Synthesis of symmetrical 1,5-bisacyloxyanthraquinone derivatives and their dual activity of cytotoxicity and lipid peroxidation

Hsu Shan Huanga, Hui Fen Chiu, Jeng Fong Chiou, Pen Fong Yeh, Chi Wei Tao, Wei Ren Jeng

研究成果: 雜誌貢獻文章同行評審

17 引文 斯高帕斯(Scopus)

摘要

Symmetrical bis-substituted anthraquinones were successfully prepared and demonstrated potent cytotoxicity against the growth of suspended murine and human tumors, i.e. rat glioma C6 cells and human hepatoma G2 cells. We report here a convenient synthetic pathway that leads to symmetrically substituted 1,5-bisacyloxyanthraquinone derivatives. Acylation of the hydroxyl group of 1,5-dihydroxyanthraquinone with the appropriate acyl chlorides in the presence of pyridine or sodium hydride, respectively, furnished this structural class of anthraquinones. The bis(butyryloxy) analog 2 b, bis(2-chlorobenzoyl) analog 2 f, and bisphenylpropionyloxy analog 2 n exhibit potent cytotoxicity in inhibition of human hep G2 cell growth in culture, as determined by using XTT colorimetric assay, while their antiproliferative activity is markedly enhanced and is comparable to that of the anticancer agent mitoxantrone. In addition, redox properties of the compounds for the inhibition of lipid peroxidation in model membranes were determined. Compounds 2n also exhibited stronger antioxidant activity than ascorbic acid, (+)-α-tocopherol, and anthrarufin. Biological evaluation and SAR studies of these symmetrical anthraquinones have been performed and the results are discussed.

原文英語
頁(從 - 到)481-486
頁數6
期刊Archiv der Pharmazie
335
發行號10
DOIs
出版狀態已發佈 - 十二月 2002

ASJC Scopus subject areas

  • 藥學科學
  • 藥物發現

指紋

深入研究「Synthesis of symmetrical 1,5-bisacyloxyanthraquinone derivatives and their dual activity of cytotoxicity and lipid peroxidation」主題。共同形成了獨特的指紋。

引用此