Phosphate alkylation in different DNA substrates: The role of local DNA sequence and electrophile character in determining the nonrandom nature of phosphotriester adduct formation

Chemical Research in Toxicology

Volumn 19, Issue 3, 2006, Pages 407-413

  Le Pla, Rachel C ^a,b   Bowman, Karen J ^a   Farmer, Peter B ^b   Jones, George D D ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; DIETHYL SULFATE; DNA; ESTER; ETHYLNITROSOUREA; METHYLNITROSOUREA; OLIGONUCLEOTIDE; OXYGEN; PHOSPHATE; PHOSPHORIC ACID TRIESTER; PURINE; UNCLASSIFIED DRUG;

ARTICLE; B LYMPHOBLAST; CELL LABELING; CELL LINE; CELL NUCLEUS; CELL STRAIN H2E1 OR; CHROMATIN; CONTROLLED STUDY; DNA ADDUCT; DNA ALKYLATION; DNA FLANKING REGION; DNA PACKAGING; DNA REPAIR; DNA SEQUENCE; ELECTRON; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; WHOLE CELL;

ALKYLATING AGENTS; ALKYLATION; AUTORADIOGRAPHY; BUFFERS; CELL LINE; CULTURE MEDIA; DNA; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ETHYLNITROSOUREA; HUMANS; METHYLNITROSOUREA; OLIGONUCLEOTIDES; OXYGEN; PHOSPHATES; SULFURIC ACID ESTERS;

EID: 33645474286     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050298c     Document Type: Article

References (29)

1. Bonassi, S., and Au, W. W. (2002) Biomarkers in molecular epidemiology studies for health risk prediction. Mutat. Res. 511, 73-86.
2. Dipple, A. (1995) DNA adducts of chemical carcinogens. Carcinogenesis 16, 437-441.
3. Gaylor, D. W., Kadlubar, F. F., and Beland, F. A. (1992) Applications of biomarkers to risk assessment. Environ. Health Perspect. 98, 139-141.
4. La, D. K., and Swenberg, J. A. (1996) DNA adducts: Biological markers of exposure and potential applications to risk assessment. Mutat. Res. 365, 129-146,
5. Poirier, M. C., Santella, R. M., and Western, A. (2000) Carcinogen rrmcromolecular adducts and their measurement. Carcinogenesis 21, 353-359.
6. Shooter, K. (1978) DNA phosphotriesters as indicators of cumulative carcinogen induced damage. Nature 274, 612-613.
7. Singer, B. (1985) In vivo formation and persistence of modified nucleosides resulting from alkylating agents. Environ. Health Perspect. 62, 41-48.
8. Maccubbin, A. E., Caballes, L., Riorclan, J. M., Huang, D. H., and Gurtoo, H. L. (1991) A cyclophosphamide/DNA phosphoester adduct formed in vitro and in vivo. Cancer Res. 51, 886-892.
9. Yates, J. M., Fennell, T. R., Turner, M. J., Recio, L., and Sumner, S. C. J. (1994) Characterization of phosphodiester adducts produced by the reaction of cyanoethylene oxide with nucleolides. Carcinogenesis 15, 277-283.
10. Guichard, Y., Jones, G. D. D., and Farmer, P. B. (2000). Detection of DNA alkylphosphotriesters by P-32 postlabeling: Evidence for the nonrandom manifestation of phosphotriester lesions in vivo. Cancer Res. 60, 1276-1282.
11. Le Pla, R. C., Guichard, Y., Bowman, K. J., Gaskell, M., Farmer, P. B., and Jones, G. D. D. (2004) Further development of P-32-postlabeling for the detection of alkylphosphotriesters: Evidence for the long-term nonrandom persistence of ethyl-phosphotriester adducts in vivo. Chem. Res. Toxicol. 17, 1491-1500.
12. MacLeod, M. C. (1995) Interaction of bulky chemical carcinogens with DNA in chromatin. Carcinogenesis 16, 2009-2014.
13. Sudhakar, S., Tew, K. D., Schein, P. S., Woolley, P. V., and Smulson, M. E. (1979) Nitrosourea interaction with chromatin and effect on poly (adenosine diphosphate ribose) polymerase activity. Cancer Res. 39, 1411-1417.
14. Berkowitz, E. M. L., and Silk, H. (1981) Methylation of chromosomal DNA by 2 alkylating-agents differing in carcinogenic potential. Cancer Lett. 12, 311-321.
15. McGhee, J. D., and Felsenfeld, G. (1979) Reaction of nucleosome DNA with dimethyl sulfate. Proc. Natl. Acad. Sci. U.S.A. 76, 2133-2137.
16. Dolan, M. E., Oplinger, M., and Pegg, A. E. (1988) Sequence specificity of guanine alkylation and repair. Carcinogenesis 9, 2139-2143.
17. Cloutier, J. F., Drouin, R., and Castonguay, A. (1999) Treatment of human cells with N-nitroso(acetoxymethyl)methylamine: Distribution patterns of piperidine-sensitive DNA damage at the nucleotide level of resolution are related to the sequence context. Chem. Res. Toxicol. 12, 840-849.
18. Hartley, J. A., Gibson, N. W., Kohn, K. W., and Mattes, W. B. (1986) DNA-Sequence selectivity of guanine-N7 alkylation by 3 antitumor chloroethylating agents. Cancer Res. 46, 1943-1947.
19. Kohn, K, W., Hartley, J. A., and Mattes, W. B. (1987) Mechanisms of DNA-Sequence selective ulkylation of guanine-N7 positions by nitrogen mustards. Nucleic Acids Res. 15, 10531-10549.
20. Mattes, W. B., Hartley, J. A., and Kohn, K. W. (1986) DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards. Nucleic Acids Res. 14, 2971-2987.
21. Beranek, D. T. (1990) Distribution of methyl and ethyl adducts following alkylation with monofunctional alkylating agents. Mutat. Res. 231, 11-30.
22. Streitweiser, A. (1956) Solvolytic displacement reactions at saturate carbon atoms. Chem. Rev. 56, 571-745.
23. Ross, W. C. J. (1962) Biological Alkylating Agents: Fundamental Chemistry and the Design of Compounds for Specific Toxicity. Butterworths, London.
24. 32P-postlabeling analysis of alkylphosphotriesters in DNA. In Postlabeling Methods for Detection of DNA Adducts (Phillips, D. H., Castegnaro, M., and Bartsch, H., Eds.) pp 127-132, IARC Scientific Publications, Lyon.
25. Saris, C. P., Damman, S. J., van den Ende, A. M. C., Westra, J. G., and den Engelse, L. (1995) A P-32 postlabeling assay for the detection of alkylphosphotriesters in DNA. Carcinogenesis 16, 1543-1548.
26. Warpehoski, M. A., and Hurley, L. H. (1988) Sequence selectivity of DNA covalent modification. Chem. Res. Toxicol. 1, 315-333.
27. Pullman, A., and Pullman, B. (1981) Molecular electrostatic potential of the nucleic-acids. Q. Rev. Biophys. 14, 289-380.
28. Kim, N. S., Zhu, Q. Q., and Lebreton, P. R. (1999) Aqueous ionization and electron-donating properties of dinucleotides: Sequence-specific electronic effects on DNA alkylation. J. Am. Chem. Soc. 12, 11516-11530.
29. Rasouli-Nia, A., Atrazheva, E., Tsujikawa, L. M., Reha-Krantz, L. J., and Weinfeld, M. (2000) Influence of DNA phosphate alkylation on DNA exonuclease activity. Proceedings of the American Association for Cancer Research #1671.