Spectral and conformational analysis of deoxyadenosine adducts derived from syn- and anti-dibenzo[a,l]pyrene diol epoxides: Fluorescence studies

Chemical Research in Toxicology

Volumn 12, Issue 9, 1999, Pages 768-777

  Jankowiak, Ryszard ^a   Lin, Cheng Huang ^b   Zamzow, Dan ^a   Roberts, Kenneth P ^a,b   Li, Kai Ming ^c   Small, Gerald J ^a,b  

^a IOWA STATE UNIVERSITY   (United States)

^b IOWA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGEN; DEOXYADENOSINE; EPOXIDE; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE;

ARTICLE; CARCINOGENESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; FLUORESCENCE; LOW TEMPERATURE; MOLECULAR DYNAMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

BENZOPYRENES; DEOXYADENOSINES; DNA; DNA ADDUCTS; EPOXY COMPOUNDS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 0032873274     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980233s     Document Type: Article

References (33)

1. Cavalieri, E. L., Higginbotham, S., RamaKrishna, N. V. S., Devanesan, P. D., Todorovic, R., Rogan, E. G., and Salmasi, S. (1991) Comparative dose-response tumorigenicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene, benzo-[a]pyrene, and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland. Carcinogenesis 12, 1939-1944.
2. Higginbotham, S., RamaKrishna, N. V. S., Johansson, S. L., Rogan, E. G., and Cavalieri, E. L. (1993) Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene at low dose in mouse skin. Carcinogenesis 14, 875-878.
3. Kozin, I. S., Gooijer, C., and Velthorst, N. H. (1995) Direct determination of dibenzo[a,l]pyrene in crude extracts of environmental samples by laser-excited Shpol'skii spectroscopy. Anal. Chem. 67, 1623-1626.
4. Mumford, J. L., Li, X., Hu, F., Lu, X. B., and Chuang, J. C. (1995) Human exposure and dosimetry of polycyclic aromatic hydrocarbons in urine from Xuan Wei, China with high lung cancer mortality associated with exposure to unvented coal smoke. Carcinogenesis 16, 3031-3036.
5. de Ratt, W. K., Kooijman, S. A. L. M., and Gielen, J. W. J. (1987) Concentrations of polycyclic hydrocarbons in airborne particles in The Netherlands and their correlation with mutagenicity. Sci. Total Environ. 66, 95-114.
6. Li, K.-M., Todorovic, R., Rogan, E. G., Cavalieri, E. L., Ariese, F., Suh, M., Jankowiak, R., and Small, G. J. (1995) Identification and quantitation of dibenzo[a,l]pyrene-DNA adducts formed by rat liver microsomes in vitro: preponderance of depurinating adducts. Biochemistry 34, 8043-8049.
7. Cavalieri, E., and Rogan, E. (1998) Mechanism of Tumor Initiation by Polycyclic Aromatic Hydrocarbons in Mammals. In The Handbook of Environmental Chemistry, Vol. 3, Part I, PAHs and Related Compounds (Neilson, A. H., Ed.) Springer-Verlag, Berlin and Heidelberg, Germany.
8. Jankowiak, R., and Small, G. J. (1998) Analysis of PAH-DNA Adducts-Fluorescence Line-Narrowing Spectroscopy. In The Handbook of Environmental Chemistry, Vol. 3, Part I, PAHs and Related Compounds (Neilson, A. H., Ed.) Springer-Verlag, Berlin and Heidelberg, Germany.
9. Cavalieri, E. L., and Rogan, E. G. (1992) The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation. Pharmacol. Ther. 55, 183-199.
10. Ralston, S. L., Seidel, A., Luch, A., Platt, K. L., and Baird, W. M. (1995) Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti-(11R,12S,13S,14R)- and (+)-syn-(11S,12R,13S,14R)-11,12-diol-13,14-epoxides which bind extensively to deoxyadenosine residues of DNA in the human mammary carcinoma cell line MCF-7. Carcinogenesis 16, 2899-2907.
11. Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic compounds. Cancer Res. 42, 4875-4910.
12. Luch, A., Glatt, H., Platt, K. L., Oesch, F., and Seidel, A. (1994) Synthesis and mutagenicity of the diastereomeric fjord-region 11,-12-dihydrodiol 13,14-epoxides of dibenzo[a,l]pyrene. Carcinogenesis 15, 2507-2516.
13. Harvey, R. G. (1991) Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, U.K.
14. Ralston, S. L., Lau, H. H. S., Seidel, A., Luch, A., Platt, K. L., and Baird, W. M. (1994) The potent carcinogen dibenzo[a,l]pyrene is metabolically activated to fjord-region 11,12-diol 13,14-epoxides in human mammary carcinoma MCF-7 cell cultures. Cancer Res. 54, 887-890.
15. Li, K.-M., RamaKrishna, N. V. S., Padmavathi, N. S., Rogan, E. G., and Cavalieri, E. L. (1994) Synthesis and structure determination of the adducts of dibenzo[a,l]pyrene diol epoxides and deoxyadenosine and deoxyguanosine. Polycyclic Aromat. Compd. 6, 207-213.
16. 32P-Postlabeling and Fluorescence Studies Chem. Res. Toxicol. 11, 674-685.
17. Jankowiak, R., and Small, G. J. (1991) Fluorescence line narrowing: a high-resolution window on DNA and protein damage from chemical carcinogens. Chem. Res. Toxicol. 4, 256-269.
18. Rogan, E. G., Devanesan, P. D., RamaKrishna, N. V. S., Higginbotham, S., Padmavathi, N. S., Chapman, K., Cavalieri, E. L., Jeong, H., Jankowiak, R., and Small, G. J. (1993) Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 356-363.
19. Devanesan, P. D., RamaKrishna, N. V. S., Padmavathi, N. S., Higginbotham, S., Rogan, E. G., Cavalieri, E. L., Marsh, G. A., Jankowiak, R., and Small, G. J. (1993) Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 8, 364-371.
20. Kok, S. J., Posthumus, R., Bakker, I., Gooijer, C., Brinkman, U. A. Th., and Velthorst, N. H. (1995) Identification of benzo[a]-pyrene tetrols by reversed-phase liquid chromatography coupled semi-on-line to fluorescence line-narrowing spectroscopy. Anal. Chim. Acta 303 3-10.
21. Marsh, G. A., Jankowiak, R., Suh, M., and Small, G. J. (1994) Sequence dependence of benzo[a]pyrene diol epoxide-DNA adduct conformer distribution: a study by laser-induced fluorescence/ polyacrylamide gel electrophoresis. Chem. Res. Toxicol. 7, 98-109.
22. 2-dG in sequence-defined oligonucleotides. Carcinogenesis 15, 2891-2898.
23. 2-dG in duplex oligonucleotides using polyacrylamide gel electrophoresis and low-temperature fluorescence spectroscopy. Biophys. Chem. 56, 281-296.
24. Ariese, F., Small, G. J., and Jankowiak, R. (1996) Conformational studies of depurinating DNA adducts from syn-dibenzo[a,l]pyrene diolepoxide. Carcinogenesis 17, 829-837.
25. Suh, M., Ariese, F., Small, G. J., Jankowiak, R., Hewer, A., and Phillips, D. H. (1995) Formation and persistence of benzo[a]-pyrene-DNA adducts in mouse epidermis in vivo: importance of adduct conformation. Carcinogenesis 16, 2561-2569.
26. Jankowiak, R., Ariese, F., Zamzow, D., Luch, A., Kroth, H., Seidel, A., and Small, G. J. (1997) Conformational Studies of Stereoisomeric Tetrols Derived from syn- and anti-Dibenzo[a,l]pyrene Diol Epoxides. Chem. Res. Toxicol. 10, 677-686.
27. Burkert, U., and Allinger, N. L. (1982) Molecular mechanics. ACS Monogr. 177.
28. Allinger, N. L. (1977) Conformational analysis 130. MM2: a hydrocarbon force field utilizing V1 and V2 torsional terms. J. Am. Chem. Soc. 99, 8127-8134.
29. Brown, J. C. (1982) Ph.D. Thesis, Iowa State University, Ames, IA.
30. Brown, J. C., Duncanson, J. A., and Small, G. J. (1980) Fluorescence line narrowing spectrometry in glasses for direct determination of polycyclic aromatic hydrocarbons in solvent-refined coal. Anal. Chem. 52, 1711-1715.
31. Herzberg, G. (1966) Molecular Spectra and Molecular Structure, III. Electronic Spectra and Electronic Structure of Polyatomic Molecules, Chapter II, van Nostrand and Reinhold Co., New York.
32. Geacintov, N. E., Cosman, M., Hingerty, B. E., Amin, S., Broyde, S., and Patel, D. J. (1997) NMR Solution Structures of Stereoisomeric Covalent Polycyclic Aromatic Carcinogen-DNA Adducts: Principles, Patterns, and Diversity. Chem. Res. Toxicol. 10, 112-146.
33. Wei, D., Maher, V., and McCormick, J. J. (1995) Site-specific rates of excision repair of benzo[a]pyrene diol epoxide adducts in the hypoxanthine phosphoribosyl transferase gene of human fibroblasts: correlation with mutation spectra. Proc. Natl. Acad. Sci. U.S.A. 92, 2204-2208.