigen or hapten. Biol. Chem. Hoppe-Seyler's 370, 343-354.
96. J. Metzger, K.H. Wiesmüller, R. Schaude, W.G. Bessler and G. Jung (1991). Synthesis of novel immunologically active tripalmitoyl-S-glycerylcysteinyl lipopeptides as useful intermediates for immunogen preparations. Int. J. Peptide Protein Res. 37, 46-57.
97. V. Braun (1975). Covalent lipoprotein from the outer membrane of Escherichia coli. Biochem. Biophys. Acta 415, 335-377.
98. K.H. Wiesmüller, W.G. Bessler and G. Jung (1992). Solid phase peptide synthesis of lipopeptide vaccines eliciting epitope-specific B-. T-helper and T-killer cell response. Int. J. Peptide Protein Res. 40, 255-260.
99. F. Melchers, V. Braun, and C. Galanos (1975). The lipoprotein of the outer membrane of Escherichia coli: a B-lymphocyte mitogen. J. Exp. Med. 142, 473-482.
100. W.G. Bessler and B.P. Ottenbreit (1977). Studies on the mitogenic principle of the lipoprotein from the outer membrane of Escherichia coli. Biochem., Biophys. Res. Commun. 76, 239-246.
101. K. Deres, H. Schild, K.H. Wiesmüller, G. Jung and H.G. Rammensee (1989). In vivo priming of virus-specific cytotoxic T-lymphocytes with synthetic lipopeptide vaccine. Nature 342, 561-564.
102. J.-P. Defoort, B. Nardelli, W. Huang, D.D. Ho and J.P. Tam (1992). Macromolecular assemblage in the design of a synthetic AIDS vaccine. Proc. Natl. Acad. Sci. USA 89, 2879-2883.
103. J.-P. Defoort, B. Nardelli, W. Huang and J.P. Tam (1992). A rational design of synthetic peptide vaccine with built-in adjuvant. A modular approach for unambiquity. Int. J. Peptide Protein Res. 40, 214-221.
104. B. Nardelli and J.P. Tam (1993). Cellular immune responses induced by in vivo priming with a lipid-conjugated multimeric antigen peptide. Immunology 79, 355-361.
105. R.M.L. Buller, K.L. Holmes, A. Hugin, T.N. Frederickson and H.C. Morse III (1987). Induction of cytotoxic T-cell responses in vivo in the absence of CD4 helper cells. Nature 328, 77-79.
106. N. Flinn, S. Coppard, W.A. Gibbons, A. Shew, P. Arturson and I. Toth. Oral absorptions studies of lipidic conjugates of thyrotropin releasing hormone (TRH) and luteinizing hormone releasing hormone (LHRH), in: Peptides: Chemistry, Structure and Biology, P.T.P. Kaumaya and R.S. Hodges, Eds, p. 165-167, Mayflower Scientific Ltd., Kingswinford, 1996.
107. G. Zhong, I. Toth, R. Reid and R.C. Brunham (1993). Immunogenicity evaluation of a lipidic amino acid-based synthetic peptide vaccine for Chlamydia trachomatis. J. Immunol. 151, 3728-3736.
108. N.J.C.M. Beekman, W.M.M. Schaaper, G.I. Tesser, K. Dalsgaard, S. Kamstrup, J.M.P. Langeveld, R.S. Boshuizen and R.H. Meloen (1997). Synthetic peptide vaccines: palmitoylation of peptide antigens by a thioester bond increases immunogenicity. J. Peptide Res. 50, 357-364.
109. W. Huang, B. Nardelli and J.P. Tam (1994). Lipophilic multiple antigen peptide system for peptide immunogen and synthetic vaccine. Mol. Immunol. 31, 1191-1199.
110. A.F. Verheul, V. Udhayakumar, D.L. Jue, R.M. Wohlhueter and A.A. Lal (1995). Monopalmitic acid-peptide conjugates induce cytotoxic T cell responses against malarial epitopes: importance of spacer amino acids. J. Immunol. Methods 182, 219-226.
111. B. Nardelli, F.B. Haser and J.P. Tam (1994). Oral administration of an antigenic synthetic lipopeptide (MAP-P3C) evokes salivary antibodies and systemic humoral and cellular responses. Vaccine 12, 1335-1339.
112. G.F. Springer (1984). T and Tn, general carcinoma autoantigens. Science 224, 1198-1206.
113. S.I. Hakomori (1991). Possible functions of tumor-associated carbohydrate antigens. Curr. Opin. Immunol. 3, 646-653.
114. G.F. Springer and P.R. Desai. Pancarcinoma T and Tn epitopes: autoimmunogens and diagnostic markers that reveal incipient carcinomas and help establish prognosis, in: immunodiagnosis of Cancer, 2nd Edition, R.B. Herberman and D.W. Mercer, Eds, p. 587-612, Marcel Dekker, New York, 1990.
115. J. Huang, J.C. Byrd, B. Siddiki, M. Yuan, E. Lau and Y.S. Kim (1992). Monoclonal antibodies against partially deglycosylated colon cancer mucin that recognize Tn antigen. Dis. Markers 10, 81-94.
116. G.F. Springer (1989). Tn epitope (N-acetyl-D-galactosamine-O-serine/threonine) density in primary breast carcinoma: a functional predictor of aggresiveness. Mol. Immunol. 26, 1-5.
117. J.E.S. Hansen, H. Clausen, S.L. Hu, J.O. Nielsen and S. Olofsson (1992). An O-linked carbohydrate neutralization epitope of HIV-1 gp 120 is expressed by HIV-1 env gene recombinant vaccinia virus. Arch. Virol. 126, 11-20.
118. A.K. Singhal, M. Fohn and S. Hakomori (1991). Induction of alpha-N-acetylgalactosamine-O-serine/ threonine (Tn) antigen-mediated cellular immune response for active immunotherapy in mice. Cancer Res. 51, 1406-1411.
119. P.Y. Fung, M. Madej, R.R. Koganty and B.M. Longenecker (1990). Active specific inmmunotherapy of a murine mammary adenocarcinoma using a synthetic tumor-associated glycoconjugate. Cancer. Res. 50, 4308-4314.
120. F. Helling, S. Zhang, A. Shang, S. Adluri, M. Calves, R. Koganty, B.M. Longenecker, T.J. Yao, H.F. Oettgen and P.O. Livingston (1995). GM2-KLH conjugate vaccine: increased immunogenicity in melanoma patients after administration with immunological adjuvant QS-21. Cancer. Res. 55, 2783-2788.
121. M. Zheng, M. Gobbo, L. Biondi, F. Filira, S. Hakomori and R. Rocchi (1994). Synthetic immunochemistry of glycohexapeptide analogues characteristic of oncofetal fibronectin. Solid phase synthesis and antigenic activity. Int. J. Peptide Protein Res. 43, 230-238.
122. T. Toyokuni, B. Dean, S. Cai, D. Boivin, S. Hakomori and A.K. Singhal (1994). Synthetic vaccines: Synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins. J. Am. Chem. Soc. 116, 395-396.
123. M. Elofsson and L.A. Salvador (1997). Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120. Tetrahedron 53, 369-390.
124. B. Liebe and H. Kunz (1997). Solid-phase synthesis of a tumour-associated sialyl-Tn antigen glycopeptide with a partial sequence of the 'tandem repeat' of the MUC-1 mucin. Angew. Chem. Int. Ed. Engl. 36, 618-620.
125. J. Kihlberg and M. Elofsson (1997). Solid-phase synthesis of glycopeptides: immunological studies with T cell stimulating glycopeptides. Curr. Med. Chem. 4, 85-116.
126. H.G. Garg, K. von dem Bruch and H. Kunz (1994). Developments In the synthesis of glycopeptides containing glycosyl L-asparagine, L-serine, and L-threonine. Adv. Corbohydr. Chem. Biochem. 50, 277-310.
127. M. Meldal. Glycopeptide synthesis, in: Neoglycoconjugates: Preparation and Applications, Y.C. Lee and R.T. Lee, Eds, p. 145-198, Academic Press, San Diego, 1994.
128. J. Ježek, J. Velek, T. Trnka, M. Písačka and F. Mareček. Solid phase synthesis of glycopeptide dendrimers with Tn antIgenic structure and their biological activities, in: Peptides 1996, R. Ramage and R. Epton, Eds, p. 503-504, Mayflower Scientific Ltd., London, 1998.
129. S. Butz, S. Rawer, W. Rapp and U. Birsner (1994). Immunization and affinity purification of antibodies using resin-immobilized lysine-branched synthetic peptides. Peptide Res. 7, 20-23.
130. J. Velek, J. Ježek, P. Vepřek, V. Velková, T. Trnka, J. Pecka and M. Písačka. Synthetic glycopeptide dendrimers with Tn antigenic structure: immunological study. Part II, in: Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Libraries 1997, London, 1998 (in press).
131. T. Toyokuni and A.K. Singhal (1995). Synthetic carbohydrate vaccines based on tumour-associated antigens. Chem. Soc. Rev. 24, 231-242.
132. M. Marguerite, M. Bossus, C. Mazingue, I. Wolowczuk, H. Gras-Masse, A. Tartar, A. Capron and C. Auriault (1992). Analysis of antigenicity and immunogenicity of five different chemically defined constructs of a peptide. Mol. Immunol. 29, 793-800.
133. H.S. Marsden, A.M. Owsianka, S. Graham, G.W. McLean, C.A. Robertson and J.H. Subak-Sharpe (1992). Advantages of branched peptides in serodiagnosis. Detection of HIV-specific antibodies and the use of glycine spacers to increase sensitivity. J. Immunol. Methods 147, 65-72.
134. G. Fassina, A. Corti and G. Cassani (1992). Affinity enhancement of complementary peptide recognition. Int. J. Peptide Protein Res. 30, 549-556.
135. M. Nomizu, K. Yamamura, H.K. Kleinman and Y. Yamada (1993). Multimeric forms of Tyr-Ile-Gly-Ser-Arg (YIGSR) peptide enhance the inhibition of tumor growth and metastasis. Cancer Res. 53, 3459-3461.
136. P. Sinnis, P. Clavijo, D. Fenyo, B.T. Chait, C. Cerami and V. Nussenzweig (1994). Structural and functional properties of region II-plus of the malaria circumsporozoite protein. J. Exp. Med. 180, 297-306.
137. J.P. Tam. Synthesis and applications of branched peptides in immunological methods and vaccines, in: Peptides: Synthesis, Structures, and Applications, B. Gutte, Ed., p. 455-500, Academic Press, San Diego, 1995.
138. J.M. Calvo-Calle, J. Hammer, F. Sinigaglia, P. Clavijo, Z.R. Moya-Castro and E.H. Nardin (1997). Binding of malaria T cell epitopes to DR and DQ molecules in vitro correlates with immunogenicity in vivo: identification of a universal T cell epitope in the Plasmodium falciparum circumsporozoite protein. J. Immunol. 159, 1362-1373.
139. E.H. Nardin, J.M. Calvo-Calle, G.A. Oliveira, P. Clavijo, R. Nussenzweig, R. Simon, W. Zeng and K. Rose (1998). Plasmodium falciparum polyoximes: highly immunogenic synthetic vaccines constructed by chemoselective ligation of repeat B-cell epitopes and a universal T-cell epitope of CS protein. Vaccine 16, 590-600.
140. N. Ahlborg, E.H. Nardin, P. Perlmann, K. Berzins, R. Andersson (1998). Immunogenicity of chimeric multiple antigen peptides based on Plasmodium falciparum antigens: impact of epitope orientation. Vaccine 16, 38-44.
141. S. Herrera, C. De Plata, M. Gonzales, B.L. Perlaza, F. Bettens, G. Corradin and M. Arevalo-Herrera (1997). Antigenicity and immunogenicity of multiple antigen peptides containing P. vivax CS epitopes in Aotus monkeys. Parasite Immunol. 19, 161-170.
142. R. Wang, Y. Charoenvit, G. Corradin, R.L. Porrozzi, R. Hunter, G. Glenn, C.R. Alving, P. Church and S.K. Hoffman (1995). Induction of protective polyclonal antibodies by immunization with a Plasmodium yoelii circumsporozoite protein multiple antigen peptide vaccine. J. Immunol. 154, 2784-2793.
143. E.D. Franke, G. Corradin and S.L. Hoffman (1997). Induction of protective CTL responses against the Plasmodium yoelii circumsporozoite protein by immunization with peptides. J. Immunol. 159, 3424-3433.
144. S. Anderson, M. Momoeda, M. Kawase, S. Kajigaya and N.S. Young (1995). Peptides derived from the unique region of B19 parvovirus minor capsid protein elicit neutralizing antibodies in rabbits. Virology 206, 626-632.
145. E. Baba, M. Nakamura, K. Ohkuma, J. Kira, Y. Tanaka, S. Nakano and Y. Niho (1995). A peptide-based human T cell leukemia virus type I vaccine containing T and B cell epitopes that induces high titers of neutralizing antibodies. J. Immunol. 154, 399-412.
146. B. Železná, L. Veselský and J. Velek (1997). Antibody against angiotensin II receptor AT2 type as a tool for the study of receptor function. Rev. Clin. Pharm. Pharmacokinet. Int. Ed. 11, 85-87.
147. J.A. James, T. Gross, H.R. Scofield and J.B. Harley (1995). Immunoglobulin epitope spreading and autoimmune disease after peptide immunization: Sm B/B′-derived PPPGMRPP and PPPGIRGP induce spliceosome autoimmunity. J. Exp. Med. 181, 453-461.
148. M. Digweed, U. Gunthert, R. Schneider, H. Seyschab, R. Friedl and K. Sperling (1995). Irreversible repression of DNA synthesis in Fanconi anemia cells is alleviated by the product of a novel cyclin-related gene. Mol. Cell. Biol. 15, 305-314.
149. G. Sa, G. Murugesan, M. Jaye, Y. Ivashchenko and P.L. Fox (1995). Activation of cytosolic phospholipase A2 by basic flbroblast growth factor via a p42 mitogen-activated protein kinase-dependent phosphorylation pathway in endothelial cells. J. Biol. Chem. 270, 2360-2366.
150. Z.G. Wo and R.E. Oswald (1995). A topological analysis of goldfish kainate receptors predicts three transmembrane segments. J. Biol. Chem. 270, 2000-2009.
151. N. Ahlborg, S. Paulie and S. Braesch-Andersen (1997). Generation of antibodies to human IL-12 and amphiregulin by immunization of Balb/c mice with diepitope multiple antigen peptides. J. Immunol. Methods 204, 23-32.
152. M.A. Rigby, N. Mackay, G. Reid, R. Osborne, J.C. Neil and O. Jarrett (1996). Immunogenicity of a peptide from a major neutralising determinant of the feline immunodeficiency virus surface glycoprotein. Vaccine 14, 1095-1102.
153. J.N. Flynn, C.A. Cannon, G. Reid, M.A. Rigby, J.C. Neil and O. Jarrett (1995). Induction of feline immunodeficiency virus-specific cell-mediated and humoral immune responses following immunization with a multiple antigenic peptide from the envelope V3 domain. Immunology 85, 171-175.
154. N. Ahlborg, R. Andersson, P. Perlmann and K. Berzins (1996). Immune responses in congenec mice to multiple antigen peptides based on defined epitopes from the malaria antigen Pf332. Immunology 88, 630-635.
155. N. Ahlborg, J. Iqbal, M. Hansson, M. Uhlen, D. Mattel, P. Perlmann, S. Stahl and K. Berzins (1995). Immunogens containing sequences from antigen Pf332 induce Plasmodium falciparum-reactive antibodies which inhibit parasite growth but not cytoadherence. Parasite Immunol. 17, 341-352.
156. L. Jaso-Friedmann, J.H. Leary, Z. Weisman and D.L. Evans (1996). Activation of nonspecific cytotoxic cells with a multiple antigenic peptide: specifity and requirements for receptor crosslinkage. Cell. Immunol. 170, 195-201.
157. S.D. Mahale, J. Pereira, U. Natraj and K.S. Iyer (1996). Comparison of antibodies raised against the peptide 10-24 of chicken riboflavin carrier protein (cRCP) by classical and multiple antigen peptide (MAP) approaches. J. Immunol. Methods 190, 215-219.
158. M. Gilardeau Truffinet, M. Bossus, D. Camus, P. Delplace, C. Mazingue, E. Diesis, A. Tartar, S. Moreau, H. Gras-Masse and D.M. Banic (1996). Induction of anybodies against the Plasmodium falciparum p126 antigen in non-responder H-2b and partial-responder H-2d mice using synthetic peptides. Peptide Res. 9, 61-70.
159. A. Basak, A. Boudreault, A. Chen, M. Chretien, N.G. Seidah and C. Lazure (1995). Application of the multiple antigenic peptides (MAP) strategy to the production of prohormone convertases antibodies: synthesis, characterization and use of 8-branched immunogenic peptides. J. Peptide Sci. 1, 385-395.
160. K. Rose, W. Zeng, L.E. Brown and D.C. Jackson (1995). A synthetic peptide-based polyoxime vaccine construct of high purity and activity. Mol. Immunol. 32, 1031-1037.
161. T. Yokoyama, K. Kimura, Y. Tagawa and N. Yuasa (1995). Preparation and characterization of antibodies against mouse prion protein (PrP) peptides. Clin. Diagn. Lab. Immunol. 2, 172-176.
162. M.E. Schott, D.T. Well, J. Schlom and S.I. Abrams (1996). Comparison of linear and branched peptide forms (MAPs) in the introduction of T helper responses to point-mutated ras immunogens. Cell. Immunol. 174, 199-209.
163. N. Aoki, M. Mori, K. Kato, Y. Sakamoto, K. Noda, M. Tajima and H. Shimada (1996). Antibody against synthetic multiple antigen peptides (MAP) of JC virus capsid protein (VP1) without cross reaction to BK virus: a diagnostic tool for progressive multifocal leukoencephalopathy. Neurosci. Lett. 205, 111-114.
164. P. Kanda, D.A. Fritz, D.A. Gage and K.R. Shuler (1995). Dependence of murine antibody response to an anti-CDR2 VH peptide on immunogen formulation. Mol. Immunol. 32, 1319-1328.
165. P.J. Duriez, S. Desnoyers, J.C. Hoflack, G.M. Shah, B. Morelle, S. Bourassa, G.G. Poirier and B. Talbot (1997). Characterization of anti-peptide antibodies directed towards the automodification domain and apoptotic fragment of poly (ADP-ribose) polymerase. Biochim. Biophys. Acta 1334, 65-72.
166. I. Toth, N. Flinn, W.A. Gibbons, M. Good, W. Hayman and F. Brown. Immunological evaluation of the Lipid-Core-Peptide (LCP) adjuvant/carrier system, in: Peptides, Chemistry, Structure and Biology, P.T.P. Kaumaya and R.S. Hodges, Eds, p. 810-811. Mayflower Scientific Ltd., Kingswinford, 1996.
167. D.J. Smith, B. Shoushtari, R.L. Heschel, W.F. King and M.A. Taubman (1997). Immunogenicity and protective immunity induced by synthetic peptides associated with a catalytic subdomain of mutans group streptococcal glucosyltransferase. Infect. Immun. 65, 4424-4430.
168. M.W. Jackwood (1995). Production and immunogenicity of multiple antigenic peptide (MAP) constructs derived from the S1 glycoprotein of infectious bronchitis virus (IBV). Adv. Exp. Med. Biol. 380, 213-219.
169. M. Singh, J.P. McGee, X.M. Li, W. Koff, T. Zamb, C.Y. Wang, D.T. O'Hagan (1997). Biodegradable microparticles with an entrapped branched octameric peptide as a controlled-release HIV-1 vaccine. J. Pharm. Sci. 86, 1229-1233.
170. L. Caponi, S. Perogano, V. Di Bartolo, P. Rovero, R. Revoltella and S. Bombardieri (1995). Autoantibodies directed against ribosomal P proteins: use of a multiple antigen peptide as the coating agent in ELISA. J. Immunol. Methods 179, 193-202.
171. T. Vogel, R. Kurth and S. Norley (1994). The majority of neutralizing Abs in HIV-1-infected patients recognize linear V3 loop sequences. Studies using HIV-1MN multiple antigenic peptides. J. Immunol. 153, 1895-1904.
172. T. Firsova, J.A. Pérez, I.V. Kruglov, F. Reig and I. Haro. Synthesis of a diepitope multiple antigen peptide containing sequences from VP1 and VP3 proteins of hepatitis A virus and its use in hepatitis diagnosis, in: Book of Abstracts, 24th Symposium oj the EPS, Abstract No. 24, Edinburgh, Scotland, 1996.
173. B. Marchini, M.P. Dolcher, A. Sabbatini, G. Klein and P. Mogliorini (1994). Immune response to different sequences of the EBNA I molecule in Epstein-Barr virus-related disorders and in autoimmune diseases. J. Autoimmun. 7, 179-191.
174. N. Yahi, J. Sabatier, S. Baghdiguian, F. Gonzales-Scarano and J. Fantini (1995). Synthetic multimeric peptides derived from the principal neutralization domain (V3 loop) of human immunodeficiency virus type 1 (HIV-1) gp120 bind to galactosylceramide and block HIV-1 infection in a human CD4-negative mucosal epithelial cell line. J. Virol. 69, 320-325.
175. N. Yahi, J. Fantini, S. Baghdiguian, K. Mabrouk, C. Tamalet, H. Rochat, J. van Rietschoten and J.M. Sabatier (1995). SPC3, a synthetic peptide derived from the V3 domain of human immunodeficiency virus type 1 (HIV-1) gp120, inhibits HIV-1 entry into CD4 + and CD4-cells by two distinct mechanisms. Proc. Natl. Acad. Sci. USA 92, 4867-4871.
176. N. Yahi, J. Fantini, K. Mabrouk, C. Tamalet, P. DeMicco, J. van Rietschoten, H. Rochat and J.M. Sabatier (1994). Multibranched V3 peptides inhibit human immunodeficiency virus infection in human lymphocytes and macrophages. J. Virol. 68, 5714-5720.
177. N. Yahi, J.M. Sabatier, P. Nickel, K. Mabrouk, F. Gonzales-Scarano and J. Fantini (1994). Suramin inhibits binding of the V3 region of HIV-1 envelope glycoprotein gp120 to galactosylceramide, the receptor for HIV-1 gp120 on human colon epithelial cells. J. Biol. Chem. 269, 24349-24353.
178. B. Weeks, M. Nomizu, A. Otaka, C. Weston, A. Okusu, H. Tamamura, A. Matsumoto, N. Yamamoto and N. Fujii (1994). Lymphocytes and promonocytes attach to the synthetic [Tyr5, 12, Lys7] polyphemusin II peptide. Biochem. Biophys. Res. Commun. 202, 470-475.
179. A. Wallace, S. Altamura, C. Toniatti, A. Vitelli, E. Bianchi, P. Delmastro, G. Ciliberto and A. Pessi (1994). A multimeric synthetic peptide combinatorial library. Peptide Res. 7, 27-31.
180. G. Fassina, G. Cassani, P. Gnocchi, M.C. Fornasiero and A.M. Isetta (1995). Inhibition of interleukin-2/p55 receptor subunit interaction by complementary peptides. Arch. Btochem. Biophys. 318, 37-45.
181. K.C. Ingham, S.A. Brew and M. Migliorini (1994). An unusual heparin-binding peptide from the carboxy-termlnal hep-2 region of fibronectin. Arch. Biochem. Biophys. 314, 242-246.
182. F. Chillemi, P. Francescato, R. Bossa, A. Fraccari, I. Galatulas (1997). Enhancement of cytotoxic activity by synthesis of peptide multimeric forms. Anticancer Res. 17, 3609-3611.
183. K. Sheldon, D. Liu, J. Ferguson and J. Gariepy (1995). Loligomers: design of de novo peptide-based intracellular vehicle. Proc. Natl. Acad. Sci. USA 92, 2056-2060.
184. D.L. Wiegandt, W. Ma and A.F. Spatola. Homooligomeric and hetero-oligomeric multifunctional peptide analogs, in: Peptides, Chemistry, Structure and Biology, P.T.P. Kaumaya and R.S. Hodges, Eds, p. 555-557, Mayflower Scientific Ltd., Kingswinford, 1996.
185. A. Verdoliva, M. Ruvo, G. Cassani and G. Fassina. Antigenic cross-recognition of retro and inverso peptides, in: Peptides in Immunology, C.H. Schneider, Ed., p. 205-211, John Wiley & Sons, Chichester, 1996.
186. G. Fassina, A. Verdoliva, M.R. Odierna, M. Ruvo and J. Cassini (1996). Protein A mimetic peptide ligand for affinity purification of antibodies. J. Mol. Recognit. 9, 564-569.
187. A. Verdoliva, G. Cassani and G. Fassina (1995). Affinity purification of polyclonal antibodies using immobilized multimeric peptides. J. Chromatogr. B, Biomed. Appl. 664, 175-183.
188. S. Butz, S. Rawer, W. Rapp and U. Birsner (1994). Immunization and affinity purification of antibodies using resin-immobilized lysine-branched synthetic peptides. Peptide Res. 7, 20-23.