title: An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells.
abstract: A highly efficient synthesis of the biologically important fluorescent probe dansyl α-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding α-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl α-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented.
authors.affiliation: Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
authors.forename: Janice M H
authors.initials: JM
authors.lastname: Cheng
authors.forename: Stephanie H
authors.initials: SH
authors.lastname: Chee
authors.forename: Deborah A
authors.initials: DA
authors.lastname: Knight
authors.forename: Hans
authors.initials: H
authors.lastname: Acha-Orbea
authors.forename: Ian F
authors.initials: IF
authors.lastname: Hermans
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
mesh_terms: D000818:Animals; D003619:Dansyl Compounds / Q000138:chemical synthesis*; D003713:Dendritic Cells / Q000187:drug effects / Q000378:metabolism; D005456:Fluorescent Dyes / Q000138:chemical synthesis; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology; D006017:Glycolipids / Q000378:metabolism; D051379:Mice; D055611:Natural Killer T-Cells / Q000187:drug effects / Q000378:metabolism
chemical_list: D003619:Dansyl Compounds; D005456:Fluorescent Dyes; D005699:Galactosylceramides; D006017:Glycolipids; C493154:alpha-galactosylceramide