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© William Beaucardet
Consultation au Centre médical de l'Institut Pasteur (CMIP).
Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Organic & biomolecular chemistry - 20 Dec 2016

Ganneau C, Simenel C, Emptas E, Courtiol T, Coïc YM, Artaud C, Dériaud E, Bonhomme F, Delepierre M, Leclerc C, Lo-Man R, Bay S

Link to Pubmed [PMID] – 27812586

Org. Biomol. Chem. 2016 Dec;15(1):114-123

Herein, we report a new process that enables the gram-scale production of a fully synthetic anti-cancer vaccine for human use. This therapeutic vaccine candidate, named MAG-Tn3, is a high-molecular-weight tetrameric glycopeptide encompassing carbohydrate tumor-associated Tn antigen clusters and peptidic CD4 T-cell epitopes. The synthetic process involves (i) the stepwise solid-phase assembly of protected amino acids, including the high value-added Tn building blocks with only 1.5 equivalents, (ii) a single isolated intermediate, and (iii) the simultaneous deprotection of 36 hindered protective groups. The resulting MAG-Tn3 was unambiguously characterized using a combination of techniques, including a structural analysis by nuclear magnetic resonance spectroscopy. The four peptidic chains are flexible in solution, with a more constrained but extended conformation at the Tn3 antigen motif. Finally, we demonstrate that, when injected into HLA-DR1-expressing transgenic mice, this vaccine induces Tn-specific antibodies that mediate the killing of human Tn-positive tumor cells. These studies led to a clinical batch of the MAG-Tn3, currently investigated in breast cancer patients (phase I clinical trial). The current study demonstrates the feasibility of the multigram-scale synthesis of a highly pure complex glycopeptide, and it opens new avenues for the use of synthetic glycopeptides as drugs in humans.

https://www.ncbi.nlm.nih.gov/pubmed/27812586