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Toxicologic Pathology
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Journal Article

Fluorescence Measurements of DNA-bound Metabolites of Benzo(a)pyrene Derivatives with Different Carcinogenic Effects

Astrid Gräslund

Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm (Sweden), and Department of Forensic Medicine, Karolinska Institutet, Box 60400, S-204 01 Stockholm (Sweden)

Bengt Jernström

Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm (Sweden), and Department of Forensic Medicine, Karolinska Institutet, Box 60400, S-204 01 Stockholm (Sweden)

Ola Undeman

Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm (Sweden), and Department of Forensic Medicine, Karolinska Institutet, Box 60400, S-204 01 Stockholm (Sweden)

Lennart Dock

Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm (Sweden), and Department of Forensic Medicine, Karolinska Institutet, Box 60400, S-204 01 Stockholm (Sweden)

Anders Ehrenberg

Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm (Sweden), and Department of Forensic Medicine, Karolinska Institutet, Box 60400, S-204 01 Stockholm (Sweden)

Torbjörn Astlind

Department of Biophysics, University of Stockholm, Arrhenius Laboratory, S-106 91 Stockholm (Sweden), and Department of Forensic Medicine, Karolinska Institutet, Box 60400, S-204 01 Stockholm (Sweden)

(±)-trans-dihydroxy-7,8-dihydrobenzo(a)pyrene (BP-7,8-diol) and 9-hydroxybenzo(a)pyrene (9-OH-BP) were metabolized by rat liver microsomes in the presence of calf thymus DNA, resulting in preferential DNA binding of fluorescent (+)-anti-BP-7,8-diol-9,10-epoxide (BPDE) and 9-OH-BP-4,5-epoxide, respectively. When the DNA is denatured the fluorescence intensities of the bound metabolites change in a characteristic manner. Fluorescence decay measurements show that the intensity changes are due to changes in lifetimes of the excited states. Model substances for the bound metabolites were studied in solvents of different polarity. We found that the fluorescence changes observed after denaturation of the DNA may be explained as solvent polarity effects, so that denaturation forces the bound metabolites from a more hydrophobic environment to a hydrophilic one. Fluorescence depolarization studies as a function of temperature in combination with previous linear dichroism studies show that both BPDE and 9-0H-BP-4,S-epoxide form rigidly associated complexes with native DNA.

Toxicologic Pathology, Vol. 12, No. 2, 179-184 (1984)
DOI: 10.1177/019262338401200211
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