One electron transfer oxidation of 7,12-dimethylbenz[.alpha.]anthracene, a model for the metabolic activation of carcinogenic hydrocarbons

Fried, Josef; Schumm, Dorothy E.

doi:10.1021/ja00997a069

Cited by 47 publications

(18 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has been proposed by others that highly carcinogenic, methylated polycyclic hydrocarbons are metabolically activated by carbonium-ion formation on the methyl groups (39) or by mechanisms involving radical cations at methyl groups or other positions (40,41). Additional studies are required in order to clarify the generality of the epoxide mechanism of metabolic activation.…”

Section: Discussionmentioning

confidence: 99%

In Vitro Transformation of Rodent Cells by K-Region Derivatives of Polycyclic Hydrocarbons

Grover

Sims

Huberman

et al. 1971

Proc. Natl. Acad. Sci. U.S.A.

152

View full text Add to dashboard Cite

The K-region epoxides and cis-dihydrodiols derived from benz(a)anthracene and from dibenz(a,h)-anthracene have been found to be more active in the production of malignant transformation in hamster embryo cells than the hydrocarbons or the corresponding K-region phenols. The K-region epoxides derived from benz(a)-anthracene and from 3-methylcholanthrene were also active in transforming a clone of ventral prostate cells from the C3H mouse that was not readily transformed by the parent hydrocarbons. The phenols were the most toxic compounds tested but did not transform cells; this confirms that toxicity and transformation are not directly related events. The results obtained support the view that metabolism of polycyclic hydrocarbons precedes toxicity and transformation in rodent cells in culture.

show abstract

Section: Discussionmentioning

confidence: 99%

In Vitro Transformation of Rodent Cells by K-Region Derivatives of Polycyclic Hydrocarbons

Grover

Sims

Huberman

et al. 1971

Proc. Natl. Acad. Sci. U.S.A.

152

View full text Add to dashboard Cite

show abstract

“…A few of the most common representative PAH are presented in Figure 2. It is well known that PAH radical cations can be produced in chemical systems with Fe3' (35)(36)(37)(38) and iodine (35,37,(39)(40)(41)(42). Iron-containing enzymes with the metal in the higher oxidative forms (Fe3+ to Fe5") are possible oxidants in biological systems.…”

Section: Chemical Properties Of Pah Radical Cationsmentioning

confidence: 99%

Role of Radical Cations in Aromatic Hydrocarbon Carcinogenesis

Cavalieri¹,

Rogan²

1985

Environmental Health Perspectives

View full text Add to dashboard Cite

Carcinogenic activation of polycyclic aromatic hydrocarbons (PAH) involves two main pathways: oneelectron oxidation and monooxygenation. One-electron oxidation produces PAH radical cations, which can react with cellular nucleophiles. Results from biochemical and biological experiments indicate that only PAH with ionization potentials below ca. 7.35 eV can be metabolically activated by one-electron oxidation. In addition, the radical cations of carcinogenic PAH must have relatively high charge localization to react effectively with macromolecules in target cells. Metabolic formation of PAH quinones proceeds through radical cation intermediates. Binding of benzo[a]pyrene (BP) to mouse skin DNA occurs predominantly at C-6, the position of highest charge localization in the BP radical cation, and binding of 6-methylBP to DNA in mouse skin yields a major adduct with the 6-methyl group bound to the 2-amino group of deoxyguanosine. Studies of carcinogenicity by direct application of PAH to rat mammary gland indicate that only PAH with ionization potentials low enough for activation by one-electron oxidation produce tumors in this target tissue. These constitute some of the results which provide evidence for the involvement of one-electron oxidation in PAH carcinogenesis.

show abstract

“…(14) and Fried and Schumm (15). Since these first reports, much circumstantial evidence has been presented for the biological involvement of BaP cation radicals.…”

Section: Evidence For Biological Involvement Of Bap Radicals Bap Catimentioning

confidence: 99%

“…potential that it can be oxidized chemically by weak oxidants such as I2 or FeC13 to give radical species which can be observed by EPR or trapped by various nucleophiles (10,(16)(17)(18). Since I2 and other Fe(III) compounds have been shown to oxidize other polycyclic hydrocarbons to their respective cation radicals (19)(20) it is hypothesized that, in vivo, BaP could be oxidized by a one-electron transfer to cytochrome-P-450 [Eq.…”

Section: Evidence For Biological Involvement Of Bap Radicals Bap Catimentioning

confidence: 99%

Free Radicals of Benzo(a)pyrene and Derivatives

Sullivan¹

1985

Environmental Health Perspectives

View full text Add to dashboard Cite

show abstract

One electron transfer oxidation of 7,12-dimethylbenz[.alpha.]anthracene, a model for the metabolic activation of carcinogenic hydrocarbons

Cited by 47 publications

References 0 publications

In Vitro Transformation of Rodent Cells by K-Region Derivatives of Polycyclic Hydrocarbons

In Vitro Transformation of Rodent Cells by K-Region Derivatives of Polycyclic Hydrocarbons

Role of Radical Cations in Aromatic Hydrocarbon Carcinogenesis

Free Radicals of Benzo(a)pyrene and Derivatives

Contact Info

Product

Resources

About