ArticleJournal of the American Chemical Society2008
Multinuclear NMR and kinetic analysis of DNA interstrand cross-link formation.
Article in Journal of the American Chemical Society, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Chemical Insights into Oxidative and Nitrative Modifications of DNA.International journal of molecular sciences · 2023Review
- Formation and repair of unavoidable, endogenous interstrand cross-links in cellular DNA.DNA repair · 2021Review
- The AT Interstrand Cross-Link: Structure, Electronic Properties, and Influence on Charge Transfer in dsDNA.Molecular therapy. Nucleic acids · 2018Article
- Chemo-enzymatic synthesis of the exocyclic olefin isomer of thymidine monophosphate.Bioorganic & medicinal chemistry · 2018Article
- Independent Generation and Reactivity of Thymidine Radical Cations.The Journal of organic chemistry · 2017Article
- Interstrand cross-linking implies contrasting structural consequences for DNA: insights from molecular dynamics.Nucleic acids research · 2017Article
- Identification of proximal sites for unwound DNA substrate in Escherichia coli topoisomerase I with oxidative crosslinking.FEBS letters · 2017Article
- Reactivity of Nucleic Acid Radicals.Advances in physical organic chemistry · 2016Article
- Bromopyridone Nucleotide Analogues, Anoxic Selective Radiosensitizing Agents That Are Incorporated in DNA by Polymerases.The Journal of organic chemistry · 2015Article
- Probing interactions between lysine residues in histone tails and nucleosomal DNA via product and kinetic analysis.ACS chemical biology · 2015Article
- Interstrand cross-link and bioconjugate formation in RNA from a modified nucleotide.The Journal of organic chemistry · 2014Article
- DNA interstrand cross-linking upon irradiation of aryl halide C-nucleotides.The Journal of organic chemistry · 2014Article
- Interstrand DNA-DNA cross-link formation between adenine residues and abasic sites in duplex DNA.Journal of the American Chemical Society · 2014Article
- Deconvoluting the reactivity of two intermediates formed from modified pyrimidines.Organic letters · 2013Article
- Oxidation and reduction of the 5-(2'-deoxyuridinyl)methyl radical.Angewandte Chemie (International ed. in English) · 2013Article
- Mechanistic studies of the spore photoproduct lyase via a single cysteine mutation.Biochemistry · 2012Article
- DNA damage by C1027 involves hydrogen atom abstraction and addition to nucleobases.Bioorganic & medicinal chemistry · 2012Article
- DNA damage and interstrand cross-link formation upon irradiation of aryl iodide C-nucleotide analogues.The Journal of organic chemistry · 2010Article
- Nucleotide excision repair of a DNA interstrand cross-link produces single- and double-strand breaks.Biochemistry · 2010Article
- An overview of chemical processes that damage cellular DNA: spontaneous hydrolysis, alkylation, and reactions with radicals.Chemical research in toxicology · 2009Review
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Recently, a phenylselenyl-modified thymidine (2) was shown to produce DNA interstrand cross-links (ICLs) via two mechanisms. Photolysis of 2 generates 5-(2'-deoxyuridinyl)methyl radical (1), the reactive intermediate that results from formal hydrogen atom abstraction from the thymine methyl group. This reactive intermediate reacts with the opposing dA and is the first example of a DNA radical that produces ICLs. Kinetic competition studies support the proposal that the rate-limiting step in ICL formation from 1 involves rotation about the glycosidic bond and that the rate constant for this process is influenced by the flanking sequence. Cross-links also form with the opposing dA when 2 is treated with mild oxidants that result in the formation of an intermediate methide-like species (4). Kinetic experiments reveal that 4 reacts with azide, a model nucleophile, via an S(N)2' pathway. Previous experiments suggested that the same product is produced via 1 or 4 but that the initially formed cross-link rearranges during the enzyme digestion and isolation procedures. In situ product analysis by NMR using synthetic, doubly labeled duplex DNA containing (13)C-2 and (15)N(1)-dA provides definitive evidence that the kinetic ICL products formed via the radical and oxidative pathways are the same and correspond to that arising from formal alkylation of N(1)-dA. Furthermore, analysis of the thermodynamic product formed upon rearrangement indicates that the primary product isomerizes via an associative mechanism in DNA.
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