Synthesis and biological evaluation of an anticancer vaccine containing the C-glycoside analogue of the Tn epitope

Bioconjugate Chemistry

Volumn 12, Issue 3, 2001, Pages 325-328

  Peri, Francesco ^a   Cipolla, Laura ^a   Rescigno, Maria ^a   La Ferla, Barbara ^a   Nicotra, Francesco ^a  

^a UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOLOGY; MAMMALS; MOLECULES; PEPTIDES; SUGARS; T-CELLS; VACCINES;

BIOLOGICAL EVALUATION; C-GLYCOSIDES; CHEMOSELECTIVE; EPITOPE PEPTIDE; SPLEEN CELLS; SYNTHESIS EVALUATION; SYNTHETIC APPROACH; SYNTHETIC VACCINES; T-CELL EPITOPES; TRANSGENICS;

EPITOPES;

EID: 0035023854     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc000143a     Document Type: Article

References (17)

1. Danishefsky, S. J., and Allen, J. R. (2000) From the Laboratory to the Clinic: A Retrospective on Fully Synthetic Carbohydrate-Based Anticancer Vaccines. Angew. Chem., Int. Ed. 39, 836-863.
2. Hakomori, S. (1989) Aberrant glycosylation in tumors and tumor-associated carbohydrate antigens. Adv. Cancer Res. 52, 257-331.
3. Toyokuni, T., and Singhal, A. K. (1995) Synthetic carbohydrate Vaccines Based on Tumour-Associated Antigens. Chem. Soc. Rev. 231-242.
4. Springer, G. F. (1984) T and Tn, general carcinoma autoantigens. Science 224, 1198-1206.
5. Francis, M. J. (1991) in Vaccines: Recent Trends and Progress (Gregoriadis, G., Allison, A. C., Poste, G., Ed.) Plenum Press, New York.
6. Toyokuni, T., Hakomori, S., and Singhal, A. K. (1994) Synthetic carbohydrate vaccines: synthesis and immunogenicity of Tn antigen conjugates. Bioorg. Med. Chem. 2(11), 1119-1132.
7. Wiesmuller, K. H., Jung, G., and Hess, G. (1989) Novel low-molecular-weight synthetic vaccineagainst foot-and-mouth disease containing a potent B-cell and macrophage activator. Vaccine 7(1), 29-33.
8. Bessler, W. G., and Jung, G. (1992) Synthetic lipopeptides as novel adjuvants. Res. Immunol. 143(5), 548-553.
9. Wiesmuller, K. H., Bessler, W. G., and Jung, G. (1992) Solid-phase peptide synthesis of lipopeptidevaccines eliciting epitope-specific B-, T-helper and T-killer cell response. Intl. J. Pept. Protein Res. 40(3-4), 255-260.
10. Reichel, F., Ashton, P. R., and Boons, G.-J. (1997) Synthetic carbohydrate-based vaccines: synthesis of an L-glycero-D-manno-heptose antigen-T-epitope-lipopeptide conjugate. Chem. Commun. 2087-2088.
11. Banchereau, J., and Steinman, R. M. Dendritic cells and the control of immunity. Nature 392(6673), 245-252.
12. Murphy, K. M., Heimberger, A. B., and Loh, D. Y. (1990) Induction by antigen of intrathymic apoptosis of CD4+CD8+TCRlo thymocytes in vivo. Science 250(4988), 1720-1723.
13. Shingal, A., Fohn, M., and Hakomori, S.-I. (1991) Induction of α-N-Acetylgalactosamine-O-serine/Threonine (Tn) Antigen-mediated Cellular Immune Response for Active Immunoterapy in Mice. Cancer Res. 51, 1406-1411.
14. Peri, F., Cipolla, L., La Ferla, B., Dumy, P., and Nicotra, F. (1999) Chemoselective synthesis of C-glycopeptides: an highly convergent approach to O- and N-linked glycopeptide analogues. Glycoconjugate J. 16(8), 399-404.
15. Cipolla, L., La Ferla, B., Lay, L., Peri, F., and Nicotra, F. (2000) Synthesis of C-analogue of N-acetylgalactosamine. Tetrahedron Asymmetry 11, 295-303.
16. Fields, G. B., and Noble, R. L. (1990) Solid-phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Intl. J. Pept. Protein Res. 35(3), 161-221.
17. Winzler, C., Rovere, P., Rescigno, M., Granucci, F., Penna, G., Adorini, L., Zimmermann, V. S., Davoust, J., and Ricciardi-Castagnoli, P. (1997) Maturation stages of mouse dendritic cells in growth factor-dependent long-term cultures. J. Expl. Med. 185(2), 317-328.