2-O-beta-d-glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation.
New sulfoquinovosyldiacylglycerols derived from 2-O-beta-d-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).
Dangate
Milind
M
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Italy.
Franchini
Laura
L
Ronchetti
Fiamma
F
Arai
Takanari
T
Iida
Akira
A
Tokuda
Harukuni
H
Colombo
Diego
D
D000956:Antigens, Viral / Q000187:drug effects*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology
D000956:Antigens, Viral; D000970:Antineoplastic Agents; C033305:Epstein-Barr virus early antigen; D006017:Glycolipids; C013694:sulfoquinovosyl diglyceride; D013755:Tetradecanoylphorbol Acetate