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

D. E. Stack, P. Cremonesi, A. Hanson, Eleanor G Rogan, Ercole Cavalieri

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Abstract

1. Oxidation of benzo[α]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-ClBP.+ 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.

Original languageEnglish (US)
Pages (from-to)755-760
Number of pages6
JournalXenobiotica
Volume25
Issue number7
DOIs
StatePublished - Jan 1 1995

Fingerprint

Nucleophiles
Cations
Derivatives
DNA
Perchlorates
Quinones
Benzene
Complexation
Reaction products
Free Radicals
Salts
perchlorate
pyrene
Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Toxicology
  • Pharmacology
  • Health, Toxicology and Mutagenesis

Cite this

Radical cations of benzo[α]pyrene and 6-substituted derivatives : Reaction with nucleophiles and DNA. / Stack, D. E.; Cremonesi, P.; Hanson, A.; Rogan, Eleanor G; Cavalieri, Ercole.

In: Xenobiotica, Vol. 25, No. 7, 01.01.1995, p. 755-760.

Research output: Contribution to journalArticle

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abstract = "1. Oxidation of benzo[α]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-ClBP.+ 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.",
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N2 - 1. Oxidation of benzo[α]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-ClBP.+ 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.

AB - 1. Oxidation of benzo[α]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-ClBP.+ 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.

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