Replication-coupled repair of crotonaldehyde/acetaldehyde-induced guanine-guanine interstrand cross-links and their mutagenicity

Biochemistry

Volumn 45, Issue 42, 2006, Pages 12898-12905

  Liu, Xiang ^a,c   Lao, Yanbin ^b   Yang, In Young ^a   Hecht, Stephen S ^b   Moriya, Masaaki ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c UNIVERSITY OF MEDICINE AND DENTISTRY OF NEW JERSEY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; BIOSYNTHESIS; CELLS; CROSSLINKING; DERIVATIVES; DNA; ESCHERICHIA COLI;

MONOADDUCTS; MUTATION; NUCLEOTIDE EXCISION REPAIR (NER); TRANSCRIPTIONAL EVENTS;

PROTEINS;

1,3 BIS(2' DEOXYGUANOS N2 YL) BUTANE DERIVATIVE; 3 (2 DEOXYRIBOS 1 YL) 5,6,7,8 (N2 DEOXYGUANOSYL) 6 METHYLPYRIMIDO[1,2 ALPHA]PURINE 10(3H) ONE; ACETALDEHYDE; CROTONALDEHYDE; DNA; GUANINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DNA CROSS LINKING; DNA REPAIR; DNA REPLICATION; ESCHERICHIA COLI; EXCISION REPAIR; HUMAN; HUMAN CELL; MUTAGENICITY; MUTATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PLASMID; PRIORITY JOURNAL;

ACETALDEHYDE; ALDEHYDES; BASE SEQUENCE; CROSS-LINKING REAGENTS; DNA REPAIR; ESCHERICHIA COLI; GENETIC VECTORS; GUANINE; HUMANS; MOLECULAR SEQUENCE DATA; MUTAGENS; PLASMIDS; XERODERMA PIGMENTOSUM;

ESCHERICHIA COLI; EUKARYOTA; MAMMALIA;

EID: 33750309537     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi060792v     Document Type: Article

References (32)

1. U.S. Department of Health and Human Services (2004) Report on Carcinogens, 11th ed., pp III-1-III-3, Research Triangle Park, NC.
2. International Agency for Research on Cancer (2004) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Volume 83, Tobacco Smoke and Involuntary Smoking, pp 53-94, Lyon, France.
3. International Agency for Research on Cancer (1995) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Volume 63, Dry Cleaning, Some Chlorinated Solvents and Other Industrial Chemicals, pp 272-391, Lyon, France.
4. Chung, F. L., Chen, H. J. C., and Nath, R. G. (1996) Lipid peroxidation as a potential source for the formation of exocyclic DNA adducts, Carcinogenesis 17, 2105-2111.
5. 2-propanodeoxyguanosine adducts, Mutat. Res. 424, 71-81.
6. Wang, M., McIntee, E. J., Cheng, G., Shi, Y., Villalta, P. W., and Hecht, S. S. (2000) Identification of DNA adducts and acetaldehyde, Chem. Res. Toxicol. 13, 1149-1157.
7. Kozekov, I. D., Nechev, L. V., Moseley, M. S., Harris, C. M., Rizzo, C. J., Stone, M. P., and Harris, T. M. (2003) DNA interchain cross-links formed by acrolein and crotonaldehyde, J. Am. Chem. Soc. 125, 50-61.
8. Kozekov, I. D., Nechev, L. V., Sanchez, A., Harris, C. M., Lloyd, R. S., and Harris, T. M. (2001) Interchain cross-linking of DNA mediated by the principal adduct of acrolein, Chem. Res. Toxicol. 14, 1482-1485.
9. 2-propano-2′-deoxyguanosine adducts in the 5′-CpG-3′ sequence, Chem. Res. Toxicol. 19, 195-208.
10. Dooley, P. A., Tsarouhtsis, D., Korbel, G. A., Nechev, K. L., Shearer, J., Zegar, I. S., Harris, C. M., Stone, M. P., and Harris, T. M. (2001) Structural studies of an oligonucleotide containing a trimethylene interstrand cross-link in a 5′-(CpG) motif: Model of a malondialdehyde cross-link, J. Am. Chem. Soc. 123, 1730-1739.
11. Dronkert, M. L. G., and Kanaar, R. (2001) Repair of DNA interstrand cross-links, Mutat. Res. 486, 217-247.
12. de Silva, I. U., McHugh, P. J., Clingen, P. H., and Hartley, J. A. (2000) Defining the roles of nucleotide excision repair and recombination in the repair of DNA interstrand cross-links in mammalian cells, Mol. Cell. Biol. 20, 7980-7990.
13. Kuraoka, I., Kobertz, W. R., Ariza, R. R., Biggerstaff, M., Essigmann, J. M., and Wood, R. D. (2000) Repair of an interstrand DNA cross-link initiated by ERCC1-XPF repair/recombinational nuclease, J. Biol. Chem. 275, 26632-26636.
14. Niedernhofer, L. J., Odijk, H., Budzowska, M., van Drunen, E., Maas, A., Theil, A. F., de Wit, J., Jaspers, N. G. J., Beverloo, H. B., Hoeijmakers, J. H. J., and Kanaar, R. (2004) The structure-specific endonuclease Ercc1-Xpf is required to resolve DNA interstrand cross-link-induced double-strand breaks, Mol. Cell. Biol. 24, 5776-5787.
15. Bessho, T. (2003) Induction of DNA replication-mediated double strand breaks by psoralen DNA interstrand cross-links, J. Biol. Chem. 278, 5250-5254.
16. Wang, X., Peterson, C. A., Zheng, H., Nairn, R. S., Legerski, R. J., and Li, L. (2001) Involvement of nucleotide excision repair in a recombination-independent and error-prone pathway of DNA interstrand cross-link repair, Mol. Cell. Biol. 21, 713-720.
17. Zheng, H., Wang, X., Warren, A. J., Legerski, R. J., Nairn, R. S., Hamilton, J. W., and Li, L. (2003) Nucleotide excision repair- and polymerase η-mediated error-prone removal of mitomycin C interstrand cross-links, Mol. Cell. Biol. 23, 754-761.
18. Lao, Y., and Hecht, S. S. (2005) Synthesis and properties of an acetaldehyde-derived oligonucleotide interstrand cross-link, Chem. Res. Toxicol. 18, 711-721.
19. Yang, I.-Y., Johnson, F., Grollman, A. P., and Moriya, M. (2002) Genotoxic mechanism for the major acrolein-derived deoxyguanosine adduct in human cells, Chem. Res. Toxicol. 15, 160-164.
20. Hirt, B. (1967) Selective extraction of polyoma DNA from infected mouse cell cultures, J. Mol. Biol. 26, 365-369.
21. Yang, I.-Y., Hossain, M., Miller, H., Khullar, S., Johnson, F., Grollman, A. P., and Moriya, M. (2001) Responses to the major acrolein-derived deoxyguanosine adduct in Escherichia coli, J. Biol. Chem. 276, 9071-9076.
22. 2- propanodeoxyguanosine DNA adducts in human cells, Mutat. Res. (in press).
23. Cole, R. S. (1973) Repair of DNA containing interstrand crosslinks in Escherichia coli: Sequential excision and recombination, Proc. Natl. Acad. Sci. U.S.A. 70, 1064-1068.
24. de Laat, W. L., Appeldoorn, E., Jaspers, N. G. J., and Hoeijmakers, J. H. J. (1998) DNA structural elements required for ERCC1-XPF endonuclease activity, J. Biol. Chem. 273, 7835-7842.
25. Berardini, M., Mackay, W., and Loechler, E. L. (1997) Evidence for a recombination-independent pathway for the repair of DNA interstrand corss-links based on a site-specific study with nitrogen mustard, Biochemistry 36, 3506-3513.
26. Gentil, A., Cabral-Neto, J. B., Mariage-Samson, R., Margot, A., Imbach, J. L., Rayner, B., and Sarasin, A. (1992) Mutagenicity of a unique apurinic/apyrimidinic site in mammalian cells, J. Mol. Biol. 227, 981-984.
27. Takeshita, M., and Eisenberg, W. (1994) Mechanism of mutation on DNA templates containing synthetic abasic sites: Study with a double strand vector, Nucleic Acids Res. 22, 1897-1902.
28. Cabral Neto, J. B., Gentil, A., Caseira Cabral, R. E., and Sarasin, A. (1992) Mutation spectrum of eat-induced abasic sites on a single-stranded shuttle vector replicated in mammalian cells, J. Biol. Chem. 267, 19718-19723.
29. Fernandes, P. H., Kanuri, M., Nechev, L. V., Harris, T. M., and Lloyd, R. S. (2005) Mammalian cell mutagenesis of the DNA adducts of vinyl chloride and crotonaldehyde, Environ. Mol. Mutagen. 45, 455-459.
30. Ohmori, H., Friedberg, E. C., Fuchs, R. P. P., Goodman, M. F., Hanaoka, F., Hinkle, D., Kunkel, T. A., Lawrence, C. W., Livneh, Z., Nohmi, T., Prakash, L., Prakash, S., Todo, T., Walker, G. C., Wang, Z., and Woodgate, R. (2001) The Y-family of DNA polymerases, Mol. Cell 8, 7-8.
31. Sarkar, S., Davies, A. A., Ulrich, H. D., and McHugh, P. J. (2006) DNA interstrand crosslink repair during G1 involves nucleotide excision repair and DNA polymerase ζ, EMBO J. 25, 1285-1294.
32. Shen, X., Jun, S., O'Neal, L. E., Sonoda, E., Bemark, M., Sale, J. E., and Li, L. (2006) REV3 and REV1 play major roles in recombination-independent repair of DNA interstrand cross-links mediated by monoubiquitinated PCNA, J. Biol. Chem. 281, 13869-13872.