Nitrogen-substitution effects on the mutagenicity and cytochrome P450 isoform-selectivity of chrysene analogs

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 586, Issue 1, 2005, Pages 87-95

  Yamada, Katsuya ^a   Hakura, Atsushi ^b   Kato, Taka Aki ^a   Mizutani, Takaharu ^a   Saeki, Ken Ichi ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b EISAI CO LTD   (Japan)

Author keywords

Ames test; Aza substitution; Human liver microsome

Indexed keywords

CHRYSENE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; EPOXIDE; NITROGEN; RECOMBINANT PROTEIN;

AMES TEST; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; ATOM; BAY REGION BINDING SITE; CATALYSIS; COMPARATIVE STUDY; CONTROLLED STUDY; CORRELATION ANALYSIS; GENE ACTIVATION; GENOTOXICITY; HUMAN; HUMAN CELL; INSECT CELL; LIVER MICROSOME; METABOLIC ACTIVATION; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; RAT; REVERTANT; SALMONELLA TYPHIMURIUM; SUBSTITUTION REACTION;

ANIMALS; CHRYSENES; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; ISOENZYMES; LIVER; MICROSOMES, LIVER; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; MUTAGENS; MUTATION; NITROGEN; QUINOLINES; RATS; SALMONELLA TYPHIMURIUM;

INSECTA; SALMONELLA TYPHIMURIUM;

EID: 23644445516     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrgentox.2005.06.006     Document Type: Article

References (44)

1. C.R. Engel, and E. Sawicki A superior thin-layer chromatographic procedure for the separation of aza arenes and its application to air pollution J. Chromatogr. 31 1967 109 119
2. D. Brocco, A. Cimmino, and M. Possanzini Determination of aza-heterocyclic compounds in atmospheric dust by a combination of thin-layer and gas chromatography J. Chromatogr. 84 1973 371 377
3. I. Schmeltz, and D. Hoffmann Nitrogen-containing compounds in tobacco and tobacco smoke Chem. Rev. 77 1977 295 311
4. T. Kosuge, H. Zenda, H. Nukaya, A. Terada, T. Okamoto, K. Shudo, K. Yamaguchi, Y. Iitaka, T. Sugimura, M. Nagao, K. Wakabayashi, A. Kosugi, and H. Saito Isolation and structural determination of mutagenic substances in coal tar Chem. Pharm. Bull. 30 1982 1535 1538
5. T. Matsumoto, D. Yoshida, S. Mizusaki, H. Tomita, and K. Koshimizu Structural requirements for mutagenic activities of N-heterocyclic bases in the Salmonella test system Agric. Biol. Chem. 42 1978 861 864
6. Y. Kitahara, H. Okuda, K. Shudo, T. Okamoto, M. Nagao, Y. Seino, and T. Sugimura Synthesis and mutagenicity of 10-azabenzo[a]pyrene-4,5-oxide and other pentacyclic aza-arene oxides Chem. Pharm. Bull. 26 1978 1950 1953
7. T. Hashimoto, T. Negishi, T. Namba, S. Hayakawa, and H. Hayatsu Mutagenicity of quinoline derivatives and analogs-quinoxaline 1,4-dioxide is a potent mutagen Chem. Pharm. Bull. 27 1979 1954 1956
8. C.H. Ho, B.R. Clark, M.R. Guerin, B.D. Barkenbus, T.K. Rao, and J.L. Epler Analytical biological analysis of test materials from the synthetic fuel technologies Mutat. Res. 85 1981 335 345
9. R. Shinohara, and A. Kido Determination of trace azaarenes in water by gas chromatography and gas chromarography-mass spectrometry J. Chromatogr. 256 1983 81 91
10. J. McCann, E. Choi, E. Yamasaki, and B.N. Ames Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals Proc. Natl. Acad. Sci. U.S.A. 72 1975 5135 5139
11. D.A. Kaden, R.A. Hites, and W.G. Thilly Mutagenicity of soot and associated polycyclic aromatic hydrocarbons to Salmonella typhimurium Cancer Res. 39 1979 4152 4159
12. D.M. Jerina, R.E. Lehr, H. Yagi, O. Hernandez, P.M. Dansette, P.G. Wislocki, A.W. Wood, R.L. Chang, W. Levin, and A.H. Conney In vitro Metabolic Activation in Mutagenesis Testing 1976 Elsevier-North Holland Biochem. Press Amesterdam pp. 159-177
13. A.W. Wood, R.L. Chang, W. Levin, D.E. Ryan, P.E. Thomas, H.D. Mah, J.M. Karle, H. Yagi, D.M. Jerina, and A.H. Conney Mutagenicity and tumorigenicity of phenanthrene and chrysene epoxides and diol epoxides Cancer Res. 39 1979 4069 4077
14. K. Yamada, T. Suzuki, A. Kohara, M. Hayashi, A. Hakura, T. Mizutani, and K. Saeki Effect of 10-aza-substitution on benzo[a]pyrene mutagenicity in vivo and in vitro Mutat. Res. 521 2002 187 200
15. K. Yamada, T. Suzuki, A. Hakura, T. Mizutani, and K. Saeki Metabolic activation of 10-aza-substituted benzo[a]pyrene by cytochrome P450 1A2 in human liver microsomes Mutat. Res. 557 2004 159 165
16. K. Saeki, M. Tomomitsu, Y. Kawazoe, K. Momota, and H. Kimoto Fluorinated benzo[h]quinolines and benzo[f]quinolines Chem. Pharm. Bull. 44 1996 2254 2258
17. K. Saeki, T. Kato, T. Matsuda, S. Matsui, and T. Mizutani Activation of the human Ah receptor by aza-polycyclic aromatic hydrocarbons and their halogenated derivatives Biol. Pharm. Bull. 26 2003 448 452
18. S.V. Nekrasov, and A.V. El'tsov Polynuclear aza-aromatic compounds I Zh. Org. Khim. 7 1971 188 199
19. B.N. Ames, J. McCann, and E. Yamasaki Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test Mutat. Res. 31 1975 347 364
20. D.M. Maron, and B.N. Ames Revised methods for the Salmonella mutagenicity test Mutat. Res. 113 1983 173 215
21. A. Hakura, S. Suzuki, and T. Satoh Advantage of the use of human liver S9 in the Ames test Mutat. Res. 438 1999 29 36
22. A. Hakura, S. Suzuki, S. Sawada, S. Motooka, and T. Satoh An improvement of the Ames test using a modified human liver S9 preparation J. Pharmacol. Toxicol. Methods 46 2001 169 172
23. A. Hakura, S. Suzuki, S. Sawada, T. Sugihara, Y. Hori, K. Uchida, W.D. Kerns, F. Sagami, S. Motooka, and T. Satoh Use of human liver S9 in the Ames test: assay of three procarcinogens using human S9 derived from multiple donors Regul. Toxicol. Pharmacol. 37 2003 20 27
24. A. Hakura, S. Suzuki, and T. Satoh Advantage of the use of human materials in the safety assessment of chemical: the Ames test using human S9 Environ. Mutagen Res. 25 2003 135 164
25. Y.L. Cheung, T.J. Gray, and C. Ioannides Mutagenicity of chrysene, its methyl and benzo derivatives, and their interactions with cytochromes P-450 and the Ah-receptor; relevance to their carcinogenic potency Toxicology 81 1993 69 86
26. B.P. Murray, R.J. Edwards, S. Murray, A.M. Singleton, D.S. Davies, and A.R. Boobis Human hepatic CYP1A1 and CYP1A2 content, determined with specific anti-peptide antibodies, correlates with the mutagenic activation of PhIP Carcinogenesis 14 1993 585 592
27. R.J. Turesky, A. Constable, J. Richoz, N. Varga, J. Markovic, M.V. Martin, and F.P. Guengerich Activation of heterocyclic aromatic amines by rat and human liver microsomes and by purified rat and human cytochrome P450 1A2 Chem. Res. Toxicol. 11 1998 925 936
28. A.T. Drahushuk, B.P. McGarrigle, K.E. Larsen, J.J. Stegeman, and J.R. Olson Detection of CYP1A1 protein in human liver and induction by TCDD in precision-cut liver slices incubated in dynamic organ culture Carcinogenesis 19 1998 1361 1368
29. S.K. Sy, B.K. Tang, A. Pastrakuljic, E.A. Roberts, and W. Kalow Detailed characterization of experimentally derived human hepatic CYP1A1 activity and expression using differential inhibition of ethoxyresorufin O-deethylation by fluvoxamine Eur. J. Clin. Pharmacol. 57 2001 377 386
30. M.A. Butler, M. Iwasaki, F.P. Guengerich, and F.F. Kadlubar Human cytochrome P-450PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines Proc. Natl. Acad. Sci. U.S.A. 86 1989 7696 7700
31. M.A. Butler, N.P. Lang, J.F. Young, N.E. Caporaso, P. Vineis, R.B. Hayes, C.H. Teitel, J.P. Massengill, M.F. Lawsen, and F.F. Kadlubar Determination of CYP1A2 and NAT2 phenotypes in human populations by analysis of caffeine urinary metabolites Pharmacogenetics 2 1992 116 127
32. T. Shimada, H. Yamazaki, M. Mimura, Y. Inui, and F.P. Guengerich Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians J. Pharmacol. Exp. Ther. 270 1994 414 423
33. O. Pelkonen, A. Rautio, H. Raunio, and M. Pasanen CYP2A6: a human coumarin 7-hydroxylase Toxicology 144 2000 139 147
34. M. Nakajima, J.T. Kwon, N. Tanaka, T. Zenta, Y. Yamamoto, H. Yamamoto, H. Yamazaki, T. Yamamoto, Y. Kuroiwa, and T. Yokoi Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans Clin. Pharmacol. Ther. 69 2001 72 78
35. S. Yamano, J. Tatsuno, and F.J. Gonzalez The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes Biochemistry 29 1990 1322 1329
36. M. Oscarson, R.A. McLellan, H. Gullsten, Q.Y. Yue, M.A. Lang, M.L. Bernal, B. Sinues, A. Hirvonen, H. Raunio, O. Pelkonen, and M. Ingelman-Sundberg Characterisation and PCR-based detection of a CYP2A6 gene deletion found at a high frequency in a Chinese population FEBS Lett. 448 1999 105 110
37. K.I. Nunoya, T. Yokoi, K. Kimura, T. Kainuma, K. Satoh, M. Kinoshita, and T. Kamataki A new CYP2A6 gene deletion responsible for the in vivo polymorphic metabolism of (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride in humans J. Pharmacol. Exp. Ther. 289 1999 437 442
38. M. Oscarson, R.A. McLellan, H. Gullsten, J.A. Agundez, J. Benitez, A. Rautio, H. Raunio, O. Pelkonen, and M. Ingelman-Sundberg Identification and characterisation of novel polymorphisms in the CYP2A locus: implications for nicotine metabolism FEBS Lett. 460 1999 321 327
39. M. Tada, K. Takahashi, Y. Kawazoe, and N. Ito Binding of quinoline to nucleic acid in a subcellular microsomal system Chem. Biol. Interact. 29 1980 257 266
40. M. Tada, K. Takahashi, and Y. Kawazoe Metabolites of quinoline, a hepatocarcinogen, in a subcellular microsomal system Chem. Pharm. Bull. 30 1982 3834 3837
41. K. Takahashi, M. Kamiya, Y. Sengoku, K. Kohda, and Y. Kawazoe Deprivation of the mutagenic property of quinoline: inhibition of mutagenic metabolism by fluorine substitution Chem. Pharm. Bull. 36 1988 4630 4633
42. K. Saeki, K. Takahashi, and Y. Kawazoe Metabolism of mutagenicity- deprived 3-fluoroquinoline: comparison with mutagenic quinoline Biol. Pharm. Bull. 16 1993 232 234
43. G. Reigh, H. McMahon, M. Ishizaki, T. Ohara, K. Shimane, Y. Esumi, C. Green, C. Tyson, and S. Ninomiya Cytochrome P450 species involved in the metabolism of quinoline Carcinogenesis 17 1996 1989 1996
44. Z.X. Yuan, S. Kumar, and H.C. Sikka Comparative metabolism of the aza polynuclear aromatic hydrocarbon dibenz[a,h]acridine by recombinant human and rat cytochrome P450s Chem. Res. Toxicol. 17 2004 672 678