Identification of a nitrosamino aldehyde and a nitrosamino acid resulting from β-oxidation of N-nitrosodiethanolamine

Luisa Airoldi, Marina Bonfanti, Roberto Fanelli, Bruno Bove, Emilio Benfenati, Pierluigi Gariboldi

Research output: Contribution to journalArticlepeer-review

Abstract

N-nitrosodiethanolamine is converted to N-(2-hydroxyethyl)-N-(formylmethyl)nitrosamine (EFMN) and N-(2-hydroxyethyl)-N-carboxymethyl) nitrosamine (ECMN) by rat S9 liver preparation as a result of β-oxidation. The β-oxidized metabolites were isolated and identified by gas chromatography-mass spectrometry (GC-MS) by comparison with authentic standards. An original gas chromatographic method with thermal energy detection was set up to measure both metabolites quantitatively. Under the experimental conditions described, when NAD+ was used as cofactor, about 1% of N-nitrosodiethanolamine (NDELA) was converted to EFMN and about half of the latter product was in turn converted to ECMN. The β-nitrosamino aldehyde seems to transfer the nitroso moiety to other amino-compounds, even at physiological pH. The significance of the metabolic formation of EFMN in relation to the carcinogenicity of NDELA is discussed.

Original languageEnglish
Pages (from-to)103-113
Number of pages11
JournalChemico-Biological Interactions
Volume51
Issue number1
DOIs
Publication statusPublished - Sep 1 1984

Keywords

  • Gas chromatography-mass spectrometry
  • Gas chromatography-thermal energy analysis
  • N-(2-hydroxyethyl)-N-(carboxymethyl)-nitrosamine
  • N-(2-hydroxyethyl)-N-(formylmethyl)-nitrosamine
  • N-nitrosodiethanolamine
  • β-Oxidation

ASJC Scopus subject areas

  • Toxicology

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