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Galactosylsphingamides : new α-GalCer analogues to probe the F’-pocket of CD1d

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Abstract
Invariant Natural Killer T-cells (iNKT-cells) are an attractive target for immune response modulation, as upon CD1d-mediated stimulation with KRN7000, a synthetic alpha-galactosylceramide, they produce a vast amount of cytokines. Here we present a synthesis that allows swift modification of the phytosphingosine side chain by amidation of an advanced methyl ester precursor. The resulting KRN7000 derivatives, termed alpha-galactosylsphingamides, were evaluated for their capacity to stimulate iNKT-cells. While introduction of the amide-motif in the phytosphingosine chain is tolerated for CD1d binding and TCR recognition, the studied alpha-galactosylsphingamides showed compromised antigenic properties.
Keywords
KILLER T-CELLS, NKT CELLS, BIOLOGICAL EVALUATION, C-GALACTOSYLCERAMIDE, SPHINGOSINE BACKBONE, INKT CELLS, KRN7000, GLYCOLIPIDS, RECEPTOR, RECOGNITION

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Citation

Please use this url to cite or link to this publication:

Chicago
Guillaume, Joren, Jing Wang, Jonas Janssens, Soumya G Remesh, Martijn Risseeuw, Tine Decruy, Mathy Froeyen, Dirk Elewaut, Dirk M Zajonc, and Serge Van Calenbergh. 2017. “Galactosylsphingamides : New α-GalCer Analogues to Probe the F’-pocket of CD1d.” Scientific Reports 7.
APA
Guillaume, J., Wang, J., Janssens, J., Remesh, S. G., Risseeuw, M., Decruy, T., Froeyen, M., et al. (2017). Galactosylsphingamides : new α-GalCer analogues to probe the F’-pocket of CD1d. SCIENTIFIC REPORTS, 7.
Vancouver
1.
Guillaume J, Wang J, Janssens J, Remesh SG, Risseeuw M, Decruy T, et al. Galactosylsphingamides : new α-GalCer analogues to probe the F’-pocket of CD1d. SCIENTIFIC REPORTS. 2017;7.
MLA
Guillaume, Joren, Jing Wang, Jonas Janssens, et al. “Galactosylsphingamides : New α-GalCer Analogues to Probe the F’-pocket of CD1d.” SCIENTIFIC REPORTS 7 (2017): n. pag. Print.
@article{8525336,
  abstract     = {Invariant Natural Killer T-cells (iNKT-cells) are an attractive target for immune response modulation, as upon CD1d-mediated stimulation with KRN7000, a synthetic alpha-galactosylceramide, they produce a vast amount of cytokines. Here we present a synthesis that allows swift modification of the phytosphingosine side chain by amidation of an advanced methyl ester precursor. The resulting KRN7000 derivatives, termed alpha-galactosylsphingamides, were evaluated for their capacity to stimulate iNKT-cells. While introduction of the amide-motif in the phytosphingosine chain is tolerated for CD1d binding and TCR recognition, the studied alpha-galactosylsphingamides showed compromised antigenic properties.},
  articleno    = {4276},
  author       = {Guillaume, Joren and Wang, Jing and Janssens, Jonas and Remesh, Soumya G and Risseeuw, Martijn and Decruy, Tine and Froeyen, Mathy and Elewaut, Dirk and Zajonc, Dirk M and Van Calenbergh, Serge},
  issn         = {2045-2322},
  journal      = {SCIENTIFIC REPORTS},
  keyword      = {KILLER T-CELLS,NKT CELLS,BIOLOGICAL EVALUATION,C-GALACTOSYLCERAMIDE,SPHINGOSINE BACKBONE,INKT CELLS,KRN7000,GLYCOLIPIDS,RECEPTOR,RECOGNITION},
  language     = {eng},
  pages        = {18},
  title        = {Galactosylsphingamides : new \ensuremath{\alpha}-GalCer analogues to probe the F{\textquoteright}-pocket of CD1d},
  url          = {http://dx.doi.org/10.1038/s41598-017-04461-7},
  volume       = {7},
  year         = {2017},
}

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