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Metabolismus von nitrosaminen in vivo

I. Über die β-Oxidation aliphatischer Di-n-alkylnitrosamine: Die Bildung von 7-Methylguanin neben 7-Propyl- bzw. 7-Butylguanin nach Applikation von Di-n-propyloder Di-n-butylnitrosamin

On the metabolism of nitrosamines in vivo

I. Evidence for β-oxydation of aliphatic di-n-alkylnitrosamines: the simultaneous formation of 7-methylguanine besides 7-propyl- or 7-butylguanine after application of di-n-propyl- or di-n-butyhiitrosamine

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Summary

The in vivo application of 1-[14C]-di-n-propyl- and 1-[14C]-di-n-butylnitrosamine leads to formation of 7-[14C]-n-propyl- and 7-[14C]-n-butylguanine in the RNA of rat liver. 7-[14C]-methylguanine is simultaneously formed after application of both compounds. No labelled [14C]-7-methylguanine, however, could be detected when 2-[14C]-di-n-propylnitrosamines was applied. In this case only 7-[14C]-n-propylguanine was found. This leads to the conclusion that the aliphatic chains of di-n-alkylnitrosamines are metabolically split between the α- and the β-carbon during metabolism forming a methylatmg compound.

Zusammenfassung

Nach in vivo Applikation von 1-[14C]-Di-n-propyl- und 1-[14C]-Din-butylnitrosamin bei Batten können 7-[14C]-n-Propyl- bzw. 7-[14C]-n-Butylguanin sowie 7-[14C]-Methylguanin in den Ribonucleinsäuren der Leber nachgewiesen werden. Nach Gabe von 2-[14C]-Di-n-propylnitrosamm war eine Bildung von [14C]-7-Methylguanin nicht nachweisbar. Es wurde im RNS-Hydrolysat nur 7-[14C]-n-Propylguanin gefunden. Aus diesen Befunden wird geschlossen, daß die Alkylketten von Di-n-Alkylnitrosaminen in vivo metabolisch zwischen dem α- und dem β-C-Atom unter Bildung einer methylierenden Verbindung gespalten werden.

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  1. Institut für experimentelle Toxikologie und Chemotherapie am Deutschen Krebsforschungszentrum, Heidelberg

    F. W. Krüger

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  1. F. W. Krüger
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Für finanzielle Unterstützung zur Durchführung dieser Arbeit danke ich der Deutschen Forschungsgemeinschaft sowie dem Verein zur Förderung der Krebsforschung in Deutschland e.V. Für techn. Assistenz danke ich Herrn H. Braun.

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Krüger, F.W. Metabolismus von nitrosaminen in vivo. Z. Krebsforsch. 76, 145–154 (1971). https://doi.org/10.1007/BF00284425

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  • DOI: https://doi.org/10.1007/BF00284425

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