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Alpha-S-GalCer: synthesis and evaluation for iNKT cell stimulation.

ABSTRACT: The synthesis and evaluation for iNKT stimulation of alpha-S-galactosylceramide is reported. Prepared by alkylation of a galactosylthiol, this analog of the potent immunostimulatory agent, KRN7000, did not stimulate iNKT cells either in vitro or in vivo.

SUBMITTER: Blauvelt ML

PROVIDER: S-EPMC2628538 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Alpha-S-GalCer: synthesis and evaluation for iNKT cell stimulation.

Blauvelt Marisa L ML Khalili Maryam M Jaung Weonjoo W Paulsen Janet J Anderson Amy C AC Brian Wilson S S Howell Amy R AR

Bioorganic & medicinal chemistry letters 20081101 24

The synthesis and evaluation for iNKT stimulation of alpha-S-galactosylceramide is reported. Prepared by alkylation of a galactosylthiol, this analog of the potent immunostimulatory agent, KRN7000, did not stimulate iNKT cells either in vitro or in vivo. ...[more]

PMID: 18993065

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Synthesis and evaluation of amino-modified alpha-GalCer analogues.

Project description:Alpha-GalCer analogues featuring a phytoceramide 3- and 4-amino group have been synthesized. A Mitsunobu reaction involving phthalimide was employed for the introduction of the amino groups at the 3- and 4-positions of suitable phytosphingosine-derived precursors. The influence of these modifications on the interaction with the T-cell receptor of NKT cells was investigated, as well as the capacity of the amino-modified analogues to induce a cytokine response after in vivo administration.

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Repeated α-GalCer Administration Induces a Type 2 Cytokine-Biased iNKT Cell Response and Exacerbates Atopic Skin Inflammation in Vα14Tg NC/Nga Mice.

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Design, Synthesis, and Immunological Evaluation of Benzyloxyalkyl-Substituted 1,2,3-Triazolyl ?-GalCer Analogues.

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Alpha-galactosylceramide (?GalCer) enhances vaccine-induced protection in a model of ricin intoxication.

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4"-O-Alkylated α-Galactosylceramide Analogues as iNKT-Cell Antigens: Synthetic, Biological, and Structural Studies.

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