ArticleJournal of the American Chemical Society2017
Fluorescence Turn-On Sensing of DNA Duplex Formation by a Tricyclic Cytidine Analogue.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 67 citations in OpenAlex.
- A turn-on fluorescent nucleoside enabling sequence-insensitive DNA labeling.Nucleic acids research · 2026Article
- Impacts of sequence and structure on pyrrolocytosine fluorescence in RNA.Nucleic acids research · 2025Article
- 1Molecules (Basel, Switzerland) · 2024Article
- Synthesis and Evaluation of Diguanosine Cap Analogs Modified at the C8-Position by Suzuki-Miyaura Cross-Coupling: Discovery of 7-Methylguanosine-Based Molecular Rotors.The Journal of organic chemistry · 2023Article
- A modular aldol approach for internal fluorescent molecular rotor chalcone surrogates for DNA biosensing applications.Chemical science · 2023Article
- Live-Cell RNA Imaging with Metabolically Incorporated Fluorescent Nucleosides.Journal of the American Chemical Society · 2022Article
- The Critical Role of Tetrahydrobiopterin (BH4) Metabolism in Modulating Radiosensitivity: BH4/NOS Axis as an Angel or a Devil.Frontiers in oncology · 2021Review
- Single-molecule fluorescence detection of a tricyclic nucleoside analogue.Chemical science · 2020Article
- Nucleotide-Bearing Benzylidene-Tetrahydroxanthylium Near-IR Fluorophore for Sensing DNA Replication, Secondary Structures and Interactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Designing Dihydrofolate Reductase Inhibitors as X-ray Radiosensitizers to Reverse Radioresistance of Cervical Cancer.ACS medicinal chemistry letters · 2020Article
- Flexibility and Preorganization of Fluorescent Nucleobase-Pyrene Conjugates Control DNA and RNA Recognition.Molecules (Basel, Switzerland) · 2020Article
- Single-Molecule Detection of a Fluorescent Nucleobase Analogue via Multiphoton Excitation.The journal of physical chemistry letters · 2019Article
- Electronic Modifications of Fluorescent Cytidine Analogues Control Photophysics and Fluorescent Responses to Base Stacking and Pairing.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Synthesis of Fluorescence Turn-On DNA Hybridization Probe Using theCurrent protocols in nucleic acid chemistry · 2018Article
- 4-Cyanoindole-2'-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue.Organic letters · 2018Article
- Pentacyclic adenine: a versatile and exceptionally bright fluorescent DNA base analogue.Chemical science · 2018Article
- Single-Labeled Oligonucleotides Showing Fluorescence Changes Upon Hybridization with Target Nucleic Acids.Molecules (Basel, Switzerland) · 2018Review
- Fluorescent nucleobases as tools for studying DNA and RNA.Nature chemistry · 2017Review
- DNA Aptamer-Target Binding Motif Revealed Using a Fluorescent Guanine Probe: Implications for Food Toxin Detection.ACS omega · 2017Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Most fluorescent nucleoside analogues are quenched when base stacked and some maintain their brightness, but there has been little progress toward developing nucleoside analogues that markedly increase their fluorescence upon duplex formation. Here, we report on the design and synthesis of a new tricyclic cytidine analogue, 8-diethylamino-tC (8-DEA-tC), that responds to DNA duplex formation with up to a 20-fold increase in fluorescent quantum yield as compared with the free nucleoside, depending on neighboring bases. This turn-on response to duplex formation is the greatest of any reported nucleoside analogue that can participate in Watson-Crick base pairing. Measurements of the quantum yield of 8-DEA-tC mispaired with adenosine and, separately, opposite an abasic site show that there is almost no fluorescence increase without the formation of correct Watson-Crick hydrogen bonds. Kinetic isotope effects from the use of deuterated buffer show that the duplex protects 8-DEA-tC against quenching by excited state proton transfer. These results, supported by DFT calculations, suggest a rationale for the observed photophysical properties that is dependent on duplex integrity and the electronic structure of the analogue.
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Registered trials
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