Effects of 9,10-dihydroxy-4,4-dimethyl-5,8-dihydro-1(4H)-anthracenone derivatives on tumor cell respiration

Ramiro Araya-Maturana, Wilson Cardona, Bruce K. Cassels, Tomás Delgado-Castro, Jorge Ferreira, Dante Miranda, Mario Pavani, Hernán Pessoa-Mahana, Jorge Soto-Delgado, Boris Weiss-López

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)


A series of tricyclic hydroquinones, incorporating a carbonyl group in the ortho position relative to the phenol function, were tested as inhibitors of oxygen uptake against the TA3 mouse carcinoma cell line and its multidrug-resistant variant TA3-MTX-R. The title compound, which proved to be the most active one, also exhibited low micromolar dose-dependent growth inhibition of the human tumor U937 cell line (human monocytic leukemia). A tentative structure-activity relationship is proposed for these substances. A comparison between the cytotoxicities of the title compound and 4,4-dimethyl-5,8-dihydroxynaphthalene-1-one, with their activities as inhibitors of oxygen uptake by the TA3-MTX-R cell line, is presented. Also, the inhibition of oxygen uptake by 6-(4-methylpent-3-enyl)-1,4-naphthoquinone was determined and compared with its reported cytotoxicity toward P-388 (murine lymphocytic leukemia), A-549 (human lung carcinoma), HT-29 (human colon carcinoma), and MEL-28 (human melanoma) cells. The inhibition of oxygen uptake by TA3-MTX-R cells is useful as a quick test for preliminary screening of possible anticancer activity.

Original languageEnglish
Pages (from-to)4664-4669
Number of pages6
JournalBioorganic and Medicinal Chemistry
Issue number13
Publication statusPublished - 1 Jul 2006


  • Anticancer activity
  • Hydroquinones
  • Inhibitors of oxygen uptake
  • Quinones

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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