Evaluation of the anti-inflammatory and cytotoxic effects of anthraquinones and anthracenes derivatives in human leucocytes

Rong Fu Chen, Yuh Chiang Shen, Hsu Shan Huang, Jyh Fei Liao, Li Kang Ho, Yueh Ching Chou, Wen Yen Wang, Chieh Fu Chen

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Abstract

A variety of anthracene- and anthraquinone-related derivatives, modified from three types of lead structures, including 9-acyloxy 1,5-dichloroanthracene (type I), 1,5-bisacyloxy-anthraquinones with O-linked substituents (type II) and 1,5-bisacyloxy-anthraquinones with S-linked substituents (type III), were synthesized and evaluated by an in-vitro bioassay for their anti-inflammatory and cytotoxic effects in human leucocytes. Among these derivatives, type I compounds displayed potent anti-inflammatory activity against phorbol-12-myristate-13-acetate (PMA)-induced superoxide anion production, a bio-marker of inflammatory mediator production by neutrophils, with 50% inhibition (IC50) concentrations (μM) for compounds 1f, 1g, 1h and 1m being 13.8 ± 3.0, 6.3 ± 4.1, 33.2 ± 1.3 and 33.9 ± 5.7, respectively. Type II and type III derivatives (i.e., 1,5-bisacyloxy anthraquinone-related compounds) and the reference compound, emodin, exhibited relatively minor (20-40%) inhibitory effect against superoxide production by neutrophils. Furthermore, none of these compounds showed a significant cytotoxic effect in human neutrophils. In conclusion, these results suggest that compounds modified from 9-acyloxy 1,5-dichloroanthracence (type I) are more powerful than the other two types as anti-inflammatory drugs. This is the first demonstration that derivatives modified from anthracenes or anthraquinones possess anti-inflammatory activity with no significant cytotoxicity in human neutrophils.

Original languageEnglish
Pages (from-to)915-919
Number of pages5
JournalJournal of Pharmacy and Pharmacology
Volume56
Issue number7
DOIs
Publication statusPublished - Jul 2004
Externally publishedYes

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ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

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