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

Bioorg Med Chem. 2003 Mar 20;11(6):909-12. doi: 10.1016/s0968-0896(02)00543-6.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

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