Advanced search
Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 25, 1995 - Issue 7
Submit an article Journal homepage
17
Views
9
CrossRef citations to date
0
Altmetric
Original Article

Radical cations of benzo[α]pyrene and 6-substituted derivatives: reaction with nucleophiles and DNA

D. E. Stack Eppley Institute for Research in Cancer, University of Nebraska Medical Center, 600 South 42nd Street, Omaha, NE, 68198-6805, USA
,
P. Cremonesi Eppley Institute for Research in Cancer, University of Nebraska Medical Center, 600 South 42nd Street, Omaha, NE, 68198-6805, USA
,
A. Hanson Eppley Institute for Research in Cancer, University of Nebraska Medical Center, 600 South 42nd Street, Omaha, NE, 68198-6805, USA
,
E. G. Rogan Eppley Institute for Research in Cancer, University of Nebraska Medical Center, 600 South 42nd Street, Omaha, NE, 68198-6805, USA
&
E. L. Cavalieri Eppley Institute for Research in Cancer, University of Nebraska Medical Center, 600 South 42nd Street, Omaha, NE, 68198-6805, USA
Pages 755-760 | Received 12 Nov 1994, Published online: 27 Aug 2009

References

  • Cavalieri E. L., Devanesan P., Rogan E. Radical cations in the horseradish peroxidase and prostaglandin H synthase mediated metabolism and binding of benzo[α]pyrene to DNA. Biochemical Pharmacology 1988a; 37: 2183–2188
  • Cavalieri E. L., Rogan E. G. One-electron and two-electron oxidation in aromatic hydrocarbon carcinogens. Free Radicals in Biology, W. A. Pryor. Academic, New York 1984; Vol. VI: 323–369
  • Cavalieri E. L., Rogan E. G. The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation. Pharmacology and Therapeutics 1992; 55: 183–199
  • Cavalieri E. L., Rogan E. G., Cremonesi P., Devanesan P. D. Radical cations as precursors in the metabolic formation of quinones from benzo[α] pyrene and 6-fluorobenzo [α]pyrene. Fluoro substitution as a probe for one-electron oxidation in aromatic substrates. Biochemical Pharmacology 1988b; 37: 2173–2182
  • Cavalieri E. L., Rogan E. G., Devanesan P. D., Cremonesi P., Cerny R. L., Gross M. L., Bodell W. J. Binding of benzo[α] pyrene to DNA by cytochrome P-450-catalyzed one-electron oxidation in rat liver microsomes and nuclei. Biochemistry 1990; 29: 4820–4827
  • Cremonesi P., Cavalieri E., Rogan E. One-electron oxidation of 6-substituted benzo[α]pyrenes by manganic acetate. A model for metabolic activation. Journal of Organic Chemistry 1989; 54: 3561–3570
  • Cremonesi P., Stack D. E., Rogan E. G., Cavalieri E. L. Radical cations of benzo[α]pyrene and 6-substituted derivatives: synthesis and reaction with nucleophiles. Journal of Organic Chemistry 1994; 59: 7683–7687
  • Devanesan P. D., Rama Krishna N. V. S., Todorovic R., Rogan E. G., Cavalieri E. L., Jeong H., Jankowiak R., Small G. J. Identification and quantitation of benzo[α]pyrene-DNA adducts formed by rat liver microsomes in vitro. Chemical Research in Toxicology 1992; 5: 302–309
  • Jeftic L., Adams R. N. Electrochemical oxidation pathways of benzo[α]pyrene. Journal of the American Chemical Society 1970; 92: 1332–1337
  • Murata Y., Shine H. S. Ion radicals XVIII. Reactions of thianthenium perchlorate and thianthienium trichlorodiiodide. Journal of Organic Chemistry 1969; 34: 3368–3372
  • Rama Krishna N. V. S., Gao F., Padmavathi N. S., Cavalieri E. L., Rogan E. G., Cerny R. L., Gross M. L. Model adducts of benzo[α]pyrene and nucleosides formed from its radical cation and diol epoxide. Chemical Research in Toxicology 1992; 5: 293–302
  • Ristagno C. V., Shine H. J. Ion Radicals, XXIII. Some reactions of the perylene cation radical. Journal of Organic Chemistry 1971; 36: 4050–4055
  • Rogan E. G., Cavalieri E. L., Tibbels S. R., Cremonesi P., Warner C. D., Nagel D. L., Tomer K. B., Cerny R. L., Gross M. L. Synthesis and identification of benzo[α]pyrene-guanine nucleoside adducts formed by electrochemical oxidation and by horseradish peroxidase catalyzed reaction of benzo[α]pyrene with DNA. Journal of the American Chemical Society 1988; 110: 4023–4029
  • Rogan E., Katomski P. A., Roth R., Cavalieri E. Horseradish peroxidase/hydrogen peroxide-catalyzed binding of polycyclic aromatic hydrocarbons to DNA. Journal of Biological Chemistry 1979; 254: 7055–7059
  • Sullivan P. D., Bannoura F., Daub G. J. 13C and 1H analysis of the benzo[α]pyrene cation radical. Journal of the American Chemical Society 1985; 107: 32–35

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.