Synthesis and in vitro evaluation of alpha-GalCer epimers.
alpha-GalCer (also known as KRN7000) is an immunomodulatory glycolipid that is known to potently activate invariant natural killer T (NKT) cells upon CD1d-mediated stimulation. Because Th1 and Th2 cytokines, which are released after alpha-GalCer presentation, antagonize each other's effects, alpha-GalCer analogues that induce a biased Th1/Th2 response are highly awaited. In this context, we report the synthesis and in vitro evaluation of alpha-Gal-D-xylo-Cer and two alpha-Gal-L-lyxo-Cer analogues, one with the natural acyl chain, the other with a truncated chain.
Trappeniers
Matthias
M
Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, 9000 Gent, Belgium.
Goormans
Stijn
S
Van Beneden
Katrien
K
Decruy
Tine
T
Linclau
Bruno
B
Al-Shamkhani
Aymen
A
Elliott
Tim
T
Ottensmeier
Christian
C
Werner
Joern M
JM
Elewaut
Dirk
D
Van Calenbergh
Serge
S
D000818:Animals; D018949:Antigens, CD1; D016207:Cytokines / Q000276:immunology / Q000378:metabolism; D005699:Galactosylceramides / Q000138:chemical synthesis / Q000494:pharmacology*; D006017:Glycolipids / Q000138:chemical synthesis / Q000494:pharmacology*; D007694:Killer Cells, Natural / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism; D051379:Mice; D008810:Mice, Inbred C57BL; D013154:Spleen / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D018417:Th1 Cells / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism; D018418:Th2 Cells / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism
D018949:Antigens, CD1; D016207:Cytokines; D005699:Galactosylceramides; D006017:Glycolipids; C493154:alpha-galactosylceramide; C103873:KRN 7000