21247-98-3Relevant articles and documents
Radical cations of benzo[a]pyrene and 6-substituted derivatives: Reaction with nucleophiles and DNA
Stack,Cremonesi,Hanson,Rogan,Cavalieri
, p. 755 - 760 (2007/10/03)
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.
Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures
Glatt, Hansruedi,Pauly, Karin,Piee-Staffa, Andrea,Seidel, Albrecht,Hornhardt, Sabine,Czich, Andreas
, p. 13 - 22 (2007/10/03)
various environmental chemical are metabolised to chemically reactive sulfuric acid esters, which may covalently bind to cellular macromoleculaes and induce mutations and tumours. This activation pathway is usually not taken into account in external xenobiotic-metabolising systems used in short-term tests. We therefore analysed the abilities of cytosols from mammalian cell lines to activate benzylic alcohols (1-hydroxymethylpyrene and 9-hydroxymethylanthracene) to mutagens detectable in Salmonella typhimurium TA98. No activation was observed in cell lines which are commonly used in mutagenicity and cell transformation assays, and only low activities were found in epithelial cell lines in culture. We have therefore constructed Chineses hamster V79-derived cell lines which stably express a heterologous sulfotransferase, rat hydroxysteroid sulfotransferase a. Cytosol of these cells effectively activated 1-hydroxymethylpyrene and 9-hydroxymethylanthracene to mutagens detected in S. pyphimurium. The hepatocarcinogen 6-hydroxymethylbenzopyrene induced gene mutations in sulfotransferase-expressing V79-derived cells, whereas it elicited only marginal effects in sulfotransferase-deficient control cells. The new cell lines may allow the detection of novel classes of mutagens, since some externally generated reactive sulfuric acid esters may not readily penetrate target cells due to their short life span and their ionization. - Keywords: Benzylic alcohols; Bioactivation; Sulfotransferase; Sulfuric acid esters; V79 cells
EPR and ENDOR Studies of 6-Substituted Benzopyrene Cation Radicals
Sullivan, Paul D.,Ocasio, Ignacio J.,Chen, Xinhua,Bannoura, Fouad
, p. 257 - 260 (2007/10/02)
The EPR spectrum of 6-methylbenzopyrene (6-CH3-BaP) in thallium(III)tris(trifluoroacetate)-trifluoroacetic acid (TTFA/TFA) solutions has been analyzed in terms of the 6-CH3-BaP cation radical with the aid of the ENDOR spectrum.Benzopyren (BaP) in TTFA/TFA gives an EPR and ENDOR spectra which are assigned and analyzed as the 6-(trifluoroacetoxy)benzopyrene cation radical.The EPR of several other 6-substituted BaP's have been investigated in both H2SO4 and TTFA/TFA solutions.Reactions of 6-CH3-BaP and 6-F-BaP in H2SO4 were observed.The EPR spectrum of 6-CH3-BaP(+.) changes over a period of an hour into the spectrum identical with that of 6-CH2OH-BaP(+.).Similarly, the EPR spectrum of 6-F-BaP(+.) in H2SO4 changes to one identical with 6-OH-BaP(+.).These observations are discussed in terms of their possible significance to the metabolic reactions of these compounds.