ArticleNucleic acids research2005
Fluorescent properties of DNA base analogue tC upon incorporation into DNA--negligible influence of neighbouring bases on fluorescence quantum yield.
Article in Nucleic acids research, 2005. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.
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Who cites it
42 citing papers in PubMed.
- Increased brightness of fluorescent uridine, qU, inside single- and double-stranded RNA.Scientific reports · 2026Article
- Studies upon Fluorescent Modulation of Silver Nanoclusters Formed on Bifunctional DNA Template.International journal of molecular sciences · 2025Article
- Evidence for intrinsic DNA dynamics and deformability in damage sensing by the Rad4/XPC nucleotide excision repair complex.Nucleic acids research · 2025Article
- Metabolic RNA labeling in non-engineered cells following spontaneous uptake of fluorescent nucleoside phosphate analogues.Nucleic acids research · 2024Article
- Evaluation by Experimentation and Simulation of a FRET Pair Comprising Fluorescent Nucleobase Analogs in Nucleosomes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Determination of two-photon absorption in nucleobase analogues: a QR-DFT perspective.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2022Article
- Determination of two-photon absorption in nucleobase analogues: a QR-DFT perspective.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2022Article
- A DNA-Based Two-Component Excitonic Switch Utilizing High-Performance Diarylethenes.Angewandte Chemie (International ed. in English) · 2022Article
- Fluorescent base analogues in gapmers enable stealth labeling of antisense oligonucleotide therapeutics.Scientific reports · 2021Article
- 2',4'-BNA/LNA with 9-(2-Aminoethoxy)-1,3-diaza-2-oxophenoxazine Efficiently Forms Duplexes and Has Enhanced Enzymatic Resistance*.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Getting DNA and RNA out of the dark with 2CNqA: a bright adenine analogue and interbase FRET donor.Nucleic acids research · 2020Article
- Flexibility and Preorganization of Fluorescent Nucleobase-Pyrene Conjugates Control DNA and RNA Recognition.Molecules (Basel, Switzerland) · 2020Article
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- Monitoring of pH Using an i-Motif-Forming Sequence Containing a Fluorescent Cytosine Analogue, tC.Molecules (Basel, Switzerland) · 2019Article
- Electronic Modifications of Fluorescent Cytidine Analogues Control Photophysics and Fluorescent Responses to Base Stacking and Pairing.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Structure guided fluorescence labeling reveals a two-step binding mechanism of neomycin to its RNA aptamer.Nucleic acids research · 2019Article
- 4-Cyanoindole-2'-deoxyribonucleoside (4CIN): A Universal Fluorescent Nucleoside Analogue.Organic letters · 2018Article
- A Lucifer-Based Environment-Sensitive Fluorescent PNA Probe for Imaging Poly(A) RNAs.Chembiochem : a European journal of chemical biology · 2018Article
- Pentacyclic adenine: a versatile and exceptionally bright fluorescent DNA base analogue.Chemical science · 2018Article
- Fluorescent nucleobase analogues for base-base FRET in nucleic acids: synthesis, photophysics and applications.Beilstein journal of organic chemistry · 2018Review
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6 authors.
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Abstract
The quantum yield of the fluorescent tricyclic cytosine analogue, 1,3-diaza-2-oxophenothiazine, tC, is high and virtually unaffected by incorporation into both single- and double-stranded DNA irrespective of neighbouring bases (0.17-0.24 and 0.16-0.21, respectively) and the corresponding fluorescence decay curves are all mono-exponential, properties that are unmatched by any base analogue so far. The fluorescence lifetimes increase when going from tC free in solution (3.2 ns) to single- and double-stranded DNA (on average 5.7 and 6.3 ns, respectively). The mono-exponential decays further support previous NMR results where it was found that tC has a well-defined position and geometry within the DNA helix. Furthermore, we find that the oxidation potential of tC is 0.4 V lower than for deoxyguanosine, the natural base with the lowest oxidation potential. This suggests that tC may be of interest in charge transfer studies in DNA as an electron hole acceptor. We also present a novel synthetic route to the phosphoramidite form of tC. The results presented here together with previous work show that tC is a very good C-analogue that induces minimal perturbation to the native structure of DNA. This makes tC unique as a fluorescent base analogue and is thus highly interesting in a range of applications for studying e.g. structure, dynamics and kinetics in nucleic acid systems.
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