Comparison of crystal structure and theory for 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

Chemical Research in Toxicology

Volumn 9, Issue 3, 1996, Pages 574-579

  Parkin, Sean ^a   Marsch, Glenn A ^a   Hope, Håkon ^b   Whitney, Erin ^c   Winter, Nick W ^a   Colvin, Michael E ^d   Felton, James S ^a   Turteltaub, Kenneth W ^a  

^a LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c WILLIAMS COLLEGE   (United States)

^d SANDIA NATIONAL LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; MUTAGENIC AGENT; WATER;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDRATION; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; IMIDAZOLES; MODELS, MOLECULAR; MUTAGENS; QUANTUM THEORY; WATER;

EID: 0029863863     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950168b     Document Type: Review

References (35)

1. 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.
2. Felton, J. S., and Knize, M. G. (1991) Occurrence, identification, and bacterial mutagenicity of heterocyclic amines in cooked food. Mutat. Res. 259, 205-217.
3. 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.
4. Manabe, S., Tohyama, K., Wada, O., and Aramaki, T. (1991) Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), in cigarette smoke condensate. Carcinogenesis 12, 1945-1947.
5. Manabe, S., Suzuki, H., Wada, O., and Ueki, A. (1993) Detection of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in beer and wine. Carcinogenesis 14, 899-901.
6. Knize, M. G., Cunningham, P. L., Griffin, E. A., Jr., Jones, A. L., and Felton, J. S. (1994) Characterization of mutagenic activity in cooked grain food products. Food Chem. Toxicol. 32, 15-21
7. Skog, K., Knize, M. G., Felton, J. S., and Jagerstad, M. (1992) Formation of new heterocyclic amine mutagens by heating creatinine, alanine, threonine, and glucose. Mutat. Res. 268, 191-197.
8. Jagerstad, M., Skog, K., Grivas, S , and Olsson, K. (1991) Formation of heterocyclic amines using model systems. Mutat. Res. 259, 219-233.
9. Sinha, R., Rothman, N., Brown, E. D., Salmon, C. P., Knize, M. G., Swanson, C. A., Rossi, S. C., Mark, S. D., Levander, O. A., and Felton, J. S. (1995) High concentrations of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) can occur in chicken but are dependent on the cooking method. Cancer Res. 55, 4516-4519.
10. Felton, J. S., and Knize, M. G. (1990) Heterocyclic amine mutagens/carcinogens in foods. In Handbook of Experimental Pharmacology (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/I, pp 471-502, Springer-Verlag, Berlin and Heidelberg.
11. Knize, M. G., and Felton, J. S. (1986) The synthesis of the cooked-beef mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and its 3-methyl isomer. Heterocycles 24, 1815-1819.
12. Wakabayashi, K., Nagao, M., Esumi, H., and Sugimura, T. (1992) Food-derived mutagens and carcinogens. Cancer Res. 52, 2092s-2098s.
13. Esumi, H., Ohgaki, H., Kohzen, E., Takayama, S., and Sugimura, T. (1989) Induction of lymphoma in CDF1 mice by the food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Jpn. J. Cancer Res. 80, 1176-1178.
14. Ito, N., Hasegawa, E., 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.
15. Autrup, H. (1990) Carcinogen metabolism in cultured human tissues and cells. Carcmogenesis 11, 707-712.
16. Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic compounds. Cancer Res. 42, 4875-4917.
17. Turteltaub, K. W., Knize, M. G , Buonarati, M. H., McManus, M. E., Veronese, 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 isozymes. Carcinogenesis 11, 941-946.
18. Holme, J. A., Wallin, H., Brunborg, G., Soderlund, 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-hydroxyamino-PhIP, a direct-acting genotoxic metabolite. Carcinogenesis 10, 1389-1396.
19. Frandsen, H., Rasmussen, E. S., Nielsen, P. A., Farmer, P., Dragsted, L , and Larsen, J 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.
20. 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.
21. Kaderlik, K. R., Minchin, R. F., Mulder, G. J., Ilett, K. F., Daugaard-Jensen, M , Teitel, C H., and Kadlubar, F. F. (1994) Metabolic activation pathway for the formation of DNA adducts of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat extrahepatic tissues. Carcinogenesis 15, 1703-1709.
22. Turesky, R. J., Lang, N. P., Butler, M. A , Teitel, C. H., and Kadlubar, F. F (1991) Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon. Carcinogenesis 12, 1839-1845.
23. Nagaoka, H., Wakabayashi, K., Kim, S.-B., Kim, I.-S., Tanaka, Y., Ochiai, M., Tada, A., Nukaya, H., Sugimura, T , and Nagao, M (1992) Adduct formation at C-8 of guanine on in vitro reaction of the ultimate form of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine with 2′-deoxyguanosine and its phosphate esters. Jpn. J Cancer Res. 83, 1025-1029.
24. Lin, D., Kaderlik, K. R., Turesky, R. J., Miller, D. W., Lay, J O., Jr., and Kadlubar, F. F. (1992) Identification of N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA. Chem. Res. Toxicol. 5, 691-697.
25. 2-(2′-deoxyguanosin-8-yl)-PhIP. Carcinogenesis 13, 629-635.
26. Marsch, G. A., Goldman, E. N , Fultz, E., Shen, N. H., and Turteltaub, K. W. (1995) Heterogeneous DNA adduct formation in vitro by the acetylated food mutagen 2-(acetoxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine: a fluorescence spectroscopic study Chem. Res. Toxicol 8, 659-670.
27. Marsch, G. A., Ward, R. L., Colvin, M., and Turteltaub, K. W. (1994) Noncovalent DNA groove-binding by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Nucleic Acids Res. 22, 5408-5415.
28. Carothers, A. M., Yuan, W., Hingerty, B. E., Broyde, S., Grunberger, D., and Snyderwine, 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.
29. Sheldrick, G. M. (1990) TREF in Siemens SHELXTL. An integrated system for solving, refining and displaying crystal structures from diffraction data, version 4.2. Siemens Analytical X-Ray Instruments, Madison, WI, USA.
30. Sheldrick, G. M. (1993) SHELXL93 crystal structure refinement program. University of Gottingen, Germany.
31. Parkin, S., Moezzi, B., and Hope, H. (1995) XABS2 - An empirical absorption correction program. J. Appl. Crystallogr. 28, 53-56.
32. Hariharan, P. C., and Pople, J. A. (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor. Chim. Acta 28, 213-222.
33. Johnson, B. G., Gill, P. M. W., and Pople, J. A. (1993) The performance of a family of density functional methods. J Chem. Phys. 98, 5612-5626.
34. Coppens, P., Sabine, T. M., Delaplane, R. G., and Ibers, J. A. (1969) An experimental determination of the asphericity of the atomic charge distribution in oxalic acid dihydrate. Acta Crystallogr. B25, 2451-2458.
35. Bernstein, J. (1992) Effect of crystal environment on molecular structure. In Accurate Molecular Structures (Domenicano, A., and Hargittai, I., Eds.) pp 469-497, Oxford University Press.