Interference of benzo[a]pyrene diol epoxide-deoxyguanosine adducts in a GC box with binding of the transcription factor Sp1

Molecular Carcinogenesis

Volumn 16, Issue 1, 1996, Pages 44-52

  MacLeod, Michael C ^a   Powell, K Leslie ^a   Kuzmin, Vladimir A ^b,c   Kolbanovskiy, Aleksandr ^b   Geacintov, Nicholas E ^b  

^a UNIVERSITY OF TEXAS   (United States)

^b NEW YORK UNIVERSITY   (United States)

^c SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

DNA adducts; polycyclic aromatic hydrocarbons; transcription factor Sp1

Indexed keywords

DEOXYGUANOSINE; DIHYDROXYBENZO[A]PYRENE OXIDE; TRANSCRIPTION FACTOR;

ARTICLE; CONTROLLED STUDY; DNA ADDUCT; HUMAN; PRIORITY JOURNAL;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; BASE SEQUENCE; BINDING SITES; DEOXYGUANOSINE; DNA ADDUCTS; DNA-BINDING PROTEINS; HELA CELLS; HUMANS; MOLECULAR SEQUENCE DATA; OLIGODEOXYRIBONUCLEOTIDES; PROMOTER REGIONS (GENETICS); PROTEIN BINDING; SP1 TRANSCRIPTION FACTOR;

EID: 0029905340     PISSN: 08991987     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2744(199605)16:1<44::AID-MC6>3.0.CO;2-O     Document Type: Article

References (38)

1. Miller JA. Carcinogenesis by chemicals: An overview. Cancer Res 30:559-576, 1970.
2. Miller EC, Miller JA. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer 47:2327-2345, 1981.
3. Jeffrey AM. DNA modification by chemical carcinogens. In: Huberman E and Goff S (eds), Mechanism of Cellular Transformation by Carcinogenic Agents. Pergamon Press, Elmsford, NY, 1987, pp. 33-71.
4. Beland FA, Poirier MC. DNA adductsand carcinogenesis. In: Sirica AE (ed), The Pathobiology of Neoplasia. Plenum Press, NY, 1989, pp. 57-78.
5. Harvey RG. Polycydic Aromatic Hydrocarbons. Chemistry and Carcinogenicity. Cambridge University Press, New York, 1991.
6. Weinberg RA. Oncogenes, tumor suppressor genes and cell transformation: Trying to put it all together. In: Brugge J, Curran T, Harlow E, and McCormick F (eds) Origins of Human Cancer. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, 1991, pp. 1-16.
7. Marshall CJ, Vousden KH, Phillips DH. Activation of c-Ha-ras-1 proto-oncogene by in vitro modification with a chemical carcinogen, benzo[a]pyrene diol epoxide. Nature 310:586-589, 1984.
8. Kennedy AR. Is there a critical target gene for the first step in carcinogenesis? Environ Health Perspect 93:199-203, 1991.
9. Kamiya K, Yasukawa-Barnes J, Mitchen JM, Gould MN, Clifton KH. Evidence that carcinogenesis involves an imbalance between epigenetic high-frequency initiation and suppression of promotion. Proc Natl Acad Sci USA 92:1332-1336, 1995.
10. Barren JC, T'so POP. Relationship between somatic mutation and neoplastic transformation. Proc Natl Acad Sci USA 75:3297-3301, 1978.
11. Treiber DK, Zhai X, Jantzen H-M, Essigman JM. Cisplatin-DNA adducts are molecular decoys for the ribosomal transcription factor hUBF (human upstream binding factor). Proc Natl Acad Sci USA 91:5672-5676, 1994.
12. Sun D, Hurley LH. Demonstration of the asymmetric TBP-induced unwinding of the region immediately downstream of the TATA box using the intercalating DNA-reactive drug pluramycin. Abstract. Proceedings of the American Association for Cancer Research 36:534, 1995.
13. MacLeod MC, Powell KL, Tran N. Binding of the transcription factor, Sp1, to non-target sites in DNA modified by benzo[a]pyrene diol epoxide. Carcinogenesis 16:975-983, 1995.
14. MacLeod MC, Lew L. A rapid, spectrophotometric assay for the integrity of diol epoxides. Carcinogenesis 9:2133-2135, 1988.
15. Nalbantoglu J, Phear GA, Meuth M. Nucleotide sequence of hamster adenine phosphoribosyl transferase (aprt) gene. Nucleic Acids Res 14:1914, 1986.
16. Park J-H, Taylor MW. Analysis of signals controlling expression of the Chinese hamster ovary aprt gene. Mol Cell Biol 8:2536-2544, 1988.
17. Cosman M, Ibanez V, Geacintov NE, Harvey RG. Preparation and isolation of adducts in high yield derived from the binding of two benzo[a]pyrene-7,8-dihydroxy-9,10-oxide stereoisomers to the oligonucleotide d(ATATGTATA). Carcinogenesis 11:1667-1672, 1990.
18. Mao B, Xu J, Li B, et al. Synthesis and characterization of covalent adducts derived from the binding of benzo[a]pyrene diol epoxide to a -GGG sequence in a deoxyoligonucleotide. Carcinogenesis 16:357-365, 1995.
19. Mao B, Margulis LA, Li B, et al. Direct synthesis and identification of benzo[a]pyrene diol epoxide-deoxyguanosine binding sites in modified oligodeoxynudeotides. Chem Res Toxicol 5:773-778, 1992.
20. Maxam AM, Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol 65:497-559, 1980.
21. Boles TC, Hogan ME. Site specific carcinogen binding to DNA. Proc Natl Acad Sci USA 81:5623-5627, 1984.
22. Boles TC, Hogan ME. High-resolution mapping of carcinogen binding sites on DNA. Biochemistry 25:3039-3043, 1986.
23. Dittrich KA, Krugh TR. Analysis of site-specific binding of (±)-anti-benzo[a)pyrene diol epoxide to restriction fragments of pBR322 DNA via photochemical mapping. Chem Res Toxicol 4:270-276, 1991.
24. Li B, Mao B, Liu T-M, et al. Laser-induced photochemical strand cleavage of site-specifically and covalently modified (+)-anti-benzo[a]pyrene diol epoxide-oligonucleotide adducts. Chem Res Toxicol 8:396-402, 1995.
25. Gidoni G, Dynan WS, Tjian R. Multiple specific contacts between a mammalian transcrption factor and its cognate promoters. Nature 312:409-413, 1984.
26. Sun D, Hurley LH. Cooperative bending of the 21-base pair repeats of the SV40 viral early promoter by human Sp1. Biochemistry 33:9578-9587, 1994.
27. Xu R, Mao B, Xu J, et al. Stereochemistry-dependent bending in oligonucleotide duplexes induced by site-specific covalent benzo[a]pyrene diol epoxide-guanine lesions Nucleic Acids Res 23:2314-2319, 1995.
28. Cosman M, de los Santos C, Fiala R, et al. Solution conformation of the major adduct between the carcinogen (+)-anti-benzo[a]pyrene diol epoxide and DNA. Proc Natl Acad Sci USA 89:1914-1918, 1992.
29. de los Santos C, Cosman M, Hingerty BE, et al. Influence of benzo[a]pyrene diol epoxide chirality on solution conformations of DMA covalent adducts: The (-)-trans-anti-[BP]G-C adduct structure and comparison with the (+)-trans-anti-[BP]G-C enantiomer. Biochemistry 315245-5252, 1992.
30. Cosman M, de los Santos C, Fiala R, et al. Solution conformation of the (+)-cis-anti-[BP]dG adduct in a DNA duplex: Intercalation of the covalently attached benzo[a]pyrenyl ring into the helix and displacement of the modified deoxyguanosine. Biochemistry 32:4145-4155, 1993.
31. Brown WC, Romano LJ. Benzo[a]pyrene-DNA adducts inhibit translocation by the gene 4 protein of bacteriophage T7. J Biol Chem 264:6748-6754, 1989.
32. Yong Y, Romano LJ. Benzo[a]pyrene-DNA adducts inhibit the DNA helicase activity of the bacteriophage T7 gene 4 protein. Chem Res Toxicol 9:179-187, 1996.
33. Kim SK, Takahashi M, Jernstrom B, Norden B. Enhancement of binding rate of RecA protein to DNA by carcinogenic benzo[a]pyrene derivatives and selective change of adduct conformation. Carcinogenesis 14:311-313, 1993.
34. Moore P, Strauss BS. Sites of inhibition of in vitro DNA synthesis in carcinogen- and UV-treated φ×174 DNA. Nature 278:664-666, 1979.
35. Nath ST, Lee M-S, Romano U. Effect of carcinogenic adducts on transcription byT7 RNA polymerase. Nucleic Acids Res 15:4257-4271, 1987.
36. Kootstra A, Lew LK, Nairn RS, MacLeod MC. Preferential modification of GC boxes by benzo|a]pyrene-7,8-diol-9,10 epoxide. Mol Carcinog 1:239-244, 1989.
37. Choi D-J, Marino-Alessandri DJ, Geacintov NE, Scicchitano DA. Site-specific benzo[a]pyrene diol epoxide-DNA adducts inhibit transcription elongation by bacteriophage T7 RNA polymerase Biochemistry 33:780-787, 1994.
38. MacLeod MC. A possible role in chemical carcinogenesis for epigenetic, heritable changes in gene expression. Mol Carcinog, in press.