%0 Journal Article
%T Synthesis of 5-Thio-¦Á-GalCer Analogues with Fluorinated Acyl Chain on Lipid Residue and Their Biological Evaluation
%J -
%D 2019
%R https://doi.org/10.1021/acsmedchemlett.8b00640
%X Invariant natural killer T (iNKT) cells are a subclass of T cells that initiates the secretion of T helper 1 and 2 cytokines after recognizing CD1d protein presented glycolipid antigens. In this Letter, we designed and synthesized a novel series of CD1d ligand ¦Á-galactosylceramides (¦Á-GalCers) in which the acyl chain backbone of the lipid was incorporated with fluorine atoms. The in vivo evaluation of immunostimulatory activities revealed that the synthesized ¦Á-5-thio-galactopyranosyl-N-perfluorooctanoyl phytosphingosine exhibited a remarkable potency toward selectively enhancing TH1 cytokine production with the IFN ¦Ã/IL-4 ratio of 9/1, while its perfluorotetradecanoyl counterpart showed TH2 profile with an IFN ¦Ã/IL-4 ratio of 0.59/1. The analogues synthesized here would be used as probes to study lipid¨Cprotein interactions in ¦Á-GalCer/CD1d complexes
%U https://pubs.acs.org/doi/10.1021/acsmedchemlett.8b00640