Skip to main content
SpringerLink
Log in

Heterocyclic Amines: New Mutagens and Carcinogenes in Cooked Foods

  • Chapter
Biological Reactive Intermediates IV

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 283))

Abstract

Studies on heterocyclic amines (HAs), mutagens and carcinogens were initiated by the simple idea that smoke produced with broiling fish and meat should contain carcinogenic compounds as cigarette smoke does. Soon it was found that not only smoke produced by cooking fish and met, but also charred parts on fish and meat contained high mutagenic activity (Sugimura, T., et al., 1977). Among pyrolysates of food components, only that of protein showed strong mutagenic activity (Nago, M., et al., 1977). This led to the isolations of mutagens from pyrolysates of amino acids and proteins. Microbial assay using Salmonella typhimurium TA98 with metabolic activation was used for montoring the purifications of mutagens, and HAs such as Trp-P-1, Trp-P-2, Glu-P-1-2, A α C and MeA α C (see Table 1 for full names) were isolated as new mutagens (Sugimura, T., et al., 1982; Sugimura, T., et al. 1986; Sugimura T., et al., 1988; Yoshida, D., et al., 1978).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  • Adamson, R.H., Thorgeirsson, U.P., Snyderwine, E.G., Thorgeirsson, S.S., Reeves, J., Dalgard, D.W., Takayama, S. and Sugimura, T. (1990). Carcinogenicity of 2amino-3-methylimidazo[4,5-f)-quinoline in nonhuman primates: Induction of tumors in three Macaques. Jpn. J. Cancer Res. 81, 10–14.

    Article  CAS  PubMed  Google Scholar 

  • Aoyama, T., Gonzalez, F.J. and Gelboin, H.V. (1989). Mutagen activation by cDNAexpressed P1450, P3450, and P450a. Mol. Carcinog. 1, 253–259.

    Article  CAS  PubMed  Google Scholar 

  • Barnes, W.S., Lovelette, C.A., tong, C., Wiliams, G.M. and Weisburger, J.H. (1985). Genotoxicity of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and analogs. Carcinogenesis 6, 441–444.

    Article  CAS  PubMed  Google Scholar 

  • Becher, G., Knize, M.G., Nes, I.F. and Felton, J.S. (1988). Isolation and identification of mutagens from a fried Norwegian meat product. Carcinogenesis 9, 247–253.

    Article  CAS  PubMed  Google Scholar 

  • Caderni, G., Kreamer, B.L. and Dolara, P. (1983). DNA damage of mammalian cells by the beef extract mutagen 2-amino-3-methylimidaxo[4,5-f]quinoline. Food. Chem. Toxicol. 21, 641–643.

    Article  CAS  PubMed  Google Scholar 

  • Cortesi, E. and Dolara, P. (1983). Neoplastic transformation of BALB 3T3 mouse embryo fibroblasts by the beef extract mutagen 2-amino-3-methylimidazo[4,5f)quinoline. Cancer Lett. 20, 43–47.

    Article  CAS  PubMed  Google Scholar 

  • Esumi, H., Ohgaki, H., Kohzen, E., Takayama, S., and Sugimura, T. (1989). Induction of lymphoma in CDF1 mice by the food mutagen, 2-amino-l-methyl-6phenylimidazo[4,5–12]pyridine. Jpn. J. Cancer Res. 80, 1176–1178.

    Article  CAS  PubMed  Google Scholar 

  • Felton, J.S., Knize, M.G., Shen, N.H., Lewis, P.R., Andreson, B.D., Happe, J. and Hatch, F.T. (1986). The isolation and identification of a new mutagen from fried ground beef: 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP). Carcinogenesis 7, 1081–1086.

    Article  CAS  PubMed  Google Scholar 

  • Felton, J.S., Knize, M.G., Wood, C., Wuebbles, B.J., Healy, S.K., Stuermer, D.H., Bjeldanes, L.F., Kimble, B.H. and Hatch, F.T. (1984). Isolation and characterization of new mutagens from fried ground beef. Carcinogenesis 5, 95102.

    Article  Google Scholar 

  • Grivas, S., Nyhammar, T., Olsson, K. and Jägerstad, M. (1985). Formatin of a new mutagenic DiMeIQx compound in a model system by heating creatinine, alanine and fructose. Mutat. Res. 151, 177–183.

    Article  CAS  PubMed  Google Scholar 

  • Grivas, S., Nyhammar, T., Olsson, K. and Jägerstad, M. (1986). Isolation and identification of the food mutagens IQ and McIQx from a heated model system of creatinine, glycine and fructose. Food Chem. 20, 127–136.

    Article  CAS  Google Scholar 

  • Grose, K.R., Grant, J.L., Bjeldanes, L.F., Andreson, B.D., Heales, S.K., Lewis, P.R., Felton, J.S. and Hatch, F.T. (1986). Isolation of the carcinogen IQ from fried egg patties. J. Agric. Food. Cehm. 34, 201–202.

    Article  CAS  Google Scholar 

  • Gross, G.A., Philippossian, G. and Aeschbacher, H.U. (1989). An efficient and convenient method for the purification of mutagenic heterocyclic amines in heated meat products. Carcinogenesis 10, 1175–1182.

    Article  CAS  PubMed  Google Scholar 

  • Hargraves, W.A. and Pariza, M.W. (1983). Pruification and mass spectral characterization of bacterial mutagens from commercial beef extract. Cancer Res. 43, 1467–1472.

    CAS  PubMed  Google Scholar 

  • Hashimoto, Y., Shudo, K. and Okamoto, T. (1980). Metabolic activation of a mutagen, 2-amino-6-methyldipyrido[1,2-a:31,21-dlimidazole. Identification of 2- hydroxyamino-6-methyldipyrido[1,2-a:31,21-sgimidazole and its reaction with DNA. Biochem. Biophys. Res. Commun. 92, 971–976.

    Article  CAS  PubMed  Google Scholar 

  • Hashimoto, Y., Shudo, K. and Okamoto, T. (1980). Activation of a mutagen, 3-amino-1-methy1–5H-pyrido[4,3–12]indole. Identification of 3-hydroxyamino-l-methyl-5H-pyrido[4,3–12]indole and its reaction with DNA. Biochem. Biophys. Res. Commun. 96, 355–362.

    Article  CAS  PubMed  Google Scholar 

  • Hayatsu, H., Matsui, Y., Ohara, Y., Oka, T. and Hayatsu, T. (1983). Characterization of mutagenic fractions in beef extract and in cooked ground beef. Use of blue-cotton for efficient extration. Gann. 74, 472–482.

    CAS  PubMed  Google Scholar 

  • Hayatsu, H., Oka, T., Wakata, A., Ohara, Y., Hayatsu, T., Kobayashi, H., and Arimoto, S. (1983). Adsorption of mutagens to cotton bearing covalently bound trisulfocopper-phthalocyanine. Mutat. Res., 119, 233–238.

    Article  CAS  PubMed  Google Scholar 

  • Hayatsu, H., Hayatsu, T., and Ohara, Y. (1985). Mutagenicity of human urine caused by ingestion of fried ground beef. Jpn. J. Cancer. Res. (Gann) 76, 445–448.

    CAS  Google Scholar 

  • Hayatsu, H. (1990). Blue cotton-broad possibility in assessing mutagens/carcinogens in the environment. In, Advances in Mutagenesis Research-1, G. Obe, ed., pp. 1–26, Springer-Verlag, Berlin.

    Chapter  Google Scholar 

  • Holme, J.A., Wallin, H., Brunborg, G., Soderlund, E.J., Hongslo, J.K. and Alexander, J. (1989). Genotoxicity of the food mutagen 2-amino-l-methy1–6- phenylimidazo[4,5–12]pyridine (PhIP): formation of 2-hydroxamino-PhIP, a directly acting genotoxic metabolite. CcuTinogenesis 10, 1389–1396.

    Article  CAS  Google Scholar 

  • Int. Agency Res. Cancer (1987), “IARC Monographs on the Evaluation of Carcinogenic Risks to Humans” Supplement 6, Genetic and related effects: an updating of selected IARC Monographs from Volumes 1 to 42, Int. Agency Res. Cancer, Lyon, pp. 40–45.

    Google Scholar 

  • Ishida, Y., Negishi, C., Umemoto, A., Fujita, Y., Sato, S., Sugimura, T., Thorgeirsson, S.S. and Adamson, R.H. (1987). Activation of mutagenic and carcinogenic heterocyclic amines by S-9 from the liver of a rhesus monkey. Toxic. In Vitro 1, 45–48.

    Google Scholar 

  • Ishidate, M. (1983). Chromosomal aberration test in vitro (M. Ishidate, ed.) p. 256, Realize Inc., Tokyo.

    Google Scholar 

  • Ishikawa, T., Takayama, S., Kitagawa, T., Kawachi, T., Kinebuchi, M., Matsukura, N., Uchida, E. and Sugimura, T. (1979). In vivo experiments on tryptophan pyrolysis products. In, Naturally Occurring Carcinogens-Mutagens and Modulators of Carcinogenesis. E.C. Miller, J.A. Miller, I. Hirono, T. Sugimura, and S. Takayama eds., pp. 159–167, Japan Scientific Societies Press/University Park Press, Tokyo/Baltimore.

    Google Scholar 

  • Jägerstad, M., Olsson, K., Grivas, S., Negishi, C., Wakabayashi, K., Tsuda, M., Sato, S. and Sugimura, T. (1984). Formation of 2-amino-3,8-dimethylimidazo[4,5- fiquinoxaline in a model system by heating creatinine, glycine and glucose. Mutat. Res. 126, 239–244.

    Article  PubMed  Google Scholar 

  • Kato, R., and Yamazoe, Y. (1987). Metabolic activation and covalent binding to nucleic acids of carcinogenic heterocyclic amines from cooked foods and amino acid pyrolysates. Jpn. J. Cancer Res. (Gann), 78, 297–311.

    CAS  Google Scholar 

  • Kikugawa, K., Kato, T. and Takahashi, S. (1989). Possible presence of 2-amino-3,4- dimethylimidazo[4,5-flquinoline and other heterocyclic amine-like mutagens in roasted coffee beans. J. Agric. Food. Chem. 37, 881–886.

    Article  CAS  Google Scholar 

  • Knudson, A.G. (1985). Hereditary cancer, oncogenes, and antioncogenes. Cancer Res. 45, 1437–1443.

    CAS  PubMed  Google Scholar 

  • Kondo, S., and Ichikawa-Ryo, H. (1973). Testing and classification of mutagenicity of furylfuramide in Escherichia coli. Jpn. J. Genet., 48, 295–300.

    Google Scholar 

  • Matsumoto, T., Yoshida, D. and Tomita, H. (1981). Determination of mutagens, amino-carbolines in grilled foods and cigarette smoke condensate. Cancer Lett. 12, 105–110.

    Article  CAS  PubMed  Google Scholar 

  • McManus, M.E., Felton, J.S., Knize, M.G., Burgess, W.M., roberts-Thomson, S., Pond, S.M., Stupans, I. and Veronese, M.E. (1989). Activation of the food-derived mutagen 2-amino-l-methy1–6-phenylimidazo-[4,5-blpyridine by rabbit and human liver microsomes and purified forms of cytochrome P-450. Carcinogenesis 10, 357–363.

    Article  CAS  PubMed  Google Scholar 

  • Mori, N., Yokota, J., Oshimura, M., Cavenee, W.K., Mizoguchi, H., Noguchi, M., Shimosato, Y., Sugimura, T. and Terada, M. (1989). Concordant deletions of chromosome 3p and loss of heterozygosity for chromosomes 13 and 17 in small cell lung carcinoma. Cancer Res. 49, 5130–5135.

    CAS  PubMed  Google Scholar 

  • Murray, S., Gooderham, N.J., Boobis, A.R. and Davies, D.S. (1988). Measurement of McIQx and DiMeIQx in fried beef by capillary column gas chromatography electron capture negative ion chemical ionisation mass spectrometry. Carcinogenesis 9, 321–325.

    Article  CAS  PubMed  Google Scholar 

  • Nagao, M., Honda, M., Seino, Y., Yahagi, T., Kawachi, T. and Sugimura, T. (1977). Mutagenicities of protein pyrolysates. Cancer Lett. 2, 335–340.

    Article  CAS  PubMed  Google Scholar 

  • Nakayasu, M., Nakasato, F., Sakamoto, H., Terada, M. and Sugimura, T. (1983). Mutagenic activity of heterocyclic amines in Chinese hamster lung cells with diphtheria toxin resistance as a mrker. Mutat. Res. 118, 91–102.

    Article  CAS  PubMed  Google Scholar 

  • Negishi, C., Wakabayashi, K., Tsuda, M., Sato, S., Sugimura, T., Saito, H., Maeda, M. and Jägerstad, M. (1984). Formation of 2-amino-3,7,8-trimethylimidazo[4,5f]quinoxaline, a new mutagen, by heating a mixture of creatinine, glucose and glycine. Mutat. Res., 140, 55–59.

    Article  CAS  PubMed  Google Scholar 

  • Negishi, C., Wakabayashi, K., Yamaizumi, Z., Saito, H., Sato, S., Sugimura, T. and Jägerstad, M. (1985). Identification of 4,8-DiMeIQx, a new mutagen,. Selected Abstracts of Papers presented at the 13th Annual Meeting of the Environemntal Mutagen Society of Japan, 12–13 Oct. 1984, Yokyo (Japan). Mutat. Res. 147, 267–268.

    Google Scholar 

  • Nemoto, N. and Takayama, S. (1984). Activation of 2-amino-6-methyl-dipyrido[1,2a:3’,2’-Jimidazole, a mutagenic pyrolysis product of glutamic acid, to bind to microsomal protein by NADPH-dependent and -independent enzyme systems. Carcinogenesis 5, 653–656.

    Article  CAS  PubMed  Google Scholar 

  • Petry, T.W., Josephy, P.D., Pagano, D.A., Zeiger, E., Knecht, K.T. and Eling, T.E. (1989). Prostaglandin hydroperoxidase-dependent activation of heterocyclic aromatic amines. Carcinogenesis 10, 2201–2207.

    Article  CAS  PubMed  Google Scholar 

  • Sato, H., Takahashi, M., Furukawa, F., Miyakawa, Y., Hasegawa, R., Toyada, K., Hayashi, Y. (1987). Initiating activity in a two-stage mouse skin model of nine mutagenic pyrolysates of amino acids, soybean globulin and proteinaceous food. Carcinogenesis 8, 1231–1234.

    Article  CAS  PubMed  Google Scholar 

  • Snyderwine, E.G., Yamashita, K., Adamson, R.H., Sato, S., Nagao, M., Sugimura, T. and Thorgeirsson, S.S. (1988). Use of the 32P-postlabeling method to detect DNA adducts of 2-amino-3-methylimidazo[4,5-flquinoline (IQ) in monkeys fed IQ: identification of the N-(deoxyguanosin-8-yl)-IQ adduct. Carcinogenesis 9, 1739–1743.

    Article  CAS  PubMed  Google Scholar 

  • Snyderwine, E.G., Wirth, P.J., Roller, P.P., Adamson, R.H., Sato, S. and Thorgeirsson, S.S. (1988). Mutagenicity and in vitro covalent DNA binding of 2-hydroxyamino3-methylimidazolo[4,5-flquinoline. Carcinogenesis 9, 411–418.

    Article  CAS  PubMed  Google Scholar 

  • Snyderwine, E.G., Roller, P.P., Adamson, R.H., Sato, S. and Thorgeirsson, S.S. (1988). Reaction of N-hydroxylamine and N-acetoxy derivatives of 2-amino-3methylimidazo[4,5-f]quinoline with DNA. Synthesis and identification of N(deoxyguanosin-8-yl)-IQ. Carcinogenesis 9, 1061–1065.

    CAS  Google Scholar 

  • Snyderwine, E.G. and Battula, N. (1989). Selective mutagenic activation by cytochrome P3–450 of carcinogenic arylamines found in foods. J. Natl. Cancer Inst. 81, 223–227.

    Article  CAS  PubMed  Google Scholar 

  • Sugimura, T., Nagao, M., Kawachi, T., Honda, M., Yahagi, T., Seino, Y., Sato, S., Matsukura, N., Matsushima, T., Shirai, A., Sawamura, M. and Matsumoto, H. (1977) Mutagen-carcinogens in food, with special reference to highly mutagenic pyrolytic products in broiled foods. In, Origins of Human Cancer ( H.H. Hiatt, J.D. Watson, and J.A. Winsten, eds.), pp. 1561–1577. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.

    Google Scholar 

  • Sugimura, T. (1982). Mutagens, carcinogens, and tumor promoters in our daily food. Cancer 49, 1970–1984.

    Article  CAS  PubMed  Google Scholar 

  • Sugimura, T. (1986). Studies on environmental chemical carcinogenesis in Japan. Science, 233, 312–318.

    Article  CAS  PubMed  Google Scholar 

  • Sugimura, T., Sato, S. and Wakabayashi, K. (1988). Mutagens/carcinogens in pyrolysates of amino acids and proteins and in cooked foods: heterocyclic aromatic amines. In Chemical Induction of Cancer, Structural Bases and Biological Mechanisms (Y-T. Woo, D.Y. Lai, J.C. Arcos, and M.F. Argus eds.), Vol. IIIC, pp, 681–710, Academic Press, San Deigo.

    Google Scholar 

  • Takahashi, M., Wakabayashi, K., Nagao, M., Yamamoto, M., Masui, T., Goto, T., Kinae, N., Tomita, I. and Sugimura T. (1985). Quantification of 2-amino-3- methylimidazo[4,5–1quinoline (IQ) and 2-amino-3-dimethylimidazo[4,5- flquinoxaline (MeIQx) in beef extracts by liquid chromatography with electrochemical detection (LCEC). Carcinogenesis 6, 1195–1199.

    Article  CAS  PubMed  Google Scholar 

  • Takahashi, M., Furukawa, F., Miyakawa, Y., Sato, H., Hasegawa, R. and Hayashi, Y. (1986). 3-Amino-l-methy1–5H-pyrido[4,3-blindole initiates two-stage carcinogenesis in mouse skin but is not a complete carcinogen. Jpn. J. Cancer. Res. (Gann) 77, 509–513.

    Google Scholar 

  • Takayama, S., Katoh, Y., Tanaka, M., Nagao, M., Wakabayashi, K., and Sugimura, T. (1977). In vitro transformation of hamster embryo cells with tryptophan pyrolysis products. Proc. Jpn. Acad. 53B, 126–129.

    CAS  Google Scholar 

  • Takayama, S., Hirakawa, T., Tanaka, M., Kawachi, T. and Sugimura, T. (1979). In vitro transformation of hamster embryo cells with a glutamic acid pyrolysis product. Toxicol. Lett. 4, 281–284.

    CAS  Google Scholar 

  • Tanaka, T., Barnes, W.S., Williams, G.M. and Weisburger, J.H. (1985). Multipotential carcinogenicity of the fried food mutgen 2-amino-3-methylimidazo[4,5- flquinoline in rats. Jpn. J. Cancer Res. (Gann) 76, 570–576.

    CAS  Google Scholar 

  • Thompson, L.H., Carrano, A.V., Salazar, E., Felton, J.S. and Hatch, F.T. (1983). Comparative genotoxic effects of the cooked-food-related mutagens Trp-P-2 and IQ in bacteria and cultured mammalian cells. Mutat. Res. 117, 243–257.

    Article  CAS  PubMed  Google Scholar 

  • Tohda, H., Oikawa, A., Kawachi, T. and Sugimura, T. (1980). Induction of sister-chromatid exchanges by mutgens from amino acid and protein pyrolysates. Mutat. Res. 77, 65–69.

    Article  CAS  PubMed  Google Scholar 

  • Tsuda, H., Asamoto, M., Ogiso, T., Inoue, T., Ito, N. and Nagao, M. (1988). Dose-dependent induction of liver and thyroid neoplastic lesions by short-term administration of 2-amino-3-methylimidazo[4,5-flquinoline combined with partial hepatectomy followed by phenobarbital or low dose 3’-methy1–4- dimethylaminoazobenzene promotion. Jpn. J. Cancer. Res. (Gann) 79, 691–697.

    Article  CAS  Google Scholar 

  • Turesky, R.J., Wishnok, J.S., Tannenbaum, S.R., Pfund, R.A. and Buchi, G.H. (1983). Qualitative and quantitative characterization of mutagens in commercial beef extract. Carcinogenesis 4, 863–866.

    Article  CAS  PubMed  Google Scholar 

  • Turesky, R.J., Bur, H., Huynh-Ba, T., Aeschbacher, H.U. and Milon, H. (1988). Analysis of mutagenic heterocyclic amines in cooked beef products by high-performance liquid chromatography in combination with mass spectrometry. Fd. Chem. Toxic. 26, 501–509.

    Article  CAS  Google Scholar 

  • Vogelstein, B., Fearon, E.R., Hamilton, S.R., Kern, S.E., Preisinger, A.C., Leppert, M., Nakamura, Y., White, R., Smits, A.M.M. and bos, J.L. (1988). Genetic alterations during colorectal-tumor development. N. Engl. J. Med. 319, 525–532.

    Article  CAS  PubMed  Google Scholar 

  • Wild, D. and Degen, G.H. (1987). Prostaglandin H synthase-dependent mutagenic activation of heterocyclic aromatic amines of the IQ-type. Carcinogenesis 8, 541–545.

    Article  CAS  PubMed  Google Scholar 

  • Yahagi, T., Nagao, M., Hara, K., Matsushima, T., Sugimura, T. and Bryan, G.T. (1974). Relationships between the carcinogenic and mutagenic or DNA-modifying effects of nitrofuran derivatives, including 2-(2-fury1)-3-(5-nitro-2- furyl)acrylamide, a food additive. Cancer Res. 34, 2266–2273.

    CAS  PubMed  Google Scholar 

  • Yamada, H., Yoshida, T., Sakamoto, H., Terada, M. and Sugimura, T. (1986). Establishment of a human pancreatic adenocarcinoma cell line (PSN-1) with amplifications of both c-myc and activated c-Ki-ras by a point mutation. Biochem. Biophys. Res. Commun. 140, 167–173.

    Article  CAS  Google Scholar 

  • Yamaguchi, K., Shudo, K., Okamoto, T., Sugimura, T. and Kosuge, T. (1980). Presence of 2-aminodipyrido[1,2-a:3’,2’4imidazole in broiled cuttlefish. Gann. 71, 743–744.

    CAS  PubMed  Google Scholar 

  • Yamaizumi, Z., Shiomi, T., Kasai, H., Nishimura, S., Takahashi, Y., Nagao, M. and Sugimura, T. (1980). Detection of potent mutagens, Trp-P-1 and Trp-P-2, in broiled fish. Cancer Lett. 9, 75–83.

    Article  CAS  PubMed  Google Scholar 

  • Yamaizumi, Z., Kasai, H., Nishimura, S., Edmonds, C.G. and McCloskey, J.A. (1986). Stable isotope dilution quantification of mutagens in cooked foods by combined liquid chromatography-thermospray mass spectrometry. Mutat. Res. 173, 1–7.

    Article  CAS  PubMed  Google Scholar 

  • Yamashita, K., Adachi, M., Kato, S., Nakagama, H., Ochiai, M., Wakabayashi, K., Sato, S., Nagao, M. and Sugimura, T. (1990). DNA adducts formed by 2-amino-3,8- dimethylimidazo[4,5-nquinoxaline in rat liver: dose-response on chronic administration. Jpn. J. Cancer. Res. in press.

    Google Scholar 

  • Yamazoe, Y., Abu-Zeid, M., Yamaguchi, K., and Kato, R. (1988). Metabolic activation of pyrolysate arylamines by human liver microsomes: possible involvement of a P-448-H type cytochrome P-450. Jpn. J. Cancer Res. (Gann) 79, 1159–1167.

    Article  CAS  PubMed  Google Scholar 

  • Yamazoe, Y., Abu-Zeid, M., Manabe, S., Toyama, S. and Kato, R. (1988). Metabolic activation of a protein pyrolysate promutagen 2-amino-3,8-dimethylimidazo[4,5- flquinoxaline by rat liver microsomes and purified cytochrome P450. Carcinogenesis 9, 05–109.

    Google Scholar 

  • Yokota, J., Wada, M., Shimosato, Y., Terada, M. and Sugimura, T. (1987). Loss of heterozygosity on chromosomes 3, 13, and 17 in small-cell carcinoma and on chromosome 3 in adenocarcinoma of the lung. Proc. Natl. Acad. Sci. USA 84, 9252–9256.

    Article  CAS  PubMed  Google Scholar 

  • Yokota, J., Tsukada, Y., Nakajima, T., Gotoh, M., Shimosato, Y., Mori, N., Tsunokawa, Y., Sugimura, T. and Terada, M. (1989). Loss of heterozygosity on the short arm of chromosome 3 in carcinoma of the uterine cervix. Cancer Res. 49, 3598–3601.

    CAS  PubMed  Google Scholar 

  • Yoo, M.A., Ryo, H., Todo, T. and Kondo, S. (1985). Mutagenic potency of heterocyclic amines in the Drosophila wing spot test and its correlation to carcinogenic potency. Jpn. J. Cancer Res. (Gann), 76, 468–473.

    CAS  PubMed  Google Scholar 

  • Yoshida, D., Matsumoto, T., Yoshimura, R., and Matsuzaki, T. (1978). Mutagenicity of amino-a-carbolines in pyrolysis products of soybean globulin. Biochem. Biophys. Res. Commun. 83, 915–920.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, X-M., Wakabayashi, K., Liu, Z-C., Sugimura, T. and Nagao, M. (1988). Mutagenic and carcinogenic heterocyclic amines in Chinese cooked foods. Mutat. Res. 201, 181–188.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National Cancer Center, 1-1, Tsukiji 5-Chome, Chuo-ku Tokyo 104, Japan

    Takashi Sugimura & Keiji Wakabayashi

Authors
  1. Takashi Sugimura
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Keiji Wakabayashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Rutgers University, Piscataway, New Jersey, USA

    Charlotte M. Witmer  & Robert R. Snyder  & 

  2. Medical University of South Carolina, Charleston, South Carolina, USA

    David J. Jollow

  3. Thomas Jefferson University, Philadelphia, Pennsylvania, USA

    George F. Kalf  & James J. Kocsis  & 

  4. University of Arizona, Tucson, Arizona, USA

    I. Glenn Sipes

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Plenum Press, New York

About this chapter

Cite this chapter

Sugimura, T., Wakabayashi, K. (1991). Heterocyclic Amines: New Mutagens and Carcinogenes in Cooked Foods. In: Witmer, C.M., Snyder, R.R., Jollow, D.J., Kalf, G.F., Kocsis, J.J., Sipes, I.G. (eds) Biological Reactive Intermediates IV. Advances in Experimental Medicine and Biology, vol 283. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5877-0_72

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-5877-0_72

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5879-4

  • Online ISBN: 978-1-4684-5877-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation