Fluorescence study of DNA-complexes formed after metabolic activation of benzo(a)pyrene derivatives |
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Authors: | Lennart Dock Ola Undeman Astrid Gräslund Bengt Jernström |
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Affiliation: | 1. Department of Forensic Medicine, Karolinska Institutet, S-104 01 Stockholm Sweden;2. Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm, Sweden |
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Abstract: | Benzo(a)pyrene derivatives (1-, 2-, 3-, 7-, and 9-hydroxy-benzo(a)pyrene and trans-9,10-dihydro-9,10-dihydroxy-, -4,5-dihydro-4,5-dihydroxy-, and -7,8-dihydro-7,8-dihydroxy-benzo(a)pyrene) were metabolized by liver microsomes isolated from 3-methylcholanthrene-treated rats in the presence of calf thymus DNA. The isolated DNA was then assayed by fluorescence for bound metabolic products. Only 2-hydroxy-benzo(a)pyrene, 9-hydroxy-benzo(a)pyrene and trans-7,8-dihydro-7,8-dihydroxy-benzo(a)pyrene yielded detectable amounts of DNA-bound products. In contrast to the product(s) from 9-hydroxy-benzo(a)pyrene, the metabolites of 2-hydroxy-benzo(a)pyrene and trans-7,8-dihydro-7,8-dihydroxy-benzo(a)pyrene, both strong carcinogens, had similar excitation spectra and gave considerably increased fluorescence intensities when the DNA was denatured. These data indicate structural similarities in the DNA complexes formed after metabolic activation of 2-hydroxy-benzo(a)pyrene and trans-7,8-dihydro-7,8-dihydroxy-benzo(a)pyrene. |
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Keywords: | PCH polycyclic aromatic hydrocarbons BP benzo(a)pyrene AHH aryl hydrocarbon hydroxylase BP-7,8-dihydrodiol trans-7,8-dihydro-7,8-dihydroxy-benzo(a)pyrene BP-4,5-dihydrodiol trans-4,5-dihydro-4,5-dihydroxy-benzo(a)pyrene BP-9,10-dihydrodiol trans-9,10-dihydro-9,10-dihydroxy-benzo(a)pyrene 1-, 2-, 3-, 7- and 9-OH-BP, 1-, 2-, 3-, 7- and 9-hydroxy-benzo(a)pyrene 3-MC 3-methylcholanthrene |
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