ArticleAngewandte Chemie (International ed. in English)2014
Photoswitchable formation of a DNA interstrand cross-link by a coumarin-modified nucleotide.
Article in Angewandte Chemie (International ed. in English), 2014. 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.
- Chemical and photoinduced interstrand crosslinking of oligo DNA duplexes containing 2'-deoxythioguanosines.Communications chemistry · 2025Article
- A Photoinducible DNA Cross-Linking Agent with Potent Cytotoxicity and Selectivity Toward Triple-Negative Breast Cancer Cell Line.Chemical research in toxicology · 2025Article
- Crosslinker-modified nucleic acid probes for improved target identification and biomarker detection.RSC chemical biology · 2021Review
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- Interstrand DNA Cross-Links Derived from Reaction of a 2-Aminopurine Residue with an Abasic Site.ACS chemical biology · 2019Article
- 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
- Photochemical Generation of Benzyl Cations That Selectively Cross-Link Guanine and Cytosine in DNA.Organic letters · 2016Article
- Simple, High-Yield Syntheses of DNA Duplexes Containing Interstrand DNA-DNA Cross-Links Between an N(4) -Aminocytidine Residue and an Abasic Site.Current protocols in nucleic acid chemistry · 2016Article
- A Nanosystem Capable of Releasing a Photosensitizer Bioprecursor under Two-Photon Irradiation for Photodynamic Therapy.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2016Article
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Authors and funding
5 authors.
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Abstract
A coumarin-modified pyrimidine nucleoside (1) has been synthesized using a Cu(I)-catalyzed click reaction and incorporated into oligodeoxynucleotides (ODNs). Interstrand cross-links are produced upon irradiation of ODNs containing 1 at 350 nm. Cross-linking occurs through a [2+2] cycloaddition reaction with the opposing thymidine, 2'-deoxycytidine, or 2'-deoxyadenosine. A much higher reactivity was observed with dT than dC or dA. Irradiation of the dT-1 and dC-1 cross-linked products at 254 nm leads to a reversible ring-opening reaction, while such phenomena were not observed with dA-1 adducts. The reversible reaction is ultrafast and complete within 50-90 s. Consistent photoswitching behavior was observed over 6 cycles of irradiation at 350 nm and 254 nm. To the best of our knowledge, this is the first example of photoswitchable interstrand cross-linking formation induced by a modified pyrimidine nucleoside.
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