Heterocyclic aromatic amines mass spectrometry

Bianchi, F. et al. Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair hquid chromatography coupled with tandem mass spectrometry the role of ion-pair reagents on LC-MS/MS sensitivity. J. Chromatogr. B. 2005, 825, 193-200. 

Calbiani, F. et al. Validation of an ion-pair liquid chromatography-electrospray-tandem mass spectrometry method for the determination of heterocyclic aromatic amines in meat-based infant foods. FoodAddit. Contam. 2007, 24, 833-841. 

Richling E., Kleinschnitz, M. and Schreier P. Analysis of heterocyclic aromatic amines by high resolution gas chromatography-mass spectrometry a suitable technique for the routine control of food and process flavors. European Food Research and Technology. 210,68.1999. 

Many publications exist in the field of food analyses. Gerda Morlock described in 2004 the determination of heterocyclic aromatic amines after a 6-step AMD-separation. She used an HPTLC-MS online extractor, developed by Luftmarm [93a]. In 2004 a patent application was made for the mode of operation of this so-called ChromeXtrakt device [93b]. In her latest paper (2006), the quantification of isopropylthioxanthon (ITX) in food using HPTLC/FLD coupled with ESI-MS and DART-MS was reported. The prepared samples were separated on a HPTLC-plate and determined by a fluorescence detector (FLD). Positive results have been verified by ESI-MS (Electrospray-Ionisation-Mass-Spectrometry) and DART-MS (Direct Analysis in Real Trme-Mass-Spectrometry) [93c]. 

Riching, E., Herderich, M., and Schreier, P., High performance liquid chromatography-electrospray tandum mass spectrometry (HPLC-ESI-MS-MS) for the analysis of heterocyclic aromatic amines (HAA), Chromatographia, 42, 7-11, 1996. 

Jamin, E., Chevolleau, S., Touzet, C., Tulliez, J., and Debrauwer, L. 2007. Assessment of metastable atom bombardment (MAB) ionization mass spectrometry for the fast determination of heterocyclic aromatic amines in cooked meat Anal. Bioanal. Chem. 387 2931-2941. 

Richling, E., Decker, C., Haring, D., Herderich, M., and Schraier P. 1997. Analysis of heterocyclic aromatic amines in wine by high-performance hquid chromatography-electrospray tandem mass spectrometry. J. Chromatogr. A 791 71-77. 

Casal, S., Mendes, E., Fernandes, J. O., Ohveira, M. B. P. P., and Ferreira, M. A. 2004. Analysis of heterocyclic aromatic amines in foods by gas chromatography-mass spectrometry as their tert.-butyldimethylsilyl derivatives. J. Chromatogr. A 1040 105-114. 

Barceld-Barrachina, E., Moyano, E., Puignou, L., and Galceran, M. T. 2004a. Evaluation of reversed-phase columns for the analysis of heterocyclic aromatic amines by liquid chromatography-electrospray mass spectrometry. J. Chromatogr. B 802 45-59. 

Guy, P. A., Gremaud, E., Richoz, J., and Turesky, R. J. 2000. Quantitative analysis of mutagenic heterocyclic aromatic amines in cooked meat using liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry. J. Chromatogr. A 883 89-102. 

Ni W., McNaughton L., Lemaster D.M., Sinha R., Turesky R.J. Quantitation of 13 heterocyclic aromatic amines in cooked beef, pork, and chicken by liquid chromatography-electrospray ionization/tandem mass spectrometry. Journal of Agricultural and Food Chemistry, 56 ... 

Sentellas S, Moyano E, Puignou L, Galceran MT (2003) Determination of heterocyclic aromatic amines by capillary electrophoresis coupled to mass spectrometry using in-line preconcentration. Electrophoresis 24 3075-3082. doi 10.1002/elps.200305523... 

Reactions of 5f/-2-methyl-l,2,4-triazepino[2,3- ]benzimidazol-4-one 71, prepared by reaction of 1,2-diaminobenz-imidazole 72 with acetoacetic ester 73, with different reagents was described, in the search of new heterocycles with biological activity <2002CHE598>. When lactam 71 was treated with aromatic aldehydes in boiling 1-BuOH with addition of piperidine 74, 577-3-arylidene-2-methyl-l,2,4-triazepino[2,3- ]benzimidazol-4-ones 75a-c were obtained (Scheme 7). Coupling lactam 71 with phenyldiazonium chloride 76 in dioxane afforded the 3-phenylazo-substituted tricycle 77. When 71 was treated with phosphorus pentasulfide 78 in boiling dioxane or pyridine, its thio analog 79 was obtained. The reaction proceeded most efficiently when lactam 71 was refluxed with twofold excess of 78 in dry dioxane. These thiones 79 react with ammonia and amines by nucleophilic substitution. When 79 was refluxed with ammonia, benzylamine, piperidine, or morpholine, the 4-amino-substituted tricycles 80a-d were obtained. All the described compounds were identified by NMR, mass spectrometry, and IR spectroscopy. 

HA, heterocyclic amine AA, aromatic amine PA, polyamine Al, aliphatic amine N, nitrosamine BCD, electrochemical UV, ultraviolet FL, fluorescence TSI, thermospray ionization ESI, electrospray ionization MS, MS-tandem mass spectrometry SIM, selected ion monitoring A, air H, water W, waste. 

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