Preparation, isolation, and characterization of dibenzo[a,l]pyrene diol epoxide-deoxyribonucleoside monophosphate adducts by HPLC and fluorescence line-narrowing spectroscopy

Chemical Research in Toxicology

Volumn 12, Issue 9, 1999, Pages 789-795

  Devanesan, Prabu ^a   Ariese, Freek ^b,c   Jankowiak, Ryszard ^b   Small, Gerald J ^b   Rogan, Eleanor G ^a   Cavalieri, Ercole L ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b IOWA STATE UNIVERSITY   (United States)

^c VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

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

ARTICLE; CARCINOGEN DNA INTERACTION; CARCINOGENESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DNA ADDUCT; FLUORESCENCE SPECTROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

BENZOPYRENES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANINE NUCLEOTIDES; DINITROBENZENES; DNA ADDUCTS; EPOXY COMPOUNDS; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 0032871770     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980202x     Document Type: Article

References (22)

1. Cavalieri, E. L., Rogan, E. G., Higginbotham, S., Cremonesi, P., and Salmasi, S. (1989) Tumor-initiating activity in mouse skin and carcinogenicity in rat mammary gland of dibenzo[a]pyrenes: The very potent activity of dibenzo[a,l]pyrene. J. Cancer Res. Clin. Oncol. 115, 67-72.
2. 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 vs 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.
3. 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 doses in mouse skin. Carcinogenesis 14, 875-878.
4. Lavoie, E. J., He, J.-M., Meegalla, R. L., and Weyand, E. H. (1993) Exceptional tumor-initiating activity of 4-fluorobenzo[j]fluoranthene on mouse skin: comparison with benzo[j]fluoranthene, 10-fluoro-benzo[j]fluoranthene, benzo[a]pyrene, dibenzo[a,l]pyrene and 7,12-dimethylbenz[a]anthracene. Cancer Lett. 70, 7-14.
5. Snook, M. E., Severson, R. F., Arrendale, R. F., Higman, H. C., and Chortyk, O. T. (1977) The identification of high molecular weight polynuclear aromatic hydrocarbons in a biologically active fraction of cigarette smoke condensate. Beitr. Tabakforsch. 9, 79-101.
6. Mumford, J. L., Harris, D. B., and Williams, K. (1987) Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion. Environ. Sci. Technol. 21, 308-311.
7. 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.
8. 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.
9. Devanesan, P., Ariese, F., Jankowiak, R., Small, G. J., Rogan, E. G., and Cavalieri, E. L. (1999) A novel method for the isolation and identification of stable DNA adducts formed by dibenzo[a,l]-pyrene and dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides in vitro. Chem. Res. Toxicol. 12, 796-801.
10. NIH Guidelines for the Laboratory Use of Chemical Carcinogens (1981) NIH Publication 81-2385, U.S. Government Printing Office, Washington, DC.
11. 32P-postlabeling assay. Carcinogenesis 12, 1109-1114.
12. Jankowiak, R., and Small, G. J. (1989) Fluorescence line-narrowing spectroscopy in the study of chemical carcinogenesis. Anal. Chem. 61, 1023A-1032A.
13. 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.
14. Luch, A., Seidel, A., Glatt, H. R., and Platt, K. L. (1997) Metabolic activation of the (+)-S,S-and (-)-R,R-enantiomers of trans-11,-12-dihydroxy-11,12-dihydrodibenzo[a,l]pyrene: Stereoselectivity, DNA adduct formation, and mutagenicity in Chinese hamster V79 cells. Chem. Res. Toxicol. 10, 1161-1170.
15. 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.
16. Jankowiak, R., Ariese, F., Zamzow, D., Luch, A., Kroth, H., Seidel, A., and Small, G. J. (1997) Conformational studies of stereoisomeric tetraols derived from syn-and anti-dibenzo[a,l]pyrene diolepoxides. Chem. Res. Toxicol. 10, 677-686.
17. Li, K.-M., George, M., Gross, M. L., Seidel, A., Luch, A., Rogan, E. G., and Cavalieri, E. L. (1999) Structure elucidation of the adducts formed by fjord-region dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides with deoxyadenosine. Chem. Res. Toxicol. 12, 758-767.
18. Li, K.-M., George, M., Gross, M. L., Lin, C.-H., Jankowiak, R., Small, G. J., Seidel, A., Kroth, H., Rogan, E. G., and Cavalieri, E. L. (1999) Structure elucidation of the adducts formed by fjord-region dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides with deoxyguanosine. Chem. Res. Toxicol. 12, 749-757.
19. Jankowiak, R., Lin, C.-H., Zamzow, D., Roberts, K., Li, K.-M., and Small, G. J. (1999) Spectral and conformational analysis of deoxyadenosine adducts derived from syn-and anti-dibenzo[a,l]-pyrene diol epoxides: Fluorescence studies. Chem. Res. Toxicol. 12, 768-777.
20. Jankowiak, R., and Small, J. G. (1998) Analysis of PAH-DNA adducts: fluorescence line-narrowing spectroscopy. In The Handbook of Environmental Chemistry, PAHs and Related Compounds (Neilson, A. H., Ed.) Vol. 3J, pp 119-145, Springer, Heidelberg, Germany.
21. 2-dG in duplex oligonucleotides using polyacrylamide electrophoresis and low-temperature fluorescence spectroscopy. Biophys. Chem. 56, 281-296.
22. Roberts, K. P., Lin, C.-H., Jankowiak, R., and Small, G. J. (1999) On-line Identification of diastereometric dibenzo [a,l]pyrene diolepoxide-derived deoxyadenosine adducts by capillary electrophoresis: fluorescence line-narrowing and non-line narrowing spectroscopy. J. Chromat. (in press).