title: 2-O-beta-d-glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation.
abstract: 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).
authors.affiliation: Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Italy.
authors.forename: Milind
authors.initials: M
authors.lastname: Dangate
authors.forename: Laura
authors.initials: L
authors.lastname: Franchini
authors.forename: Fiamma
authors.initials: F
authors.lastname: Ronchetti
authors.forename: Takanari
authors.initials: T
authors.lastname: Arai
authors.forename: Akira
authors.initials: A
authors.lastname: Iida
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.forename: Diego
authors.initials: D
authors.lastname: Colombo
mesh_terms: 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
chemical_list: D000956:Antigens, Viral; D000970:Antineoplastic Agents; C033305:Epstein-Barr virus early antigen; D006017:Glycolipids; C013694:sulfoquinovosyl diglyceride; D013755:Tetradecanoylphorbol Acetate