Involvement of superoxide in the interaction of 2,3-dichloro-1,4-naphthoquinone with mitochondrial membranes

Pritsos, Chris A.; Jensen, David E.; Pisani, David E.; Pardini, Ronald S.

doi:10.1016/0003-9861(82)90483-0

Cited by 35 publications

(3 citation statements)

References 25 publications

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“…The cytotoxic potencies of 5,8-dihydroxy-l,4-NQ (Ollinger and Brunmark 1991) and dichlone (Pritsos et al 1982) have been associated with the induction of reactive oxygen intermediates. Thus, enhancement of the potencies of these two NQs with BSO pretreatment and the lack of potentiation by pretreatment with dicoumarol, coupled with the lowering of intracellular glutathione when the BF-2 and HepG2 cells were exposed to these two NQs, are consistent with the one-electron reduction reaction as the dominant pathway.…”

Section: Discussionmentioning

confidence: 98%

Naphthoquinone cytotoxicity to bluegill sunfish BF-2 cells

Babich

Palace

Borenfreund

et al. 1994

Arch. Environ. Contam. Toxicol.

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Bluegill sunfish BF-2 fibroblasts were used to evaluate the in vitro cytotoxicities of 1,4-naphthoquinone (NQ), 5,8-dihydroxy-1,4-NQ, and 2,3-dichloro-1, 4-NQ (dichlone); comparisons were made with previously obtained data on the response of human hepatoma HepG2 cells. For both cell types, the sequence of potency was 5,8-dihydroxy-1,4-NQ > 1,4-NQ > dichlone. Dichlone, and, although to a lesser extent, 1,4-NQ and 5,8-dihydroxy-1-4-NQ, induced endoreduplication in the BF-2 cells; for the HepG2 cells, endoreduplication was induced only with dichlone. Exposures to the three NQs reduced intracellular glutathione levels in both cell types. For the BF-2 and HepG2 cells, pretreatments with buthionine sulfoximine (BSO), a glutathione-depleting agent, potentiated the cytotoxicity of 5,8-hydroxy-1,4-NQ and dichlone; pretreatment with dicoumarol, an inhibitor of DT-diaphorase, had no effect on toxicity of these two NQs. Apparently, for these two quinones the predominant metabolic pathway in both the BF-2 and HepG2 cells involved redox cycling via a one-electron reduction reaction, generating reactive oxygen intermediates that consumed intracellular glutathione. Pretreatment of the BF-2 cells with BSO, but not with dicoumarol, potentiated the toxicity of 1,4-NQ, again indicating that metabolism occurred via one electron reduction. However, for the HepG2 cells, pretreatment with dicoumarol, but not with BSO, potentiated the cytotoxicity of 1,4-NQ. Apparently, in the HepG2, as compared to the BF-2, cells, 1,4-NQ was metabolized by DT-diaphorase in a reaction involving a two electron reduction.

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Section: Discussionmentioning

confidence: 98%

Naphthoquinone cytotoxicity to bluegill sunfish BF-2 cells

Babich

Palace

Borenfreund

et al. 1994

Arch. Environ. Contam. Toxicol.

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“…NADH oxidation in respiratory electron transport chain is also one of the superoxide-anion-generating systems (Nohl 1986). The production of superoxide anion coupled with NADH oxidation can be stimulated by some organic xenobiotics such as quinones (Pritsos et al 1982), flavonoids (Hodnick et al 1994), and nitroaromatic compounds (Martinez et al 1995). Fusarubin stimulated O 2 -generation in bacterial membrane when NADH was used as an electron donor.…”

Section: Discussionmentioning

confidence: 99%

Respiratory stimulation and generation of superoxide radicals in Pseudomonas aeruginosa by fungal naphthoquinones

Haraguchi

Yokoyama

Oike

et al. 1997

Archives of Microbiology

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The mechanism of action of antimicrobial naphthoquinones from the fungus Fusarium was studied by using Pseudomonas aeruginosa. Bostricoidin, methyl ether fusarubin, and fusarubin stimulated the oxygen consumption of bacterial cells and induced cyanide-insensitive oxygen consumption. These activities of the tested compounds were also observed in bacterial membrane preparations in a dose-dependent manner. Naphthoquinones stimulated the generation of superoxide anion and hydrogen peroxide. The naphthoquinone effectively acted as the electron acceptors for bacterial diaphorase, which could explain the antibacterial activity of Fusarium naphthoquinones since electron acceptors lead to the stimulation of respiratory activity and the generation of oxygen radical species.

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“…Redox cycling with concomitant production of highly reactive oxygen and semiquinone radicals has been associated with inhibition of mitochondrial respiration by other natural products (Hodnick et al, 1986) and quinones (Pritsos et al, 1982). Therefore, the ability of hypericin to redox cycle with the mitochondrial electron transport chain was investigated to test the hypothesis that oxygen or semiquinone radicals were generated to inactivate succinoxidase in the dark.…”

Section: Inhibition Of Mitochondrial Succinoxidasementioning

confidence: 99%

Photoactivation of Hypericin Generates Singlet Oxygen in Mitochondria and Inhibits Succinoxidase

Thomas

MacGill

Miller

et al. 1992

Photochem & Photobiology

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154

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Photosensitized inhibition of mitochondrial succinoxidase by hypericin was measured in vitro and found to be drug-dose, light-dose, and wavelength dependent. Singlet oxygen generation, monitored using the singlet oxygen trap tetramethylethylene, and oxygen consumption in isolated mitochondria sensitized by hypericin were also light-dose and wavelength dependent. Unequivocal evidence for the generation of singlet oxygen was obtained using kinetic isotope ratios of products from the reaction between singlet oxygen and geminally deuterated tetramethylethylene. An action spectrum for the inhibition of succinoxidase was measured at wavelengths between 400 and 700 nm and found to parallel the recorded visible absorption spectrum of hypericin in isolated mitochondria. The greatest singlet oxygen generation, oxygen consumption, and succinoxidase inhibition occurred with white light or 600 nm irradiation. These data are consistent with a type II singlet-oxygen-mediated mechanism for hypericin induced photosensitized inhibition of mitochondrial succinoxidase.

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Involvement of superoxide in the interaction of 2,3-dichloro-1,4-naphthoquinone with mitochondrial membranes

Cited by 35 publications

References 25 publications

Naphthoquinone cytotoxicity to bluegill sunfish BF-2 cells

Naphthoquinone cytotoxicity to bluegill sunfish BF-2 cells

Respiratory stimulation and generation of superoxide radicals in Pseudomonas aeruginosa by fungal naphthoquinones

Photoactivation of Hypericin Generates Singlet Oxygen in Mitochondria and Inhibits Succinoxidase

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