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Chem Res Toxicol
2006 Jan 01;191:16-9. doi: 10.1021/tx050250z.
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The 5'-GNC site for DNA interstrand cross-linking is conserved for diepoxybutane stereoisomers.
Millard JT
,
Hanly TC
,
Murphy K
,
Tretyakova N
.
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The bifunctional alkylating agent 1,2,3,4-diepoxybutane forms interstrand DNA-DNA cross-links between the N7 positions of deoxyguanosine residues on opposite strands of the duplex. For racemic diepoxybutane, these cross-links predominate within 5'-GNC/3'CNG sequences, where N is any nucleotide. We used denaturing polyacrylamide gel electrophoresis (dPAGE) to examine the role of stereochemistry in the cross-linking reaction, subjecting a restriction fragment to cross-linking with S,S-DEB, R,R-DEB, or meso-DEB. DNA cross-links generated by each isomer were isolated by dPAGE, and the sites of cross-linking were identified by sequencing gel analysis of DNA fragments generated by hot piperidine cleavage. We found that the 5'-GNC consensus sequence of racemic DEB is conserved, but the efficiencies of cross-linking vary, with S,S- > R,R- > meso-DEB. These results help explain the observed differences between the biological activities of DEB stereoisomers.
Albertini,
The use of non-tumor data in cancer risk assessment: reflections on butadiene, vinyl chloride, and benzene.
2003, Pubmed
Albertini,
The use of non-tumor data in cancer risk assessment: reflections on butadiene, vinyl chloride, and benzene.
2003,
Pubmed
Brookes,
The reaction of mono- and di-functional alkylating agents with nucleic acids.
1961,
Pubmed
Carmical,
Butadiene-induced intrastrand DNA cross-links: a possible role in deletion mutagenesis.
2000,
Pubmed
Cochrane,
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.
1994,
Pubmed
Divine,
Cancer mortality among workers at a butadiene production facility.
1993,
Pubmed
Divine,
An update on mortality among workers at a 1,3-butadiene facility--preliminary results.
1990,
Pubmed
Doerr,
Species difference in the ovarian toxicity of 1,3-butadiene epoxides in B6C3F1 mice and Sprague-Dawley rats.
1996,
Pubmed
Ehrenberg,
Genetic toxicity of some important epoxides.
1981,
Pubmed
Fischhaber,
Direct demonstration in synthetic oligonucleotides that N,N'-bis(2-chloroethyl)-nitrosourea cross links N1 of deoxyguanosine to N3 of deoxycytidine on opposite strands of duplex DNA.
1999,
Pubmed
Hartley,
DNA alkylation and interstrand cross-linking by treosulfan.
1999,
Pubmed
Hartley,
DNA sequence selectivity of guanine-N7 alkylation by three antitumor chloroethylating agents.
1986,
Pubmed
Johnson,
Selective recognition of the m5CpG dinucleotide sequence in DNA by mitomycin C for alkylation and cross-linking.
1995,
Pubmed
Kuduvalli,
Cleavage by calicheamicin gamma 1I of DNA in a nucleosome formed on the 5S RNA gene of Xenopus borealis.
1995,
Pubmed
,
Xenbase
Lee,
Mutations induced by 1,3-butadiene metabolites, butadiene diolepoxide, and 1,2,3,4-diepoxybutane at the Hprt locus in CHO-K1 cells.
2002,
Pubmed
Li,
C5 cytosine methylation at CpG sites enhances sequence selectivity of mitomycin C-DNA bonding.
2000,
Pubmed
Luce,
Chemical cross-linking of drugs to DNA.
2001,
Pubmed
Macaluso,
Leukemia and cumulative exposure to butadiene, styrene and benzene among workers in the synthetic rubber industry.
1996,
Pubmed
Matagne,
Induction of chromosomal aberrations and mutations with isomeric forms of L-threitol-I,4-bismethanesulfonate in plant materials.
1969,
Pubmed
Mattes,
DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards.
1986,
Pubmed
Millard,
Sequence preferences of DNA interstrand crosslinking agents: quantitation of interstrand crosslink locations in DNA duplex fragments containing multiple crosslinkable sites.
1991,
Pubmed
Millard,
Cytosine methylation enhances mitomycin C cross-linking.
1993,
Pubmed
Millard,
Diepoxybutane and diepoxyoctane interstrand cross-linking of the 5S DNA nucleosomal core particle.
2001,
Pubmed
,
Xenbase
Millard,
Effect of nucleosome structure on DNA interstrand cross-linking reactions.
1998,
Pubmed
,
Xenbase
Millard,
Diepoxybutane cross-links DNA at 5'-GNC sequences.
1993,
Pubmed
Ojwang,
Synthesis of a duplex oligonucleotide containing a nitrogen mustard interstrand DNA-DNA cross-link.
1989,
Pubmed
Park,
Structural characterization of the major DNA-DNA cross-link of 1,2,3,4-diepoxybutane.
2004,
Pubmed
Park,
Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: role of stereochemistry.
2005,
Pubmed
Rajski,
DNA Cross-Linking Agents as Antitumor Drugs.
1998,
Pubmed
Said,
Nearest neighbor effects on carcinogen binding to guanine runs in DNA.
1991,
Pubmed
Sawyer,
Flanking sequences modulate diepoxide and mustard cross-linking efficiencies at the 5'-GNC site.
2004,
Pubmed
Sunters,
The cytotoxicity, DNA crosslinking ability and DNA sequence selectivity of the aniline mustards melphalan, chlorambucil and 4-[bis(2-chloroethyl)amino] benzoic acid.
1992,
Pubmed
Verly,
Inactivation of the T7 coliphage by the diepoxybutane stereoisomers.
1971,
Pubmed
Yarema,
Mutagenic and genotoxic effects of DNA adducts formed by the anticancer drug cis-diamminedichloroplatinum(II).
1995,
Pubmed
Yunes,
1,2,5,6-Diepoxyhexane and 1,2,7,8-diepoxyoctane cross-link duplex DNA at 5'-GNC sequences.
1996,
Pubmed
