TY - JOUR
T1 - Identification of a nitrosamino aldehyde and a nitrosamino acid resulting from β-oxidation of N-nitrosodiethanolamine
AU - Airoldi, Luisa
AU - Bonfanti, Marina
AU - Fanelli, Roberto
AU - Bove, Bruno
AU - Benfenati, Emilio
AU - Gariboldi, Pierluigi
PY - 1984/9/1
Y1 - 1984/9/1
N2 - 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.
AB - 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.
KW - Gas chromatography-mass spectrometry
KW - Gas chromatography-thermal energy analysis
KW - N-(2-hydroxyethyl)-N-(carboxymethyl)-nitrosamine
KW - N-(2-hydroxyethyl)-N-(formylmethyl)-nitrosamine
KW - N-nitrosodiethanolamine
KW - β-Oxidation
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U2 - 10.1016/0009-2797(84)90023-1
DO - 10.1016/0009-2797(84)90023-1
M3 - Article
C2 - 6547642
AN - SCOPUS:0021253768
VL - 51
SP - 103
EP - 113
JO - Chemico-Biological Interactions
JF - Chemico-Biological Interactions
SN - 0009-2797
IS - 1
ER -