Fluorescence hplc methods for detecting benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide-deoxyadenosine adducts in enzyme-digests of modified dna: Improved sensitivity

Carcinogenesis

Volumn 14, Issue 5, 1993, Pages 1049-1051

  Chen, Junxin ^a   Macleod, Michael C ^a,b   Zhao, Rushen ^a   E geacintov, Nicholas ^a  

^a NEW YORK UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE 7,8 DIHYDRODIOL 9,10 OXIDE; DEOXYADENOSINE; DEOXYGUANOSINE;

ARTICLE; DNA ADDUCT; DNA DEGRADATION; DNA MODIFICATION; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYADENOSINES; DNA; MICROCHEMISTRY; SPECTROMETRY, FLUORESCENCE; SUPPORT, U.S. GOV'T, NON-P.H.S.; SUPPORT, U.S. GOV'T, P.H.S.; TRITIUM;

EID: 0027276369     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/14.5.1049     Document Type: Article

References (16)

1. Weinstein, I.B, Jeffrey, A.M., Jennette, K.W., Blobstien, S.H., Harvey, R.G., Harris, C., Autnip, H., Kasai, H. and Nakanishi, K. (1976) Benzo[a]pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo. Science, 193, 592-594
2. Koreeda, M., Moore, P.D., Wislocki, P.G., Levin, W., Conney, A.H., Yagi, H. and Jerina, D.M. (1978) Binding of benzo[a]pyrene 7, 8-dkl-9, 10-epoxides to DNA, RNA and protein of mouse slnn occurs whh high stereoselectivity. Science, 199, 778-781
3. Meehan, T. and Straub A (1979) Double stranded DNA steitosdectively binds benzo[a]pyrene diol epoxides. Nature, 21, 410-412
4. Brookes, P. and Osborne, M.R. (1982) Mutation in mammalian cells by stereoisomers of anri-benzo[a]pyrene diol epoxide in relation to the extent and nature of the DNA reaction products. Carcinogenesis, 3, 1223-1226
5. Cheng, S.C., Hilton, B.D., Roman, J.M. and Dipple, A. (1989) DNA adducts from carcinogenic and noocarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide. Chem. Res. Toxicol, 2, 334-340
6. Jeffrey AM., Grzeskowiak, K., Weinstein, I.B., Nakanishi, K., Roller, P. and Harvey, R.G. (1979) Benzo(a]pyrene-7, 8-dihydrodiol 9, 10-oxide adenosine and deoxyadenosine adducts: Structure and stereochemistry. Science, 206, 1309-1311
7. Cheng, S.C., Prakash, A.S., Pigott, M.A., Hilton, B.D., Lee, H., Harvey, R.G. and Dipple, A. (1988) A metabolite of the carcinogen 7, 12-dimethylbenz[a]-anthracene that reacts predominantly with adenine residues in DNA. Carcinogenesis, 9, 1721-1723
8. Dipple, A., Pigott, M.A., Agarwal, S.K., Yagi, H., Sayer, J.M. and Jerina JYM. (1989) Optically active benzo[c]phenanthrene diol epoxides bind extensively to adenine in DNA. Nature, 327, 535-536
9. Bigger, C.A.H., Strandberg, J., Yagi, H., Jerina, D.M. and Dipple, A. (1989) Mutagenic specificity of a potent carcinogen, benzo[a]phenanihrene (4R, 3S)-dihydrodiol (2S, lR)-epoxide, which reacts with adenine and guanine in DNA. Proc. Natl. Acad. Sa. USA, 86, 2291-2295
10. MacLeod, M.C. and Tang, M.-S. (1985) Interactions of benzo[a]pyrene diol epoxides with linear and supercoiled DNA. Cancer Res., 45, 51-56
11. Ibanez, V., Geacintov, N.E., Gagliano, A.G., Brandimaite, S. and Harvey, R.G. (1980) Physical binding of tetraols derived from 7, 8-dihydroxy-9, 10-epoxy-bezo(a]pyrene to DNA. J. Am. Chem. Soc., 102, 5661-5666
12. Geacintov, N.E., Mao, B., France, L.L., Zhao, R., Cben, J., Liu, T.M., Ya, N.-Q., Margulis, L.A. and Sutherland J.C. (1992) Photoinduced electron transfer and fluorescence mechanisms in covalently linked polynuclear aromatic-nucleotide complexes. SPIE Vol. 1640, Time-Resolved Laser Spectroscopy in Biochemistry III, 774-783
13. Margulis, L., Pluzhnikov, P.F., Mao, B., Kuzmin, V.A., Chang, Y.-J., Scott, T.W. and Geacintov, N.E. (1991) Photoinduced electron transfer in a covalent benzo[a]pyrene diol epoxide-2'-deoxyguanosine complex. Chem. Phys. Lett., 187, 597-603
14. Yamamoto J., Subramaniam, R., Wolfe, A.R. and Meehan, T. (1990) The formation of covalent adducts between benzo[a]pyrenediol epoxide and RNA structural analysis by mass spectrometry. Biochemistry, 29, 3966-3972
15. Macleod, M.C., Adair, G. and Humphrey, R.M. (1988) Differential efficiency of mutagenesis at three genetic loci in CHO cells by benzo[a]pyrene diol epoxide. Mutat. Res., 199, 243-254
16. MacLeod, M.C., Mann, K.L., Thai, G., Cod, C.J. and Reiners, J.J. Jr (1991) Inhibition by 2, 6-dithiopurine and thiopurinol of binding of a benzo[a]pyrene diol epoxide to DNA in mouse epidermis and of the initiation phase of two-stage tumorigenesis. Cancer Res., 51, 4859-4864