Diepoxybutane interstrand cross-links induce DNA bending

Biochimie

Volumn 94, Issue 2, 2012, Pages 574-577

  Millard, Julie T ^a   McGowan, Erin E ^a   Bradley, Sharonda Q ^a  

^a Colby College   (United States)

Author keywords

Alkylating agent; Diepoxybutane; DNA bending; DNA cross linking; DNA damage

Indexed keywords

ADENINE; BUTADIENE DIEPOXIDE; BUTANEDIOL; CURVED DNA; DEOXYGUANOSINE; OLIGOMER;

ARTICLE; CONTROLLED STUDY; DNA CROSS LINKING; DNA SEQUENCE; ELECTROPHORETIC MOBILITY; GENE TARGETING;

BASE SEQUENCE; BUTADIENES; CARCINOGENS; CROSS-LINKING REAGENTS; DNA; DNA DAMAGE; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ELECTROPHORETIC MOBILITY SHIFT ASSAY; EPOXY COMPOUNDS; MOLECULAR SEQUENCE DATA; NUCLEIC ACID CONFORMATION; STEREOISOMERISM;

EID: 84855829071     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2011.07.030     Document Type: Article

References (32)

1. J.A. Bond, and M.A. Medinsky Insights into the toxicokinetics and toxicodynamics of 1,3-butadiene Chemico-Biol. Interact 135-136 2001 599 614 (Pubitemid 32530511)
2. IARC IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 1,3-Butadiene, Ethylene Oxide and Vinyl Halides (Vinyl Fluoride, Vinyl Chloride and Vinyl Bromide) vol. 97 2007 IARC Working Group on the Evaluation of Carcinogenic Risks to Humans Lyon, France pp. 45-184
3. A.-M. Steen, K.G. Meyer, and L. Recio Analysis of hprt mutations occurring in human TK6 lymphoblastoid cells following exposure to 1,2:3,4-diepoxybutane Mutagenesis 12 1997 61 67 (Pubitemid 27153692)
4. N. Sathiakumar, E. Delzell, M. Hovinga, M. Macaluso, J.A. Julian, R. Larson, P. Cole, and D.C. Muir Mortality from cancer and other causes of death among synthetic rubber workers Occup. Environ. Med. 55 1998 230 235 (Pubitemid 28179973)
5. S. Park, and N. Tretyakova Structural characterization of the major DNA-DNA cross-link of 1,2,3,4-diepoxybutane Chem. Res. Toxicol. 17 2004 129 136 (Pubitemid 38252491)
6. S. Park, J. Hodge, C. Anderson, and N.Y. Tretyakova Guanine-adenine cross-linking by 1,2,3,4-diepoxybutane: potential basis for biological activity Chem. Res. Toxicol. 17 2004 1638 1651 (Pubitemid 39665556)
7. M. Goggin, J.A. Swenberg, V.E. Walker, and N. Tretyakova Molecular dosimetry of 1,2,3,4-diepoxybutane-induced DNA-DNA cross-links in B6C3F1 mice and F344 rats exposed to 1,3-butadiene by inhalation Cancer Res. 69 2009 2479 2486
8. J.T. Millard, and M.M. White Diepoxybutane cross-links DNA at 5′-GNC sequences Biochemistry 32 1993 2120 2124 (Pubitemid 23086068)
9. G.A. Sawyer, E.D. Frederick, and J.T. Millard Flanking sequences modulate diepoxide and mustard cross-linking efficiencies at the 5′-GNC site Chem. Res. Toxicol. 17 2004 1057 1063 (Pubitemid 39115329)
10. S. Park, C. Anderson, R. Loeber, M. Seetharaman, R. Jones, and N. Tretyakova Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: role of stereochemistry J. Am. Chem. Soc. 127 2005 4355 4365
11. P. Brookes, and P.D. Lawley The alkylation of guanosine and guanylic acid J. Chem. Soc. 1961 3923
12. J.O. Ojwang, D.A. Grueneberg, and E.L. Loechler Synthesis of a duplex oligonucleotide containing a nitrogen mustard interstrand DNA-DNA cross-link Cancer Res. 49 1989 6529 6537 (Pubitemid 20008781)
13. J.T. Millard, S. Raucher, and P.B. Hopkins Mechlorethamine cross-links deoxyguanosine residues at 5′-GNC sequences in duplex DNA fragments J. Am. Chem. Soc. 112 1990 2459 2460 (Pubitemid 20144466)
14. B.L. Van Duuren Carcinogenic epoxides, lactones, and halo-ethers and their mode of action Ann. NY Acad. Sci. 163 1969 633 651
15. P.B. Hopkins, J.T. Millard, J. Woo, M.F. Weidner, J.J. Kirchner, S.T. Sigurdsson, and S. Raucher Sequence preferences of DNA interstrand cross-linking agents: importance of minimal DNA structural reorganization in the cross-linking reactions of mechlorethamine, cisplatin, and mitomycin C Tetrahedron 47 1991 2475 2489
16. S.M. Rink, and P.B. Hopkins A mechlorethamine-induced DNA interstrand cross-link bends duplex DNA Biochemistry 34 1995 1439 1445
17. H.S. Koo, and D.M. Crothers Calibration of DNA curvature and a unified description of sequence-directed bending Proc. Natl. Acad. Sci. U S A 85 1988 1763 1767 (Pubitemid 24315762)
18. J. Sambrook, E.F. Fritsch, and T. Maniatis Molecular Cloning: A Laboratory Manual second ed. 1989 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
19. M. Zewail-Foote, and L.H. Hurley Ecteinascidin 743: a minor groove alkylator that bends DNA toward the major groove J. Med. Chem. 42 1999 2493 2497 (Pubitemid 29344290)
20. M. Leng DNA bending induced by covalently bound drugs. Gel electrophoresis and chemical probe studies Biophys. Chem. 35 1990 155 163 (Pubitemid 20185435)
21. B.A. Wadugu, C. Ng, B.L. Bartley, R.J. Rowe, and J.T. Millard DNA interstrand cross-linking activity of (1-chloroethenyl)oxirane, a metabolite of beta-chloroprene Chem. Res. Toxicol. 23 2010 235 239
22. H.S. Koo, H.M. Wu, and D.M. Crothers DNA bending at adenine-thymine tracts Nature 320 1986 501 506
23. P. Brooks, and P.D. Lawley The reaction of mono- and di-functional alkylating agents with nucleic acids Biochem. J. 80 1961 496 503
24. J.A. Rice, D.M. Crothers, A.L. Pinto, and S.J. Lippard The major adduct of the antitumor drug cis-diamminedichloroplatinum(II) with DNA bends the duplex by ∼40 degrees toward the major groove Proc. Natl. Acad. Sci. U S A 85 1988 4158 4161
25. P.P. Pil, and S.J. Lippard Specific binding of chromosomal protein HMG1 to DNA damaged by the anticancer drug cisplatin Science 256 1992 234 237
26. S.J. Brown, P.J. Kellett, and S.J. Lippard Ixr1, a yeast protein that binds to platinated DNA and confers sensitivity to cisplain Science 261 1993 603 605 (Pubitemid 23278370)
27. I. Ugrinova, S. Zlateva, I.G. Pashev, and E.A. Pasheva Native HMGB1 protein inhibits repair of cisplatin-damaged nucleosomes in vitro Int. J. Biochem. Cell Biol. 41 2009 1556 1562
28. S. Park, and S.J. Lippard Redox state-dependent interaction of HMGB1 and cisplatin-modified DNA Biochemistry 50 2011 2567 2574
29. Q. He, C.H. Liang, and S.J. Lippard Steroid hormones induce HMG1 overexpression and sensitize breast cancer cells to capsulation and carboplatin Proc. Natl. Acad. Sci. U S A 97 2000 5768 5772 (Pubitemid 30367473)
30. M.C. MacLeod, K.L. Powell, and N. Tran Binding of the transcription factor, Sp1, to non-target sites in DNA modified by benzo[a]pyrene diol epoxide Carcinogenesis 16 1995 975 983
31. E.D. Michaelson-Richie, R.L. Loeber, S.G. Codreanu, X. Ming, D.C. Liebler, C. Campbell, and N.Y. Tretyakova DNA-protein cross-linking by 1,2,3,4-diepoxybutane J. Proteome Res. 9 2010 4356 4367
32. M. Goggin, D. Sangaraju, V.E. Walker, J. Wickliffe, J.A. Swenberg, and N. Tretyakova Persistence and repair of bifunctional DNA adducts in tissues of laboratory animals exposed to 1,3-butadiene by inhalation Chem. Res. Toxicol 24 2011 809 817