Formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in a model system by heating creatinine, glycine and glucose |
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| Authors: | Margaretha Jägerstad Kjell Olsson Spiros Grivas Chie Negishi Keiji Wakabayashi Mitsuhiro Tsuda |
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| Institution: | 1. Department of Nutrition, Chemical Center, University of Lund, P.O. Box 740, S-220 07 Lund Sweden;2. Department of Chemistry and Molecular Biology, Swedish University of Agricultural Sciences, S-750 07 Uppsala Sweden;3. Biochemistry Division, National Cancer Center Research Institute, 1-1, Tsukiji 5 chome, Chuo-ku, Tokyo 104 Japan |
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| Abstract: | A mixture of creatinine, glucose and glycine was heated in diethylene glycol containing 14% water for 2 h at 128 degrees C, and the mutagens formed were purified by XAD-2 column chromatography, acid-base partition, Sephadex LH-20 column chromatography, 'blue cotton' treatment and HPLC. Two mutagenic substances were isolated by HPLC. The major mutagen was identified by its UV absorption and mass and NMR spectra as 2-amino-3,8- dimethylimidazo 4,5-f]quinoxaline, which was originally isolated from fried beef. This finding supported the idea that creatinine, amino acids and sugars present in meat are precursors in the formation of the mutagenic imidazoquinoxaline derivative. |
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| Keywords: | Trp-P-1 Trp-P2 Glu-P-1 Glu-P-2 Orn-P-1 Phe-P-1 2-amino-5-phenylpyridine 33421-40-8 AαC MeAαC IQ MeIQ MeIQx HPLC high performance liquid chromatography |
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