Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines

Koushik Saha, Kok Wai Lam, Faridah Abas, A. Sazali Hamzah, Johnson Stanslas, Lim Siang Hui, Nordin H. Lajis

Research output: Contribution to journalArticle

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Abstract

Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2-8 μM. Structure-activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.

Original languageEnglish
Pages (from-to)2093-2104
Number of pages12
JournalMedicinal Chemistry Research
Volume22
Issue number5
DOIs
Publication statusPublished - May 2013

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Anthraquinones
Cells
Cell Line
Assays
Antioxidants
Neoplasms
Structure-Activity Relationship
Cytotoxicity
Hydroxyl Radical
Inhibitory Concentration 50
damnacanthal
9,10-anthraquinone
nordamnacanthal

Keywords

  • Anthraquinones
  • Antioxidant activity
  • Cytotoxicity
  • Synthesis

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines. / Saha, Koushik; Lam, Kok Wai; Abas, Faridah; Sazali Hamzah, A.; Stanslas, Johnson; Hui, Lim Siang; Lajis, Nordin H.

In: Medicinal Chemistry Research, Vol. 22, No. 5, 05.2013, p. 2093-2104.

Research output: Contribution to journalArticle

Saha, Koushik ; Lam, Kok Wai ; Abas, Faridah ; Sazali Hamzah, A. ; Stanslas, Johnson ; Hui, Lim Siang ; Lajis, Nordin H. / Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines. In: Medicinal Chemistry Research. 2013 ; Vol. 22, No. 5. pp. 2093-2104.
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