title: Synthesis and human NKT cell stimulating properties of 3-O-sulfo-alpha/beta-galactosylceramides.
abstract: Two novel hybrid molecules 3-O-sulfo-alpha/beta-galactosylceramide 3 and 4, which are derived from an immunostimulatory agent alpha-GalCer 1 and self-glycolipid ligand sulfatide 2, were designed and synthesized. Compound 3 was shown to efficiently stimulate human NKT cells to secret IL-4 and IFN-gamma, with activities similar to 1, suggesting that modification of the 3''-OH position of the galactose moiety with sulfate has no significant effect on NKT cell stimulation. As a comparison, the beta-isomer 4 has no affinity to NKT cells, which demonstrates that the alpha-glycosidic bond of galactosylceramide is crucial to the NKT cells activation.
authors.affiliation: Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: Guo-Wen
authors.initials: GW
authors.lastname: Xing
authors.forename: Douglass
authors.initials: D
authors.lastname: Wu
authors.forename: Michael A
authors.initials: MA
authors.lastname: Poles
authors.forename: Amir
authors.initials: A
authors.lastname: Horowitz
authors.forename: Moriya
authors.initials: M
authors.lastname: Tsuji
authors.forename: David D
authors.initials: DD
authors.lastname: Ho
authors.forename: Chi-Huey
authors.initials: CH
authors.lastname: Wong
mesh_terms: D002460:Cell Line; D015195:Drug Design; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007371:Interferon-gamma / Q000378:metabolism; D015847:Interleukin-4 / Q000378:metabolism; D007694:Killer Cells, Natural / Q000187:drug effects* / Q000378:metabolism
chemical_list: D005699:Galactosylceramides; D015847:Interleukin-4; D007371:Interferon-gamma