Analysis of mutagenic heterocyclic amines in cooked beef products by high-performance liquid chromatography in combination with mass spectrometry

Turesky, Robert J.; Bur, H.; Huynh-Ba, T.; Aeschbacher, H.U.; Milon, H.

doi:10.1016/0278-6915(88)90002-6

Cited by 105 publications

(47 citation statements)

References 23 publications

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“…The design of the Shanghai Cohort study has been described previously (28,29). In brief, between January 1, 1986 and September 30,1989, all male residents of four, small, geographically defined communities in Shanghai, China, who were ages 45 to 64 years and had no history of cancer, were invited to participate in a prospective study of diet and cancer. At enrollment, participants were interviewed in person using a structured questionnaire that included lifetime history of tobacco use, and each participant provided a 10-mL blood and a single-void urine sample.…”

Section: Methodsmentioning

confidence: 99%

Tobacco Smoking and Urinary Levels of 2-Amino-9H-Pyrido[2,3-b]Indole in Men of Shanghai, China

Turesky

Yuan²,

Wang

et al. 2007

Cancer Epidemiology, Biomarkers &Amp; Prevention

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Carcinogenic heterocyclic aromatic amines (HAA) are formed in cooked meats, poultry, and fish and arise in tobacco smoke. We measured the concentrations of four prevalent HAAs in spot urine samples collected at baseline from 170 participants of the Shanghai Cohort study, a population-based cohort study of adult men recruited during 1986 to 1989 in Shanghai, China. Sixteen (18.6%) of 86 nonsmokers were positive for urinary 2-amino-9H-pyrido[2,3-b]indole (AAC) versus 41 (48.8%) of 84 cigarette smokers; the difference was statistically significant (P < 0.001). The number of cigarettes smoked per day was positively and significantly related to urinary levels of AAC in study subjects (P < 0.001); the mean level among nonsmokers was 2.54 ng/g creatinine, whereas the means for light (1-19 cigarettes per day) and heavy (20+ cigarettes per day) smokers were 7.50 and 11.92 ng/g creatinine, respectively. 2-Amino-3,4,8-trimethylimidazo [4,5-f] quinoxaline was undetected in the urine of the 170 subjects. Only 5 (2.9%) and 6 (3.5%) subjects, respectively, showed detectable levels of urinary 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine and 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline, and smoking status was unrelated to levels of either HAA. Quantitative measurements of HAAs in commonly eaten pork and chicken dishes in Shanghai showed low concentrations of HAAs (<1 ng/g meat). Our data indicate that AAC represents a major HAA exposure in adult men of Shanghai, China, and that tobacco smoke is an important point source of their AAC exposure. (Cancer Epidemiol Biomarkers Prev 2007;16(8):1554 -60)

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Section: Methodsmentioning

confidence: 99%

Tobacco Smoking and Urinary Levels of 2-Amino-9H-Pyrido[2,3-b]Indole in Men of Shanghai, China

Turesky

Yuan²,

Wang

et al. 2007

Cancer Epidemiology, Biomarkers &Amp; Prevention

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“…Thus, estimates were variable and it was not possible to accurately assess the amount of carcinogens consumed in the daily diet. More recently HPLC with electrochemical detection (9) or mass spectrometry (10,11) has been used for quantitative analysis. While this has led to more accurate estimates of the heterocyclic amine content, there remains a need for more rapid sample preparation for the practical application of analyzing many samples.…”

Section: Introductionmentioning

confidence: 99%

“…In this report we present a rapid purification scheme utilizing XAD-2 treatment followed by monoclonal antibody affinity chromatography to purify IQ and MelQx from heated meat products. (7, were synthesized as previously described (11). Bacterial-grade beef extract was purchased from Difco Laboratories, Detroit and food-grade beef extracts were purchased from several food suppliers.…”

Section: Introductionmentioning

confidence: 99%

Purification of the food-borne carcinogens 2-amino-3-methylimidazo [4,5-f]quinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in heated meat products by immunoaffinity chromatography

Turesky¹,

Forster²,

Aeschbacher³

et al. 1989

Carcinogenesis

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“…Quantification was done by HPLC with UV or mass spectrometry detection (2,3). Analysis by solid-phase tandem extraction gave similar values, but enabled the measurement of other heterocyclic amines, including 2-amino-i-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) and 2-amino-9H-pyrido [2,3-b]indole (2-AaC), which do not cross-react with the antibodies (4).…”

Section: Methodsmentioning

confidence: 99%

“…Methods have been developed to rapidly quantitate carcinogenic heterocyclic amines formed in cooked foods such as meat and fish (1)(2)(3)(4). However, measurement of these contaminants in food only provides a crude estimate ofexposure and does not account for absorption and metabolism ofthese procarcinogens to biologically active species or to detoxified products.…”

Section: Introductionmentioning

confidence: 99%

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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Analysis of mutagenic heterocyclic amines in cooked beef products by high-performance liquid chromatography in combination with mass spectrometry

Cited by 105 publications

References 23 publications

Tobacco Smoking and Urinary Levels of 2-Amino-9H-Pyrido[2,3-b]Indole in Men of Shanghai, China

Tobacco Smoking and Urinary Levels of 2-Amino-9H-Pyrido[2,3-b]Indole in Men of Shanghai, China

Purification of the food-borne carcinogens 2-amino-3-methylimidazo [4,5-f]quinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in heated meat products by immunoaffinity chromatography

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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