Identification and Quantification of the Depurinating DNA Adducts Formed in Mouse Skin Treated with Dibenzo[a,l]pyrene (DB[a,l]P) or Its Metabolites and in Rat Mammary Gland Treated with DB[a,l]P

Chemical Research in Toxicology - Tập 18 Số 6 - Trang 976-983 - 2005
Ercole L. Cavalieri1, Eleanor G. Rogan1, Kai-Ming Li1, Rosa Todorovic1, Freek Ariese1, Ryszard Jankowiak1, Nikica Grubor1, Gerald J. Small1
1Eppley Institute for Research in Cancer and Allied Diseases, University of Nebraska Medical Center, 986805 Nebraska Medical Center, Omaha, Nebraska 68198-6805, Ash Stevens, Inc., 5861 John C. Lodge Freeway, Detroit, Michigan 48202-3398, Department of Analytical Chemistry and Applied Spectroscopy, Laser Centre, Vrije Universiteit, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands, and Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111

Tóm tắt

Từ khóa


Tài liệu tham khảo

Cavalieri E. L., 1989, J. Cancer Res. Clin. Oncol., 115, 72, 10.1007/BF00391602

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[α,l]pyrene versus 7,12-dimethylbenz[α]anthracene, 982 benzo[α]pyrene and two dibenzo[α,l]pyrene dihydrodiols in mouse skin and rat mammary gland.Carcinogenesis12, 1939−1944.

Higginbotham S., 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, 10.1093/carcin/14.5.875

LaVoie E. J., 1993, Cancer Lett., 70, 14, 10.1016/0304-3835(93)90068-K

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 mourse skin of dibenzo[a,l]pyrenesyn- andanti-fjord-region diolepoxides.Carcinogenesis 15, 2455−2460.

Snook M. E., 1977, Beitrag. Tabakforsch., 9, 101

IARC (1983)IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, Vol. 32:  Polynuclear Aromatic Compounds, Part 1, Chemical, Environmental and Experimental Data, pp 33−104, 327−347, IARC, Lyon.

Mumford, J. L., He, X. Z., Chapman, R. S., Cao, S. R., Harris, D. B., Li, X. M., Xian, Y. L., Jiang, W. Z., Xu, C. W., Chuang, J. C., Wilson, W. E., and Cooke, M. (1987) Lung cancer and indoor air pollution in Xuan Wei, China.Science 235, 217−220.

Mumford J. L., 1995, China, with high lung cancer mortality associated with exposure to unvented coal smoke. Carcinogenesis 16, 3031−3036.

Schubert, P., Schantz, M. M., Sander, L. C., and Wise, S. A. (2003) Determination of polycyclic aromatic hydrocarbons with molecular weight 300 and 302 in environmental-matrix standard reference materials by gas chromatography/mass spectrometry.Anal. Chem.75, 234−246.

Li K. M., 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

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.

Todorovic R., 2005, Identification and quantification of stable DNA adducts of dibenzo[a,l]pyrene formed in mouse skin and rat mammary gland. Chem. Res. Toxicol. 18, 984−990

RamaKrishna N. V. S., 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

Hanson A. A., 1998, Synthesis of adducts formed by iodine oxidation of aromatic hydrocarbons in the presence of deoxyribonucleosides and nucleobases. Chem. Res. Toxicol. 11, 1201−1208

Li K.-M., 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

Li K.-M., 1994, Synthesis and structure determination of the adducts of dibenzo[a,l]pyrene diol epoxides and deoxyadenosine or deoxyguanosine. Polycyclic Aromat. Compd. 6, 207−213

Li K.-M., 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

Li K.-M., 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, 778−788

Chen L., 1996, Expanded analysis of benzo[a]pyrene-DNA adducts formed in vitro and in mouse skin:  Their significance in tumor initiation. Chem. Res. Toxicol. 9, 897−903

Mulder, P. P. J., Chen, L., Sekhar, B. C., George, M., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (1996) Synthesis and structure determination of the adducts formed by electrochemical oxidation of 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthracene in the presence of deoxyribonucleosides or adenine.Chem. Res. Toxicol. 9, 1264−1277.

Li K.-M., 2004, Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo. Carcinogenesis 25, 289−297

Guidelines, 1981, NIH Publication No. 81-2385

Jankowiak R., 1989, Fluorescence line narrowing spectroscopy in the study of chemical carcinogenesis. Anal. Chem. 60, 1023A−1032A

Lu P., 1991, Chem. Res. Toxicol., 4, 69

Devanesan P. D., 1992, Identification and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes in vitro. Chem. Res. Toxicol. 5, 302−309

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.

Ariese F., 1996, Conformational studies of depurinating DNA adducts from syn-dibenzo[a,l]pyrene diolepoxide. Carcinogenesis 17, 829−837

Jankowiak R., 1997, Conformational studies of stereoisomeric tetrols derived from syn- and anti-dibenzo[a,l]pyrene diol epoxides. Chem. Res. Toxicol. 10, 677−686

Devanesan P. D., 1990, Metabolism and mutagenicity of dibenzo[a,e]pyrene and the very potent environmental carcinogen dibenzo[a,l]pyrene. Chem. Res. Toxicol. 3, 580−586

Cremonesi P., 1992, J. Org. Chem., 57, 10.1021/jo00038a015

Todorovic R., 1997, Determination of benzo[a]pyrene- and 7,12-dimethylbenz[a]anthracene-DNA adducts formed in rat mammary glands. Chem. Res. Toxicol. 10, 941−947

Chakravarti D., 1995, Proc. Natl. Acad. Sci. U.S.A. 92

Chakravarti D., 1998, Detection of dibenzo[a,l]pyrene-induced H-ras codon 61 mutant genes in preneoplastic SENCAR mouse skin using a new PCR−RFLP method. Oncogene 16, 3203−3210

Chakravarti D., 2000, Mutat. Res., 456, 32, 10.1016/S0027-5107(00)00102-0

Colapietro A.-M., 1993, Characterization of benzo[a]pyrene-initiated mouse skin papillomas for Ha-ras mutations and protein kinase C levels. Carcinogenesis 14, 2289−2295

Slaga T. J., 1976, Cancer Lett., 2, 10.1016/S0304-3835(76)80020-1

Slaga T. L., 1977, Comparison of the tumor-initiating activities of benzo[a]pyrene arene oxides and diol-epoxides. Cancer Res. 37, 4130−4133

Quintanilla M., 1986, Nature, 322, 80, 10.1038/322078a0

Brown K., 1990, Proc. Natl. Acad. Sci. U.S.A. 87

Devanesan P. D., 1993, Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 364−371

Casse C., 2003, Mutat. Res., 528, 27, 10.1016/S0027-5107(03)00078-2

Hofseth L. J., 2003, J. Clin. Invest., 112, 10.1172/JCI19757

Sossou M., 2005, APE1 overexpression in XRCC1-deficient cells complements the defective repair of oxidative single strand breaks but increases genomic instability. Nucleic Acids Res. 33, 298−306

Frechet M., 2001, FEBS Lett., 505, 10.1016/S0014-5793(01)02834-4

Lang T., 2004, Proc. Natl. Acad. Sci. U.S.A. 101