ArticleNucleic acids research2006
A modified thymine for the synthesis of site-specific thymine-guanine DNA interstrand crosslinks.
Article in Nucleic acids research, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 23 citations in OpenAlex.
- Synthesis of structurally diverse major groove DNA interstrand crosslinks using three different aldehyde precursors.Nucleic acids research · 2014Article
- Reversibly locked thionucleobase pairs in DNA to study base flipping enzymes.Beilstein journal of organic chemistry · 2014Article
- New synthetic substrates of mammalian nucleotide excision repair system.Nucleic acids research · 2013Article
- Using synthetic DNA interstrand crosslinks to elucidate repair pathways and identify new therapeutic targets for cancer chemotherapy.Cellular and molecular life sciences : CMLS · 2010Review
- Synthesis and molecular modeling of a nitrogen mustard DNA interstrand crosslink.Chemistry (Weinheim an der Bergstrasse, Germany) · 2010Article
- 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
- Furan-modified oligonucleotides for fast, high-yielding and site-selective DNA inter-strand cross-linking with non-modified complements.Nucleic acids research · 2009Article
- Generation of DNA interstrand cross-links by post-synthetic reductive amination.Organic letters · 2009Article
- Multinuclear NMR and kinetic analysis of DNA interstrand cross-link formation.Journal of the American Chemical Society · 2008Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
DNA interstrand crosslinks (ICLs) are highly cytotoxic lesions formed by a variety of important anti-tumor agents. Despite the clinical importance of ICLs, the mechanisms by which these lesions are repaired in mammalian cells have so far remained elusive. One of the obstacles in the study of ICL repair has been the limited availability of suitable methods for the synthesis of defined site-specific ICLs. We report here the synthesis of a site-specific ICL containing an ethylene-bridged G-T base pair based on the incorporation of a crosslink precursor containing a selectively reactive group on one strand using solid-phase synthesis. 3-(2-chloroethyl)thymidine was incorporated into oligonucleotides and underwent ICL formation upon annealing to a complementary strand by reacting with the base opposite to the modified T residue. A strong preference for ICL formation with a G residue opposite the reactive T was observed. Detailed characterization of the reaction product revealed that the alkylation reaction occurred with the O-6 group of G and a mechanism accounting for this preference is proposed. These G-T crosslinks introduced here will be useful for studies of ICL repair.
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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.