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

Hsu Shan Huanga, Hui F. Chiu, Jeng Fong Chiou, Pen Fong Yeh, Chi W. Tao, Wei R. Jeng

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)481-486
Number of pages6
JournalArchiv der Pharmazie
Volume335
Issue number10
DOIs
Publication statusPublished - Dec 2002

Fingerprint

Anthraquinones
Cytotoxicity
Lipid Peroxidation
Derivatives
Lipids
Acylation
Mitoxantrone
Tocopherols
Hep G2 Cells
Cell growth
Growth
Cell culture
Glioma
Hydroxyl Radical
Antineoplastic Agents
Ascorbic Acid
Oxidation-Reduction
Rats
Chlorides
Tumors

Keywords

  • Anthraquinone
  • Cytotoxicity
  • Human hepatoma G2 cells
  • Lipid peroxidation
  • Rat glioma C6 cells
  • XTT colormetric assay

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Synthesis of symmetrical 1,5-bisacyloxyanthraquinone derivatives and their dual activity of cytotoxicity and lipid peroxidation. / Huanga, Hsu Shan; Chiu, Hui F.; Chiou, Jeng Fong; Yeh, Pen Fong; Tao, Chi W.; Jeng, Wei R.

In: Archiv der Pharmazie, Vol. 335, No. 10, 12.2002, p. 481-486.

Research output: Contribution to journalArticle

Huanga, Hsu Shan ; Chiu, Hui F. ; Chiou, Jeng Fong ; Yeh, Pen Fong ; Tao, Chi W. ; Jeng, Wei R. / Synthesis of symmetrical 1,5-bisacyloxyanthraquinone derivatives and their dual activity of cytotoxicity and lipid peroxidation. In: Archiv der Pharmazie. 2002 ; Vol. 335, No. 10. pp. 481-486.
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