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2- O -β- d -Glucopyranosyl- sn -glycerol based analogues of sulfoquinovosyldiacylglycerols (SQDG) and their role in inhibiting Epstein-Barr virus early antigen activation

Bioorganic & Medicinal Chemistry, ISSN: 0968-0896, Vol: 17, Issue: 16, Page: 5968-5973
2009
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Article Description

New sulfoquinovosyldiacylglycerols derived from 2- O -β- 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).

Bibliographic Details

Dangate, Milind; Franchini, Laura; Ronchetti, Fiamma; Arai, Takanari; Iida, Akira; Tokuda, Harukuni; Colombo, Diego

Elsevier BV

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry

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