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Synthesis 2009(8): 1355-1369  
DOI: 10.1055/s-0028-1088033
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Dendrimers of Vaccines Consisting of Tumor-Associated Glycopeptide Antigens and T Cell Epitope Peptides

Stefanie Keil, Anton Kaiser, Fauziya Syed, Horst Kunz*
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Fax: +49(6131)3924786; e-Mail: hokunz@uni-mainz.de;
Further Information

Publication History

Received 17 October 2008
Publication Date:
25 March 2009 (online)

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Abstract

According to the principle of multiple antigen presentation (MAP), a di-lysyl lysine core was used for the synthesis of tetramers of a glycododecapeptide antigen from the tandem-repeat sequence of the tumor-associated mucin, MUC1, which carries a sialyl TN-antigen saccharide side chain. The methodology was extended to the analogous construction of a tetrameric vaccine consisting of a T cell epitope from tetanus toxoid and the sialyl TN-glycododecapeptide of MUC1.

Key words

tumor-associated antigens - glycopeptides - fragment condensation - MUC1 - multiple antigen presentation

    References

  • For reviews, see:
  • 1a Taylor-Papadimitriou J. Burchell JM. Miles DW. Daziel M. Biochim. Biophys. Acta  1999,  1455:  301 
    Google Scholar
  • 1b Hanisch FG. Ninkovic T. Curr. Protein Pept. Sci.  2006,  7:  307 
    Google Scholar
  • 2 Burchell JM. Mungul A. Taylor-Papadimitriou J. J. Mammary Gland Biol. Neoplasia  2001,  6:  355 
    CrossrefGoogle Scholar
  • 3a For a review, see: Liakatos A. Kunz H. Curr. Opin. Mol. Ther.  2007,  9:  35 
    Google Scholar
  • 3b Becker T. Dziadek S. Wittrock S. Kunz H. Curr. Cancer Drug Targets  2006,  6:  491 
    Google Scholar
  • 4 Muller S. In Synthetic Peptides as Antigens   Vol. 28:  Pillai S. van der Vliet PC. Elsevier; Amsterdam: 1999.  p.79-31  
    Google Scholar
  • 5a Kunz H. Birnbach S. Angew. Chem.  1986,  98:  354 
    Google Scholar
  • 5b Kagan E. Ragupathi G. Yi SS. Reis CA. Gildersleeve J. Kahne D. Clausen H. Danishefsky SJ. Livingston PO. Cancer Immunol. Immunother.  2005,  54:  424 
    Google Scholar
  • 5c Wittrock S. Becker T. Kunz H. Angew. Chem. Int. Ed.  2007,  46:  5226 ; Angew. Chem. 2007, 119, 5319, and references cited therein
    Google Scholar
  • 6a Buskas T. Ingale S. Boons G.-J. Angew. Chem. Int. Ed.  2005,  44:  5985 ; Angew. Chem. 2005, 117, 6139-6142
    Google Scholar
  • 6b Dziadek S. Hobel A. Schmitt E. Kunz H. Angew. Chem. Int. Ed.  2005,  44:  7630 ; Angew. Chem. 2005, 117, 7803
    Google Scholar
  • 7 Tam JP. Proc. Natl. Acad. Sci. U.S.A.  1988,  85:  5409 
    CrossrefPubMedGoogle Scholar
  • 8 Keil S. Claus C. Dippold W. Kunz H. Angew. Chem. Int. Ed.  2001,  40:  366 ; Angew. Chem. 2001, 113, 379
    CrossrefGoogle Scholar
  • 9a Rock KL. Immunol. Today  1996,  17:  131 
    Google Scholar
  • 9b Ota S. Ono T. Morita A. Uenaka A. Harada M. Nakayama E. Cancer Res.  2002,  62:  1471 
    Google Scholar
  • 10 Roy R. Drug Discovery Today: Technologies  2004,  1:  327 
    CrossrefGoogle Scholar
  • 11 Seitz O. Kunz H. J. Org. Chem.  1997,  62:  813 
    CrossrefGoogle Scholar
  • 12 Knorr R. Trceziak A. Bannwarth W. Gillessen D. Tetrahedron Lett.  1989,  30:  1927 
    CrossrefGoogle Scholar
  • 13 König W. Geiger R. Chem. Ber.  1970,  103:  788 
    CrossrefPubMedGoogle Scholar
  • 14 Carpino L. El-Faham A. Minor CA. Albericio F. J. Chem. Soc., Chem. Commun.  1994,  2001 
    Google Scholar
  • 15 Wagner M. Dziadek S. Kunz H. Chem. Eur. J.  2003,  9:  6018 
    PubMedGoogle Scholar
  • 16 Kitaguchi H. Hiroshi M. Itoh I. Isamu K. Alexander M. Agric. Biol. Chem.  1991,  55:  3067 
    Google Scholar
  • 17 Perrin DD. Armarego WLF. Purification of Laboratory Chemicals   3rd ed.:  Pergamon Press; Oxford: 1988. 
    Google Scholar
  • 18 Belleau B. Malik G. J. Am. Chem. Soc.  1968,  90:  1651 
    CrossrefGoogle Scholar