Synthesis and evaluation of human T cell stimulating activity of an alpha-sulfatide analogue.
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.
Franchini
Laura
L
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133 Milano, Italy.
Matto
Pamela
P
Ronchetti
Fiamma
F
Panza
Luigi
L
Barbieri
Lucia
L
Costantino
Valeria
V
Mangoni
Alfonso
A
Cavallari
Marco
M
Mori
Lucia
L
De Libero
Gennaro
G
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
D018949:Antigens, CD1; D055610:Antigens, CD1d; C526877:CD1D protein, human; D005699:Galactosylceramides; D013433:Sulfoglycosphingolipids