Carcinogenic heterocyclic amines in model systems and cooked foods: a review on formation, occurrence and intake.

Frying or grilling of meat and fish products may generate low ppb levels of mutagenic/carcinogenic heterocyclic amines (HAs). Many heterocyclic amines are formed via the Maillard reaction from creatine, free amino acids and monosaccharides; compounds naturally occurring in protein-rich foods of animal origin. The formation and yield of HAs are dependent on physical parameters, such as cooking temperature and time, cooking technique and equipment, heat and mass transport, and on chemical parameters, especially the precursors to HAs. This paper reviews the current knowledge on the formation of HAs in cooked foods and model systems, and summarizes data on the content of HAs in various cooked foods, and estimates of the dietary intake of HAs. It should be noted that the presence of carcinogens of other types in food (e.g. nitrosamines, aromatic amines, cholesterol oxide products) and that their generation during frying and grilling are outside the scope of this review.

[1]  Influence of oxidized deep-frying fat and iron on the formation of food mutagens in a model system. , 1993, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[2]  E. Hopmans,et al.  The identification of a new heterocyclic amine mutagen from a heated mixture of creatine, glutamic acid and glucose. , 1991, Mutation research.

[3]  S. Mizusaki,et al.  Isolation of 2-Amino-3-methyl-imidazo- [4,5-f]quinoline as Mutagen from the Heated Product of a Mixture of Creatine and Proline , 1984 .

[4]  B. Stavric,et al.  Analysis of commercial bouillons for trace levels of mutagens. , 1993, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[5]  J. Gustafsson,et al.  Effect of Lactobacillus acidophilus Supplements on Mutagen Excretion in Faeces and Urine in Humans , 1992 .

[6]  H. Hayatsu,et al.  Occurrence of the mutagens, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-MeIQx) in some Japanese smoked, dried fish products , 1986 .

[7]  B. Commoner,et al.  Formation of mutagens in beef and beef extract during cooking. , 1978, Science.

[8]  T. Sugimura,et al.  Formation of 2-amino-3,7,8-trimethylimidazo [4,5-f]quinoxaline, a new mutagen, by heating a mixture of creatinine, glucose and glycine. , 1984, Mutation research.

[9]  M. Jägerstad,et al.  Influence of amino acids on the formation of mutagenic/carcinogenic heterocyclic amines in a model system. , 1995, Carcinogenesis.

[10]  M. Pariza,et al.  Anticarcinogens from fried ground beef: heat-altered derivatives of linoleic acid. , 1987, Carcinogenesis.

[11]  P. Schreier,et al.  Analysis of heterocyclic aromatic amines in wine by high-performance liquid chromatography-electrospray tandem mass spectrometry. , 1997, Journal of chromatography. A.

[12]  S. Manabe,et al.  Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), in cigarette smoke condensate. , 1991, Carcinogenesis.

[13]  M. Knize,et al.  Formation of mutagenic activity from amino acids heated at cooking temperatures. , 1994, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[14]  K. Latva-Kala,et al.  Effect of commercial marinades on the mutagenic activity, sensory quality and amount of heterocyclic amines in chicken grilled under different conditions. , 1996, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[15]  M. Jägerstad,et al.  Influence of pro- and antioxidants on the formation of mutagenic-carcinogenic heterocyclic amines in a model system , 1996 .

[16]  M. Jägerstad,et al.  Creatin(in)e and Maillard reaction products as precursors of mutagenic compounds: Effects of various amino acids , 1983 .

[17]  J. Gray,et al.  Effects of synthetic antioxidants (BHA, BHT and PG) on the mutagenicity of IQ-like compounds☆ , 1992 .

[18]  S. Chan,et al.  Formation and identification of carcinogenic heterocyclic aromatic amines in boiled pork juice. , 1994, Mutation research.

[19]  M. Jägerstad,et al.  Formation of a new mutagenic DiMeIQx compound in a model system by heating creatinine, alanine and fructose. , 1985, Mutation research.

[20]  M. Knize,et al.  Proposed structures for an amino-dimethylimidazofuropyridine mutagen in cooked meats. , 1990, Carcinogenesis.

[21]  W. Iwaoka,et al.  Formation of mutagens during the frying of Hawaiian fish: correlation with creatine and creatinine content. , 1990, Mutation research.

[22]  M. Knize,et al.  Characterization of mutagenic activity in cooked-grain-food products. , 1994, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[23]  M. Lin,et al.  Characterization of the mutagen 2-amino-3-methylimidazo[4,5-f]quinoline prepared from a 2-methylpyridine/creatinine/acetylformaldehyde model system. , 1994, Mutagenesis.

[24]  R. Sinha,et al.  Pan-fried meat containing high levels of heterocyclic aromatic amines but low levels of polycyclic aromatic hydrocarbons induces cytochrome P4501A2 activity in humans. , 1994, Cancer research.

[25]  J. Weisburger,et al.  Inhibition of Aminoimidazoquinoxalinc‐type and Aminoimidazol‐4‐one‐type Mutagen Formation in Liquid Reflux Models by l‐Tryptophan and Other Selected Indoles , 1988, Japanese journal of cancer research : Gann.

[26]  T. Matsushima,et al.  Formations of MeIQx and 4,8-DiMeIQx by heating mixtures of creatinine, amino acids and monosaccharides , 1985 .

[27]  R. Edenharder,et al.  Modifying actions of solvent extracts from fruit and vegetable residues on 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and 2-amino-3,4-dimethylimidazo[4,5-f]quinoxaline (MeIQx) induced mutagenesis in Salmonella typhimurium TA 98. , 1995, Mutation research.

[28]  M. Knize,et al.  Effects of marinating on heterocyclic amine carcinogen formation in grilled chicken. , 1997, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[29]  L. Bjeldanes,et al.  Effects of temperature, patty thickness and fat content on the production of mutagens in fried ground beef. , 1985, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[30]  M. Namiki,et al.  A New Mechanism of the Maillard Reaction Involving Sugar Fragmentation and Free Radical Formation , 1983 .

[31]  J. Weisburger,et al.  High-pressure liquid chromatographic method for the analysis of 2-amino-3-methylimidazo[4,5-f]quinoline, a mutagen formed during the cooking of food , 1983 .

[32]  K T Bogen,et al.  Cancer risk of heterocyclic amines in cooked foods: an analysis and implications for research. , 1995, Carcinogenesis.

[33]  M. Knize,et al.  Heterocyclic-Amine Mutagens/Carcinogens in Foods , 1990 .

[34]  J. Felton,et al.  Characterization of mutagenic activity in instant hot beverage powders , 1995, Environmental and molecular mutagenesis.

[35]  E. Widmark,et al.  Presence of Cancer-producing Substances in Roasted Food , 1939, Nature.

[36]  M. Galceran,et al.  Determination of heterocyclic amines by pneumatically assisted electrospray liquid chromatography-mass spectrometry. , 1996, Journal of chromatography. A.

[37]  G. Becher,et al.  Heterocyclic aromatic amines in human urine following a fried meat meal. , 1997, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[38]  M. Knize,et al.  Analysis of cooked muscle meats for heterocyclic aromatic amine carcinogens. , 1997, Mutation research.

[39]  M. Galceran,et al.  Solid-phase extraction for the selective isolation of polycyclic aromatic hydrocarbons, azaarenes and heterocyclic aromatic amines in charcoal-grilled meat. , 1996, Journal of chromatography. A.

[40]  M. Jägerstad,et al.  Occurrence of mutagenic/carcinogenic heterocyclic amines in meat and fish products, including pan residues, prepared under domestic conditions. , 1994, Carcinogenesis.

[41]  H. Kataoka Methods for the determination of mutagenic heterocyclic amines and their applications in environmental analysis. , 1997, Journal of chromatography. A.

[42]  M. Galceran,et al.  Liquid chromatography-atmospheric-pressure chemical ionization mass spectrometry as a routine method for the analysis of mutagenic amines in beef extracts. , 1997, Journal of chromatography. A.

[43]  S. Aust,et al.  Mechanism(s) involved in meat mutagen formation and inhibition. , 1992, Free Radical Biology & Medicine.

[44]  I. Munro,et al.  Safety assessment of ingested heterocyclic amines: initial report. , 1993, Regulatory toxicology and pharmacology : RTP.

[45]  F. Dolbeare,et al.  Effect of microwave pretreatment on heterocyclic aromatic amine mutagens/carcinogens in fried beef patties. , 1994, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[46]  J. Gustafsson,et al.  Influence of creatine, amino acids and water on the formation of the mutagenic heterocyclic amines found in cooked meat. , 1989, Carcinogenesis.

[47]  Paul A. Kuzmicky,et al.  Mutagenicity and Chemical Analysis of Fumes from Cooking Meat , 1994 .

[48]  T. Sugimura,et al.  Identification of 4,8-DiMeIQx, a new mutagen , 1985 .

[49]  P. Kuzmicky,et al.  Airborne mutagens produced by frying beef, pork and a soy-based food. , 1995, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[50]  E. Hopmans,et al.  Health risks of heterocyclic amines. , 1997, Mutation research.

[51]  M. Knize,et al.  Mutagen formation in muscle meats and model heating systems , 1991 .

[52]  M. Jägerstad,et al.  Formation of new heterocyclic amine mutagens by heating creatinine, alanine, threonine and glucose. , 1992, Mutation research.

[53]  I. Rowland,et al.  Effects of plant-derived flavonoids and polyphenolic acids on the activity of mutagens from cooked food. , 1986, Mutation research.

[54]  G. Williams,et al.  Species and sex differences in genotoxicity of heterocyclic amine pyrolysis and cooking products in the hepatocyte primary culture/DNA repair test using rat, mouse, and hamster hepatocytes. , 1988, Environmental and molecular mutagenesis.

[55]  T. Sugimura,et al.  Formation of a mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]-pyridine (PhIP) in cooked beef, by heating a mixture containing creatinine, phenylalanine and glucose. , 1987, Mutation research.

[56]  K. Latva-Kala,et al.  Screening of heat-processed Finnish foods for the mutagens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. , 1993, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[57]  J. Casal,et al.  Determination of heterocyclic aromatic amines by capillary zone electrophoresis in a meat extract , 1997 .

[58]  G. Steineck,et al.  Effect of cooking temperature on the formation of heterocyclic amines in fried meat products and pan residues. , 1995, Carcinogenesis.

[59]  B. Caemmerer,et al.  Investigation of the contribution of radicals to the mechanism of the early stage of the Maillard reaction , 1996 .

[60]  S. Robbana-Barnat,et al.  Heterocyclic amines: occurrence and prevention in cooked food. , 1996, Environmental health perspectives.

[61]  H. Ohgaki,et al.  Carcinogenicities of heterocyclic amines in cooked food. , 1991, Mutation research.

[62]  M. Jägerstad,et al.  Trigonelline, a naturally occurring constituent of green coffee beans behind the mutagenic activity of roasted coffee? , 1997, Mutation research.

[63]  S. Manabe,et al.  Detection of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in beer and wine. , 1993, Carcinogenesis.

[64]  S. Thorgeirsson,et al.  Carcinogenicity of 2‐Amino‐3‐methylimidazo[4,5‐f]quinoline in Nonhuman Primates: Induction of Tumors in Three Macaques , 1990, Japanese journal of cancer research : Gann.

[65]  L B Fay,et al.  Heterocyclic aromatic amine formation in grilled bacon, beef and fish and in grill scrapings. , 1993, Carcinogenesis.

[66]  C. Shi,et al.  Determination of heterocyclic amines in flame-grilled fish patty by capillary electrophoresis. , 1996, Food additives and contaminants.

[67]  M. Churchwell,et al.  MULTI‐RESIDUE DETERMINATION AND CONFIRMATION OF TEN HETEROCYCLIC AMINES IN COOKED MEATS , 1996 .

[68]  G. Steineck,et al.  Assessment of the human exposure to heterocyclic amines. , 1997, Carcinogenesis.

[69]  J. A. Newell,et al.  Formation of pyrazine compounds in sugar-amino acid model systems , 1969 .

[70]  M. Feather,et al.  The Maillard reaction in foods and nutrition , 1983 .

[71]  T. Sugimura,et al.  Detection of 2‐Amino‐1‐methyl‐6‐(4‐hydroxyphenyl)imidazo[4,5‐b]pyridine in Broiled Beef , 1992, Japanese journal of cancer research : Gann.

[72]  M. Murkovic,et al.  Heterocyclic aromatic amines in fried poultry meat , 1997 .

[73]  M. Jägerstad,et al.  Mutagenicity of pan-fried bovine tissues in relation to their content of creatine, creatinine, monosaccharides and free amino acids. , 1987, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[74]  G. Becher,et al.  Isolation and identification of mutagens from a fried Norwegian meat product. , 1988, Carcinogenesis.

[75]  A. Arnoldi,et al.  Effect of Lipids in the Maillard Reaction , 1990 .

[76]  M. Galceran,et al.  Liquid chromatography-electrospray mass spectrometry with in-source fragmentation for the identification and quantification of fourteen mutagenic amines in beef extracts. , 1997, Journal of chromatography. A.

[77]  M. Galceran,et al.  Isolation by solid-phase extraction and liquid chromatographic determination of mutagenic amines in beef extracts. , 1996, Journal of chromatography. A.

[78]  L. Jackson,et al.  Heterocyclic aromatic amine content of selected beef flavors. , 1994, Mutation research.

[79]  T. Sugimura,et al.  Formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in a model system by heating creatinine, glycine and glucose. , 1984, Mutation research.

[80]  M. Jägerstad,et al.  Inhibitory effect of carbohydrates on the formation of mutagens in fried beef patties. , 1992, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[81]  T. Sugimura,et al.  Isolation and identification of a new mutagen, 2-amino-4-hydroxy-methyl-3,8-dimethylimidazo[4,5-f]quinoxaline (4-CH2OH-8-MeIQx), from beef extract. , 1994, Carcinogenesis.

[82]  T. Sugimura,et al.  Mutagenicities of smoke condensates and the charred surface of fish and meat. , 1977, Cancer letters.

[83]  G Eisenbrand,et al.  Food-borne heterocyclic amines. Chemistry, formation, occurrence and biological activities. A literature review. , 1993, Toxicology.

[84]  Formation of mutagens in cooked foods. IV. Effect of fat content in fried beef patties. , 1981, Cancer letters.

[85]  B. Henderson,et al.  MeIQx (2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline): metabolism in humans and urinary metabolites in human populations. , 1995, Princess Takamatsu symposia.

[86]  L. Klungsøyr,et al.  Reversible binding of the cooked food mutagen MeIQx to lignin-enriched preparations from wheat bran. , 1992, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[87]  M. Jägerstad,et al.  Effects of glucose on the formation of PhIP in a model system. , 1991, Carcinogenesis.

[88]  S. Tsai,et al.  Flavone inhibits mutagen formation during heating in a glycine/creatine/glucose model system , 1992 .

[89]  M. Jägerstad,et al.  Formation of heterocyclic amines using model systems. , 1991, Mutation research.

[90]  M. Jägerstad,et al.  Creatinine and Maillard Reaction Products as Precursors of Mutagenic Compounds Formed in Fried Beef , 1983 .

[91]  M. Jägerstad,et al.  Binding of 14C-labeled food mutagens (IQ, MeIQ, MeIQx) by dietary fiber in vitro. , 1985 .

[92]  A. Truswell,et al.  Mutagenicity of basic fractions derived from lamb and beef cooked by common household methods. , 1990, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[93]  T. Sugimura,et al.  Food-derived mutagens and carcinogens. , 1992, Cancer research.

[94]  M. Jägerstad,et al.  Incorporation of carbon atoms from glucose into the food mutagens MeIQx and 4,8-DiMeIQx using 14C-labelled glucose in a model system. , 1993, Carcinogenesis.

[95]  Chi-Tang Ho,et al.  Thermal generation of aromas , 1989 .

[96]  J. Čanadanović-Brunet,et al.  Synthesis of some heterocyclic aminoimidazoazarenes , 1993 .

[97]  F. Dolbeare,et al.  Mutagenic activity and heterocyclic amine content of the human diet. , 1995, Princess Takamatsu symposia.

[98]  E. Hopmans,et al.  Analysis of foods for heterocyclic aromatic amine carcinogens by solid-phase extraction and high-performance liquid chromatography. , 1997, Journal of chromatography. A.

[99]  L. Fay,et al.  Determination of heterocyclic aromatic amines in food products: automation of the sample preparation method prior to HPLC and HPLC-MS quantification. , 1997, Mutation research.

[100]  Lauren S. Jackson,et al.  Effects of Time and Temperature on the Formation of MeIQx and DiMeIQx in a Model System Containing Threonine, Glucose, and Creatine , 1995 .

[101]  R. Doll,et al.  The causes of cancer: quantitative estimates of avoidable risks of cancer in the United States today. , 1981, Journal of the National Cancer Institute.

[102]  M. Jägerstad,et al.  Effects of edible oils and fatty acids on the formation of mutagenic heterocyclic amines in a model system. , 1993, Carcinogenesis.

[103]  S. Vainiotalo,et al.  GC/MS determination of the mutagenic heterocyclic amines MeIQx and DiMeIQx in cooking fumes , 1993 .

[104]  K. Kikugawa,et al.  Formation of the mutagenic/carcinogenic imidazoquinoxaline-type heterocyclic amines through the unstable free radical Maillard intermediates and its inhibition by phenolic antioxidants. , 1996, Carcinogenesis.

[105]  K. Skog,et al.  Cooking procedures and food mutagens: a literature review. , 1993, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[106]  G. Perfetti Determination of Heterocyclic Aromatic Amines in Process Flavors by a Modified Liquid Chromatographic Method , 1996 .

[107]  I. Rowland,et al.  Counteraction of the genotoxicity of some cooked-food mutagens by biogenic amines. , 1987, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[108]  T. Kato,et al.  The presence of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in smoked dry bonito (katsuobushi). , 1986, Japanese journal of cancer research : Gann.

[109]  Kerstin Skog,et al.  Kinetics of Formation of Polar Heterocyclic Amines in a Meat Model System , 1997 .

[110]  R. Sinha,et al.  FORMATION OF HETEROCYCLIC AMINE MUTAGENS/CARCINOGENS DURING HOME AND COMMERCIAL COOKING OF MUSCLE FOODS , 1996 .

[111]  M. Galceran,et al.  High-performance liquid chromatographic determination of ten heterocyclic aromatic amines with electrochemical detection , 1993 .

[112]  B. Lau,et al.  Heterocyclic aromatic amine content in pre-processed meat cuts produced in Canada. , 1997, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[113]  M. Jägerstad,et al.  Influence of frying fat on the formation of heterocyclic amines in fried beefburgers and pan residues. , 1995, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[114]  M. Jägerstad,et al.  Isolation and identification of the food mutagens IQ and MeIQx from a heated model system of creatinine, glycine and fructose , 1986 .

[115]  E. Snyderwine,et al.  Excretion of food-derived heterocyclic amine carcinogens into breast milk of lactating rats and formation of DNA adducts in the newborn. , 1993, Carcinogenesis.

[116]  M. Jägerstad,et al.  Effects of monosaccharides and disaccharides on the formation of food mutagens in model systems. , 1990, Mutation research.

[117]  R. Sinha,et al.  High concentrations of the carcinogen 2-amino-1-methyl-6-phenylimidazo- [4,5-b]pyridine (PhIP) occur in chicken but are dependent on the cooking method. , 1995, Cancer research.

[118]  T. Sugimura,et al.  Presence of carcinogenic heterocyclic amines in urine of healthy volunteers eating normal diet, but not of inpatients receiving parenteral alimentation. , 1991, Carcinogenesis.

[119]  T. Sugimura,et al.  Overview of carcinogenic heterocyclic amines. , 1997, Mutation research.

[120]  F. Dolbeare,et al.  Effect of cooking time and temperature on the heterocyclic amine content of fried beef patties. , 1994, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[121]  William A. Pryor,et al.  Electron-spin resonance study of mainstream and sidestream cigarette smoke: nature of the free radicals in gas-phase smoke and in cigarette tar. , 1983, Environmental health perspectives.

[122]  J. Weisburger,et al.  Formation of mutagens in cooked foods. V. The mutagen reducing effect of soy protein concentrates and antioxidants during frying of beef. , 1982, Cancer letters.

[123]  Lawrence M. Seiford,et al.  Recent developments in dea : the mathematical programming approach to frontier analysis , 1990 .

[124]  B. Lau,et al.  Mutagenic heterocyclic aromatic amines (HAAs) in 'processed food flavour' samples. , 1997, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[125]  R. Vikse,et al.  Mutagenicity, Creatine and Nutrient Contents of Pan Fried Meat from Various Animal Species , 1993, Acta Veterinaria Scandinavica.

[126]  A. Y. Lu,et al.  Tumorigenicity of nitrated derivatives of pyrene, benz[a]anthracene, chrysene and benzo[a]pyrene in the newborn mouse assay. , 1986, Carcinogenesis.

[127]  A. Lynch,et al.  Quantification of the carcinogens 2-amino-3,8-dimethyl- and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in food using a combined assay based on gas chromatography-negative ion mass spectrometry. , 1993, Journal of chromatography.

[128]  A. Karlsson,et al.  Transfer of the food mutagen PhIP to foetuses and newborn mice following maternal exposure. , 1994, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[129]  C. Meester Genotoxic potential of beta-carbolines: a review. , 1995 .

[130]  B. Ames,et al.  Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. , 1975, Mutation research.

[131]  L. Bjeldanes,et al.  Isolation and characterization of new mutagens from fried ground beef. , 1984, Carcinogenesis.

[132]  N. Kurihara,et al.  Formation of PhIP in a mixture of creatinine, phenylalanine and sugar or aldehyde by aqueous heating. , 1992, Carcinogenesis.

[133]  J. Westra,et al.  Comparative carcinogenicity of the food pyrolysis product, 2-amino-5-phenylpyridine, and the known human carcinogen, 4-aminobiphenyl, in the neonatal B6C3F1 mouse. , 1988, Cancer letters.

[134]  G. Steineck,et al.  Polar and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues. , 1997, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[135]  G. Gross,et al.  Quantitation of mutagenic/carcinogenic heterocyclic aromatic amines in food products. , 1992, Journal of chromatography.

[136]  H. Hayatsu,et al.  Inhibitory effect of the ether extract of human feces on activities of mutagens: inhibition by oleic and linoleic acids. , 1981, Mutation research.

[137]  R. Sinha,et al.  Heterocyclic amine content in fast-food meat products. , 1995, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[138]  L. Bjeldanes,et al.  Identification of the mutagens in cooked beef. , 1986, Environmental health perspectives.

[139]  N. Kurihara,et al.  Nucleic acids induce the formation of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in a model system. , 1993, Carcinogenesis.

[140]  T. Sugimura,et al.  Structural determination of a new mutagenic heterocyclic amine, 2-amino-1,7,9-trimethylimidazo[4,5-g]quinoxaline (7,9-DiMeIgQx), present in beef extract. , 1994, Carcinogenesis.