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).
2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation / M. Dangate, L. Franchini, F. Ronchetti, T. Arai, A. Iida, H. Tokuda, D. Colombo. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 17:16(2009 Aug 15), pp. 5968-5973.
|Titolo:||2-O-β-d-Glucopyranosyl-sn-glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation|
DANGATE, MILIND SHRINIVAS (Primo)
FRANCHINI, LAURA (Secondo)
COLOMBO, DIEGO RODOLFO (Ultimo)
|Parole Chiave:||Cancer chemoprevention; EBV-EA; Glycoglycerolipids; Sulfo-glycolipids|
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||15-ago-2009|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/j.bmc.2009.06.064|
|Appare nelle tipologie:||01 - Articolo su periodico|