Synthesis and anti-tumor-promoting activity of glycoglycerolipid analogues lacking the glycerol backbone.

Abstract

Glycoglycerolipid analogues lacking the glycerol backbone were prepared through a lipase catalyzed transesterification of beta-D-galactosylethylene glycol. The inhibitory effect of the resultant isomeric hexanoates at the primary alcoholic positions, beta-D-galactosylethylene glycol itself and nonyl beta-D-galactopyranoside, was tested on Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), as a primary screening test for inhibitors of tumor promotion. All the compounds assayed were found to be less active than the reference 2-O-beta-D-galactopyranosylglycerol derivatives, of which they are simplified models, indicating that the anti-tumor-promoting activity is very closely related to the presence of a free hydroxymethylene group on the glycerol-like aglycone moiety.

• Authors: Diego Colombo, Fiamma Ronchetti, Antonio Scala, Lucio Toma, Harukuni Tokuda, Hoyoku Nishino
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 11 Issue 6 Pg. 909-12 (Mar 20 2003) ISSN: 0968-0896 [Print] England
• PMID: 12614876 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anticarcinogenic Agents
• Antigens, Viral
• Carcinogens
• Epstein-Barr virus early antigen
• Glycolipids
• glycerolglycolipids
• Lipase
• Tetradecanoylphorbol Acetate
• Glycerol

Topics

• Anticarcinogenic Agents (chemical synthesis, pharmacology)
• Antigens, Viral (metabolism)
• Candida (metabolism)
• Carcinogens (antagonists & inhibitors, toxicity)
• Drug Screening Assays, Antitumor
• Glycerol (chemistry)
• Glycolipids (chemical synthesis, chemistry, pharmacology)
• Humans
• Lipase (metabolism)
• Pseudomonas (enzymology)
• Tetradecanoylphorbol Acetate (antagonists & inhibitors, toxicity)