Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation

Hsu Shan Huang, Jeng Fong Chiou, Hui Fen Chiu, Jing Min Hwang, Pen Yuan Lin, Chi Wei Tao, Pen Fong Yeh, Wei Ren Jeng

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The synthesis of a series of anthraquinone moieties bearing symmetrical sulfur-linked substituents in the 1 and 5 positions is described. These compounds were evaluated for their ability to inhibit the growth of suspended rat glioma C6 cells and human hepatoma G2 cells, respectively. In addition, the redox property of the compounds was determined based on the inhibition of lipid peroxidation in model membranes. Compounds 2a and 2h in this series compared favorably and exhibited the most potent cytotoxicity (0.02, 0.05 μM) against C6 cells in the XTT colorimetric assay. As far as redox properties are concerned, all bis-thio-anthraquinones show potential lipid peroxidation in model membranes very close to that of mitoxantrone (MX), and 2a, 2d, 2e, 2i, 2j, and 2k have more potential than that of MX. The lack of cytotoxicity of compound 2i cannot be related to lipid peroxidation, but the steric and electronic properties of the side-chain substituent maybe impair effective recognition of the cleavable complex. In contrast to MX, 2a and 2h are cytotoxic in rat glioma C6 cells and do not enhance lipid peroxidation in model membranes.

Original languageEnglish
Pages (from-to)1491-1494
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume50
Issue number11
DOIs
Publication statusPublished - Nov 2002

Fingerprint

Cultured Tumor Cells
Anthraquinones
Cytotoxicity
Mitoxantrone
Lipid Peroxidation
Tumors
Cells
Lipids
Membranes
Glioma
Oxidation-Reduction
Rats
Bearings (structural)
Sulfur
Electronic properties
Hepatocellular Carcinoma
Assays
Growth

Keywords

  • Anthraquinone
  • Cytotoxicity
  • Human hepatoma G2 cell
  • Lipid peroxidation
  • Rat glioma C6 cell

ASJC Scopus subject areas

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

Cite this

Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation. / Huang, Hsu Shan; Chiou, Jeng Fong; Chiu, Hui Fen; Hwang, Jing Min; Lin, Pen Yuan; Tao, Chi Wei; Yeh, Pen Fong; Jeng, Wei Ren.

In: Chemical and Pharmaceutical Bulletin, Vol. 50, No. 11, 11.2002, p. 1491-1494.

Research output: Contribution to journalArticle

Huang, Hsu Shan ; Chiou, Jeng Fong ; Chiu, Hui Fen ; Hwang, Jing Min ; Lin, Pen Yuan ; Tao, Chi Wei ; Yeh, Pen Fong ; Jeng, Wei Ren. / Synthesis of symmetrical 1,5-bis-thio-substituted anthraquinones for cytotoxicity in cultured tumor cells and lipid peroxidation. In: Chemical and Pharmaceutical Bulletin. 2002 ; Vol. 50, No. 11. pp. 1491-1494.
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