Mutational spectra of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) at the Chinese hamster hprt locus

Carcinogenesis

Volumn 17, Issue 4, 1996, Pages 617-624

  Yadollahi Farsani, Masoud ^a   Gooderham, Nigel J ^a   Davies, Donald S ^a   Boobis, Alan R ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; ADENINE; CARCINOGEN; CYTOCHROME P450; GUANINE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; TIOGUANINE;

ANIMAL CELL; ARTICLE; CELL CULTURE; CHINESE HAMSTER; COLON TUMOR; CONTROLLED STUDY; DNA ADDUCT; DNA REPAIR; DNA SEQUENCE; DNA TRANSCRIPTION; DOSE RESPONSE; FRAMESHIFT MUTATION; GENE LOCUS; GENE MUTATION; MUTATION RATE; NONHUMAN; NUCLEIC ACID BASE SUBSTITUTION; PRIORITY JOURNAL; TUMOR SUPPRESSOR GENE;

ANIMALS; BASE SEQUENCE; CARCINOGENS; CELL LINE; CRICETINAE; CRICETULUS; DNA ADDUCTS; DNA MUTATIONAL ANALYSIS; DNA PRIMERS; HUMANS; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; IMIDAZOLES; MOLECULAR SEQUENCE DATA; MUTAGENS;

EID: 0029970360     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/17.4.617     Document Type: Article

References (70)

1. Doll,R. and Peto,R. (1981) The Causes of Cancer. Oxford Medical Publications, Oxford University Press, Oxford. pp. 1226-1235.
2. Doll,R. (1992) The lesson of life: Keynote address to the nutrition and cancer conference. Cancer Res., 52 (Suppl.), 2024s-2029s.
3. Gerhardsson de Verdier,M., Hagman,U., Peters,R.K., Steineck,G. and Overvik,E. (1991) Meat, cooking methods and colorectal cancer: a cause-referent study in Stockholm. Int. J. Cancer, 49, 520-525.
4. Sugimura,T. and Sato,S. (1983) Mutagens-carcinogens in foods. Cancer Res., 43 (Suppl.), 2415s-2421s.
5. Felton,J.S , Knize,M.G., Shen,N.H., Andresen,B D., Bjeldanes,L.F. and Hatch,F.T. (1986) Identification of the mutagens in cooked beef. Environ. Health Perspect., 67, 17-24.
6. Felton,J.S. and Knize,M.G. (1990) Heterocyclic-amine mutagens/ carcinogens in foods. In Cooper,C.S. and Grover,P.L. (eds), Handbook of Experimental Pharmacology, vol 94, Springer-Verlag, Berlin, pp. 471-502.
7. Esumi,H , Ohgaki,H., Kohzen,E., Takayama,S and Sugimura,T. (1989) Identification of lymphoma in CDF1 mice by the food mutagen 2-amino-1-methyl-6-phenylimidazo[4.5-b]pyridine (PhIP). Jpn J. Cancer Res., 80, 1176-1178.
8. Ito,N., Hasegawa,R , Sano,M., Tamano,S , Esumi,H., Takayama,S. and Sugimura,T. (1991) A new colon and mammary carcinogen in cooked food, 2-amino-1-methyl-6-phenylimidazo[4.5-b]pyridine (PhIP). Carcinogenesis, 12, 1503-1506.
9. Rich,K., Murray,B.P., Lewis,.I., Rendell,N., Davies,D.S., Gooderham,N.J. and Boobis,A.R. (1992) N-hydroxy-MeIQx is the major microsomal oxidation product of the dietary carcinogen MeIQx with human liver. Carcinogenesis, 13, 2221-2226.
10. Zhao,K., Gooderham,N.J., Rich,K., Boobis,A.R. and Davies,D.S. (1992) Metabolic activation of the cooked food mutagen PhIP is via N-hydroxylation, catalysed by CYP1A2, in human liver microsomes. Taxicol. Lett. (Suppl.), 303.
11. Boobis,A.R., Sesardic,D., Murray,B P et al (1990) Species variation in the response of the cytochrome P450-dependent monooxygenase system to inducers and inhibitors. Xenobiotica, 20, 1139-1161.
12. Buonarati,M H., Turteltaub,K.W., Shen,N.H. and Felton,J.S. (1990) Role of sulfation and acetylation in the activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine to intermediates which bind DNA. Mutat. Res., 245, 185-190.
13. 1 induces the transversion of G→T in codon 249 of the p53 tumor suppressor gene in human hepatocytes. Proc. Natl Acad. Sci. USA. 90, 8586-8590
14. 32P-postlabelling analysis of IQ, MeIQx and PhIP adducts formed in vitro in DNA and polynucleotides and found in vivo in hepatic DNA from IQ-. MeIQx- and PhIP-treated monkeys. Carcinogenesis. 14, 1389-1395.
15. 32P-postlabelling. Hum. Exp. Toxicol., 13, 641.
16. Wölfel,C., Heinrich-Hirsch,B., Schulz-Schalge,T. et al. (1992) Genetically engineered V79 Chinese hamster cells for stable expression of human cytochrome P450IA2. Eur. J. Pharmacol., 228, 95-102.
17. Konecki,D.S., Brennand,J., Fuscoe,J.C., Caskey,C.T. and Chinault,A.C. (1982) Hypoxanthine-guanine phosphoribosyltransferase genes of mouse and Chinese hamster construction and sequence analysis of cDNA recombinants. Nucleic Acids Res., 10, 6763-6775.
18. Xu,Z., Yu,Y., Gibbs,R.A., Caskey,C.T. and Hsie,A.W. (1993) Multiplex DNA amplification and solid-phase direct sequencing for mutation analysis at the hprt locus in Chinese hamster cells. Mutat. Res., 288, 237-248.
19. Holme,J.A., Wallin,H., Brunborg,G., Soderland,E.J., Hongslo,J.K. and Alexander,J. (1989) Genotoxicity of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP): formation of 2-hydroxamino-PhIP, a direct acting genotoxic metabolite. Carcinogenesis, 10, 1389-1396.
20. Turteltaub,K.W., Knize,M.G , Buonarati,M.H., McManus,M.E., Veroneses,M.E., Mazrimas,J.A. and Felton,J.S. (1990) Metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) by liver microsomes and isolated rabbit cytochrome P450 isoenzymes. Carcinogenesis, 11, 941-946.
21. Wallin,H., Mikalsen,A., Guengerich,F.P., Ingelman-Sundberg,M., Solberg,K.E. and Rossland,J. (1990) Differential rates of metabolic activation and detoxification of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by different cytochrome P450 enzymes. Carcinogenesis, 11, 489-492.
22. Frandsen,H., Rasmussen,E.S., Nielsen,P.A., Farmer,P., Dragsted,L. and Larsen,C. (1991) Metabolic formation, synthesis and genotoxicity of the N-hydroxy derivative of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Mutagenesis, 6, 93-98.
23. Buonarati,M.H., Tucker,J.D., Minkler,J.L., Wu,R.W., Thompson,L.I.I. and Felton,J.S. (1991) Metabolic activation and cytogenetic effects of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in Chinese hamster ovary cells expressing murine cytochrome P450 IA2. Mutagenesis, 6, 253-259.
24. Zhao,K., Murray,S., Davies,D.S., Boobis,A.R. and Gooderham,N.J. (1994) Metabolism of the food derived mutagen and carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) by human liver microsomes. Carcinogenesis, 15, 1285-1288.
25. Buonarati,M.H. and Felton,J.S. (1990) Activation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]]pyridine (PhIP) to mutagenic metabolites. Carcinogenesis, 11, 1133-1138.
26. Morgenthaler,P M. and Holzhäuser,D. (1995) Analysis of mutations induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in human lymphoblastoid cells. Carcinogenesis. 16, 713-718.
27. Carothers,A.M., Yuan,W., Hingerty,B.E., Broyde,S., Grunberger,D. and Synderwine,E.G. (1994) Mutation and repair induced by the carcinogen 2-(hydroxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine (N-OH-PhIP) in the dihydrofolate reductase gene of Chinese hamster ovary cells and conformational modeling of the dG-C8-PhIP adduct in DNA. Chem. Res. Toxicol., 7, 209-218.
28. 32P-postlabelling method. Jpn J. Cancer Res., 85, 113-117.
29. 32P-postlabelling analysis of DNA adducts formed by food-drived heterocyclic amines: evidence for incomplete hydrolysis and a procedure for adduct pattern simplification. Curcinogenesis, 15, 877-882.
30. Turesky,R.J. and Markovic,J (1994) DNA adduct formation of the food carcinogen 2-amino-3-methylimidazo[4.5-f]quinoline at the C-8 and N2 atoms of guanine. Chem. Res. Toxicol., 6, 752-761.
31. 7 position. Proc. Natl Acad. Sci. USA, 89, 8278-8282
32. Loeb,L.A. and Preston,B D. (1986) Mutagenesis by apurinic and apyrimidinic sites. Annu. Rev. Genet., 20, 201-230.
33. Chetsanga,C J. and Lindahl,T. (1979) Release of 7-methylguanine residues whose imidazole rings have been opened from damaged DNA by a DNA glycosylase from Escherichia coli Nucleic Acids Res., 6, 3673-3684.
34. 1 imidazole ring-opened guanine adducts from DNA by formamidopyrimidine DNA glycosylase. Carcinogenesis, 4, 997-1000.
35. Chetsanga,C.J., Polidori,G and Mainwarinng,M (1982) Analysis and excision of ring-opened phosphoramide mustard-deoxyguanosine adducts in DNA. Cancer Res., 42, 2616-2621.
36. Boiteux,S., Bichara,M., Fuchs,R.P. and Lava,J. (1989) Excision of the imidazole ring-opened form of N-2-aminofluorene-C(8)-guanine adduct in poly(dG-dC) by Escherichia coli formamidopyrimidine-DNA glycosylase. Carcinogenesis, 10, 1905-1909.
37. Tarpley,W.G., Miller,J.A. and Miller,E.C. (1982) Rapid release of carcinogen-guanine adducts from DNA after reaction with acetoxy-2-acetylaminofluorene or N-benzoyloxy-N-methyl-4-aminoazobenzene Carcinogenesis, 3, 81-88.
38. Kunkel,T.A. (1984) Mutational specificity of depurination. Proc. Natl Acad. Sci. USA, 81, 1494-1498.
39. Kakiuchi,H., Watanabe,M., Ushijima,T., Toyota,M., Imai,K., Weisburger,J.H., Sugimura,T. and Nagao,M (1995) Specific 5′-GGGA-3′→5′-GGA-3′ mutation of the APC gene in rat colon tumors induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Proc. Natl Acad. Sci. USA, 92, 910-914.
40. Powell,S.M., Zilz,N., Beazer-Barclay,Y., Bryan,T.M., Hamilton,S.R., Thiobodeau,S.N., Vogelstein,B. and Kinzler,K.W. (1992) APC mutations occur early during colorectal tumorigenesis. Nature, 359, 235-237.
41. Joslyn,G., Carlson,M., Thliveris,A. et al (1991) Identification of deletion mutations and three new genes at the familial polyposis locus. Cell, 66, 601-613.
42. Koffel-Schwartz,N., Verdier,J M., Bichara,M., Freund,A.M., Daune,M.P. and Fuchs,R.P.P. (1984) Genetic control of AAF-induced mutagenesis at alternating GC sequences: an additional role for RecA. J. Mol. Biol., 177, 33-51.
43. Lambert,I.B., Napolitano,R.I. and Fuchs,R.P.P. (1992) Carcingen-induced frameshift mutagenesis in repetitive sequences Proc. Natl Acad. Sci. USA. 89, 1310-1314.
44. Napolitano,R.L , Lambert,I.B. and Fuchs,R.P.P. (1994) DNA sequence determinants of carcinogen-induced frameshift mutagenesis. Biochemistry, 33, 1311-1315
45. Zhang,L.-H., Vrieling,H., vanZeeland,A.A. and Jenssen,D. (1992) Spectrum of spontaneously occurring mutations in the hprt gene of V79 Chinese hamster cells. J. Mol. Biol., 223, 627-635.
46. Vrieling,H., van Rooijen,M.L., Groen,N.A., Zdzienicka,M.Z., Simons, J.W.I.M., Lohman,P.H.M. and van Zeeland,A.A. (1989) DNA strand specificity for UV-induced mutations in mammalian cell. Mol. Cell. Biol., 9, 1277-1283.
47. Vrieling,H., Venema,J., van Rooijen,M.-L., van Hoffen,A., Menichini, P., Zdzienicka,M.Z., Simons,J W.I.M., Mullenders,L.H.F. and van Zeeland,A.A. (1991) Strand specificity for UV-induced DNA repair and mutations in the Chinese hamster HPRT gene. Nucleic Acids Res., 19, 2411-2415.
48. Carothers,A M., Steigerwalt,R.W., Urlaub,G., Chasin,L.A. and Grunberger,D. (1989) DNA base changes and RNA levels in N-acetoxy-2-acetylaminofluorene-induced dihydrofolate reductase mutants of Chinese hamster ovary cells. J. Mol. Biol., 208, 417-428.
49. Carothers,A.M. and Grunberger,D. (1990) DNA base changes in benzo[a]pyrene diol epoxide-induced dihydrofolate reductase mutants of Chinese hamster ovary cells. Carcinogenesis, 11, 189-192.
50. Yang,J.-L., Chen,R.-H., Maher,V.M. and McCormick,J.J. (1991) Kinds and location of mutations induced by (-±)-7β.8α-dihydroxy-9α,10α-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene in the coding region of the hypoxanthine (guanine) phosphoribosyltransferase gene in diploid human fibroblasts. Carcinogenesis, 12, 71-75.
51. McGregor,W G., Chen,R.-H., Lukash,L., Maher,V.M. and McCormick,J.J. (1991) Cell cycle-dependent strand bias for uv-induced mutations in the transcribed strand of excision repair-proficient human fibroblasts but not in repair-deficient cells. Mol. Cell. Biol., 11, 1927-1934.
52. Chen,R.-H., Maher,V.M. and McCormick,J.J. (1990) Effects of excision repair by diploid human fibroblasts on the kinds and locations of mutations induced by (±)-7β,8α-dihydroxy-9α, 10α-epoxy-7,8.9,10-tetrahydrobenzo[a]pyrene in the coding region of the hgprt gene. Proc. Natl Acad. Sci. USA, 87, 8680-8684.
53. Chen,R.-H , Maher,V.M., Brouwer,J., Van de Putte,P. and McCormick,J.J. (1992) Preferential repair and strand-specific repair of benzo[a]pyrene diol epoxide adducts in the hgprt gene of diploid human fibroblasts. Proc. Natl Acad. Sci. USA, 89, 5413-5417.
54. Wu,R.W., Wu,E.M., Thompson,L.H. and Felton,J.S. (1995) Identification of aprt gene mutations induced in repair-deficient and P450-expressing CHO cells by the food-related mutagen/carcinogen. PhIP Carcinogenesis, 16, 1207-1213.
55. - Escherichia coli to N-methyl-N′-nitro-N-nitrosoguanine. Mol. Gen. Genet., 209, 526-532.
56. Richardson,K.K., Richardson,F.C., Crosby,R.M., Swenberg,J.A. and Skopek,T.R. (1987) DNA base changes and alkylation following in vivo exposure of Escherichia coli to N-methyt-N-nitrosourea. Proc. Natl Acad. Sci. USA, 84, 344-348.
57. 6-alkylguanine. FASEB J., 6, 2302-2310.
58. Zarbl,H., Sukumar,S., Arthur,A.V., Martin-Zenace,D. and Barbacid,M. (1985) Direct mutagenesis of H-ras-1 oncogenes by nitroso-methylurea during initiation of mammary carcinogenesis in rats. Nature, 318, 382-385.
59. Barbacid,M. (1987) ras Genes Annu. Rev. Biochem., 56, 779-827.
60. Mazur,M. and Glickman,B.W. (1988) Sequence specificity of mutations induced by benzo[a]pyrene-7,8-diol-9,10-epoxide at endogenous aprt gene in CHO cells. Somat. Cell Mol. Genet., 14, 393-400.
61. Singer,B. and Dosanjh,M.K. (1990) Site-directed mutagenesis for quantitation of base-base interactions at defined sites. Mutat. Res., 233, 45-51.
62. Pullman,A. and Pullman,B. (1981) Molecular electrostatic potential of the nucleic acids. Q. Rev. Biophys., 14, 289-380.
63. 6-methylguanine at specific sites in a synthetic oligonucleotide designed to resemble a known mutagenic hotspot. J. Biol. Chem., 264, 838-841.
64. 6-substituted guanine-induced mutagenesis of ras oncogenes. Proc. Natl Acad. Sci. USA. 86, 8650-8654.
65. Miyaki,M., Konishi,M., Kikuchi-Yanoshita,R., Enomoto,M., Iyari,T. and Tanaka,K (1994) Characteristics of somatic mutations of the adenomatous polyposis coli gene in colorectal tumors. Cancer Res., 54, 3011-3020.
66. Nagase,H. and Nakamura,Y. (1993) Mutations of the apc (adenomatous polyposis coli) gene. Human Mutat., 2, 425-434.
67. Miyoshi,Y., Nagase,H , Ando,H. et al. (1992) Somatic mutations of the APC gene in colorectal tumors: mutation cluster region in the apc gene. Hum. Mol. Genet., 1, 229-233.
68. Mandl,M., Paffenholz,R., Friedl,W. et al (1994) Frequency of common and novel inactivating apc mutations in 202 families with familial adenomatous polyposis. Hum. Mol. Genet., 3, 181-184.
69. De Benedetti,L., Sciallero,S., Gismondi,V. et al. (1994) Association of apc gene mutations and histological characteristics of colorectal adenomas. Cancer Res., 54, 3553-3556.
70. Toyooka,M., Konishi,M., Kikuchi-Yanoshita,R., Iwama,T. and Miyaki,M. (1995) Somatic mutations of the adenomatous polyposis coli gene in gastroduodenal tumors from patients with familial adenomatous polyposis. Cancer Res., 55, 3165-3170.