Cytotoxic properties of iron-hydroxynaphthoquinone complexes in rat hepatocytes |
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| Authors: | Avinash Kumbhar Subhash Padhye David Ross |
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| Affiliation: | (1) Department of Chemistry, University of Pune, Pune, India;(2) School of Pharmacy, University of Colorado, Denver, CO, USA;(3) Department of Chemistry, University of Pune, 411007 Pune, India |
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| Abstract: | The mechanisms of toxicity to isolated rat hepatocytes of Fe(II) and Fe(III) complexes of two structurally related naphthoquinones have been studied. All complexes were found to show a dose-dependent toxicity which precedes cell death. Within the naphthoquinone series the order of toxicity is Fe(II) > parent naphthoquinone > Fe(III). The iron complexes of 5-OH-1,4 naphthoquinone (5-OH-1,4 NQ; Juglone) are more toxic than the iron complexes of 2-OH-1,4 naphthoquinone (2-OH-1,4 NQ; Lawsone) indicating that the mechanisms of toxicity are different. Electrochemical studies on these complexes shows that 5-OH-1,4 NQ facilitates formation of stable semiquinone species while 2-OH-1,4 NQ does not. The low redox potential of 2-OH-1,4 NQ makes it a poor substrate for metabolism by reductases. |
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| Keywords: | iron-naphthoquinone complexes cytotoxicity hepatocytes redox cycling glutathione cyclic voltammetry |
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