Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine, in airborne particles and diesel-exhaust particles

Manabe, Shigeo; Kurihara, Nobutaka; Wada, Osamu; Izumikawa, Sekio; Asakuno, Kunihiko; Morita, Masatoshi

doi:10.1016/0269-7491(93)90049-t

Cited by 67 publications

(33 citation statements)

References 21 publications

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“…HAs are formed from the Maillard reaction, involving creatine, creatinine, carbohydrates and free amino acids present in raw protein-rich food [3]. Other sources of exposure to HAs include diesel-exhaust particles [4,5], tobacco fumes [6] and cooking fumes [7 -9]. Based on evidences from animal experiments, the International Agency for Research on Cancer (IARC) classified eight HAs as possible human carcinogens (class 2B) and 1 as a probable human carcinogen (class 2A) [10].…”

Section: Introductionmentioning

confidence: 99%

Quantification of heterocyclic amines from thermally processed meats selected from a small‐scale population‐based study

Busquets

Mitjans

Puignou

et al. 2008

Molecular Nutrition Food Res

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Heterocyclic amines (HAs) are potent mutagens that form at high temperatures in cooked, protein-rich food. Due to their frequent intake, these compounds are considered a risk factor for human cancer. Cooking conditions and eating habits strongly influence the level of HA exposure. Thus, it is difficult to assess the intake of HAs in a large population. Food-frequency questionnaires (FFQs), designed to provide data on parameters that affect HA formation, were used to survey a small population (459 persons) from Barcelona (NE Spain). Subsequently, the most-consumed food items named were cooked according to the preferences of the population surveyed and analyzed for HAs using SPE and LC-MS/MS. In the population studied, the estimated intake via consumption of 13 meat dishes was 285.6 ng of mutagenic HAs per capita and day. PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) was the HA to which the population was most exposed, mainly from fried chicken and griddled beef. When the co-mutagens norharman and harman are included, the mean daily intake of HAs rises to 475.6 ng per capita and day. A novel putative DMIP regioisomer was detected in the cooked meats, which was analyzed in the present study by multistage MS

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Section: Introductionmentioning

confidence: 99%

Quantification of heterocyclic amines from thermally processed meats selected from a small‐scale population‐based study

Busquets

Mitjans

Puignou

et al. 2008

Molecular Nutrition Food Res

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show abstract

“…They also have been detected in processed food flavorings, beer, wine, cigarette smoke, smoke condensate formed during frying of beef patties and bacon, and in aerosol from cooking of stir-fried fish (National Toxicology Program, 2005). PhIP has been detected in airborne particles, diesel-exhaust particles, and incineration ash from garbage-burning plants (Manabe et al, 1993). …”

mentioning

confidence: 99%

Effect of N-Acetyltransferase 2 Polymorphism on Tumor Target Tissue DNA Adduct Levels in Rapid and Slow Acetylator Congenic Rats Administered 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine or 2-Amino-3,8-dimethylimidazo-[4,5-f]quinoxaline

Metry¹,

Neale²,

Bendaly³

et al. 2009

Drug Metab Dispos

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ABSTRACT:2-Amino-3,8-dimethylimidazo-[4,5-f ]quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) are suspected human carcinogens generated in well done meats. After N-hydroxylation, they are O-acetylated by N-acetyltransferase 2 (NAT2) to electrophiles that form DNA adducts. dG-C8-MeIQx and dG-C8-PhIP adducts have been identified in human tissues. In the female rat, administration of PhIP leads to mammary and colon tumors, whereas MeIQx induces liver tumors. Both humans and rats exhibit NAT2 genetic polymorphism yielding rapid and slow acetylator phenotypes. Because O-acetylation is an activation pathway, we hypothesized that MeIQx-and PhIP-induced DNA damage would be greater in tumor target tissues and higher in rapid than slow NAT2 acetylators. Adult female rapid and slow acetylator rats congenic at the Nat2 locus received a single dose of 25 mg/kg MeIQx or 50 mg/kg PhIP by gavage, and tissue DNA was isolated after 24 h. Deoxyribonucleoside adducts were identified and quantified by capillary liquid chromatography-tandem mass spectrometry using isotope dilution methods with deuterated internal standards. Major adducts were those bound to the C8 position of deoxyguanosine. dG-C8-PhIP DNA adducts were highest in colon, lowest in liver and did not significantly differ between rapid and slow acetylator congenic rats in any tissue tested. In contrast, dG-C8-MeIQx adducts were highest in liver and significantly (p < 0.001) higher in rapid acetylator liver than in slow acetylator liver. Our results are consistent with the tumor target specificity of PhIP and MeIQx and with increased susceptibility to MeIQx-induced liver tumors in rapid NAT2 acetylators. -3,8-dimethylimidazo-[4,5-f ]quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) are potent and abundant mutagens in the human diet, formed during high temperature cooking of meats (Keating and Bogen, 2004). They also have been detected in processed food flavorings, beer, wine, cigarette smoke, smoke condensate formed during frying of beef patties and bacon, and in aerosol from cooking of stir-fried fish (National Toxicology Program, 2005). PhIP has been detected in airborne particles, diesel-exhaust particles, and incineration ash from garbage-burning plants (Manabe et al., 1993). 2-AminoBoth MeIQx and PhIP induce tumors in the rat (Sugimura et al., 2004) and are designated as "reasonably anticipated to be a human carcinogen" (National Toxicology Program, 2005). MeIQx induces liver tumors in mice (Ohgaki et al., 1987) and up to 100% incidence of hepatic tumors in rats (Kato et al., 1988;Kushida et al., 1994). PhIP target organ specificity differs from MeIQx in the rat because it induces tumors in colon, prostate, and mammary tissue (Sugimura et al., 2004). MeIQx-and PhIP-induced DNA adduct formation and carcinogenesis require N-hydroxylation, which occurs at relatively high rates in humans (Stil1well et al., 1999;Turesky 2002). N-Hydroxy-MeIQx and -PhIP are further O-acetylated by N-acetyltransferase 2 (NAT2) to a...

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“…These HAAs have been isolated from proteinaceous foods including cooked meats and fish, meat extracts or process flavours. They are also present in cooking fumes (Yen & Hsieh, 1994), several foods (Knize, Kunningham, Griffin, Jones, & Felton, 1994) coffee (Casal, Mendes, Fernandes, Oliveira, & Ferreira, 2004), alcohol beverages (Richling, Decker, Haring, Herderich, & Schraier, 1997), and from environmental sources, such as cigarette smoke (Manabe et al, 1993), air (Manabe et al, 1993), river and rain water (Wu, Wong, Lee, & Ong, 1995). Also, some HAAs have been detected in human tissues (Prabhu et al, 2001), hair (Hegstag et al, 2000), and in biological fluids, such as plasma, urine o bile (Friesen, Garren, Bereziat, Kadlubar, & Lin, 1993), as well as in milk of healthy women (DeBruin, Martos, & Josephy, 2001).…”

Section: Introductionmentioning

confidence: 97%

Determination of mutagenic amines in water and food samples by high pressure liquid chromatography with amperometric detection using a multiwall carbon nanotubes-glassy carbon electrode

et al. 2016

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Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine, in airborne particles and diesel-exhaust particles

Cited by 67 publications

References 21 publications

Quantification of heterocyclic amines from thermally processed meats selected from a small‐scale population‐based study

Quantification of heterocyclic amines from thermally processed meats selected from a small‐scale population‐based study

Effect of N-Acetyltransferase 2 Polymorphism on Tumor Target Tissue DNA Adduct Levels in Rapid and Slow Acetylator Congenic Rats Administered 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine or 2-Amino-3,8-dimethylimidazo-[4,5-f]quinoxaline

Determination of mutagenic amines in water and food samples by high pressure liquid chromatography with amperometric detection using a multiwall carbon nanotubes-glassy carbon electrode

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