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

Article abstract of DOI:10.3109/00498259509061890

1. Oxidation of benzo[a]pyrene (BP) by I₂ in the presence of AgClO₄ in benzene generates the BP^.+ ClO₄^- · AgI complex. This same method was used to produce radical cations from 6-FBP, 6-ClBP, 6-BrBP and 6-CH₃BP. 2. Reaction of the BP,6-FBP,6-ClBP and 6-BrBP radical cation perchlorates with H₂O produced BP 1,6-, 3,6- and 6,12- dione, whereas 6-CH₃BP^.+ClO₄^- · AgI yielded 6-CH₂OHBP. 3. When BP^.+ClO₄^- · AgI and 6-FBP^.+ClO₄^- · AgI were reacted with NaOAc in H₂O/CH₃CN (9:1), 6-OAcBP was formed, in addition to the quinones. In the case of 6-CIBP^.+ClO₄^- · AgI, a small amount of 1-OAc-6-ClBP and 3-OAc-6-ClBP was formed in, addition to the diones, whereas for 6-BrBP and 6-CH₃BP the reaction products were BP diones and 6-CH₂OHBP respectively. 4. These results confirm the localization of charge in the BP^.+ at C-6, followed by C-1 and C-3. 5. The reaction of BP with NOBF₄ in CH₂Cl₂ produced BP^.+ BF₄^-, radical cation free of complexation with inorganic salts. 6. Reaction of BP^.+BF₄^- with DNA produced the depurinating adducts BP-6-C8Gua, BP-6-C8dGua and BP-6-N7Gua.

Full text of DOI:10.3109/00498259509061890

Xenobiotica
the fate of foreign compounds in biological systems
ISSN: 0049-8254 (Print) 1366-5928 (Online) Journal homepage: http://www.tandfonline.com/loi/ixen20
Radical cations of benzo[α]pyrene and 6-
substituted derivatives: reaction with nucleophiles
and DNA
D. E. Stack, P. Cremonesi, A. Hanson, E. G. Rogan & E. L. Cavalieri
To cite this article: D. E. Stack, P. Cremonesi, A. Hanson, E. G. Rogan & E. L. Cavalieri (1995)
Radical cations of benzo[α]pyrene and 6-substituted derivatives: reaction with nucleophiles
and DNA, Xenobiotica, 25:7, 755-760
To link to this article: http://dx.doi.org/10.3109/00498259509061890
Published online: 27 Aug 2009.
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Date: 06 November 2015, At: 04:48