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Título: | Galacto-Configured Aminocyclitol Phytoceramides Are Potent in Vivo Invariant Natural Killer T Cell Stimulators |
Autor: | Harrak Serifi, Youssef CSIC; Barra, Carolina M.; Delgado Huertas, Antonio CSIC ORCID ; Castaño, A. Raúl; Llebaria, Amadeu CSIC ORCID | Fecha de publicación: | 2011 | Editor: | American Chemical Society | Citación: | Journal of the American Chemical Society | Resumen: | A new class of α-galactosylceramide (αGC) nonglycosidic analogues bearing galacto-configured aminocyclitols as sugar surrogates have been obtained. The aminocyclohexane having a hydroxyl substitution pattern similar to an α-galactoside is efficiently obtained by a sequence involving Evans aldol reaction and ring-closing metathesis with a Grubbs catalyst to give a key intermediate cyclohexene, which has been converted in galacto-aminocyclohexanes that are linked through a secondary amine to a phytoceramide lipid having a cerotyl N-acyl group. Natural Killer T (NKT) cellular assays have resulted in the identification of an active compound, HS161, which has been found to promote NKT cell expansion in vitro in a similar fashion but more weakly than αGC. This compound stimulates the release of Interferon-γ (IFNγ) and Interleukin-4 (IL-4) in iNKT cell culture but with lower potency than αGC. The activation of Invariant Natural Killer T (iNKT) cells by this compound has been confirmed in flow cytometry experiments. Remarkably, when tested in mice, HS161 selectively induces a very strong production of IFN-γ indicative of a potent Th1 cytokine profile. Overall, these data confirm the agonist activity of αGC lipid analogues having charged amino-substituted polar heads and their capacity to modulate the response arising from iNKT cell activation in vivo. | Versión del editor: | http://dx.doi.org/10.1021/ja202610x | URI: | http://hdl.handle.net/10261/48566 | DOI: | 10.1021/ja202610x | ISSN: | 0002-7863 | E-ISSN: | 1520-5126 |
Aparece en las colecciones: | (IQAC) Artículos |
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