Synthesis and immunological evaluation of an antitumor neoglycopeptide vaccine bearing a novel homoserine Tn antigen. - Archive ouverte HAL Access content directly
Journal Articles Bioorganic and Medicinal Chemistry Letters Year : 2004

Synthesis and immunological evaluation of an antitumor neoglycopeptide vaccine bearing a novel homoserine Tn antigen.

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Abstract

As part of our program on Tn-specific anti-tumor immunotherapy, our aim was to vary the nature of the aglyconic part of the tumor-associated Tn antigen (alpha-d-GalNAc-Ser/Thr). This report describes the synthesis of Fmoc-hSer-(alpha-d-GalNAc)-OH (4) in 19% overall yield from protected aspartic acid. The building block 4 was incorporated as trimeric clusters into a glycopeptide vaccine [MAG:Tn(hSer)3-PV], using solid-phase peptide synthesis. When injected in mice, the resulting MAG induces a strong antibody response, which recognizes native tumor-associated antigens (TAA) at the surface of human tumor cells. This approach may be extended to the use of other nonnatural TAA in order to improve half-life of synthetic anti-cancer vaccines.

Dates and versions

pasteur-00166850 , version 1 (10-08-2007)

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Sophie Vichier-Guerre, Richard Lo-Man, Valérie Huteau, Edith Dériaud, Claude Leclerc, et al.. Synthesis and immunological evaluation of an antitumor neoglycopeptide vaccine bearing a novel homoserine Tn antigen.. Bioorganic and Medicinal Chemistry Letters, 2004, 14 (13), pp.3567-70. ⟨10.1016/j.bmcl.2004.04.047⟩. ⟨pasteur-00166850⟩

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