Comparison of glutathione reductase activity and the intracellular glutathione reducing effects of 13 derivatives of 1'-acetoxychavicol acetate in Ehrlich ascites tumor cells.

Abstract

In a previous study, we showed that (1'S)-acetoxychavicol acetate ((S)-ACA) caused a rapid decrease in glutathione (GSH) levels less than 15 min after exposure. (S)-ACA-induced cell death was reversed by the addition of N-acetylcysteine. In the current study, we investigated the inhibitory activities of 13 derivatives of (S)-ACA on tumor cell viability, intracellular GSH level and GR activity. Correlations were found among a decrease in cell viability, intracellular GSH levels and the activity of GR in Ehrlich ascites tumor cells treated with the various ACA analogues. A test of the 13 derivatives revealed that the structural factors regulating activity were as follows: (1) the para or 1'-position of acetoxyl group (or other acyl group) was essential, (2) the presence of a C2'-C3' double or triple bond was essential, and (3) the S configuration of the 1'-acetoxyl group was preferable.

• Authors: Shenghui Xu, Akiko Kojima-Yuasa, Hideki Azuma, David Opare Kennedy, Yotaro Konishi, Isao Matsui-Yuasa
• Journal: Chemico-biological interactions (Chem Biol Interact) Vol. 185 Issue 3 Pg. 235-40 (May 14 2010) ISSN: 1872-7786 [Electronic] Ireland
• PMID: 20230805 (Publication Type: Comparative Study, Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright 2010 Elsevier Ireland Ltd. All rights reserved.

Chemical References

• Benzyl Alcohols
• Glutathione Reductase
• Glutathione
• 1'-acetoxychavicol acetate

Topics

• Animals
• Benzyl Alcohols (chemistry, pharmacology)
• Carcinoma, Ehrlich Tumor (metabolism)
• Cell Survival (drug effects)
• Glutathione (metabolism)
• Glutathione Reductase (metabolism)
• Molecular Structure
• Structure-Activity Relationship