title: Synthesis and in vitro evaluation of alpha-GalCer epimers.
abstract: 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.
authors.affiliation: Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, 9000 Gent, Belgium.
authors.forename: Matthias
authors.initials: M
authors.lastname: Trappeniers
authors.forename: Stijn
authors.initials: S
authors.lastname: Goormans
authors.forename: Katrien
authors.initials: K
authors.lastname: Van Beneden
authors.forename: Tine
authors.initials: T
authors.lastname: Decruy
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau
authors.forename: Aymen
authors.initials: A
authors.lastname: Al-Shamkhani
authors.forename: Tim
authors.initials: T
authors.lastname: Elliott
authors.forename: Christian
authors.initials: C
authors.lastname: Ottensmeier
authors.forename: Joern M
authors.initials: JM
authors.lastname: Werner
authors.forename: Dirk
authors.initials: D
authors.lastname: Elewaut
authors.forename: Serge
authors.initials: S
authors.lastname: Van Calenbergh
mesh_terms: 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
chemical_list: D018949:Antigens, CD1; D016207:Cytokines; D005699:Galactosylceramides; D006017:Glycolipids; C493154:alpha-galactosylceramide; C103873:KRN 7000