9,10-Phenanthraquinone in diesel exhaust particles downregulates Cu,Zn–SOD and HO-1 in human pulmonary epithelial cells: Intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis

Sugimoto, Rika; Kumagai, Yoshito; Nakai, Yoshinobu; Ishii, Tetsuro

doi:10.1016/j.freeradbiomed.2004.11.003

Cited by 73 publications

(33 citation statements)

References 39 publications

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“…Some drugs have quinone structures, such as daunorubicin and doxorubicin, which are used as anti-tumor drugs [5]. Moreover, quinones existed in environment, including 9,10-phenanthrenequinone, have become the focus of attention owing to their potential harmful effects on human health [6][7][8]. It is reported that quinones serves as a potent inhibitor of some biological functions such as nitric oxide synthase activity [9] and progesterone secretion [10].…”

Section: Introductionmentioning

confidence: 99%

Chemiluminescence assay for quinones based on generation of reactive oxygen species through the redox cycle of quinone

et al. 2008

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A sensitive and selective chemiluminescence assay for the determination of quinones was developed. The method was based on generation of reactive oxygen species through the redox reaction between quinone and dithiothreitol as reductant, and then the generated reactive oxygen was detected by luminol chemiluminescence. The chemiluminescence was intense, long-lived and proportional to quinone concentration. It is concluded that superoxide anion was involved in the proposed chemiluminescence reaction because the chemiluminescence intensity was decreased only in the presence of superoxide dismutase. Among the tested quinones, the chemiluminescence was observed from 9,10-phenanthrenequinone, 1,2-naphthoquinone and 1,4-naphthoquinone, whereas it was not observed from 9,10-anthraquinone and 1,4-benzoquinone. The chemiluminescence property was greatly different according to the structure of quinones.The chemiluminescence was also observed for biologically important quinones such as ubiquinone. Therefore, simple and rapid assay for ubiquinone in pharmaceutical preparation was developed based on the proposed chemiluminescence reaction. The detection limit (blank + 3SD) of ubiquinone was 0.05 µM (9 ng/assay) with an analysis time of 30 seconds per sample. The developed assay allowed the direct determination of ubiquinone in pharmaceutical preparation without any purification procedure.

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Section: Introductionmentioning

confidence: 99%

Chemiluminescence assay for quinones based on generation of reactive oxygen species through the redox cycle of quinone

et al. 2008

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“…9,10-Phenanthroquinone, a major quinone contained in atmospheric particulates, generates ROS through redox cycling that causes iron-mediated oxidative damage (Sugimoto et al 2005) . Analysis showed that the quinone-enriched fraction from particulates is more potent than the PAH fraction as regards generation of ROS and induction of apoptosis (Xia et al 2004) .…”

Section: Particulatesmentioning

confidence: 99%

Pulmonary Toxicity and Environmental Contamination: Radicals, Electron Transfer, and Protection by Antioxidants

Kovacic

Somanathan

2009

Reviews of Environmental Contamination and Toxicology Vol 201

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The atmosphere is replete with a mixture of toxic substances, both natural and man-made. Inhalation of toxic substances produces a variety of insults to the pulmonary system. Lung poisons include industrial materials, particulates from mining and combustion, agricultural chemicals, cigarette smoke, ozone, and nitrogen oxides, among a large number of other chemicals and environmental contaminants. Many proposals have been advanced to explain the mode of action of pulmonary toxicants. In this review we focus on mechanisms of pulmonary toxicity that involve ET, ROS, and OS. The vast majority of toxicants or their metabolites possess chemical ET functionalities that can undergo redox cycling. Such recycling may generate ROS that can injure various cellular constituents in the lung and in other tissues. ET agents include quinones, metal complexes, aromatic nitro compounds, and conjugated iminium ions. Often, these agents are formed metabolically from parent toxicants. Such metabolic reactions are often catalytic and require only small amounts of the offending material. Oxidative attack is commonly associated with lipid peroxidation and oxidation of DNA, and it may result in strand cleavage and 8-OH-DG production. Toxicity is often accompanied by depletion of natural AOs, which further exacerbates the toxic effect. It is not surprising that the use of AOs, both natural in fruits and vegetables, as well as synthetic, may provide protection from the adverse effects of toxicant exposure. The mechanistic framework described earlier is also applicable to some of the more prominent pulmonary illnesses, such as asthma, COPD, and cancer.

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“…11) In reductive activation of 9,10-PQ to generate ROS, there are two reduced 9,10-PQ species of biological importance, its semiquinone radical (9,10-PQ ·− ) and its hydroquinone (9,10-dihydroxyphenanthrene, 9,10-PQH 2 ). Although detoxification of quinones is generally thought to be two-electron reduction forming hydroquinones, we found that 9,10-PQ form disproportionately with 9,10-PQH 2 formed by aldo-keto reductase (AKR) isozymes, producing 9,10-PQ ·− which reacts easily with molecular oxygen to yield superoxide.…”

Section: Biotransformation Associated With the Initiation And Terminamentioning

confidence: 99%

Polycyclic Aromatic Hydrocarbon Quinones as Redox and Electrophilic Chemicals Contaminated in the Atmosphere

Kumagai

2009

JOURNAL OF HEALTH SCIENCE

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Polycyclic aromatic hydrocarbon quinones (PAHQs) produced by combustion of gasoline exhibit two chemical characteristics; one is their electron transfer abilitiy, transferring electrons from reducing agents to molecular oxygen to generate reactive oxygen species (ROS) associated with oxidative stress and the other is their ability to arylate cellular proteins, resulting in the disruption of signal transduction pathways. This review summarizes toxicological and pharmacological significances of such envirnmental chemicals through redox cycling and covalent modification.

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9,10-Phenanthraquinone in diesel exhaust particles downregulates Cu,Zn–SOD and HO-1 in human pulmonary epithelial cells: Intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis

Cited by 73 publications

References 39 publications

Chemiluminescence assay for quinones based on generation of reactive oxygen species through the redox cycle of quinone

Chemiluminescence assay for quinones based on generation of reactive oxygen species through the redox cycle of quinone

Pulmonary Toxicity and Environmental Contamination: Radicals, Electron Transfer, and Protection by Antioxidants

Polycyclic Aromatic Hydrocarbon Quinones as Redox and Electrophilic Chemicals Contaminated in the Atmosphere

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