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© 1984 Oxford University Press

other

The identification of bases in DNA involved in covalent binding of the reactive metabolite from 9-hydroxybenzo[a]pyrene

John A. Robertson , Magnus Nordenskjöld 1 and Bengt Jernström  2

Department of Forensic Medicine, Karolinska Institutet S-104 01 Stockholm, Sweden
1Department of Clinical Genetics, Karolinska Hospital S-104 01 Stockholm, Sweden

2To whom reprint requests should be sent

Unlabelled 9-hydroxybenzo[a]pyrene (9-OH-BP) was incubated with a microsomal metabolic system and plasmid Col E1 DNA that had been radiolabelled by nick-translation with a tritiated deoxyribonucleotide. After the addition of an excess of a similar incubate that substituted calf thymus for plasmid DNA, a fraction obtained from DNA hydrolysates of these incubation mixtures was analysed by reverse-phase, h.p.l.c. for fluorescence and radioactivity of eluates. The presence of radioactivity with fluorescence activity in the same eluate fractions indicated the presence of 9-OH-BP-derived adducts with that radiolabelled nucleoside. These analyses showed the presence of at least four adducts with dG, a single adduct with dA, and no adducts with either dC or dT in plasmid DNA. This enabled the identification of components of similar h.p.l.c. profiles obtained from incubates with calf thymus DNA and [3H]9-OH-BP. No major qualitative or quantitative differences were found. As both the identities and extent of binding to these bases were similar to these previously reported for the ultimately carcinogenic BP-diolepoxides, we conclude that the non-cardnogenidty of 9-OH-BP is not, therefore, attributed to a difference in the base moieties involved in adduct formation. H.p.l.c. and spectrofluorimetric analyses indicated that an isolated metabolite of 9-OH-BP is indistinguishable from its 4,5-dihydrodiol. This is interpreted as evidence for the formation of 9-OH-BP-4, 5-oxide as the reactive, DNA-binding intermediate.


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This article has been cited by other articles:


Home page
 Toxicol PatholHome page
A. Graslund, B. Jernstrom, O. Undeman, L. Dock, A. Ehrenberg, and T. Astlind
Fluorescence Measurements of DNA-bound Metabolites of Benzo(a)pyrene Derivatives with Different Carcinogenic Effects
Toxicol Pathol, February 1, 1984; 12(2): 179 - 184.
[Abstract] [PDF]


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