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Article Dans Une Revue ChemBioChem Année : 2003

Total Enantioselective Synthesis and In Vivo Biological Evaluation of a Novel Fluorescent BODIPY α-Galactosylceramide

Résumé

Natural killer T (NKT) cells are a distinct subset of mature lymphocytes endowed with features of activated and regulatory T cells. alpha-Galactosylceramides (alpha-GalCers), the synthetic prototype of which is KRN7000, are the only natural reagents recognised by the T-cell receptor of NKT cells. The alpha-GalCer-activated NKT cells promptly release IFN gamma and IL-4 (IFN=interferon; IL=interleukin) and undergo apoptotic death within hours. In mice, activated NKT cells are responsible for antitumour activity and protection against autoimmune diseases. KRN7000 can thus be considered as the root of a family of novel immunoregulatory drugs. To get insights into the in vivo behaviour of alpha-galactosylceramides, an original fluorescent derivative has been prepared by following a convergent synthetic scheme. This strategy allows the introduction of different acyl chains, carbohydrate residues and various labels in the final steps of the synthesis. The fluorescent BODIPY probe derived from a versatile glycolipid precursor is as active as KRN7000 for inducing apoptosis of liver NKT cells. Fluorescence was detected in peritoneal macrophages and splenic antigen-presenting cells, in Kupffer-like cells in the liver, but not in lymphocytes.

Dates et versions

hal-03531886 , version 1 (18-01-2022)

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Citer

Yen Vo-Hoang, Laurent Micouin, Catherine Ronet, Gabriel Gachelin, Martine Bonin. Total Enantioselective Synthesis and In Vivo Biological Evaluation of a Novel Fluorescent BODIPY α-Galactosylceramide. ChemBioChem, 2003, 4 (1), pp.27-33. ⟨10.1002/cbic.200390009⟩. ⟨hal-03531886⟩
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