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© 1993 Oxford University Press

research-article

Studies on guanine adducts excreted in rat urine after benzene exposure

E. Krewet, C. Verkoyen 1, G. Müller, C. Schell, W. Popp and K. Norpoth

Institut für Hygiene und Arbeitsmedizin, Universitats-Klinikum Gesamthochschule Essen, D-4300 Essen 1
1DLR-Projekttragerschaft Arbeit und Technik Südstraße 125, D-5300 Bonn 2, Germany

Investigations with [14C]benzene indicate the formation of base adducts in vivo. Experiments to separate adducts from urine of [14C]benzene-exposed rats suggest the excretion of eight labeled compounds different from benzene metabolites. In order to obtain information about their structure we synthesized N7-, O6-, C8- and N2-phenylguanine. With regard to their chromatographic properties we compared these phenylguanines with products obtained by alkylation of guanine by metabolites of unlabeled and 14C-labeled benzene in vivo with HPLC with UV detection and liquid scintillation counting. Furthermore GC/MS and ELISA techniques were used to detect N7-phenylguanine. Phenylguanines could not be identified in collected DNA fractions. The labeled compounds detected in urine of [14C]benzene-exposed rats also showed deviations from the HPLC elution patterns of our reference substances. Even N7-phenylguanine, formerly suspected to be a urinary metabolite of benzene in the rat, could not be detected with these refined HPLC methods. With GC/MS a compound was found in trace amounts in concentrated rat urine samples, which had a similar fragmentation pattern to N7-phenylguanine. These data could not be confirmed by a sensitive immunological assay (ELISA). No. N7-phenylguanine was detected in purified rat urine samples. The results suggest the excretion of a hydroxylated phenylguanine which may be formed in liver or bone marrow DNA by highly reactive hydroxylated intermediates. The OH group might be lost because of the high temperatures during GC/MS measurements. A hydroxy group at the phenyl-ring of N7-phenylguanine will cause other elution properties in HPLC compared to N7-phenylguanine.


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