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

Turesky, Robert J.; Forster, Christina M.; Aeschbacher, H.U.; Würzner, H P; Skipper, Paul L.; Trudel, Laura J.; Tannenbaum, Steven R.

doi:10.1093/carcin/10.1.151

Cited by 45 publications

(14 citation statements)

References 22 publications

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“…The analysis of HAs in foods has been difficult because most are present in trace amount (ppb or ppt). Many extraction and purification methods, including solvent extraction, acid-base partition, liquid-solid chromatography with silica gel, Sephadex LH 20, carboxymethylcellulose, XAD-2 or blue cotton as adsorbent, protein precipitation and immunoaffinity chromatography have been employed to extract HAs and remove impurities from foods [4,13]. However, most of these methods result in low recovery and the presence of many impurities interfere with the identification of HAs by UV detection.…”

Section: Introductionmentioning

confidence: 99%

An improved analytical method for determination of heterocyclic amines in chicken legs

Chen

Yang

1998

Chromatographia

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SummarySeveral extraction, separation and detection methods for heterocyclic amines (HAs) in chicken legs were evaluated by liquid chromatography. Results showed that the most appropriate extraction method includes the removal of macrosubstances by centrifugation and subsequent purification using a PRS (propylsulfonic acid silica gel) and a C18 cartridge, and the recovery obtained ranged between 51 and 89 %. For HPLC separation, a binary solvent system consisting of acetonitrile and 0.05 M ammonium acetate solution (pH 3.6) with gradient elution with flow rate of 1.0 mL min -1 and detection at 258 nm was used to resolve 16 HAs. With fluorescence nine HAs could be detected by employing a programmable wavelength, and the sensitivity was 100-400 times higher than that by UV detection. The detection limits for UV and fluorescence detection were 0.02-0.5 ng and 0.05-3 pg respectively, with a signal-tonoise ratio 3. The presence of HAs in fried chicken legs was also determined.

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Section: Introductionmentioning

confidence: 99%

An improved analytical method for determination of heterocyclic amines in chicken legs

Chen

Yang

1998

Chromatographia

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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%

“…Analysis of MeIQx excreted in urine of humans following consumption of fried beefwas done by the method of Murray et al (8) using negative-ion chemical ionization GC-MS except that an immunoaffinity purification step was included following the acid/base partitioning step (3). Three subjects ingested 1 lb equivalent cooked beef prepared under typical household cooking practices and then collected urine for 24 hr.…”

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%

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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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“…Applications of LC-ECD, LC-UV, and LCfluorescence detections in HA analyses were reviewed by Pais and Knize [15]. Highly specific detectors based on immunosorbent or immunoaffinity assays have also been developed [72,73]. However, these have been restricted to analyses of HAs for which antibodies are available [20].…”

Section: 4mentioning

confidence: 99%

Heterocyclic amines: Chemistry and health

Cheng¹,

Chen²,

Wang³

2006

Molecular Nutrition Food Res

105

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Heterocyclic amines (HAs) occur at the ppb range in foods. Most of them demonstrate potent mutagenicity in bacteria mutagenicity test, and some of them have been classified by the International Agency for Research on Cancer as probable/possible human carcinogens. Their capability of formation even during ordinary cooking practices implies frequent exposure by the general public. Over the past 30 years, numerous studies have been stimulated aiming to alleviate human health risk associated with HAs. These studies contribute to the understanding of their formation, characterization, and quantification in foods; their mutagenesis/carcinogenesis, mechanisms of antimutagenesis by chemical or phytogenic modulators; and strategies to inhibit their formation. The chemistry of HAs, their implications in human health, factors influencing their formation, and feasible ways of suppression will be briefly reviewed. Their occurrence in trace amounts in foods necessitates continuous development and amelioration of analytical techniques. Various inhibitory strategies, ranging from modifying cooking conditions to incorporation of different modulators, have been developed. This will remain one of the foremost areas of research in the field of food chemistry and safety.

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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

Abstract: A rapid and simple scheme has been developed for the isolation and purification of two of the major mutagenic heterocyclic amines formed in heated beef products by affinity chromatography using monoclonal antibodies which recognize 2-amino-3-methylimidazo

Cited by 45 publications

References 22 publications

An improved analytical method for determination of heterocyclic amines in chicken legs

An improved analytical method for determination of heterocyclic amines in chicken legs

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

Heterocyclic amines: Chemistry and health

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