ArticleNucleic acids research2009
Furan-modified oligonucleotides for fast, high-yielding and site-selective DNA inter-strand cross-linking with non-modified complements.
Article in Nucleic acids research, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 71 citations in OpenAlex.
- Chemical and photoinduced interstrand crosslinking of oligo DNA duplexes containing 2'-deoxythioguanosines.Communications chemistry · 2025Article
- A Photosensitized Singlet Oxygen (Molecules (Basel, Switzerland) · 2022Review
- Interrogating biological systems using visible-light-powered catalysis.Nature reviews. Chemistry · 2021Review
- Selective covalent capture of a DNA sequence corresponding to a cancer-driving C>G mutation in theRSC advances · 2019Article
- Interstrand DNA Cross-Links Derived from Reaction of a 2-Aminopurine Residue with an Abasic Site.ACS chemical biology · 2019Article
- Synthesis and Improved Cross-Linking Properties of C5-Modified Furan Bearing PNAs.Molecules (Basel, Switzerland) · 2017Article
- Risks for public health related to the presence of furan and methylfurans in food.EFSA journal. European Food Safety Authority · 2017Article
- Sequence-Specific Covalent Capture Coupled with High-Contrast Nanopore Detection of a Disease-Derived Nucleic Acid Sequence.Chembiochem : a European journal of chemical biology · 2017Article
- A role for the base excision repair enzyme NEIL3 in replication-dependent repair of interstrand DNA cross-links derived from psoralen and abasic sites.DNA repair · 2017Review
- A simple, high-yield synthesis of DNA duplexes containing a covalent, thermally cleavable interstrand cross-link at a defined location.Angewandte Chemie (International ed. in English) · 2015Article
- Photouncaged Sequence-specific Interstrand DNA Cross-Linking with Photolabile 4-oxo-enal-modified Oligonucleotides.Scientific reports · 2015Article
- Selective nucleic acid capture with shielded covalent probes.Journal of the American Chemical Society · 2013Article
- Synthesis and characterization of an O(6)-2'-deoxyguanosine-alkyl-O(6)-2'-deoxyguanosine interstrand cross-link in a 5'-GNC motif and repair by human O(6)-alkylguanine-DNA alkyltransferase.Organic & biomolecular chemistry · 2010Article
- Scope and mechanism of interstrand cross-link formation by the C4'-oxidized abasic site.Journal of the American Chemical Society · 2009Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Among the various types of DNA damage, inter-strand cross-links (ICL) represent one of the most cytotoxic lesions. Processes such as transcription and replication can be fully blocked by ICLs, as shown by the mechanism of action of some anticancer drugs. However, repair of ICLs can be a possible cause of resistance. To study the mechanisms of cross-link repair stable, site-specifically cross-linked duplexes are needed. We here report on the synthesis of site-specifically cross-linked DNA using an acyclic furan containing nucleoside. Selective in situ oxidation of the incorporated furan moiety generates a highly reactive oxo-enal that instantly reacts with the complementary base in a non-modified strand, yielding one specific stable cross-linked duplex species. Varying sequence context showed that a strong selectivity for cross-linking to either complementary A or complementary C is operating, without formation of cross-links to neighboring or distant bases. Reaction times are very short and high isolated yields are obtained using only one equivalent of modified strand. The formed covalent link is stable and the isolated cross-linked duplexes can be stored for several months without degradation. Structural characterization of the obtained ICL was possible by comparison to the natural mutagenic adducts of cis-2-butene-1,4-dial, a metabolite of furan primarily responsible for furan carcinogenicity.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.