The metal-mediated formation of hydroxyl radical by aqueous extracts of cigarette tar

Cosgrove, John P.; Borish, Edward T.; Church, Daniel F.; Pryor, William A.

doi:10.1016/0006-291x(85)91034-4

Cited by 104 publications

(51 citation statements)

References 15 publications

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“…[We had previously reported ESR spin trap spectra of the hydroxyl radical that is produced by these ACT solutions (18).] For DNA binding studie used RAM.…”

Section: Discussionmentioning

confidence: 99%

Aqueous extracts of cigarette tar containing the tar free radical cause DNA nicks in mammalian cells.

Stone

Bermúdez

Pryor

1994

Environ Health Perspect

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The ability of aqueous extracts of cigarette tar to nick DNA was investigated using viable mammalian cells. Tar extracts contain a radical with a stable electron spin resonance (ESR) signal at g = 2.0036 characteristic of a semiquinone. The association of the tar component that carries the ESR signal with DNA was demonstrated using viable rat alveolar macrophages. The formation of single-strand DNA breaks caused by cigarette tar extracts in viable rat thymocytes follows saturation kinetics, indicating a tar component associates with DNA and then nicks it. These studies support our hypothesis that tar components that contain the cigarette tar radical can enter cells, associate with, and then nick DNA. -Environ Health Perspect 102(Suppl 10): 173-178 (1994)

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“…[We had previously reported ESR spin trap spectra of the hydroxyl radical that is produced by these ACT solutions (18).] For DNA binding studie used RAM.…”

Section: Discussionmentioning

confidence: 99%

Aqueous extracts of cigarette tar containing the tar free radical cause DNA nicks in mammalian cells.

Stone

Bermúdez

Pryor

1994

Environ Health Perspect

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“…The cigarette tar semiquinone radical, as is typical of such radicals, can reduce oxygen to produce superoxide, and hence hydrogen peroxide and the hydroxyl radical. Unlike the tar radical itself, the superoxide and hydroxyl radicals are too reactive and short lived to be observable by direct ESR; but they can be detected by the use of spin trap 5, 5 -dimethyl-1 -pyrroline-N-oxide (DMPO) (78,86,87). Figure 3 Figure 2.…”

Section: Tar Radicalsmentioning

confidence: 99%

“…These ACT solutions can initiate lipid peroxidation, oxidize proteins such as the antiproteinase, a-l-protease inhibitor (88)(89)(90), and nick DNA (82,87). The quinone-hydroquinone-semiquinone system can penetrate viable mammalian cells, bind to, and nick cellular DNA (2,86,87,91,92). The nicks produced by the tar radical require multistep repair, suggesting a process that could be error prone (93).…”

Section: Tar Radicalsmentioning

confidence: 99%

Cigarette Smoke Radicals and the Role of Free Radicals in Chemical Carcinogenicity

Pryor¹

1997

Environmental Health Perspectives

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This article consists of two parts: a brief overview of the ways in which free radicals can be involved in chemical carcinogenesis, and a review of cigarette smoke chemistry. Carcinogenesis is generally agreed to involve at least three stages: initiation, promotion, and progression. It is suggested that radicals sometimes are involved in the initiation step, either in the oxidative activation of a procarcinogen (such as benzo[alpyrene) to its carcinogenic form or in the binding of the carcinogenic species to DNA, or both. The fraction of initiation events that involve radicals, as opposed to two-electron steps, is not known, but radicals probably are involved in a substantial number, although probably not a majority, of cancer initation reactions. Promotion always involves radicals, at least to some extent. Progression probably does not normally involve radicals. The second part of this article reviews the molecular mechanisms involved in cigarette-induced tumors, particularly by aqueous cigarette tar (ACT) extracts and by a model of these solutions, aged solutions of catechol. ACT solutions as well as aged solutions of catechol contain a quinone-hydroquinone-semiquinone system that can reduce oxygen to produce superoxide and hence hydrogen peroxide and the hydroxyl radical. Both the cigarette tar radical and the catecholderived radical can penetrate viable cells, bind to DNA, and cause nicks.Environ Health Perspect 1 05(Suppl 4): 875-882 (1997)

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“…4) It has been suggested that superoxide was generated by the reduction of oxygen by smoke components, possibly such phenolic components as hydroquinone and catechol. 8,17) In order to investigate the effect of oxygen on generating superoxide anion radicals from the extract, nitrogen gas was bubbled into the sample until conducting the analysis. The ESR signal was eliminated when nitrogen gas was bubbled into the sample (B in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…[8][9][10][11] Many types of DMPO adducts were detected in an earlier study on an aqueous extract of the particulate phase of cigarette smoke; 8) however, in the absence of EDTA, the intensity of the signals of DMPO-OH in the extract was only slightly different from the solution without the extract. Other reports have stated that the ESR signals of a DMPO adduct including DMPO-OOH were detected in the aqueous extract of particulate phase cigarette smoke and were eliminated by adding superoxide dismutase (SOD); 10) however, the extract would have been modified in the presence of DMSO with a high concentration (7 M).…”

mentioning

confidence: 99%

Evaluation of Superoxide Anion Radicals Generated from an Aqueous Extract of Particulate Phase Cigarette Smoke by Electron Spin Resonance Using 5,5-Dimethyl-1-pyrroline-N-oxide

Takanami

Nakayama

2011

Bioscience, Biotechnology, and Biochemistry

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The reactive oxygen species generated by an aqueous extract of the particulate phase of cigarette smoke were evaluated by an electron spin resonance (ESR) analysis, using spin-trapping agents, and by comparing with model reaction systems. The ESR signals of DMPO-OH were detected from the extract by using 5,5-dimethyl-1-pyrroline-N-oxide (DMPO). These signals were eliminated by adding superoxide dismutase, but hardly by catalase. These responses of the ESR signals to the scavengers were similar to those of a hypoxanthinexanthine oxidase system. The results indicate that the signals of DMPO-OH from the extract were derived from a reaction product of DMPO with superoxide anion radicals and clarify the mechanism by which the extract generated superoxide anion radicals.

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The metal-mediated formation of hydroxyl radical by aqueous extracts of cigarette tar

Cited by 104 publications

References 15 publications

Aqueous extracts of cigarette tar containing the tar free radical cause DNA nicks in mammalian cells.

Aqueous extracts of cigarette tar containing the tar free radical cause DNA nicks in mammalian cells.

Cigarette Smoke Radicals and the Role of Free Radicals in Chemical Carcinogenicity

Evaluation of Superoxide Anion Radicals Generated from an Aqueous Extract of Particulate Phase Cigarette Smoke by Electron Spin Resonance Using 5,5-Dimethyl-1-pyrroline-N-oxide

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