title: Cytotoxic properties of iron-hydroxynaphthoquinone complexes in rat hepatocytes.
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.
authors.affiliation: Department of Chemistry, University of Pune, India.
authors.forename: A
authors.initials: A
authors.lastname: Kumbhar
authors.forename: S
authors.initials: S
authors.lastname: Padhye
authors.forename: D
authors.initials: D
authors.lastname: Ross
mesh_terms: D000818:Animals; D002470:Cell Survival / Q000187:drug effects; D004563:Electrochemistry; D005978:Glutathione / Q000378:metabolism; D066298:In Vitro Techniques; D007501:Iron / Q000737:chemistry / Q000633:toxicity*; D008099:Liver / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D008297:Male; D009285:Naphthoquinones / Q000737:chemistry / Q000633:toxicity*; D051381:Rats; D017207:Rats, Sprague-Dawley
chemical_list: D009285:Naphthoquinones; D007501:Iron; D005978:Glutathione