Quantitation of mutagegnic/carcinogenic heterocyclic aromatic amines in food products

Gross, Gian A.; Grüter, A.

doi:10.1016/0021-9673(92)85095-b

Cited by 376 publications

(247 citation statements)

References 6 publications

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“…In domestic cooking, temperature is generally below 200ºC. Increase in cooking time and temperature lead to increase the amounts of HCAs and PhIP level is higher at higher cooking temperatures and in longer cooking time [12,50,53,54]. Bjeldanes and others [30,55] reported that mutagenic activity in grilled meat increased rapidly during the initial 10 min and then decreased.…”

Section: +mentioning

confidence: 99%

A Review on the Formation of Carcinogenic/Mutagenic Heterocyclic Aromatic Amines

Kızıl¹,

Öz²,

Besler³

2011

J Food Process Technol

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Mutagenic and/or carcinogenic heterocyclic aromatic amines (HCAs) have been found in meat and fish cooked at temperatures over 150ºC. To date, more than 25 HCAs have been isolated and identified in cooked meat and meat products as potent mutagens in the Ames/Salmonella test. HCAs are potent mutagens at ng/g levels in cooked foods and play an important role in the etiology of human cancer. Major precursors of HCAs are creatine and/or creatinine, amino acids and reducing sugars. IQ-type HCAs are formed by heat induced non enzymatic browning known as Maillard reaction which involves creati(ni)ne, amino acid and sugars whereas amino-carbolines are mainly formed by pyrolysis of amino acids and proteins at higher temperatures above 300ºC. Concentrations and variety of HCAs can be dependent on many factors such as precursor level, meat type, cooking method, cooking duration, pH and water activity, heat and mass transfer, lipid level, lipid oxidation and antioxidants. Due to better understanding, formation of HCAs has been studied both in model systems and cooked foods and this review gives an overview of the studies on the formation of carcinogenic and/or mutagenic HCAs.

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Section: +mentioning

confidence: 99%

A Review on the Formation of Carcinogenic/Mutagenic Heterocyclic Aromatic Amines

Kızıl¹,

Öz²,

Besler³

2011

J Food Process Technol

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“…The samples were extracted and processed using GPC in the same manner as the samples prepared for mutagenicity assays. The samples were then analyzed using previously reported methodology [Gross and Gunter, 1992] by a Waters (Milford, MA) HPLC system equipped with 600E pumps, 717 autosampler, a 996 photodiode array detector, and a 4.6-mm id ϫ 150-mm Cosmosil 5NPE (Phenomenex) column.…”

Section: Mutagen Recovery Analysismentioning

confidence: 99%

Evidence for the presence of mutagenic arylamines in human breast milk and DNA adducts in exfoliated breast ductal epithelial cells

Thompson

DeMarini

Kadlubar

et al. 2002

Environ and Mol Mutagen

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Aromatic and heterocyclic amines are ubiquitous environmental mutagens present in combustion emissions, fried meats, and tobacco smoke, and are suspect human mammary carcinogens. To determine the presence of arylamines in breast tissue and fluid, we examined exfoliated breast ductal epithelial cells for DNA adducts and matched human milk samples for mutagenicity. Breast milk was obtained from 50 women who were 4 -6 weeks postpartum, and exfoliated epithelial-cell DNA was evaluated for bulky, nonpolar DNA adducts by 32 P-postlabeling and thin-layer chromatography. Milk was processed by acid hydrolysis, and the extracted organics were examined in the standard plate-incorporation Ames Salmonella assay using primarily strain YG1024, which detects frameshift mutations and overexpresses aryl amine N-acetyltransferase. DNA adducts were identified in 66% of the specimens, and bulky adducts migrated in a pattern similar to that of 4-aminobiphenyl standards. The distribution of adducts did not vary by NAT2 genotype status. Of whole milk samples, 88% (22/25) had mutagenic activity.Among the samples for which we had both DNA adduct and mutagenicity data, 58% (14/19) of the samples with adducts were also mutagenic, and 85% (11/13) of the mutagenic samples had adducts. Quantitatively, no correlation was observed between the levels of adducts and the levels of mutagenicity. Separation of the milk showed that mutagenic activity was found in 69% of skimmed milk samples but in only 29% of the corresponding milk fat samples, suggesting that the breast milk mutagens were moderately polar molecules. Chemical fractionation showed that mutagenic activity was found in 67% (4/6) of the basic fractions but in only 33% (2/6) of acidic samples, indicating that the mutagens were primarily basic compounds, such as arylamines. Although pilot in nature, this study corroborates previous findings of significant levels of DNA adducts in breast tissue and mutagenicity in human breast milk and indicates that breast milk mutagens may be moderately polar basic compounds, such as arylamines.

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“…The adduct was labile to acid with quantitative recovery of the parent amine. Gross (4), and Gross and Gruter (24 The binding of MeIQx to albumin and hemoglobin was several fold lower than that observed for IQ. Hepatic cytochrome P-450 induction with PCB increased the rate of formation of the biologically reactive N-hydroxy metabolite by 20-fold in microsomal assays, but resulted in a 10-fold decrease in blood protein binding in vivo (5).…”

Section: Resultsmentioning

confidence: 89%

Metabolism of the Food-Borne Carcinogens 2-Amino-3-Methylimidazo-[4,5-f]quinoline and 2-Amino-3,8-Dimethylimidazo[4,5-f]-Quinoxaline in the Rat As a Model for Human Biomonitoring

Turesky¹,

Stillwell²,

Skipper³

et al. 1993

Environmental Health Perspectives

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Metabolism of 2-amino-3-methylimidazD[4,5-Jlquinoline (IQ) and 2-amino-3-dimethylimidazoll4,5-Jjquinoxaline (MeIQx) and their binding to blood proteins were examined in the rat to develop methods of human biomonitoring.Hemoglobin and serum albumin were among many blood proteins modified. Approximately 0.01% ofthe dose for both compounds was bound to these proteins, and induction ofcytochrome P450 with polychlorobiphenyls resulted in decreased levels of adduction. Hemoglobin sulfinic acid amide adducts could not be detected for either amine, however, as much as 10% ofthe IQ bound to albumin was characterized as an N2-cysteine(34)sulfinyl-IQ linkage. Human dosimetry ofthese carcinogens through such adducts may prove difficult due to the low kvels of protein binding. Major routes of dfiation of both contaminants included cytochrome P450-mediated ring hydroxylation at the C-S position followed by conjugation to glucuronic or sulfuric acid. Direct conjugation to the exocyclic amine group through N-glucuronidation and sulfamate formation were other important routes of inactivation, but N-acetylation was a minor pathway. The Nglucuronide conjugate of the mutagenic metabolite N-hydroxy-MeIQx was also detected in urine. Rats given MeIQx at 10 jAg/kg excreted 20% of the dose in urine within 24 hr and the remainder was recovered in feces. The N2-glucuronide was the major metabolite found in urine and accounted for 4% of the total dose. The other metabolites cited above also were excreted in urine at amounts ranging from 05 to 3% of the dose, whereas 0.5 to 2% was detected as unmetabolized MeIQx. Hunan hepatic microsomes activated IQ and MeIQx by N-hydroxylation, but neither compound was a substrate for hepatic cytosol N-acetyltransferases. Both IQ and MeIQx were substrates for hepatic cytosol sulfotransferases, forming the lf te derivatives. Immunoaf18fi chromatography was used torapidly purify MeIQx and sweral metabolites from rat urine as a model for human biomonitoring. Trace levels of MeIQx vere detected in urine of humans within 24 hr of consumption of cooked meat by analysis with negative ion GC-MS. Analytical methods are under development for measuring polar metabolites that may be present in human urine.

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Quantitation of mutagegnic/carcinogenic heterocyclic aromatic amines in food products

Cited by 376 publications

References 6 publications

A Review on the Formation of Carcinogenic/Mutagenic Heterocyclic Aromatic Amines

A Review on the Formation of Carcinogenic/Mutagenic Heterocyclic Aromatic Amines

Evidence for the presence of mutagenic arylamines in human breast milk and DNA adducts in exfoliated breast ductal epithelial cells

Metabolism of the Food-Borne Carcinogens 2-Amino-3-Methylimidazo-[4,5-f]quinoline and 2-Amino-3,8-Dimethylimidazo[4,5-f]-Quinoxaline in the Rat As a Model for Human Biomonitoring

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