Structure elucidation of the adducts formed by fjord region dibenzo[a,l]pyrene-11,12-dihydrodiol 13,14-epoxides with deoxyguanosine

Chemical Research in Toxicology

Volumn 12, Issue 9, 1999, Pages 778-788

  Li, Kai Ming ^a   George, Mathai ^b   Gross, Michael L ^b   Lin, Cheng Huang ^c   Jankowiak, Ryszard ^d   Small, Gerald J ^c,d   Seidel, Albrecht ^e   Kroth, Heiko ^f   Rogan, Eleanor G ^a   Cavalieri, Ercole L ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b WASHINGTON UNIVERSITY   (United States)

^c IOWA STATE UNIVERSITY   (United States)

^d IOWA STATE UNIVERSITY   (United States)

^e JOHANNES GUTENBERG UNIVERSITY   (Germany)

^f NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; DEOXYGUANOSINE; EPOXIDE; N,N DIMETHYLFORMAMIDE; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE;

ARTICLE; CARCINOGENESIS; CHEMICAL REACTION; FLUORESCENCE SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DIHYDROXYDIHYDROBENZOPYRENES; DNA; DNA ADDUCTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032821305     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980234k     Document Type: Article

References (23)

1. 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, 1083-1099.
2. Cavalieri, E. L., and Rogan, E. G. (1998) Mechanisms of tumor initiation by polycyclic aromatic hydrocarbons in mammals. In The Handbook of Environmental Chemistry: PAHs and Related Compounds, Vol. 3J (Neilson, A. H., Ed.) pp 81-117, Springer, Heidelberg.
3. RamaKrishna, N. V. S., Padmavathi, N. S., Cavalieri, E. L., Rogan, E. G., Cerny, R. L., and Gross, M. L. (1993) Synthesis and structure determination of the adducts formed by electrochemical oxidation of the potent carcinogen dibenzo[a,l]pyrene in the presence of nucleosides. Chem. Res. Toxicol. 6, 554-560.
4. Li, K.-M., Byun, J., Gross, M., Zamzow, D., Jankowiak, R., Rogan, E. G., and Cavalieri, E. L. (1999) Synthesis and structure determination of the adducts formed by electrochemical oxidation of dibenzo[a,l]pyrene in the presence of adenine. Chem. Res. Toxicol. 12, 749-757.
5. 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 by fjord region dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides with deoxyadenosine. Chem. Res. Toxicol. 12, 758-767.
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. 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 structures. Cancer Res. 54, 887-890.
8. Ralston, S. L., Seidel, A., Luch, A., Platt, K. L., and Baird, W. M. (1995) Stereoselective activation of dibenzo[a,l]pyrene to (-)-anti(11R12S,13S,14R)-and (+)-syn-(11S,12R,13S,14R)-11,12-diol-13,14-epoxides which bind exclusively to deoxyadenosine residues of DNA in the human mammary carcinoma cell line MCF-7. Carcinogenesis 16, 2899-2907.
9. 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.
10. 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.
11. Devanesan, P. D., RamaKrishna, N. V. S., Padmavathi, N. S., Higginbotham, S., Rogan, E. G., Cavalieri, E. L., Marsch, 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. 6, 364-371.
12. 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.
13. Marsch, 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.
14. 2-dG in sequence-defined oligonucleotides. Carcinogenesis 15, 2891-2898.
15. 2-dG in duplex oligonucleotides using polyacrylamide gel electrophoresis and low-temperature fluorescence spectroscopy. Biophys. Chem. 56, 281-296.
16. Ariese, F., Small, G. J., and Jankowiak, R. (1996) Conformational studies of depurinating DNA adducts from syn-dibenzo[a]pyrene diolepoxide. Carcinogenesis 17, 829-837.
17. 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 onti-dibenzo[a,l]-pyrene diol epoxides: Fluorescence studies. Chem. Res. Toxicol. 12, 768-777.
18. NIH Guidelines for the Laboratory Use of Chemical Carcinogens (1981), NIH Publication No. 81-2385, U.S. Government Printing Office, Washington, DC.
19. 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.
20. Frank, H., Luch, A., Oesch, F., and Seidel, A. (1996) Assignment of absolute configuration to metabolically formed trans-dihydrodiols of dibenzo[a,l]pyrene by the exciton chirality method using a new red-shifted chromophore. Polycyclic Aromat. Compd. 10, 109-116.
21. 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.
22. RamaKrishna, N. V. S., Gao, F., Padmavathi, N. S., Cavalieri, E. L., Rogan, E. G., Cerny, R. L., and Gross, M. L. (1992) Model adducts of benzo[a]pyrene and nucleosides formed from its radical cation and diol epoxide. Chem. Res. Toxicol. 5, 293-302.
23. Cerny, R., Wellemans, J. M. Y., George, M., and Gross, M. L. (1994) The use of tandem mass spectrometry for the structure determination of adducts formed between DNA and dibenzo[a,l] pyrene. Polycyclic Aromat. Compd. 6, 215-222.