Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: UMLS:C0596263 (carcinogenesis)
 64,820 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

A new mutagenic compound has been isolated from ground beef which was fried at 300 degrees C for 5.5 min on each side. The new mutagen was purified using an aqueous acid extraction, XAD-2 adsorption-solvent elution, a series of preparative and analytical h.p.l.c. purification steps, and monitored with the Ames/Salmonella assay. This study reveals a new mutagen member of the amino-imidazoazaarene class of aromatic amines, having a mol. w of 224, and a formula of C13H12N4 as determined by high-resolution mass spectrometry. N.m.r. spectrometry supports the structure, 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP), for the new mutagen. The 1-methyl and 3-methyl synthesized isomers of PhIP were compared to the purified mutagen. The two isomers had identical mass spectra to the purified compound, but only the 1-methyl isomer showed similar u.v. and n.m.r. spectra. The two synthetic isomers were separable by h.p.l.c. and the beef derived component co-eluted with the 1-methyl-PhIP isomer. PhIP has a specific activity in the Ames/Salmonella assay of 1950 revertants/microgram. Although it is not as mutagenic as other compounds isolated from fried beef (e.g. MeIQx, 58 000 revertants/microgram) it is the most abundant mutagenic compound by mass in fried beef. PhIP is present at approximately 15 p.p.b. of the original weight of uncooked beef (accounting for 75% of the mass of genotoxic material) and contributes 18% of the total mutagenicity of the fried beef.
Carcinogenesis 1986 Jul
PMID:The isolation and identification of a new mutagen from fried ground beef: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). 371 3

Frying of ground beef at 250 degrees C results in the formation of a series of mutagenic heterocyclic amines, possibly as many as 10 distinct compounds. In this study, the mutagens are separated by aqueous/acid extraction from the beef, XAD adsorption, acid/neutral/base-liquid/liquid extraction, preparative reverse phase h.p.l.c., normal phase h.p.l.c., and analytical reverse phase h.p.l.c. Identification is by low and high resolution mass spectrometry, u.v. absorption spectroscopy and nitrite sensitivity assays. More than 30% of the mutagenic material is identified as 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). The previously described beef mutagen, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) contributes less than 12% of the total mutagenicity at high temperatures (300 degrees C) and less than 4% at lower temperatures. In addition to MeIQx major mutagens are seen with molecular ions at m/z 227 (C12H13N5), 209 (C13H11N3), and 176 (C9H12N4). Two very polar and two non-polar peaks making a relatively minor contribution to the total mutagenicity (less than 16% total) have not yet been identified. Estimates of the mass of these mutagens in the original cooked beef were made from the mass spectral analysis and the mutagenic recoveries. From one kilogram of cooked ground beef, 1.0 micrograms MeIQx, 0.02 micrograms of IQ, and up to 1.5 micrograms of additional mutagens are formed.
Carcinogenesis 1984 Jan
PMID:Isolation and characterization of new mutagens from fried ground beef. 669 92