Synthesis of a resveratrol analogue with high ceramide-mediated proapoptotic activity on human breast cancer cells.

Abstract

Resveratrol, a natural product with a stilbene structure, exerts profound proapoptotic activity in human cancer cells, by triggering the accumulation of ceramide, a bioactive sphingolipid. We studied the biological effects of seven methoxylated and/or naphthalene-based resveratrol analogues and compared these compounds with resveratrol with the objective to identify an analogue with higher ceramide-mediated proapoptotic activity relative to resveratrol. Here we show that the compound with three hydroxyls and a naphthalene ring is the most effective in triggering apoptosis coupled to the induction of endogenous ceramide in human cancer cells.

• Authors: Filippo Minutolo, Giusy Sala, Annalisa Bagnacani, Simone Bertini, Isabella Carboni, Giorgio Placanica, Giovanni Prota, Simona Rapposelli, Nicoletta Sacchi, Marco Macchia, Riccardo Ghidoni
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 48 Issue 22 Pg. 6783-6 (Nov 03 2005) ISSN: 0022-2623 [Print] United States
• PMID: 16250636 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents
• Ceramides
• Stilbenes
• Resveratrol

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Apoptosis
• Breast Neoplasms
• Cell Line, Tumor
• Ceramides (biosynthesis)
• Drug Screening Assays, Antitumor
• Female
• Humans
• Resveratrol
• Stilbenes (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship