Conformational studies of stereoisomeric tetrols derived from syn- and anti-dibenzo[a,l]pyrene diol epoxides

Chemical Research in Toxicology

Volumn 10, Issue 6, 1997, Pages 677-686

  Jankowiak, Ryszard ^a   Ariese, Freek ^b,d   Zamzow, Dan ^b   Luch, Andreas ^c,e   Kroth, Heiko ^c   Seidel, Albrecht ^c   Small, Gerald J ^a,b  

^a IOWA STATE UNIVERSITY   (United States)

^b IOWA STATE UNIVERSITY   (United States)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

^d INSTITUTE FOR ENVIRONMENTAL STUDIES   (Netherlands)

^e TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PYRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DNA ADDUCT; DRUG CONFORMATION; FLUORESCENCE; MOLECULAR MODEL; NUCLEOTIDE SEQUENCE; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY;

BENZOPYRENES; CARCINOGENS; DIHYDROXYDIHYDROBENZOPYRENES; ELECTROCHEMISTRY; EPOXY COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 0030958995     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960211a     Document Type: Article

References (35)

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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-dimethyl-benz[a]anthracene and benzo[a]pyrene at low dose in mouse skin. Carcinogenesis 14, 875-878.
7. 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.
8. Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic compounds. Cancer Res. 42, 4875-4491.
9. 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.
10. Gill, H. S., Kole, P. L., Wiley, J. C., Li, K.-M., Higginbotham, S., Rogan, E. G., and Cavalieri, E. L. (1994) Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn-and anti-fjord-region diol epoxides. Carcinogenesis 15, 2455-2460.
11. 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.
12. 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. Polycycl. Aromat. Compd. 6, 207-213.
13. Devanesan, P. D., Rogan, E. G., and Cavalieri, E. L. (1995) Identification of stable DNA adducts of dibenzo[a,l]pyrene. Proc. Am. Assoc. Cancer Res. 36, 137.
14. 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.
15. 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.
16. 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.
17. 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. 6, 364-371.
18. 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.
19. 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.
20. 2-dG in sequence-defined oligonucleotides. Carcinogenesis 15, 2891-2898.
21. 2-dG in duplex oligonucleotides using polyacrylamide gel electrophoresis and low-temperature fluorescence spectroscopy. Biophys. Chem. 56, 281-296.
22. Ariese, F., Small, G. J., and Jankowiak, R. (1996) Conformational studies of depurinating DNA adducts from syn-dibenzo[a,l]pyrene diol epoxide. Carcinogenesis 17, 829-837.
23. Rodriguez, H., and Loechler, E. L. (1993) Mutagenesis by the (+)-anti diol-epoxide of benzo[a]pyrene: what controls mutagenic specificity? Biochemistry 32, 1759-1769.
24. Shibutani, S., Margulis, L. A., Geacintov, N. E., and Grollman, A. (1993) Translesional synthesis on a DNA template containing a single stereoisomer of dG-(+)-or dG-(-)-anti-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene). Biochemistry 32, 7531-7541.
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. Bushman, D. R., Grossman, S. J., Jerina, D. M., and Lehr, R. E. (1989) Synthesis of optically active fjord-region 11,12-diol 13,14-epoxides and the K-region 9,10-oxide of the carcinogen benzo[g]-chrysene. J. Org. Chem. 54, 3533-3544.
27. Burkert, U., and Allinger, N. L. (1982) Molecular mechanics, ACS Monograph Vol. 177, American Chemical Society, Washington, DC.
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. Ridley, J. E., and Zerner, M. C. (1976) Triplet states via intermediate neglect of differential overlap: benzene, pyridine, and the diazines. Theoret. Chim. Acta 42, 223-236.
30. Del Bene, J., and Jaffé, H. H. (1968) Use of the CNDO method in spectroscopy I. benzene, pyridine, and the diazines. J. Chem. Phys. 48, 1807-1813.
31. Del Bene, J., and Jaffé, H. H. (1968) Use of the CNDO method in spectroscopy II. five-membered rings. J. Chem. Phys. 48, 4050-4055.
32. Brown, J. C. (1982) Ph.D. Thesis, Iowa State University, Ames, IA.
33. 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.
34. 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.
35. Gordon, A. J., and Ford, R. A. (1972) The Chemist's Companion; a Handbook of Practical Data, Techniques, and References; John Wiley & Sons, New York.