The ESR Properties, DNA Nicking, and DNA Association of Aged Solutions of Catechol Versus Aqueous Extracts of Tar from Cigarette Smoke

Stone, Koni; Bermúdez, Eliezer; Zang, Li Yun; Carter, K. M.; Queenan, K. E.; Pryor, William A.

doi:10.1006/abbi.1995.1282

Cited by 61 publications

(36 citation statements)

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“…These ACT solutions also interfere with mitochondrial electron transport (94 Field, gauss present in aged solutions of catechol (85,95,96). Figure 4 shows the similarity in the ESR spectra obtained for solutions of ACT and aged catechol (92). Thus, the tar radical is a low-molecular-weight semiquinone radical, which exists in equilibrium with its quinone and hydroquinone derivatives.…”

Section: Tar Radicalsmentioning

confidence: 89%

“…The electron spin resonance (ESR) spectra obtained when (A) a Cambridge filter is placed in the cavity of an ESR spectrometer after the smoke from a single cigarette has been pulled through the filter, and (B) an aged solution of catechol is filtered. Both spectra can be identified as being due to a semiquinone (78,92).…”

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%

“…Figure 6 shows the ESR spectra obtained when the DNA from rat alveolar macrophages that have been incubated either with ACT or aged catechol solutions are trapped and washed on polycarbonate filters (82 or of catechol used versus DNA nicks Deferoxamine provides little protection, ws saturation behavior, suggesting that suggesting that the iron required to convert re might be certain sites in the DNA hydrogen peroxide to the hydroxyl radical are particularly prone to bind the tar is tightly associated either with the ACT cal; once these sites are saturated, bind-radical or with DNA or both (82). decreases (78,82,92). Analyses of these Glutathione also protects significantly, as ding data using Lineweaver-Burke or shown in Figure 7.…”

Section: Tar Radicalsmentioning

confidence: 99%

“…Catalase, but not SOD, provides signifRanderath and associates (97)(98)(99)(100)(101)(102)(103)(104)(105)(106) and it protection against ACT-and aged others (107,108) have used the phosphoechol-induced DNA nicks (82 Figure 6. The electron spin resonance (ESR) spectra of the material obtained when the DNA from rat alveolar macrophages (RAM) that have been incubated either with (A) ACT or (B) aged catechol solutions and then isolated on polycarbonate filters (92). No ESR signal is obtained if the RAM are not exposed to ACT or catechol (C).…”

Section: Tar Radicalsmentioning

confidence: 99%

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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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Section: Tar Radicalsmentioning

confidence: 89%

Section: Tar Radicalsmentioning

confidence: 99%

Section: Tar Radicalsmentioning

confidence: 99%

Section: Tar Radicalsmentioning

confidence: 99%

Section: Tar Radicalsmentioning

confidence: 99%

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

Pryor¹

1997

Environmental Health Perspectives

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Comparative32P-postlabeling analysis of exogenous and endogenous DNA adducts in mouse skin exposed to a wood-preserving waste extract, a complex mixture of polycyclic and polychlorinated chemicals

Randerath

Zhou

Randerath

et al. 1997

Environ. Mol. Mutagen.

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The role of catechols and free radicals in benzene toxicity: An oxidative DNA damage pathway

Barreto

Madureira

Capani

et al. 2009

Environ and Mol Mutagen

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Benzene is a widespread volatile compound and an environmental contaminant. Since it causes important toxic effects in workers exposed to low levels, long-term exposure to this compound has been extensively studied. Leukemia, blood disorders, bone marrow depression, and some types of cancer are directly related to benzene-initiated toxicity. Bioactivation of benzene can lead to the formation of hazardous metabolites such as phenol, hydroquinone, and catechol. Catechol forms semiquinones and reactive quinones that are presumed to play an important role in the generation of reactive oxygen species (ROS). ROS formation can directly induce single and double strand breaks in the DNA, oxidized nucleotides, and hyper-recombination, and consequently produces deleterious genetic changes. In this review, we have addressed the cytotoxic effects of benzene and its main metabolite, catechol, focusing on the oxidative pathway and further DNA damage.

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The ESR Properties, DNA Nicking, and DNA Association of Aged Solutions of Catechol Versus Aqueous Extracts of Tar from Cigarette Smoke

Cited by 61 publications

References 0 publications

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

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

Comparative32P-postlabeling analysis of exogenous and endogenous DNA adducts in mouse skin exposed to a wood-preserving waste extract, a complex mixture of polycyclic and polychlorinated chemicals

The role of catechols and free radicals in benzene toxicity: An oxidative DNA damage pathway

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