Cross-linking of the human DNA repair protein O6-alkylguanine DNA alkyltransferase to DNA in the presence of 1,2,3,4-diepoxybutane

Chemical Research in Toxicology

Volumn 19, Issue 5, 2006, Pages 645-654

  Loeber, Rachel ^a   Rajesh, Mathur ^a   Fang, Qingming ^b   Pegg, Anthony E ^b   Tretyakova, Natalia ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 O ALKYLGUANINE DNA ALKYLTRANSFERASE; ALANINE; ALKYLATING AGENT; AMINO ACID; BUTADIENE DIEPOXIDE; CARCINOGEN; CYSTEINE; DNA; GLYCYLASPARAGINYLPROLYLVALYLPROLYLISOLEUCYLLEUCYLISOLEUCYLPROLYLCYSTEINYLHI STIDYLARGININE; GUANINE DERIVATIVE; N7 (2' HYDROXY 3',4' EPOXYBUT 1' YL)GUANINE; OLIGODEOXYNUCLEOTIDE; PHOSPHORUS 32; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COVALENT BOND; CYTOTOXICITY; DNA ADDUCT; DNA ALKYLATION; DNA PROTEIN COMPLEX; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVE SITE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MUTAGENICITY; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN CROSS LINKING; PROTEIN EXPRESSION; SEQUENCE ANALYSIS; STANDARD; STRUCTURE ANALYSIS;

ALKYLATING AGENTS; AMINO ACID SEQUENCE; CARCINOGENS; CROSS-LINKING REAGENTS; DEOXYGUANOSINE; DNA; DNA REPAIR; EPOXY COMPOUNDS; HUMANS; MOLECULAR SEQUENCE DATA; O(6)-METHYLGUANINE-DNA METHYLTRANSFERASE; PEPTIDES;

EID: 33744501244     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0600088     Document Type: Article

References (29)

1. 6-alkylguanine by alkyltransferases. Mutat. Res. 462, 83-100.
2. Daniels, D. S., Woo, T. T., Luu, K. X., Noll, D. M., Clarke, N. D., Pegg, A. E., and Tainer, J. A. (2004) DNA binding and nucleotide flipping by the human DNA repair protein AGT. Nat. Struct. Mol. Biol. 11, 714-720.
3. Daniels, D. S., Mol, C. D., Arvai, A. S., Kanugula, S., Pegg, A. E., and Tainer, J. A. (2000) Active and alkylated human AGT structures: a novel zinc site, inhibitor and extrahelical base binding. EMBO J. 19, 1719-1730.
4. 6- alkylguanine DNA alkyltransferase. Protein Sci. 13, 301-305.
5. 6-alkylguanine-DNA alkyltransferase (AGT), Cys145-alkylated AGT and Cys145 → Met145 mutant AGT: comparison by isoelectric focusing, CD and time-resolved fluorescence spectroscopy. Biochem. J. 324 (Pt. 1), 321-328.
6. 6-benzylguanine analogues on sensitivity of human tumor cells to the cytotoxic effects of alkylating agents. Cancer Res. 51, 3367-3372.
7. 6-benzylguanine on the response to 1,3-bis-(2-chloroethyl)-1-nitrosourea in the Dunning R3327G model of prostatic cancer. Cancer Chemother. Pharmacol. 32, 221-225.
8. 6-benzylguanine. J. Med. Chem. 47, 6875-6883.
9. 6-alkylguanine-DNA alkyltransferase. Chem. Res. Toxicol. 17, 972-982.
10. Guengerich, F. P. (2005) Principles of covalent binding of reactive metabolites and examples of activation of bis-electrophiles by conjugation. Arch. Biochem. Biophys. 433, 369-378.
11. Melnick, R. L., and Kohn, M. C. (1995) Mechanistic data indicate that 1,3-butadiene is a human carcinogen. Carcinogenesis 16, 157-163.
12. Rice, J. M., and Boffetta, P. (2001) 1,3-Butadiene, isoprene and chloroprene: reviews by the IARC monographs programme, outstanding issues, and research priorities in epidemiology. Chem.-Biol. Interact. 135-136, 11-26.
13. Malvoisin, E., and Roberfroid, M. (1982) Hepatic microsomal metabolism of 1,3-butadiene. Xenobiotica 12, 137-144.
14. Himmelstein, M. W., Turner, M. J., Asgharian, B., and Bond, J. A. (1996) Metabolism of 1,3-butadiene: inhalation pharmacokinetics and tissue dosimetry of butadiene epoxides in rats and mice. Toxicology 113, 306-309.
15. Krause, R. J., and Elfarra, A. A. (1997) Oxidation of butadiene monoxide to meso- and (±)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat, and human liver microsomes: evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes. Arch. Biochem. Biophys. 337, 176-184.
16. Sasiadek, M., Norppa, H., and Sorsa, M. (1991) 1,3-Butadiene and its epoxides induce sister-chromatid exchanges in human lymphocytes in vitro. Mutat. Res. 261, 117-121.
17. Cochrane, J. E., and Skopek, T. R. (1994) Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts. Carcinogenesis 15, 713-717.
18. Henderson, R. F., Thomton-Manning, J. R., Bechtold, W. E., and Dahl, A. R. (1996) Metabolism of 1,3-butadiene: species differences. Toxicology 113, 17-22.
19. Park, S., and Tretyakova, N. (2004) Structural characterization of the major DNA-DNA cross-link of 1,2,3,4-diepoxybutane. Chem. Res. Toxicol. 17, 129-136.
20. Park, S., Hodge, J., Anderson, C., and Tretyakova, N. Y. (2004) Guanine-adenine cross-linking by 1,2,3,4-diepoxybutane: potential basis for biological activity. Chem. Res. Toxicol. 17, 1638-1651.
21. Park, S., Anderson, C., Loeber, R., Seetharaman, M., Jones, R., and Tretyakova, N. (2005) Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: role of stereochemistry. J. Am. Chem. Soc. 127, 14355-14365.
22. 6- alkylguanine-DNA alkyltransferase. J. Biol. Chem. 279, 4250-4259.
23. Jelitto, B., Vangala, R. R., and Laib, R. J. (1989) Species differences in DNA damage by butadiene: role of diepoxybutane. Arch. Toxicol., Suppl. 13, 246-249.
24. 6-alkylguanine-DNA alkyltransferase after reaction with nitric oxide. Cancer Res. 62, 3037-3043.
25. 6-benzylguanine. Cancer Res. 56, 5571-5575.
26. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Press, Cold Spring Harbor, New York.
27. Tretyakova, N. Y., Sangaiah, R., Yen, T. Y., and Swenberg, J. A. (1997) Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane. Chem. Res. Toxicol. 10, 779-785.
28. a and high reactivity of cysteine 145. Biochemistry 42, 10965-10970.
29. 6-alkylguanine-DNA alkyltransferase. J. Biol. Chem. 277, 37920-37928.