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Direct alkyl chain cleavage after C-hydroxylation of dialkylinitrosamines in rats. A new pathway of the oxidative biotransformation

Direkte Alkylkettenspaltung nach C-Hydroxylierung von Dialkylnitrosaminen in Ratten. Ein neuer Weg der oxidativen Biotransformation

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Summary

Comparative in vivo investigations on the biotransformation of di-n-butylnitrosamine (DBNA) and (2-hydroxybutyl)-n-butylnitrosamine (HBBNA) showed the known ω-oxidation. However, a new metabolic mechanism of direct oxidative alkyl chain cleavage in the vicinity of the hydroxy group of HBBNA could be demonstrated.

Zusammenfassung

Vergleichende Untersuchungen über die Biotransformation von di-n-butylnitrosamin (DBNA) und (2-hydroxybutyl)-n-butylnitrosamin (HBBNA) in vivo zeigten, daß außer der bekannten ω-Oxidation auch direkte oxidative Alkylkettenspaltung neben der OH-Gruppe von HBBNA stattfindet.

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References

  • Blattmann,L., Preussmann,R.: Struktur von Metaboliten carcinogener Dialkylnitrosamine im Rattenurin. Z. Krebsforsch. 79, 3–5 (1973)

    Google Scholar 

  • Blattmann,L., Joswig,N., Preussmann,R.: Struktur von Metaboliten des carcinogenen Methyl-n-butylnitrosamins im Rattenurin. Z. Krebsforsch. 81, 71–73 (1974)

    Google Scholar 

  • Blattmann,L., Preussmann,R.: Biotransformation von carcinogenen Dialkylnitrosaminen. Weitere Urinmetaboliten von Di-n-butyl- und Di-n-pentylnitrosamin. Z. Krebsforsch. 81, 75–78 (1974)

    Google Scholar 

  • Blattmann,L., Preussmann,R.: Metaboliten von (2-Hydroxy-butyl)-n-butylnitrosamin. Z. Krebsforsch. 83, 125–127 (1975)

    Google Scholar 

  • Blattmann,L., Preussmann,R.: Oxidative biotransformation of di-n-butylnitrosamine. Formation in vitro of aldehydes in the presence of rat liver microsomes. Z. Krebsforsch. 88, 311–314 (1977)

    Google Scholar 

  • Brouwers,J.A.J., Emmelot,P.: Microsomal N-demethylation and the effect of the hepatic carcinogen dimethylnitrosamine on amino acid incorporation into the proteins of rat liver and hepatomas. Exp. Cell. Res. 19, 467–474 (1960)

    Google Scholar 

  • Challis,B.C., Rayman,M.P.: Potential alkylating agents from oxidation of carcinogenic cyclic N-nitrosamines. Brit. J. Cancer 28, 84–84 (1973)

    Google Scholar 

  • Eisenbrand,G., Preussmann,R.: Eine neue Methode zur kolorimetrischen Bestimmung von Nitrosaminen nach Spaltung der N-Nitrosogruppe mit Bromwasserstoff in Eisessig. Arzneim.-Forsch. 20, 1513–1517 (1970)

    Google Scholar 

  • Elliott,T.H., Parke,D.V., Williams,R.T.: The metabolism of cyclo(14C)hexane and its derivatives. Biochem. J. 72, 193–200 (1959)

    Google Scholar 

  • Elliott,T.H., Hanam,J.: The metabolism of tetralin. Biochem. J. 108, 551–559 (1968)

    Google Scholar 

  • Grilli,S., Prodi,G.: Identification of dimethylnitrosamine metabolites in vitro. Gann 66, 473–480 (1975)

    Google Scholar 

  • Grilli,S., Tosi,M.R., Prodi,G.: Degradation of dimethylnitrosamine catalysed by physical and chemical agents. Gann 66, 481–488 (1975)

    Google Scholar 

  • Hashimoto,Y., Iiyoshi,M., Okada,M.: Rapid and selective induction urinary bladder cancer in rats with N-ethyl-N-(4-hydroxybutyl)nitrosamine and by its principal urinary metabolite. Gann 65, 565–566 (1974)

    Google Scholar 

  • Krüger,F.W., Bertram,B.: Metabolism of nitrosamines in vivo. Z. Krebsforsch. 83, 255–260 (1975)

    Google Scholar 

  • Neunhoeffer,O., Wilhelm,G., Lehmann,G.: Eine enzymatische Umlagerung cancerogener Nitrosamine. Z. Naturf. 25b, 302–307 (1970)

    Google Scholar 

  • Okada,M., Suzuki,E.: Metabolism of butyl (4-hydroxybutyl)-nitrosamine in rats. Gann 63, 391–392 (1972)

    Google Scholar 

  • Okada,M., Suzuki,E., Aoki,J., Iiyoshi,M., Hashimoto,Y.: Metabolism and carcinogenicity of N-butyl-N-(4-hydroxybutyl)nitrosamine and related compounds, with special reference to induction of urinary bladder tumors. Gann Monograph on Cancer Research 17, 161–176 (1975)

    Google Scholar 

  • Preussmann,R., Arjungi,K., Ebers,G.: In-vitro detection of nitrosamines and other indirect alkylating agents by reaction with 3,4-dichlorothiophenol in the presence of liver microsomes. Cancer Research 36, 2459–2462 (1976)

    Google Scholar 

  • Süss,R.: Zur Wirkungsweise der Nitrosamine. Z. Naturf. 20b, 714 (1965)

    Google Scholar 

  • Suzuki,E., Aoki,J., Okada,M.: Proc. Japan. Cancer Assoc., 31st Annu. Meet., 9 (1972)

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For Prof. Dr. A. Lüttringhaus on occasion of his 70. birthday

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Blattmann, L. Direct alkyl chain cleavage after C-hydroxylation of dialkylinitrosamines in rats. A new pathway of the oxidative biotransformation. Z. Krebsforsch. 88, 315–322 (1977). https://doi.org/10.1007/BF00305369

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  • DOI: https://doi.org/10.1007/BF00305369

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