26 Citations (Scopus)

Abstract

The dibenzo[o]pyrenes (DB[a]Ps) are carcinogenic polycyclic aromatic hydrocarbons (PAH) found as environmental pollutants. DB[a,l]P is the most potent carcinogenic PAH ever tested. To investigate the bioactivation of DB[o]Ps by one-electron oxidation, oxidation of DB[a,e]P, DB[a,h]P, DB[a,i]P, DB[a,l]P, and anthanthrene with Mn(OAc)3 was conducted and compared to that of benzo[o]pyrene (B[a]P). All five DB[a]Ps produced monoacetoxy derivatives, and all of them except DB[a,l]P also produced diacetoxy derivatives. Kinetic studies of the formation of monoacetoxy and diacetoxy derivatives of DB[a]Ps were carried out, and the results were compared to those of the parent compound B[a]P. DB[a,l]P was similar to B[a]P. DB[a,e]P reacted inefficiently to form monoacetoxy and diacetoxy products. The other three DB[a]Ps resembled one another. These results provide preliminary essential information for studies of the bioactivation of the very potent carcinogen DB[a,l]P to form DNA adducts.

Original languageEnglish (US)
Pages (from-to)3309-3312
Number of pages4
JournalJournal of Organic Chemistry
Volume57
Issue number12
DOIs
StatePublished - Jun 1 1992

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Pyrenes
Acetates
Polycyclic Aromatic Hydrocarbons
Derivatives
Oxidation
Electrons
Environmental Pollutants
DNA Adducts
Carcinogens
Kinetics
dibenzo(a,e)pyrene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

One-Electron Oxidation of Dibenzo[a]pyrenes by Manganic Acetate. / Cremonesi, Paolo; Hietbrink, Bruce; Rogan, Eleanor G; Cavalieri, Ercole.

In: Journal of Organic Chemistry, Vol. 57, No. 12, 01.06.1992, p. 3309-3312.

Research output: Contribution to journalArticle

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