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. 2017 Mar 1;8(3):2204-2208.
doi: 10.1039/c6sc04218j. Epub 2016 Dec 9.

Psychosine variants as antigens for natural killer T cells

S Deng  1 , L Kain  2 , C S Pereira  3   4 , S Mata  1 , M F Macedo  3   4   5 , A Bendelac  6 , L Teyton  2 , P B Savage  1
Affiliations

Psychosine variants as antigens for natural killer T cells

S Deng et al. Chem Sci. .

Abstract

Natural killer T (NKT) cells play a central role in the interface between innate and adaptive immunity, and alpha-galactosylceramide was recently shown to be an endogenous antigen for these cells. The source of alpha-galactosylceramide has not yet been determined; however, in vivo degradation of alpha-galactosylceramide involves generation of alpha-psychosine (alpha-galactosylsphingosine). Alpha-psychosine stimulates cytokine release from NKT cells and constitutes an endogenous antigen for these cells. Alpha-psychosine contains a single lipid chain, while most antigens for NKT cells have two lipid chains, and we have investigated if other glycolipids with one lipid chain, derived from know antigens for NKT cells, stimulate cytokine release from NKT cells. Only psychosine variants derived from the most potent NKT cell antigens cause stimulation, and this stimulation occurs in vitro as well as in vivo. Truncated forms of weak antigens for NKT cells are not stimulatory.

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Figures

Fig. 1
Fig. 1. Structures of glycolipid antigens for NKT cells.
Fig. 2
Fig. 2. Pathway for alpha-galactosylceramide degradation.
Fig. 3
Fig. 3. Psychosine variants prepared for determination of NKT cell stimulatory activity.
Scheme 1
Scheme 1. Synthesis of alpha-psychosine.
Scheme 2
Scheme 2. Synthesis of alpha-Glc-palmitoyl glycerol.
Scheme 3
Scheme 3. Synthesis of alpha-GlcA-psychosine.
Scheme 4
Scheme 4. Synthesis of lyso-iGb3.
Fig. 4
Fig. 4. Stimulation of NKT cells (DN32.D3 cells) by the indicated glycolipids presented by CD1d on RBL cells. Stimulation measured by tritium incorporation into a natural killer cell line. Alpha-galactosylceramide (■); alpha-psychosine (); alpha-psychosine (phyto) (); alpha-Glc-psychosine (); alpha-Glc-psychosine (phyto) (◆); 6′-NAc-alpha-psychosine (▲).
Fig. 5
Fig. 5. Response of two human NKT cell lines (A and B) to alpha-psychosine (■) and alpha-Glc-psychosine (). CD1d-transfected C1R cells were used for antigen presentation.
Fig. 6
Fig. 6. Expansion of NKT cells in wild-type C57BL/6J mice three days after injection (IV) with the indicated glycolipid (2.5 μg per mouse).
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