title: Synthesis and evaluation of human T cell stimulating activity of an alpha-sulfatide analogue.
abstract: A concise synthesis of alpha-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the alpha-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated beta-GalCer (sulfatide) and alpha-GalCer, which activate specific T cells. alpha-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than alpha-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.
authors.affiliation: Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133 Milano, Italy.
authors.forename: Laura
authors.initials: L
authors.lastname: Franchini
authors.forename: Pamela
authors.initials: P
authors.lastname: Matto
authors.forename: Fiamma
authors.initials: F
authors.lastname: Ronchetti
authors.forename: Luigi
authors.initials: L
authors.lastname: Panza
authors.forename: Lucia
authors.initials: L
authors.lastname: Barbieri
authors.forename: Valeria
authors.initials: V
authors.lastname: Costantino
authors.forename: Alfonso
authors.initials: A
authors.lastname: Mangoni
authors.forename: Marco
authors.initials: M
authors.lastname: Cavallari
authors.forename: Lucia
authors.initials: L
authors.lastname: Mori
authors.forename: Gennaro
authors.initials: G
authors.lastname: De Libero
mesh_terms: D018949:Antigens, CD1 / Q000378:metabolism; D055610:Antigens, CD1d; D002460:Cell Line; D005699:Galactosylceramides / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D013433:Sulfoglycosphingolipids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013601:T-Lymphocytes / Q000187:drug effects* / Q000378:metabolism
chemical_list: D018949:Antigens, CD1; D055610:Antigens, CD1d; C526877:CD1D protein, human; D005699:Galactosylceramides; D013433:Sulfoglycosphingolipids