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The -carboline compounds 9H-pyrido[3,4-b]indole (norharman) and 1methyl-9H-pyrido[3,4-b]indole (harman) are formed during the pyrolysis of
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ENDOGENOUS FORMATION OF NOVEL HAAs
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tryptophan and are present at much higher amounts in tobacco condensates and cooked foods than are other pyrolytic or AIA HAAs (Fig. 2.3.1) (29). Norharman and harman are not mutagenic in S. typhimurium in the presence or absence of liver S9 fraction mixture; however, these -carbolines become mutagenic when incubated with non-mutagenic aniline or o-toluidine in the presence of S9 fraction mixture (30). The co-mutagenic effect was attributed to the formation of novel HAAs (31). The structures of these compounds have been determined as 9-(4 -aminophenyl)-9H-pyrido[3,4-b]indole (aminophenylnorharman, APNH), 9-(4 -amino-3-methyl-phenyl)-9H-pyrido [3,4-b]indole (aminomethyl-phenylnorharman, AMPNH), and 9-(4 -aminophenyl)-1-methyl-9H-pyrido[3,4-b]indole (aminophenylharman, APH); the compounds are produced by the respective reactions of norharman with aniline, norharman and o-toluidine, and harman with aniline (32). The formation of APH derivatives is proposed to occur via a P450 complex, where an ipso attack on the aniline (or toluidine) can occur by norharman or harman to produce these compounds (Fig. 2.3.3a). Human P450s 1A2 and 3A4 are the most active of the enzyme isoforms that catalyze this process (33). APNH is a liver and colon carcinogen in F344 rats (34). Moreover, APNH is present at comparable concentrations in the urine of smokers, nonsmokers, and patients
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Figure 2.3.3 Endogenous formation of HAAs: (a) formation of 9-(4 -aminophenyl)1-methyl-9H-pyrido[3,4-b]indole (APH) via a P450 complex with aniline (adapted from Reference 32 with permission); (b) formation of IQ[4,5-b] by reaction of 2aminobenzaldehyde with creatinine.
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receiving parenteral alimentation (35). These results suggest that APNH is a novel mutagen/carcinogen that is produced endogenously. 2-Amino-1-methylimidazo[4,5-b]quinoline (IQ[4,5-b]) is a weak bacterial mutagen (36, 37) and an isomer of IQ, a powerful experimental animal carcinogen (4). The amounts of IQ[4,5-b] measured in the urine of human volunteers who consumed grilled beef ranged from 15% to 135% of the ingested dose (38). Base treatment of urine at 70 C increased the amount of IQ[4,5-b] by more than 100-fold in carnivores and also in the urine of vegetarians. Moreover, IQ[4,5-b], but not IQ, 8-MeIQx, or PhIP, arose in the urine incubated for 3 h at 37 C: creatinine and 2-aminobenzaldehyde are the likely precursors of IQ[4,5-b] (Fig. 2.3.3b). These ndings suggest that IQ[4,5-b] is present in nonmeat staples, or alternatively that this HAA occurs endogenously within the urine or other biological uids.
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2.3.4 ANALYTICAL METHODS TO MEASURE HAAs Early investigations that sought to identify HAAs in cooked meat employed multiple chromatography steps, and the compounds were monitored, by the Ames bacterial mutagenesis S. typhimurium assay, at each step of the puri cation (39, 40). The nal puri cation step was done by HPLC. IQ, MeIQ, and 8MeIQx, the rst AIAs discovered, were originally isolated from grilled or broiled sh and meat (41 44). The puri ed mutagenic fractions were characterized by 1H NMR and mass spectrometry (MS) for structural elucidation, followed by chemical synthesis for corroboration of the structure (45, 46). These methods were extremely labor-intensive, and kg quantities of grilled meat were required to produce amounts of HAAs suf cient for spectroscopic measurements (41 44). Thereafter, a number of other AIAs were identi ed in cooked meats and poultry (3, 39, 47). The identi cation of PhIP was rst reported in 1986 (48). Although the mutagenic potency of PhIP is not as great as that of IQ, MeIQ, or 8-MeIQx, PhIP was estimated to account for 75% of the mass of genotoxic material attributed to characterized HAAs in fried ground beef. Because the mutagenic potencies of HAAs vary over a range of >10,000-fold in bacterial assays (4), only HAAs possessing high mutagenic activity or present in great abundance were successfully isolated and characterized from cooked meats when bacterial mutagenicity assays were employed for screening. The analysis of HAAs in cooked foods has been simpli ed through the advances in solid-phase extraction (SPE) methods, such as blue cotton and diatomaceous earth (silica). These SPE techniques permit the rapid isolation of many different HAAs from cooked meats and provide a cost-effective method of chemical analysis. Hayatsu discovered that copper phthalocyanine trisulfonate, a blue pigment commonly used in the dye industry, had a high af nity for aromatic compounds with three or more fused rings in their structure. This pigment, bound to a cotton support matrix, served as a selective
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