- Characterization of the mutagen 2-amino-3-methylimidazoquinoline prepared from a 2-methylpyridine/creatinine/acetylformaldehyde model system
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A mixture of 2-methylpyridine, creatinine and aldehydes was heated in diethylene glycol containing 5 percent water for 1 h at 140 deg C. The mutagenic compounds were purified by XAD-2 column chromatography, acid/base partition, blue cotton treatment, thin layer chromatography and HPLC. The active substances purified from each step were monitored by their mutagenicity with Salmonella typhimurium TA98 in the presence of S9 mix. Among the mutagens collected, 2-amino-3-methylimidazoquinoline (IQ) was isolated from HPLC, and was identified by its UV and mass spectrum using a photodiode array detector and mass spectrometry. Our findings appear to be the first experimental evidence to substantiate of hypothetical pathway for the formation of IQ mutagens from a heated model system consisting of a pyridine or pyrazine derivatives, an aldehyde and creatinine or creatine.
- Lee, Huei,Lin, Ming-Yang,Lin, Shaw Tao
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- 2-amino-X-nitrobenzimidazoles as precursors of food-borne carcinogens: A new approach to IQ synthesis
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Cyclization of (non)-methylated nitro-o-phenylenediamines with cyanogen bromide provided nitro-substituted 2-aminobenzimidazoles in good up to excellent yields. Catalytic hydrogenation of 2-amino-1-methyl-5-nitrobenzimidazole yielded 2,5-diamino-1-methylbenzimidazole, which on treatment with 1,1,3,3-tetramethoxypropane in methanol and subsequently after removal of methanol in polyphosphoric acid afforded food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in 20% yield. Copyright
- Bella, Maros,Milata, Viktor,Larina, Lyudmila I.
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p. 293 - 296
(2012/06/04)
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- Synthetic Routes to the Carcinogen IQ and Related 3H-Imidazoquinolines
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2-Amino-3-methyl-3H-imidazoquinoline (IQ, 1a) and four new IQ homologues, viz. its 7-methyl, 8-methyl, 9-methyl and 7,9-dimethyl derivatives 1c-1f, have been conveniently synthesized from the appropriate 6-methoxyquinolines 3 rather than from the p
- Ronne, Erik,Grivas, Spiros,Olsson, Kjell
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p. 823 - 830
(2007/10/02)
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- THE SYNTHESIS OF THREE ISOMERS OF THE FOOD CARCINOGEN IQ
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2-Amino-3-methyl-3H-imidazoquinoline, 2-amino-3-methyl-3H-imidazoisoquinoline and 2-amino-3-methyl-3H-imidazoisoquinoline were synthesized from 7-methoxyquinoline, 6- and 7-methoxyisoquinolines in 21-28percent overall yields.
- Ronne, Erik,Grivas, Spiros
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p. 101 - 105
(2007/10/02)
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- CONVENIENT SYNTHESIS OF THE FOOD MUTAGEN 2-AMINO-3-METHYLIMIDAZOQUINOLINE (iq), AND IQ-D3
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The title compounds (5 and 10) were each prepared in four steps from commercially available 5-amino-6-nitroquinoline (1) in 41percent overall yield.The key step was the displacement of the methylsulfonyl group of 4 by sodamine.
- Ziv, Joseph,Knapp, Spencer,Rosen, Joseph D.
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p. 973 - 980
(2007/10/02)
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- A Potent Mutagen in Broiled Fish. Part 1. 2-Amino-3-methyl-3H-imidazoloquinoline
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A potent mutagen isolated from a methanol extract of sardines broiled under normal domestic conditions was strongly mutagenic to Salmonella typhimurium TA98.Its identity has been established as 2-amino-3-methyl-3H-imidazoquinoline on the basis of spectral evidence and by chemical synthesis.
- Kasai, Hiroshi,Yamaizumi, Ziro,Nishimura, Susumu,Wakabayashi, Keiji,Nagao, Minako,at al.
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p. 2290 - 2293
(2007/10/02)
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