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

Bioorganic & Medicinal Chemistry
Ramiro Araya-MaturanaBoris Weiss-López

Abstract

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.

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Citations

Dec 26, 2013·Bioorganic & Medicinal Chemistry·Diego A PedrozaShizue Mito
Oct 15, 2013·European Journal of Medicinal Chemistry·Mona A Abdel-Rahman, Ahmed M Al-Abd
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Oney Ramírez-RodríguezRamiro Araya-Maturana
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Andrés VegaRamiro Araya-Maturana
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Andrés VegaRamiro Araya-Maturana
Jul 6, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maximiliano Martínez-CifuentesRamiro Araya-Maturana
Jul 12, 2016·International Journal of Molecular Sciences·Maximiliano Martínez-CifuentesRamiro Araya-Maturana
Apr 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maximiliano Martínez-CifuentesRamiro Araya-Maturana
May 7, 2015·Chemical Communications : Chem Comm·Gleiston G DiasEufrânio N da Silva Júnior
Apr 1, 2011·Magnetic Resonance in Chemistry : MRC·Jose A DobadoRamiro Araya-Maturana
Apr 10, 2014·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Víctor Eduardo Bahamonde-PadillaBoris Enrique Weiss López
Dec 31, 2010·Rapid Communications in Mass Spectrometry : RCM·Iriux AlmodóvarRamiro Araya-Maturana

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