Literature DB >> 8448170

Diepoxybutane cross-links DNA at 5'-GNC sequences.

J T Millard1, M M White.   

Abstract

Epoxides are cancer-causing agents chemically analogous to the nitrogen mustards, a family of powerful antitumor drugs. We found that the DNA interstrand cross-linking sequence preference of diepoxybutane is the same as that of the mustard mechlorethamine: 5'-GNC. Therefore, the genomic site of cross-linking alone cannot explain why some interstrand cross-linkers act as antitumor agents whereas others are deadly toxins.

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Year:  1993        PMID: 8448170     DOI: 10.1021/bi00059a034

Source DB:  PubMed          Journal:  Biochemistry        ISSN: 0006-2960            Impact factor:   3.162


  14 in total

1.  Diepoxybutane interstrand cross-links induce DNA bending.

Authors:  Julie T Millard; Erin E McGowan; Sharonda Q Bradley
Journal:  Biochimie       Date:  2011-08-04       Impact factor: 4.079

2.  Structure of the 1,4-bis(2'-deoxyadenosin-N6-yl)-2R,3R-butanediol cross-link arising from alkylation of the human N-ras codon 61 by butadiene diepoxide.

Authors:  W Keither Merritt; Lubomir V Nechev; Tandace A Scholdberg; Stephen M Dean; Sarah E Kiehna; Johanna C Chang; Thomas M Harris; Constance M Harris; R Stephen Lloyd; Michael P Stone
Journal:  Biochemistry       Date:  2005-08-02       Impact factor: 3.162

Review 3.  A review of the role of the sequence-dependent electrostatic landscape in DNA alkylation patterns.

Authors:  Barry Gold; Luis M Marky; Michael P Stone; Loren D Williams
Journal:  Chem Res Toxicol       Date:  2006-11       Impact factor: 3.739

4.  DNA oligomers containing site-specific and stereospecific exocyclic deoxyadenosine adducts of 1,2,3,4-diepoxybutane: synthesis, characterization, and effects on DNA structure.

Authors:  Uthpala Seneviratne; Sergey Antsypovich; Danae Quirk Dorr; Thakshila Dissanayake; Srikanth Kotapati; Natalia Tretyakova
Journal:  Chem Res Toxicol       Date:  2010-09-27       Impact factor: 3.739

5.  Structure of the 1,4-Bis(2'-deoxyadenosin-N(6)-yl)-2S,3S-butanediol intrastrand DNA cross-link arising from butadiene diepoxide in the human N-ras codon 61 sequence.

Authors:  Wen Xu; W Keither Merritt; Lubomir V Nechev; Thomas M Harris; Constance M Harris; R Stephen Lloyd; Michael P Stone
Journal:  Chem Res Toxicol       Date:  2007-01-27       Impact factor: 3.739

6.  Quantitative PCR analysis of diepoxybutane and epihalohydrin damage to nuclear versus mitochondrial DNA.

Authors:  Frederick J Lariviere; Adam G Newman; Megan L Watts; Sharonda Q Bradley; Justin E Juskewitch; Paul G Greenwood; Julie T Millard
Journal:  Mutat Res       Date:  2009-02-21       Impact factor: 2.433

7.  The 5'-GNC site for DNA interstrand cross-linking is conserved for diepoxybutane stereoisomers.

Authors:  Julie T Millard; Trevor C Hanly; Kris Murphy; Natalia Tretyakova
Journal:  Chem Res Toxicol       Date:  2006-01       Impact factor: 3.739

8.  Polymerase bypass of N7-guanine monoadducts of cisplatin, diepoxybutane, and epichlorohydrin.

Authors:  Jiayu Ye; Caitlin R Farrington; Julie T Millard
Journal:  Mutat Res       Date:  2018-03-20       Impact factor: 2.433

9.  The topoisomerase II poison clerocidin alkylates non-paired guanines of DNA: implications for irreversible stimulation of DNA cleavage.

Authors:  B Gatto; S Richter; S Moro; G Capranico; M Palumbo
Journal:  Nucleic Acids Res       Date:  2001-10-15       Impact factor: 16.971

10.  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.

Authors:  Melissa Goggin; James A Swenberg; Vernon E Walker; Natalia Tretyakova
Journal:  Cancer Res       Date:  2009-03-10       Impact factor: 12.701

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